Definitions:

Consider botany. What isataxon? It is the name which identifies

aplant. A taxon is made of two parts. First, there is the genus,
whichisageneral name given toagroup of closely related plants.
Second, there is the species, which is the distinguishing name
giventoaspecific plant in that group. A taxon is always written
initalics. Thus, for example, Pachycereus pecten-aboriginum is the
nameof acactus.
Consider chemistry. What are isoquinolines? These arechemical
structures built around atwo-ring compound. This compound,
Isoquinoline, consists of abenzene ring and pyridine ring fused
together at aspecific bond. There is apattern of substitution that
givesan isoquinoline its absolute definition. Thus, for example,
Salsolineis an isoquinoline, which is a major component of the
Pachycereus pecten-aboriginum plant.
Onecanidentify aplant by what it looks like, or by what is in it.
Onecanidentify anatural compound by its structure, or by what
plant it isin. Know one, find the other. This reference book has
beendesigned to make this cross-identification easier to achieve.
TABLE OF CONTENTS
Foreword I
vi
Foreword II
xi
Introduction
xiii
Trivial Name Index
1
Structural Index
Unsubstituted
Monosubstituted
Disubstituted
5,6- 5,7- and 5,8-substituted
6,7-HO,HO-substituted
6,7-HO,MeO-substituted
6,7-MeO,HO-substituted
6,7-MeO,MeO-substituted
6,7-MDO-substituted
6,8-substituted
7,8-substituted
Trisubstituted
5,6,7-substituted
5,6,8-substituted
6,7,8-substituted
Tetrasubstituted
39
41
46
47
52
88
161
245
347
349
372
425
426
455
TaxonIndex
458
Plant Families Appendix
602
Isobenzofuranone Appendix
610
J ournal Names Appendix
616
v
vi
FOREWORDI
Thepassion of my lifeover thelast forty years has been acompelling
interest in psychedelic drugs. They have given me not only an exciting
area of research and discovery, but also apersonal understanding of just
who I am and why I am. Certainly these guides and sacraments will
eventually play an accepted role in our community and in our culture.
Almost all of these drugs have either been isolated frompsychoactive
plants, or aretheresults of subtlevariations of themolecular structures of
theseisolates.
I havealways looked at theseplants and thecompounds they contain
inthesameway that theRomans dreamt of their ultimate empire. It was
Caesar who acknowledged that all of Gaul was divided into three parts
and to understand it, to conquer it, each part had to be respected as a
separate entity. It isexactly thesameway with understanding theworld
of psychedelic drugs. There are three domains of inquiry that must be
studied independently before one canbegin to appreciate just how they
might integrate into a single concept. These three are now, I believe,
coming together.
Onepart isthelarge collection of psychoactive compounds known as
thephenethylamines. Thefirst known plant psychedelic was mescaline,
or 3,4,5-trimethoxyphenethylamine. This simple one-ring alkaloid was
discovered in the North American dumpling cactus Peyote (Anhalonium
toilliamsii) inthelatenineteenth century, and isnow known tobeacom-
ponent of over fifty other cacti. Over adozen other cactus phenethyl-
amines havebeen isolated and identified, and there areperhaps ahun-
dred synthetic analogues that arenow also known tobepsychedelic in
action. Thisbody of information hasbeen published bymy wifeAnn and
measabook entitled "PIHKAL:AChemical LoveStory." PIHKAL stands
for Phenethylamines I Have Known and Loved.
An almost-as-large chemical group contains the tryptamines. N,N-
Dimethyltryptamine (DMT), its 5-hydroxy analogue (bufotenine) and
theO-methyl ether homologue 5-methoxy-N,N-dimethyltryptamine (5-
MeO-DMT) arewidely distributed intheworld of natural plants. There
arealso thewell-established mushroom alkaloids 4-phosphoryloxy-N,N-
vii
dimethyltryptamine (psilocybin, and the dephosphorylated indolol psilo-
cin)and the mono- and didemethylated homologues baeocysteine and
norbaeocysteine. These seven natural alkaloids have provided the tem-
platefor perhaps two dozen analogue structures that are now well-estab-
lishedpsychedelic agents. Ann and I have written a companion volume
toPIHKAL called "TIHKAL: The Continuation" (TIHKAL stands for
TryptaminesI haveKnown and Loved), which has brought together most
ofthesenatural and synthetic tryptamines into asingle reference site.
Theremaining third of the above Gallic synthesis deals with what I
hadoriginallycalled the "Q" compounds, as distinguished from the "P"
compounds and the "T" compounds (the phenethylamines and the
tryptamines). Theactual parent structural element isthe isoquinoline ring
system,and myinitial plan was to give this third book aname similar to
thefirst two. IIHKAL wouldn't do it, but QIHKAL shows agood bit of
class,at least in my opinion. Or maybe THIQIHKAL because most of
themarereally tetrahydroisoquinolines. Well, all these names are now
onhold, as Ann is uncomfortable with them. No name has yet been
decidedupon, but ideas such as The Third Book, or Book Three, are
under consideration. Names like these resound with arather striking
arrogance, if nothing else.
Tounderstand the relationship of the isoquinolines to the phenethyl-
aminesand the tryptamines, the concept of ring closure must be used.
Thisisasortofsynthetic scorpion sting at themolecular level. Atryptamine
hasanindole ring as its centerpiece and from it there extends a floppy
two-carbonchain terminated by an amino nitrogen atom. A small but
veryimportant family of plant alkaloids is the product of this amine ex-
ploitingacarbonatomfromsomewhere, and making anew six-membered
ringbythat "sting" reaction back onto the parent indole ring. This family
hasthename,~-carbolines, and theformed compound is1,2,3,4-tetrahydro-
[3-carboline.
Q C N H
N
I
H
tryptamine 1,2,3,4-tetrahydro-~-carboline
Aphenethylamine has abenzene ring as its centerpiece and it, too, has
afloppytwo-carbon chain extending out from it and also terminating in
anamino group. In a reaction that is exactly analogous to that of the
tryptamines,thisamine can pick up acarbon atom and bend back to react
viii
with theparent benzene ring forming asix-member ring. Thisisthe ori-
gin of the isoquinoline family of natural products, and the formed com-
pound is l,2,3,4-tetrahydroisoquinoline.
phenethylamine 1,2,3,4-tetrahydroisoquinoline
As mentioned above, this third part of the plant psychedelic alkaloid
world involves tetrahydroisoquinolines and isthe substance of our third
book. Avery reasonable appendix tobewritten for this book would bea
search of the chemical literature for the known isoquinolines that might
beof interest as pharmacological agents. Therearecertainly many plant
products, aswell asamonster inventory of synthetics, someof which are
made based on plant examples, but many others are simply laboratory
creations of theimaginative chemist.
It was soon apparent that this compilation would become unmanage-
ablylarge. Thefirst major trimming was theelimination of thecompounds
that were synthetic, and the limitation of thelisting to those compounds
that havebeenreported asplant products. Theseisoquinolines could play
thedual roleof serving not only as potential contributors to theaction of
psychoactive plants but also as prototypes for the synthesis of new
materials that might themselves bebiologically active.
But even this restriction toonly plant compounds was not sufficiently
severe. Thereseemed tobeno end toexisting isoquinoline treasures. As
I wandered deeper into the literature, I kept finding an ever-increasing
inventory of research papers that described fantastic stuff. As a totally
make-believe example, pretend that there was a compound named
Dogabinine that has only been found in the Dogabic treein the Twathtu
rainforest, which thenatives say cures leprosy, and which has acomplex
chemical structure that just happens to carry an isoquinoline ring in its
lower southwest corner. Toinclude all such monsters would make the
appendix many thousands or even tens of thousands of pages long. And
if youweretoadd into this compilation all theknown derivatives, exten-
sions and chemical modifications of Dogabinine, then you would have a
reviewentity that would beseveral volumes inlength. If suchacollection
weretoexist, I would haveit inmy library right now. Butit does not exist
and it may never exist.
IX
Somemiddle ground, some rational compromise, had to be found. I
wantedthis collection to present all isoquinolines that are known to be
plantalkaloids, but respecting carefully defined restrictions that exclude
horrormonsters such as Dogabinine. The final compromise was to estab-
lishseparateentries for all the known two-ring isoquinolines that arefrom
natural sources, including those that carry a third ring as a substituent
(suchasabenzyl group) at the I-position. And within each of these en-
tries,thereareincluded all natural alkaloids that can be seen as products
ofahypothetical attack of an ortho hydrogen of this substituent on some
otherposition of the isoquinoline nucleus. This "ortho-X attack" is ex-
actlydefinedand illustrated intheForeword thatfollows. All plant sources
arerecorded (or representative sources if there are too many) and litera-
turecitationsarealso included in each entry.
Butevenwith these restrictions, this "appendix" to a third book was
becominglarger and larger, and it soon became apparent that it was to-
tallyinappropriate. There would be far too many pages for aminor ap-
pendixinabook that is tobe dedicated to cactus and isoquinolines. And
bythetimemy stream-of-consciousness commentary was added in the
textwhereI feltit should beadded, the mass increased to the extent that it
hadtobeareference book in its own right.
Voila.Let's try to get all that information together into asingle modest
packageand make it available to the chemists and botanists who might
wantit. Should it beareview article in Chemical Reviews or the J ournal
of Natural Products? Several factors said "No." Most botanical review
surveysarenot searchable except by taxon name (that would assume that
youwould know the plant from which it came) or by some complex and
maddeningChemical Abstracts entry that dealt with some alphabetiza-
tionthatdemanded the knowledge of the structure and the way the struc-
turewouldbelisted. And most review articles also insist on atidy format
thatiswithout editorial comment and does not contain volunteered ideas
andextrapolations.
Anobvious solution became apparent. Create asingle reference book
to contain all this information. Use the chemical substituents as an
alphabet. Visuallytravel around the structural image of the molecule ina
logicaldirection,address thesubstituent groups insome logical way which
willbecalledalphabetical, and progress until you find the target you are
searchingfor, or until you find an empty hole where it would have been
haditbeenknown. Sothis book has come into existence simply to meet
thisneed, and to relieve the potential "Third Book" readership of akiller
ofanappendix.
Thenatureof the substituents and, especially, the connection between
simplebenzylated isoquinolines and the nature of the cyclized products
oforthoattacks, arethe heart and substance of this review book.
x
One additional comment is essential in this introduction. Theexten-
siveliterature searching, and commingling of theaccumulated plant and
chemical data, taxed my capability and exceeded my patience. Thiswas
indeed acompilation that was essential tomy current cactus research for
thethird book, but thetask of its organization created adisruptive inter-
ferenceto my exploration of new psychedelics inunanalyzed cacti. The
early help given meby Ann's daughter Wendy quickly evolved into her
playing an indispensable role as my co-author. The final organization
and structuring of this book has been largely the result of her dedicated
labor. Itisanhonor tosharetheauthorship with her as, without her help,
this book would not exist today.
Alexander T.Shulgin
Xl
FOREWORD II
WhenSasha and I began this project it was meant to be an appendix
forthenextbook inthe series of PIHKAL and TIHKAL. It became so big
thatweknew after some time it could not be an appendix; it was its own
book.Sohereit is, acollection of all the information we've compiled over
thelasttwoyears. It's been adaunting project at times. If wehad included
all thevariations of isoquinolines that we had originally planned to, this
bookwould have been a series of volumes. Along the way we had to
makedecisionsabout what was important to keep in, what we could leave
out,what our focus was, what our intentions were. Wepared down con-
stantly,finallysettling on the criteria that Sasha has laid down in the in-
troduction.
Itismybelief that what we have put together here will beof great use
toanyoneinterested in this particular field of botany and chemistry. We
havetriedtomakethe information as easy to find and review as possible,
takinginto consideration what it was like for us to search through the
literature.Hopefully this compilation will make others' work much easier.
Wefound so many mistakes in the literature, and even in the Chemical
Abstracts,that we had to make educated guesses as to the correct way
somethingwas spelled, or what acertain substituent was on agiven ring;
sometimeswesimply made comments in the text about aparticular dis-
crepancy.Wewelcome corrections and comments that come to us, as we
surelyhavemade errors ourselves.
WhatI observed while going through the literature was enlightening.
Whatstood out for me was how much of the plant research done on
isoquinolineshasbeen incountries other than the United States. As many
peopleknow, thestate of objective, independent scientific research in this
countryisasad one. Research is at the mercy of special interests, govern-
mentfunding, and of harsh regulations and restrictions. It's rare to have
asituationwhere ascientist is freeto explore and discover, much less en-
couragedtodo so. Weareleft to rely on research done incountries where
thescientists' findings are not bought and paid for in advance, as hap-
pensinthis country too often. Sasha is a rare chemist indeed, working
independently for so long, free of those controls, and following his pas-
siontodiscover tools to understand the mind and the brain in the faceof
xii
much misunderstanding andmisguided assumptions about psychoactive
materials. As it is now, thepharmaceutical industry isbridging the gap
between what issocially and legally acceptable todo toone's brain chem-
istry inorder tofeel well, and what iscurrently considered unacceptable,
which isusing chemical or plant medicines tolook at why oneisnot feel-
ing well tobegin with.
Thereisgreat hypocrisy, fear, and thoughtlessness afoot intheUnited
Statesregarding psychoactive drugs. Their benefits andpotential uses are
lost in the rhetoric of the "drug war," and in the fear that it generates.
There are many examples of healthy and informed use of psychoactive
medicines throughout the world, and throughout the ages. They have
beenused inthepast, and arebeing used today, ashealing tools. Weneed
that kind of thinking inthis country, weneed that kind of healing.
Hypocrisy existsinthelaws regarding alcohol and tobacco, which are
legal, and arethemost damaging andwidely abused drugs inour culture.
Many pharmaceutical drugs arenot without their dangers and abuses as
well (it's afact that far more Americans die frompharmaceutical drugs
than illegal drugs). What arethefears of psychoactive drugs really based
on? I encourage those who start with the arguments of brain damage
caused by thisor that drug toobtain theactual scientificpapers that make
those claims (not just the titles of the papers) and read them carefully.
Theywill findmuch misinformation due topolitical pressure, economics,
and fear.
It's been ablessing to work with Sasha, who is not only abrilliant
chemist but afantastic teacher. I had nobackground inchemistry when I
began working with him; he has taught me so much. His passion and
enthusiasm for chemistry isinfectious; hehas made it adelight tolearn,
andhasshown mehowmagical it all is. Itismagical, andmysterious, this
world weliveinand thestuff that it and wearemade up of. It should be
cherished, protected, and explored, with honesty and courage.
Wendy E. Perry
Introduction
xiii
INTRODUCTION
Forthisbook toserve asacompletely satisfactory reference, it must
bestructured so that areader who comes to it with one specific word
inmindthat isrelated to the simple, natural isoquinolines, can imme-
diatelylocateall other related entries. Total cross-referencing isneeded.
Asawaytosimplify this type of search, the main part of this book is
actuallyacollection of three indices. Each index isarranged alphabeti-
cally,very much like a dictionary. The first index lists the common
trivial names, the second lists the structures of the compounds them-
selvesand the plants that contain them, and the third lists the taxo-
nomicnamesof these plants and the compounds that have been found
inthem.
Part1: Trivial names of the plant alkaloids:
Alloftheknown simple plant isoquinolines have been entered into
thisindexunder their common, or trivial names. Originally, there was
alinearstructurecodeattached tothetrivial name entry which allowed
thereader toimmediately deduce the chemical structure and to access
thecompounddirectly inthestructural index. It became apparent that
asinglepagereference would do as well. Each trivial name thus leads
tothechemical structure, the plants that contain that compound, and
appropriateliterature references.
Manycompounds have anumber of trivial names. These may be
puresynonyms for asingle compound, or they may distinguish differ-
entstructural or optical isomers. Thequaternary amine alkaloid salts
presentanunusual problem. There are three naming procedures that
arefrequently encountered. The quaternary salt may have a distinct
one-wordname. Here there is no problem. However, the other two
examplesaretwo- or three-word names, with the anion involved be-
ingincorporated into the second word. As the fourth alkyl group on
thenitrogenisusually amethyl group, theanion name would take one
of twoforms. If the parent tertiary amine is, say, the alkaloid Cana-
dine, then the methyl quaternary salt could be called either N-
Methylcanadiniumiodide or Canadine methiodide. Both are faulted
inthat thepresence of the iodide anion in the product is the work of
xiv The Simple Plant Isoquinolines
theanalyst, and it is not what was originally present in theplant. And
if fivepeople weretoindependently isolate this plant product and char-
acterize it as asalt using theanions chloride, iodide, picrate, perchlor-
ateand oxalate (all commonly found inbotanical papers) it would de-
mand five different index entries for a single plant alkaloid. In this
present compilation, N-Methylcanadine quat will be the name used.
But somequaternary amines areinternally tetra-substituted. Withcom-
pounds such as theberberines where thec-ring isaromatic, there isno
external "methyl" group to call upon. Here, using Caseadinium io-
dide asanexample, theanion will also bedropped and it will belisted
as Caseadinium quat.
Part 2: Structural formulae of theplant alkaloids:
Thesecond, and major, index isthecollection of structures and their
plant sources. This section is also organized in an alphabetical way,
but clearly the use of the classical A to Z order does not apply to the
various arrangements of atoms. Let's say you have the structure of a
simpleisoquinoline inmind, andyou would liketoknow if it isaknown
plant alkaloid. Theclassic academic process istohead over totheUni-
versity library and start going through the many collected indices of
theChemical Abstracts, and search it out by what you hope istheright
chemical name. But sadly therules of naming arecontinuously chang-
ing. Sometimes 5,6,7,8-tetramethoxy precedes l,2,3,4-tetrahydro, and
sometimes it follows it. Sometimes 6,7-methylenedioxy-l,2,3,4-
tetrahydroisoquinoline isfiledinjust that way, but sometimes it isfiled
under benzodioxolol4,5-gJ 5,6,7,8-tetrahydroisoquinoline. And just
what aretheChemical Abstracts' structural naming rules and number-
ing systems for four-ring systems such as aporphines, isopavines or
berberines?
The"alphabet" used inthis structural index istotally indifferent to
thecapricious and arbitrary rules laid down bytheChemical Abstracts.
Quite simply, it is based on the location of the substituents and their
identity in thenuclear isoquinoline skeleton before it isdistorted by a
hypothetical "ortho attack." The definition of this "atomic" alphabet
is the substance of this introduction. The nature and variety of this
"ortho attack" is addressed here as well.
Part 3: Botanical names for theplants that contain these alkaloids:
All plants have been entered into the third index alphabetically,
according togenus and species. Under each of these taxaarelisted the
trivial (or chemical) names of thealkaloids reported tobeinthat plant.
Introduction xv
Part4: Appendices:
Thereare three appendices located at the end of this volume. The
firstisalisting of the botanical families that are mentioned in this book,
andtheGenera that each contains. Second is an analysis of the non-
intuitiveprocess used by Chemical Abstracts to create the name of an
isofuranone-substituted isoquinoline. The third is the list of actual jour-
nal names that are given only as initials in the references in the struc-
tural index.
THEATOMICALPHABETIZATION OF COMPOUNDS
Thereare two "alphabets" used in the organization of this book.
Boththeindex of trivial names and the listing of the botanical binomi-
alsusethe English A to Z, 26-letter convention, like a dictionary, and
thewords can be of any length. The listing of compounds in the struc-
tural index is also "alphabetical," but it employs a hierarchy of posi-
tionallocations and structural substituents as its alphabet. Each struc-
tureisafive-lettered "word" and the priority follows the rules of the
dictionary. With the structure being sought in mind, one must go
through the list of compounds with the first "letter" (substituent) in
mind, and then the second "letter" is located, and on, and on. Below is
alist of thepriorities each substituent ("letter") follows.
(l) POSITION ON THE AROMATIC RING
Here is the primary assignment of numbered positions, and the
assignment of letters to the individual bonds, of the isoquinoline ring:
5 4a 4
600~3
7 ~ I ~N2
8 8a 1
OJ
f ed C
-: / ' " I ~
9 b
~ ~N
h i j a
Thefirst "letter" of the chemical name of the structure being sought
iscreated from the position of the substituents on the aromatic ben-
zenering. There are four positions available (5,6,7,8), and they are al-
phabetically arranged from small to large and from few to many.
xvi The Simple Plant Isoquinolines
This is the order:
none 5 5,6 5,6,7 5,6,7,8
6 5,7 5,6,8
7 5,8 5,7,8
8 6,7 6,7,8
6,8
7,8
Thus acompound with a5,6-disubstitution pattern is to be found
inthis dictionary immediately following the8-monosubstituted entries
and immediately before the 5,7-disubstituted entries. All numbering
has been taken exclusively from the assignments given to the
isoquinoline ring. There are situations such as the methylenedioxy-
isoquinolines where thenature of thesubstituent constitutes anewring.
In this case, as in many others, Chemical Abstracts would assign to-
tally different numbers to these four positions on the aromatic ring.
Currently correct numbering systems areignored here, and the primi-
tive 5,6,7 and 8 positional identifiers are used exclusively. This first
letter of the structural alphabet is used as aheading for the appropri-
ate subsection of the second index, the structural formula group.
(2) THE SUBSTITUENTSON THE AROMATIC RING
Thesecond "letter" of the chemical name is the actual substituent
or substituents found at thepositions designated by thenumbers above.
There areonly three substituents to be considered in this chemical al-
phabetical sequence; they are, in order:
code atomic common
used: connections: name:
HO HO- (hydroxy)
MeO CH30-
(methoxy)
MOO -OCH20-
(methylenedioxy)
The HO- group is exactly what it appears to be. It is ahydrogen
atombonded to an oxygen atom which is, in turn, bonded (at least in
the caseof the second letter of this chemical alphabet) to one or more
of the available positions on the aromatic ring of the isoquinoline, i.e.,
the 5,6,7and/or the 8positions. TheMeO- group, as drawn, is an ab-
Introduction
XVll
breviationfor aslightly more complex structure, amethyl group (H3
C
-
or-CH3)bonded to anoxygen atomwhich is, as above, attached to one
(ormore) of the four positions of this aromatic ring. The MOO, or
methylenedioxygroup, isyet abit more complex. It isunique inthat it
isadouble-ended substituent. It is ashort chain that involves an oxy-
genatom(0) connected to amethylene group (CH2) connected inturn
to another oxygen atom. Drawn out as a collection of atoms it is
-
OCH
2
0
-andthus requires two adjacent substituent positions and must
beassociatedwith two numbers.
Let's use the 5,6 substitution position as an illustration template,
andwe'll introduce some substitution second "letter" examples, in al-
phabetical order:
5,6HOHO
5,6HOMeO
5,6MeOHO
5,6MeOMeO
5,6MOO
precedes
precedes
precedes
precedes
Afewthings are obvious. Where athing is located (shown by the
numberor numbers) has priority over what athing is (the substituent
orsubstituents). This same locating and identifying code will beused
for the benzyl group on the I-position, but with some extensions
whichwill beexplained below.
Thereis, of course, a fourth allowable substituent. This is H (a
hydrogenatom), but it is automatically assumed to be on every num-
beredpositionnot carrying oneof thethree given oxygenated examples.
Itisgenerallyaccepted, inthe creation of aname to represent achemi-
cal structure, that if there is no substituent specified on the aromatic
ringthesubstituent ishydrogen, and is not entered. The presentation
oftheentry
5,6 MeOHO - without this exclusion, would have been
5,6,7,8 MeOHO H H
What about substituents that are groups other than HO, MeO or
MDO(andof course theunsubstituted H)? Homologues of Mea such
asethoxyandbenzyloxy (Eta, BzO), alkyl groups such asmethyl, phe-
nyl,halides, carboxy or substituted carboxy groups, esters of phenols,
xviii
The Simple Plant Isoquinolines
nitrogen-containing groups such as nitro or amino derivatives, thio
compounds, all are regularly encountered as substituents of
isoquinolines in thechemical literature. And since almost all of them
areproducts of synthesis rather than plant products, they areignored
in this compilation. Thereis an occasional exception, like anO-acetyl
derivative that appears tohavebeen isolated fromsomenatural source.
There areplant alkaloids known that can, within the plants' envi-
ronment, undergo extensive oxidation. Intheaporphine group, acom-
pound such asNorcorydine can go to thequinone, all four rings com-
pletely aromatic and acarbonyl at the 7-position where the hydroxy
group oncewas. This isthebase Pancoridine. Soaquinonic carbonyl
can appear in the aromatic ring. But its origin was ahydroxy group.
So, for all practical purposes, we are staying with the three substitu-
ents mentioned above (other than hydrogen). Thesubstituents that are
on thebenzene ring arelisted on the first line in thebox at the upper
left corner of eachcompound's entry, inthesequence that corresponds
to thenumber or numbers at the top of the page.
6-MeO 7-HO
3,4-MeO,MeO-benzyl
H IQ
(3) THE I-POSITION
Thethird "letter" of this alphabet isthesubstituent that isfound at
theI-position of theisoquinoline ring. This isthefirst involvement of
the pyridine ring position of the isoquinoline system, so anumber of
new factors must beconsidered. Therearealways two substituents at
this position but, depending on the degree of aromaticity of this ring,
oneof themmight bemeaningless. And, asthere aretwo substituents,
there must bearule that ranks them. If they aredifferent, theheavier
will precede the lighter. This lighter one will be ahydrogen or ame-
thyl group (abbreviated Me). And occasionally there will be a sub-
stituent that embraces both substituents as asingle thing. And again,
as above, there will be occasions where the unnamed substituent is
simply hydrogen, and isnot mentioned.
Here isthesequence that will beused, listed by what thesubstitu-
ents really are, and by how they will beentered.
Introduction
xix
Heavier substituent
atthe I-position:
Lighter substituent
at the [-position:
Appearance of this
third chemical letter:
H
Me
Me
OH
OH
R
R
R
H
H
Me
H
Me
H
Me
HO
H
Me
Me,Me
OH or (=0)
OH,Me
R
R,Me
R,HO
In those cases where there are two different substituents, this car-
bonatom becomes chiral. Most natural products have optical activity,
but in many plant analyses, the optical rotation is not reported and
probably not measured. In the literature there is no way to distinguish
between an unknown rotation and aracemate. In these cases, all plant
sources for a given isoquinoline have been commingled without re-
gardto the reported optical activity, unless it is known.
The "R" that is mentioned above is one of five aromatic systems,
andthese are usually substituted themselves. These aromatic systems
andtheir numbering are ranked as shown below:
.c.'
~
6cr
5 ~ 3
4 ~ 2 6 2
4
3
5
3
R=phenyl R=benzyl
R=~-phenethyl
5
5~ I 0
I 0
6 ~
6 ~
7 OH
7 0
R=isobenzofuranol, 3' -yl
R=isobenzofuranone, 3' -yl
Thepriorities for both the numbering and the substituents follow
thesamepatterns established for the first and second chemical letters.
xx
The Simple Plant Isoquinolines
Numbering priority:
none 2 2, 3
2, 3, 4 2, 3, 4, 5 2, 3, 4, 5, 6
3
2, 4
2, 3, 5
2, 3, 4, 6
4 2, 5 2, 3, 6 2, 3, 5, 6
2, 6 2, 4, 5
3, 4
2, 4, 6
3, 5 3, 4, 5
And oncethenumbers have been decided upon, then thesubstitu-
ent ischosen fromthe following sequence:
HO
MeO
MOO
Again, there are many known compounds that have phenyl, ben-
zyl or phenethyl rings at the 'l-position with substitutions other than
thesethree(andtheunderstood andunstated hydrogen atomof course).
And, as with the 5,6,7,8substitution story, most of these aresynthetic
products and arenot part of this book. Thefewunusual substitutions
that are known to be incompounds fromnatural sources, such as the
formyl (CHO) and the carboxyl group (C02H), will beincluded. The
rule of organization is: agroup bonded with acarbon atomhas prior-
ity over agroup bonded with an oxygen atom.
Occasionally there is acarbon or an oxygen substituent found on
the alpha-carbon atomof thebenzyl group. This istaken into account
inthe alphabetization. Thesesubstituents have thefollowing priority:
Mono-substituted Oi-substituted
Me (methyl)
HO (hydroxy)
AcO (acetoxy)
MeO (methoxy)
NH2 (amino)
Me,Me (dimethyl)
Me,HO (methyl, hydroxy)
= CH2 (rnethenyl)
=0 (oxo)or (keto)
Thepresence of acarbonyl at the 'l-position introduces anambigu-
ity. Inmost cases, the structure of the I-keto product can beredrawn
as a I-hydroxy tautomer with the inclusion of a double bond in the
piperidine ring to balance the equation. When this situation occurs,
the compound will beentered as the keto tautomer.
Introduction
XXI
OQ
OH
O)H
a
Thisthird letter of the atomic alphabet, the 'l-position, is entered on
thesecondlinein the box found at the upper left corner of each entry.
-~.-
6-MeO 7-HO
3,4-MeO,MeO-benzyl
H IQ
(4) THE 2-POSITION
Thefourth "letter" in this chemical alphabet is the substituent at
the2-position, the nitrogen atom, of the isoquinoline ring. The pri-
mary substituents found here are the hydrogen and methyl groups,
andthey are arranged by increasing number:
H
Me
Me (+)
Me,Me(+)
CHO
C02H
Ac (COCH3)
C
ONH
2
C02Me
C02Et
(formyl)
(carboxy)
(acetyl)
(carbamoyl, or urea)
(carbomethoxy)
(carboethoxy)
An"H" as the fourth letter does not necessarily mean that there is a
hydrogenat thisposition. It isan indicator of the absence of any substitu-
tiononthenitrogen. This, as with the absence or presence of a(+) charge
atthatposition inthemethylated examples, reflects the aromaticity of the
pyridinering. Thisisdiscussed below insection (5). There arealso found,
occasionally,amide functions on this nitrogen atom.
Oxidation at this position is frequently found. Hydroxylamines
andN-oxides are entered either as footnotes to their non-oxygenated
XXll
The Simple Plant Isoquinolines
counterparts or as entries intheir own right. There are about adozen
plant isoquinolines that havebenzyl substituents onthenitrogen atom.
They are included in this collection.
This fourth letter of theatomic alphabet isfound at the left side of
the third line in thebox at the upper left corner of each entry.
6-MeO 7-HO
3,4-MeO,MeO-benzyl
H IQ
t
(5) HYDROGENATION
Thefifth letter of the chemical alphabet is the simple statement of
the degree of hydrogenation of the pyridine ring, and the three codes
are ranked in the order of increased aromaticity,
THIQ
DHIQ
IQ
tetrahydroisoquinoline
dihydroisoquinoline
isoquinoline
THIQ is l,2,3,4-tetrahydroisoquinoline. Both double bonds in the
pyridine ring are hydrogenated. If the fourth letter is an "H," there is
indeed ahydrogen onthe nitrogen. If there are methyl groups there, a
single methyl will bewithout acharge, but two methyls will require a
(+) charge.
DHIQisspecifically 3,4-dihydroisoquinoline. If thefourth letter is
an "H," there isno substitution onthenitrogen, even though there will
be an H written on the third line on the left side. If there is amethyl
group indicated, there must be a (+) associated with it. There is an
occasional natural dihydroisoquinoline inwhich the hydrogenation is
at the l,2-positions and theunsaturation is at the3,4-positions. These
havebeen entered asafootnote under theTHIQcompound as3,4-ene.
Introduction XX111
IQisthecompletely aromatic compound. Again, inthis case, if the
4thletter isindicated as an H, there is no substituent on that nitrogen
positionand if there is amethyl there, it must have a(+) on it.
Thislast letter is noted as aTHIQ, DHIQ or IQ on the right-hand
sideof the third line in the box at the upper-left corner of the
compound'sentry.
6-MeO 7-HO
3,4-MeO,MeO-benzyl
H IQ
t
TH E oRTH o ATTACK
Oneof thelittleappreciated but totally fascinating properties shared
byperhapsadozen of theclasses of four-ring isoquinolines isthat most
ofthemcanbevisualized as resulting froman 11 ortho attack," fromthe
2- or6-hydrogen atom of the I-substituent (usually abenzyl group) to
somespecifically identified position of the isoquinoline ring. These
conversionsmay certainly have biosynthetic reality. But they have a
greatdeal more importance for this book in that they allow a simple
andfoolproof way of organizing the compounds in text. Tolocate the
targetcompound under which the four-ring material will be found,
simplymentally note the I-benzylisoquinoline that constitutes its
chemicalskeleton. Thebond forming the fourth ring can beidentified
asgoingfroman ortho-position of thebenzyl to some numbered atom
ontheisoquinoline. Belowthey are illustrated and identified as to the
alkaloidalclassname. One must keep inmind that thebenzyl ring has
twoorthohydrogens. If it is not symmetrically substituted, the nor-
malnumberingpriority sequence isused, and that will dictate whether
theorthohydrogen employed intheattack isa2- or a6-hydrogen. The
examplesbelowshow ortho (2,X)attacks. It should beunderstood that
thesubstitution pattern on the benzyl ring could require that they be
calledortho (6,X)attacks. The ortho attacks will be indicated in each
sectionin a separate box from the first. Thus, the first box in each
sectionistheparent compound, and any additional boxes will bemodi-
fications,such as an ortho attack, an N-oxide, or other changes.
xxiv The Simple Plant Isoquinolines
Spirobenzylisoquinolines
The ortho (2, 1-Me) attack
This family is classified in this collection as an ortho-attack on a
l,l-disubstituted tetrahydroisoquinoline where there is a methyl, or
someother group (an ortho (2,1-XX)attack).
Dibenzopyrrocolines
The ortho (2,N ) attack
Herethehypothetical2,N (or 2,2)attack produces afive-membered
ring. Thetetracyclic product is treated here as an isoquinoline, but it
canalsobeseenas adisubstituted dihydroindole. Theusual chemical
classification isthat of asubstituted pyrrocoline, the name for the het-
erocyclethat isthe middle two rings of this system.
Introduction xxv
Protoberberines (Berberines) and Protopines
The ortho (2,N -Me) attack
with ring C aromatic
The N -methyl oxo and oxy forms
Thisisoneof themore common ortho attacks, and gives rise to the
protoberberinesand, with aminor substitution change, theprotopines.
I havealways assumed that the protoberberines were the saturated
precursoralkaloids (proto- meaning early or source) which upon aro-
matizationgavetheberberines with anaromatic ring "c." It now looks
asiftheentiregroup isoften simply called the protoberberines. Inthe
four-ringprotoberberine with the ring "C" aromatized, the hydroxyla-
tionof thecarbon atomthat was the original N-methyl group leads to
XXVI The Simple Plant Isoquinolines
agroup of compounds called 8-oxy (or 8-oxo) berberines. This tauto-
meric interconversion isshown above.
If there isahydroxy group aswell as abenzyl group onthe I-posi-
tion and there are two N-methyls in the THIQ ring (the quaternary
salt), another family canbeexplored through this 2,N-Meattack. These
alkaloids areof the protopine class, but to understand their structures
little tautomeric manipulation isneeded.
an ortho (2,N -Me) attack Tautomeric equilibrium
A tautorner isabit of structural sophistication. Onecan move the
electrons around, without moving any of the atoms, and some end up
with quite a different looking thing. Which is it? It's abit like the
problem with theduality of thephoton. It isaparticle and it isawave,
both. It pretty much depends onhow you look at it. Themiddle struc-
ture, with an 0- and an N+, should berather soluble inwater. It isan
ionic doubly charged molecule, after all. But thestructure ontheright
is a ketone and an amine, and would probably be lipophilic, and
wouldn't dissolve inwater. Is it water soluble? Hard to use that as a
way of telling the structure because just the act of putting it inwater
might shift the electrons towards the ionic configuration. As they say
inquantum mechanics, you can't observe anything without changing
it insomeway. Thesecompounds will beportrayed inthe4-ring struc-
ture with the 0- shown as ahydroxy group inthe structural index.
Introduction
xxvii
Pavines
The ortho (2,3) attack
Thepavine family, created by the ortho-3 attack, has an unusual
propertynot shared by any other isoquinoline group. The pavine can
beviewedin either of two ways, left to right, or right to left. This is
bestseenin the above structural diagram on the right. View the left-
handbenzenering asthearomatic ring of the THIQ, and then go to the
firstcarbonatomat the 4 0'clock position. The nitrogen bond in the
centerdemarks thesecond ring of the isoquinoline, with the I-position
beingthepoint between these two locations, at the bottom. The car-
bonbondout to theright of this point shows the benzyl group.
Nowviewthe right-hand benzene ring as the aromatic ring of the
isoquinoline,and then gotothe carbon atomat the 100'clock position.
Thenitrogen bond in the center demarks the second ring of the
isoquinoline; the point above is the I-position, and the carbon bond
outtotheleft isthebenzyl group.
Thusany pavine with different substituents on the two benzene
ringscouldresult froman ortho (2,3) attack of either of two different
isoquinolines. Theseitems areentered both ways inthis book. And in
thecaseof pavines here, and the isopavines below, if there is amethyl
grouponthe nitrogen, it will be represented by the abbreviation Me
insteadof CH3.
XXV111 The Simple Plant Isoquinolines
Isopavines
4
1
4
~ 2
I
~
~
The ortho (2,4) attack
Unlike thepavines, theunusual internal N-bridged heterocycle of
the isopavines admits to an isoquinoline classification in just one di-
rection.
Morphanans
The ortho (2,4a) attack
This ortho-4a attack, forming thecarbon skeleton of themorphine
molecule, is one that is not easily visualized by non-chemists. It re-
quiresanout-of-plane manipulation tobring thebenzyl group into con-
junction with the ring-juncture 4a carbon atom. The I-benz yl-
isoquinoline is shown in its conventional formon the left. Topicture
the attack, mentally take hold of the benzyl group and bring it back,
Introduction
XXIX
out of the plane of the paper, to where the 2-position is pointing di-
rectlyat the4a-position. This is the only one of the ortho attacks that is
superficiallynot an oxidation. The consequence is that the aromatic
resonancestatus of thebenzenoid ring of the THIQ is permanently lost.
Thelocationof theresidual double bonds and other electrons depends
totallyon the substitution pattern of the isoquinoline aromatic ring.
Oncetheattack has been achieved, the plant world makes many fur-
ther chemical steps, leading to a host of alkaloids related to thebaine
andmorphine, both of which contain an additional heterocyclic furan
ring. Theyliebeyond the scope of this compila tion. An unna tural, but
fascinatingcompound is the (+) isomer of the product of this attack
witha4-methoxybenzyl on the I-position, a methyl on the nitrogen,
and hydrogenation of the resid ual benzene ring of the paren t
isoquinoline. This product is the broadly abused antitussive,
dextromethorphan, or DXM.
Another family of alkaloids, the Hasubanans, are often lumped to-
getherwiththeMorphinans because of asuperficially similar morphol-
ogy. Asanillustration:
H O
C H sO
C H sO
o OC H
s
Sinoacutine (a Morphinan)
C epharamine (a H asubanan)
Theyare actually indoles, not isoquinolines, and so they are not
includedinthis listing.
xxx The Simple Plant Isoquinolines
Azaluoranthenes
The ortho (2,8) attack (with a 1-phenyl)
Although most ring-substituents on the 'l-position of the natural
tetrahydroisoquinolines are substituted benzyl groups or isobenzo-
furanones, occasionally aphenyl groupis observed, bound directly to
the isoquinoline ring. An ortho (2,8) attack leads directly to the
indino[l,2,3-ij]isoquinolines, known commonly astheazafluoranthenes.
Aporphines
The ortho (2,8) attack (with a 1-benzyl)
This family is viewed as an ortho-attack on the S-position of the
isoquinoline ring. This produces a four-ring system known as an
aporphine.
Well over ahundred years ago it was discovered that morphine,
when treated with astrong acid, gave rise to the compound apomor-
phine, an aporphine. It is now known that the lower of the two aro-
matic rings of apomorphine is the result of the rearomatization of the
benzyl group, which was compromised by the ortho-4a attack men-
Introduction
XXXI
tionedabove. But at the time it was thought to be asimple conversion,
andforalongwhile the structure of apomorphine was thought to rep-
resenttheskeleton of morphine itself.
Cularines
Theortho(2,8-0H ) attack
Hereisthegeneration of a7-membered oxygen-containing heterocycle.
Proaporphines
The(1,8) attack
Thisis a Ll-spirobenzyl intermediate to what is quite likely the
entirefamilyof the aporphines. The "pro" part of the name suggests
thatthisisabiosynthetic precursor to these alkaloids. Very often there
isaketofunction at the4-position of the benzyl group (equivalent to a
hydroxyl group on the original benzyl), to facilitate the spiro loss of
aromaticityneeded to achieve this type of coupling. This is directly
analogoustothe(2,4a)attacks needed to get into the morphinans, where
XXXll The Simple Plant Isoquinolines
aketonic presentation of anaromatic hydroxyl group permits thebond-
ing to occur.
5-phen ylfurano [2,3,4- ij Iisoq uino 1ines
/ OH /
8-H O a-H
The a,B-H O attack
There are several reports of tetrahydroisoquinolines with afused
furan ring that could beargued (for the sake of the classification used
in this collection) as an oxidative attack by the a-hydrogen of the 1-
benzyl onto the8-HO substituent, inamanner similar to theformation
of a seven-membered ether ring seen in the cularines. It can also be
seen as a similar oxidative attack from an a-hydroxy group (a com-
monly encountered benzyl substituent) onthe8-hydrogen position. The
first of these two mechanisms (illustrated above) is used in this collec-
tion.
THE SECOISOQUINOLINES
Theprefix "seco" is an unusual term occasionally encountered in
the literature of natural products. J ust as the term "ortho-attack" indi-
cates the generation of a new ring, the term "seco" indicates the de-
struction of aring. A secoisoquinoline is formed from a 1-substituted
tetrahydroisoquinoline by the loss of the 1,2-bond. Transferring ahy-
drogen atom from the a-carbon to the nitrogen, and reshuffling the
electrons, results in the formation of anew double bond.
Introduction
Phenethylamines
a a
1,2 seeo bond loss
Inanappendix tothebook "TIHKAL: The Continuation" there were
listedanumber of the phenethylamines known to be in the cactus fam-
ily. Thesewere all of classical simplicity with the phenyl ring substi-
tutedwith one or more hydroxys and methoxys, and an occasional
methylenedioxygroup. There was also an occasional hydroxy group
onthebetaposition of the chain, and on the nitrogen atom there were
zero, one, or two methyl groups. There was no mention made of a
subclassof phenethylamines which are intimately associated with the
isoquinolines. The chemical term "seco" is a clever device for main-
tainingastructural relationship between two chemicals after having,
magically,removed astructural bond. Illustrated here is an aporphine
withtheelectrons fromthat l,2-bond having been rearranged into the
middle ring. It would probably be chemically classified as an
aminoethyl-substituted phenanthrene, rather than a phenethylamine
whichhad been fused (2,3a) with anaphthalene, but in this book it
will be listed in the section describing the parent I-benzyl-
tetrahydroisoquinoline, modified with an ortho attack if appropriate,
followedby al,2-seco bond removal.
XXX111
XXXIV The Simple Plant Isoquinolines
With the simpler l-benzyl derivatives (those which have not un-
dergone any ortho-attack), the removal of the 1,2-bond usually pro-
duces a2-styryl substituted phenethylamine. Again, this would belo-
cated in the entry that described the parent isoquinoline.
The second illustration above is a phthalide THIQ, and these
phenethylamines are sometimes referred to as secophthalide-
isoquinolines. Here, the oxygen atom of the original isofuranone ring
is substituted on the newly formed double bond. This structure can
easily open up tothecorresponding ketonic carboxylic acid. Theseseco-
modifications of the attacked isoquinoline (first example, illustrated
with an aporphine) and the simpler I-substituted isoquinolines (sec-
ond example, as illustrated by theisobenzofuranone) aretheonly ones
included in this book. The standard phenethylamines that are com-
monly found incacti, compounds which arenot fromthese seco-mecha-
nisms, have been tabulated inTIHKAL and will not be repeated here.
There have been many compounds excluded from this compila-
tion, but to give examples would increase the mass of this collection
without any useful information. They are, in a general hand-waving
sense, those compounds not explicitly allowed in the above inclusion
criteria.
Toall rules, there arealways exceptions. Thesehave been made to
allow unexpected natural isoquinolines that just happen to present
unexpected substituents that nature for some reason chose to contrib-
ute to this collection. Mention has been made of an occasional carbo-
nyl group disrupting the aromaticity of the benzene ring (this is the
basis of the quinonic isoquinolines). The nitrogen atom (position 2)
occasionally displays an amide group (these have been entered at the
fourth letter of the structural alphabet). Several natural compounds
demand a hydroxyl or methoxyl function at the isoquinoline 3- or 4-
positions. When this occurs, the compound is listed as afootnote un-
der the parent structure.
More difficult to generalize, are the isoquinolines with new rings
resulting frombiosynthetic attacks fromhere tothere that areexcluded
fromthis study. Inabroad, inclusive statement thelinehas again been
drawn to exclude everything that has not been included above.
Originally it was intended to list every plant inwhich these natu-
ral isoquinolines are found, documented with a literature reference.
The project became unmanageable in that some of the more common
alkaloids have been found in literally hundreds of plants. So, in some
cases, if there are many species fromone Genus, the plant listing will
be condensed to mention the particular Genus, the family, plus a lit-
erature reference; e.g., Corydalis spp. (Papaveraceae) jnp 51, 262 '88.
This way the broadness of distribution is established. Also, there are
Introduction xxxv
sectionsin the structural index where there is a compound that has
oneormoresynonyms. In some instances, synonyms of what are sup-
posedtobethe "same" compound have been given different lists of
plants. So,it could be that different names are given to represent dif-
ferentoptical isomers, we don't know. But in most cases the differen-
tiationwas respected, the lists of plants to a given name were kept
separatewithin agiven section.
Formuch of the plant information we are most grateful for being
allowedaccessto the NAPRALERT (sm) database at the University of
Illinoisat Chicago, and would highly recommend the use of their ser-
vicesif moredetailed information is wanted. In particular, we appre-
ciatethehelp of Douglas Trainor there. Also, we'd like to give great
thankstoJ imBauml, the Senior Biologist at the Arboretum of Los An-
gelesCounty, for helping to resolve many plant name and family is-
sues,Amy Rasmussen for her supurb proofreading skills, and Frani
Halperinfor her artwork on the cover of this book.
Trivial Name Index
TRIVIAL NAME INDEX
Acetonyl-reframidine
N-Acetylanolobine
N-Acetylanonaine
N-Acetylanhalamine
N-Acetylanhalonine
N-Acetylasimilobine
D-Acetylfumaricine
N-Acetyllaurelliptine
N-Acetyllaurolitsine
N-Acetyl-3-methoxynornantenine
N-Acetyl-3-methoxynornuciferine
N-Acetylnomantenine
N-Acetylnomuciferine
N-Acetyl-seco-N -methylla urotetanine
N-Acetylstepharine
D-Acetylsukhodianine
N-Acetylxylopine
Actinodaphnine
Acutifolidine
Adlumiceine
Adlumiceine enol lactone
Adlumidiceine
Adlumidiceine enol lactone
Adlumidine
Adlumine
Aducaine
Aequaline
Alborine
AlkaloidFk-5
AlkaloidPO-3
Allocryptopine
a-Allocryptopine
Alpinone
I
312
263
252
431
445
57
165
133
68
407
396
229
172
196
181
282
269
284
85
243
243
344
344
340
241
139
70
450
108
96
327
327
223
2 The Simple Plant Isoquinolines
Amurensine
Amurensinine
Amurine
Amurinol I
Analobine
Anaxagoreine
Anhalamine
Anhalidine
Anhalinine
Anhalonidine
Anhalonine
Anhalotine
Anibacanine
Anicanine
Anisocycline
Annocherine A
Annocherine B
Annolatine
Annonelliptine
Anolobine
Anomoline
Anomuricine
Anomurine
Anonaine
Aobamine
Aobamidine
Apocavidine
Apocrotonosine
Apocrotsparine
Apoglaziovine
Aporeine
Aporheine
Aporpheine
Argemonine
Argemonine metho hydroxide
Argemonine N-oxide
Argentinine
Argentinine N-oxide
Arizonine
Armepavine
Arosine
Arosinine
292
301
154
155
262
59
429
431
439
432
443
432
93
175
403
104
105
107
388
262
388
376
399
246
324
344
157
60
100
103
248
248
248
213
218
214
56
56
354
178
152
133
Trivial Name Index
Artabonatine A
Artabonatine B
Artavenustine
Aryapavine
Asimilobine
Asimilobine- 2-0-~-D-glucoside
Atheroline
Atherospermidine
Atherosperminine
Atherosperminine N-oxide
Aurotensine
Ayuthianine
Backebergine
Baicaline
Belemine
2-Benzazine
l-Benzylisoquinoline
Berberastine
Berbericine
Berbericinine
Berberilycine
Berberine
Berberrubine
Berbervirine
Berbine
Berbin-8-one
Berbithine
Berbitine
Berlambine
Bernumicine
Bemumidine
Bemumine
Beroline
Bharatamine
Bicuculline
Bicucullinidine
Bicucullinine
Biflorine
Bisnorargemonine
Boldine
Boldinemethiodide
Bracteoline
255
410
63
449
54
55
199
411
172
172
114
261
161
424
264
39
39
299
297
210
300
297
285
324
40
285
321
321
299
53
165
53
285
91
342
243
345
329
71, 122
67
68
138
3
4 The Simple Plant Isoquinolines
Breoganine
Bromcholitin
Bulbocapnine
Bulbocapnine methiodide
Bulbocapnine N-oxide
Bulbodoine
Buxifoline
Caaverine
Califomine
Califomidine
Calycinine
Calycotomine
Canadaline
Canadine
a-Canadine
~-Canadine
Canadinic acid
Canelilline
Capaurimine
Capaurine
Capaurine N-oxide
Capnoidine
Capnosine
Capnosinine
N-Carbamoylanonaine
N-Carbamoylasimilobine
N-Carboxamidostepharine
Carlumine
Camegine
Carpoxidine
Caryachine
Caryachine methiodide
Caseadine
Caseadine N-oxide
Caseadinium quat
Caseamine
Caseamine N-oxide
Caseanadine
Caseanidine
Caseanine
Cassamedine
Cassameridine
349
214
286
288
286
326
412
91
311
314
318
166
296
296
296
296
324
93
436
437
437
340
90
162
251
57
182
242
164
305
82, 287
83, 288
365
365
365
362
362
364
364
207
419
317
Cassyfiline
Cassyformine
Cassythicine
Cassythidine
Cassythine
Cataline
Catalpifoline
Cavidine
Celtine
Celtisine
Cephakicine
Cephamonine
Cephamuline
Cephasugine
Cerasodine
Cerasonine
Chakranine
Cheilanthifoline
Cherianoine
Cinnamolaurine
Cissaglaberrimin e
Cissamine
Oarkeanidine
Claviculine
Coclanoline B
Coclaurine
Cocsarmine
Codamine
Codamine N-oxide
Colchiethanamine
Colchiethine
Colletine
Columbamine
Constrictosin e
Coptisine
Corarnine
Coreximine
Corftaline
Corgoine
Corledine
Corlumidine
Corlumine
Trivial Name Index
5
415
415
287
418
415
217
205
230
363
349
426
428
428
426
137
147
197
81
427
275
382
128
359
349
191
97
204
141
141
85
85
106
143
42
309
121
121
335
89
86
86
242
6
The Simple Plant Isoquinolines
Corphthaline
Corunnine
Corybrachylobine
Corybulbine
Corycavidine
Corycavamine
Corycavine
Corycularicine
Corydaldine
Corydalidzine
Corydaline
Corydalisol
Corydalispirone
Corydalmine
Corydalmine methochloride
Corydalmine N-oxide
Corydecumbine
Corydine
Corydine methine
Corydine N-oxide
Corydinine
Corygovanine
Coryrnotine
Corynoxidine
Corypalline
Corypalmine
Coryphenanthrine
Coryrutine
Corysamine
Corysolidine
Corystewartine
Corytenchine
Corytenchirine
Corytensine
Corytuberine
Coryximine
Cotarnine
Cotarnoline
Coulteroberbinone
Coulteropine
Crabbine
Crassifoline
335
152
221
79
328
331
331
353
239
72
220
321
332
202
221
203
335
143
152
145
329
154
221
209
88
74
217
338
315
157
326
196
196
340
120
325
447
445
448
448
194
359
Trivial Name Index
7
Crassifoline methine
Crebanine
CrebanineN-oxide
Cristadine
Crotoflorine
Crotonosine
Crotsparine
Crotsparinine
Crychine
Crykonisine
Cryprochine
Cryptaustoline
Cryptocavine
Cryptodorine
Cryptopine
Cryptopleurospermine
Cryptostyline I
Cryptostyline II
Cryptostyline III
Cryptowolidine
Cryptowoline
Cryptowolinol
Cucoline
Culacorine
Cularicine
Cularidine
Cularidine N-oxide
Cularirnine
Cularine
Cularine N-oxide
Cyclanoline
l a-Cyclanoline
t p.cyclanoline
IDanguyelline
l
~ Dasymachaline
Dauricoside
Decumbenine
Decumbenine-C
C Decumbensine
epi~-Decurnbensine
~lucopterocereine
Deglucopterocerelne N-oxide
361
281
281
134
99
60
99
99
311
178
179
146
233
307
233
334
167
167
168
82
154
158
65
349
353
350
351
363
366
366
128
128
128
377
305
63
335
334
340
340
372
372
8 The Simple Plant Isoquinolines
Dehassiline
1,2-Dehydroanhalarnine
1,2-Dehydroanhalidinium quat
1,2-Dehydroanhalonidine
Dehvdroanonaine
Dehydroboldine
Dehydrocapaurimine
Dehydrocavidine
Dehydrocheilanthifoline
Dehydrocorybulbine
Dehydrocorydaline
Dehydrocorydalmine
Dehydrocorydine
Dehydrocorypalline
Dehydrocorytenchine
Dehydrocrebanine
Dehydrodicentrine
Dehydrodiscretamine
Dehydrodiscretine
Dehydroformouregine
Dehydroglaucentrine
Dehydroglaucine
Dehydroguattescine
1,2-Dehydroheliarnine
1,2,3,4-Dehydroheliamine
Dehydroisoboldine
3,4-Dehydroisocorydione
Dehydroisocorypalmine
Dehydroisolaureline
Dehydroisothebaine
1,2-Dehydrolemaireocereine
Dehydrolirinidine
Dehydronantenine
Dehydroneolitsine
6,6a-Dehydronorglaucine
6,6a-Dehydronorlaureline
Dehydronomuciferine
1,2-Dehydronortehuanine
1,2-Dehydronorweberine
Dehydronuciferine
Dehydroocopodine
Dehydroocoteine
108
430
432
433
247
67
437
230
81
79
221
203
146
88
196
281
302
70
76
396
146
216
271
161
161
127
238
143
268
95
370
92
227
312
206
277
169
391
455
171
323
417
Trivial Name Index
9
1,2-Dehydropach ycereine
1,2,3,4-Dehydropach ycereine
1,2-Dehydropellotinium quat
Dehydrophanostenine
Dehydrophoebine
Dehydropredicentrine
Dehydropseud ocheilanthifo line
Dehydroremerine
a-Dehydroreticuline
Dehydroroemerine
1,2-Dehydrosalso lidine
Dehydrostephalagine
Dehydrostephanine
Dehydrostesakine
Dehydrothalicmine
Dehydrothalicsimidine
Dehydroxylopine
Dehydroxyushinsunine
Delporphine
6-O-Demethyladlumi dine
6-O-Demethyladlumine
N-Demethylamurine
8-Demethylargemonine
Demethylcoclaurine
N-Demethylcolletine
1Q-O-Demethylcoryd ine
3'-0-Demethylcularine
1Q-O-Demethyldiscretine
n-0-Demeth yldiscretine
Demethyleneberberine
N-Demethylfumaritine
0-7'-Demethy1-l3-hydrastine
9-O-Demethylimeluteine
N-Demethylisocorytuberine
N-Demethyllinoferine
04-Demethy lmurarnine
3'-Demethylpapaverine
7-Demethylpapaverine
N-Demethylstephalagine
3-0-Demethylthalicthuberine
2-Demethylthalimonine
9-Demethylthalimonine
456
457
435
293
406
78
154
250
114
250
164
409
260
280
417
402
267
248
378
160
86
153
147, 203
47
105
137
360
71
66
50
157
335
393
134
201
200
190
140
409
84
237, 423
84, 423
10 The Simple Plant Isoquinolines
10-Demethylxylopinine 203
Densiberine 217
Deoxythalidastine 267
7-0-Desmethylisosalsolidine 90
Desmethylnarcotine 446
O-Desmethylweberine 455
N,O-Diacetyl-3-hydroxynornuciferine 375
N,O-Diacetylisopiline 386
N,O-Diacetylnoroliveroline 257
Dicentrine 301
Dicentrinone 306
Didehydroaporheine 250
Didehydroocoteine 417
Didehydroglaucine 216
Didehydroroemerine 250
5,6-Dihydroconstrictosine 42
Dihydrocoptisine 309
5,6-Dihydro-3,5-di-O-methylconstrictosine 43
Dihydroguattescine 271
Dihydroimenine 397
8,9-Dihydroisoroemerialinone 202
Dihydro1inaresine 322
Dihydromelosmine 387
1,2-Dihydro-6,7-methylenedioxy-l-oxoisoquinoline 333
3,4-Dihydro-l-methyl-5,6,7-trimethoxyisoquinoline 392
3,4-Dihydronigellimine 164
8,14-Dihydronorsa1utaridine 110
Dihydronudaurine 155
Dihydroorientalinone 135
11,12-Dihydroorientalinone 135
~-Dihydropallidine 124
Dihydropalmatine 209
Dihydroparfumi dine 165
Dihydrorugosinone 322
8,14-Dihydrosa1utaridine 119
Dihydrosecoquettamine 357
4,6-Dihydroxy-3-methoxymorphinandien-7-one 49
4,6-Dihydroxy-2-methyltetrahydroisoquinoline 41
3,9-Dihydroxynornuciferine 376
5,6-Dimethoxy-2,2-dimethyl-l-(4-hydroxybenzy1)-I,2,3,4- THIQquat 46
6,8-Dimethoxy-l,3-dimethylisoquinoline 348
6,7-Dimethoxy-N,N-dimethyl-l-(2-methoxy-4-hydroxybenzy1)-THIQ 188
Trivial Name Index
1,2-Dirnethoxy-ll-hydroxyaporphine
1,2-Dirnethoxy-3-hydroxynora porp hine
1,2-Dirnethoxy-3-hydroxy-5-oxonora porphine
2,9-Dimethoxy-3- hydroxypa vinane
6,7-Dirnethoxy-l-(6',7 -methy 1enedioxyisobenzofurano1, 3'-y1)-
2,2-dimethy1-1,2,3,4- THIQ
6,7-Dimethoxy-l-(3,4-meth y1enedioxypheny 1)-2-methy 1-DHIQ
6,7-Dimethoxy-l-(3,4-methy 1enedioxypheny 1)-2-methy 1-IQ
6,7-Dirnethoxy-l-( 4-methoxybenzy l)-IQ
6,8-Dirnethoxy-l-methyl-3- hydroxymethy lisoquinoline
6,7-Dimethoxy- 2-met hylisocarbostyril
6,7-Dirnethoxy- N-meth ylisoquinoline
6,7-Dirnethoxy-2-methylisoquinolium quat
N,o- Dimethy1actinoda phnine
N,o-Dimethy1armepavine
0,o-Dimethy1bo1dine
N,o-Dimethylcassyfiline
0,0- Dimethylcissamine
3,5-Di-O-methylconstrictosine
O,o-Dimethylcorytuberine
N,o-Dimethylcrotonosine
N,o-Dimethy lcrotsparine
O,o-Dimethylcyclanoline
N,o-Dimethy1hemovine
0,0- Dimethy1isobo1dine
N,o-Dimethy 1isocorydine
N,N-Dimethy llindcarpine
O,N-Dimethylliriodendronine
0,0- Dimethyllongifo1onine
0,0' -Dimethy1magnoflorine
0,o-Dimethy1munitagine
N,o-Dimethy1nandigerine
N,o-Dimethy1oreoline
N,o-Dimethy1oridine
N,N-Dimethy1pavinium quat
N,o-Dimethy 1thaicanine
Dinorargemonine
Disco1orine
Discretamine
Discretine
Discoguattine
Domesticine
175
373
373
44,106
244
168
168
184
348
240
240
162
301
185
214
323
218
43
212
179
179
218
76
214
218
68
93
186
218
212,371
300
180
180
218
403
71,122
48
70
76
320
155
11
12
The Simple Plant Isoquinolines
Domestine
Doryafranine
Doryanine
Doryfornine
Doryphornine
Doryphornine methyl ether
Duguespixine
Duguetine
Duguevanine
Duguexine
Duguexine N-oxide
Dysoxyline
Egenine
Elmerrillicine
Enneaphylline
Epiberberine
Epiglaufidine
10-Epilitsericine
6-Epioreobeiline
14-Episinomenine
Episteporphine
Escholamidine
Escholamine
Escholidine
Escholine
Escholinine (also seeunder Romneine)
Eschscholtzidine
Eschscholtzidine methiodide
Eschscholtzine
Eschscholtzine N-oxide
Eschscholtzinone
Eximine
Evoeuropine
a-Fagarine
Filiformine
Fissiceine
Fissicesine
Fissicesine N-oxide
Fissilandione
Fissisaine
Fissistigine A
Fissistigine B
226
279
334
160
160
240
58
305
419
264
264
239
340
411
360
225
145
274
124
66
249
293
312
293
129
303
225,301
228,304
311
311
317
301
178
327
416
289
183
183
326
378
318
348
Trivial Name Index
Fissistigine C
Fissoldine
F K -3000
Flavinantine
Flavinine
Floripavidine
Floripavine
Formouregine
N-Formylanhalamine
N-Formylanhalinine
N-Formylanhalonidine
N-Formylanhalonine
N-Formylanonaine
N-Formylbuxifoline
7-Formyldehydro hernanergine
N-Formyldehydronorn uciferine
7-Formyldehydrothalicsimidine
N-Formylduguevanine
N-Formylhernangerine
N-Formyl-0-meth ylan halonid ine
N-Formylnomantenine
N-Formylnornuciferine
N-Formylovigerine
N-Formylpurpureine
N-Formylputerine
N-Formylstepharine
N-Formylxylopine
Fugapavine
Fumaflorine
Fumaflorine methyl ester
Fumaramidine
Fumaramine
Fumaricine
Fumaridine
Fumariline
Fumarine
~Fumaritine
~Fumaritine N-oxide
[ Fumariz'
" me
J Fumarophycinol
IFumschleicherine
iFuzitine
13
147
318
425
138
134
56
118
395
430
440
436
445
251
413
290
173
405
420
294
442
229
173
314
404
269
181
269
275
236
236
243
346
165
339
283
329
108
108
324
108
346
189
14 The Simple Plant Isoquinolines
Gandhararnine
Gentryamine A
Gentryamine B
Gigantine
Gindarine
Glaucentrine
Glaucine
Glaucine methine
Glaucine methiodide
Glaucinone
Glaufidine
Glaufine
Glaufinine
Glaunidine
Glaunine
Glauvent
Glauvine
Glaziovine
Gnoscapine
Gorchacoine
Gortschakoine
Goudotianine
Gouregine
Govadine
Govanine
Groenlandicine
Guacolidine
Guacoline
Guadiscidine
Guadiscine
Guadiscoline
Guatterine
Guatterine N-oxide
Guattescidine
Guattescine
Guattouregidine
Guattouregine
GusanlungA
GusanlungB
GusanlungC
GusanlungD
n-Hainanine
182
348
347
373
207
143
214
219
219
222
145
63
201
152
199
214
152
102
452
358
358
376
455
137
146
81
318
320
265
273
320
410
410
265
271
387
388
285
297
44
248
79
Trivial Name Index
Heliamine
Hemiargyrine
Henderine
Hernagine
Hernandia base
Hernandia base II
Hernandia base IV
Hernandia base VIII
Hernandonine
Hernangerine
Hernovine (also see under Ovigerine)
Hexahydrofugapavine
Hexahydromecambrine
Hexahydrothalicminine
Higenamine
~-Homochelidonine
Homolaudanosine
Homolinearisine
Homomoschatoline
Humosine-A
Hunnemanine
Hydrastidine
Hydrastine
a-Hydrastine
I}-Hydrastine
Hydrastinimide
Hydrastinine
Hydrocotarnine
Hydrohydrastinine
4-Hydroxyanonaine
4-Hydroxybulbocapnine
4-Hydroxycrebanine
7-Hydroxydehydroglaucine
3-Hydroxy-6a,7 -deh ydronuciferine
8-Hydroxydehydroroemerine
4-Hydro xydicentrine
4-Hydroxyeschschol tzi dine
3-Hydroxyglaucine
N-Hydroxyhernangerine
41}- Hydroxyisocory dine
2'-Hydroxylaudanosine
lO-Hydroxyliriodenine
161
122
446
201
290
290
306
292
316
290
69
276
276
415
47
327
239
61
396
340
289
335
336
337
336
339
333
447
245
247
287
281
222
374
259
302
235,382
380
294
194
234
277
15
16
The Simple Plant Isoquinolines
1o-Hydroxymagnocurarine
13~-Hydroxy-N-rnethylstylopine quat
Hydroxynantenine
3-Hydroxynantenine
4-Hydroxynantenine
3-Hydroxynornantenine
4-Hydroxynornantenine
3-Hydroxynornuciferine
N-Hydroxynorthalicthuberine
3-Hydroxynuciferine
N-Hydroxyovigerine
8-Hydroxypseudocoptisine
4-Hydroxysarcocapnidine
4-Hydroxysarcocapnine
8-Hydroxystephenanthrine
8-Hydroxystephenanthrine N-oxide
13~-Hydroxystylopine
3-Hydroxy-2,9,10-trirnethoxytetrahydroprotoberberine
4-Hydroxywilsonirine
Hyndarin
Hypecournine
Irneluteine
Irnenine
Intebrirnine
Intebrine
Isoanhalarnine
Isoanhalidine
Isoanhalonidine
Isoapocavidine
Isoauturnnaline
Isobackebergine
Isoboldine
Isocalycinine
Isocanadine
Isococlaurine
Isocoptisine
Isocorexirnine
Isocorybulbine
Isocorydine
Isocorydine N-oxide
Isocorydione
Isocoryne
105
318
230
381
224
380
224
373
227
374
314
311
360
365
259
259
316
74
140
207
334
393
397
163
334
427
427
427
84
86
370
124
318
300
59
311
66
150
192
194
238
336
Isocorypalline
Isocorypalmine
Isocorypalmine N-oxide
Isocorytuberine
Isocularine
Isodomesticine
Isofugapavine
Isoguattouregidine
Isohydrastidine
Isolaureline
Isolaureline N-oxide
Isomoschatoline
Isonorargemonine
Isonortehuanine
Isonorweberine
Isooconovine
Isoorientalinone
Isopachycereine
Isopacodine
Isopellotine
Isopiline
Isopycnarrhine
Isoquinoline
Isoremerine
Isoroemerialinone
Isosalsolidine
Isosalsolidine N-oxide
Isosalsoline
Isosalutaridine
Isoscoulerine
Isosendaverine
Isosevanine
Isosinoacutine
Isotembetarine
Isothebaidine
Isothebaine
Isouvariopsine
Isovelucryptine
Izmirine
laculadine
[acularine
J atrorrhizine
Trivial Name Index
52
141
142
137
364
83
276
384
335
268
268
375
77, 194
391
456
389
135
457
73
428
385
52
39
248
201
164
164
90
123
65
52
284
137
361
94
95
279
62
87
60
99
75
17
18
The Simple Plant Isoquinolines
[uziphine
[uziphine N-oxide
J uzirine
Karnaline
Kikernanine
Kuafurnine
Kukoline
Laetanine
Laetine
Larnbertine
Lanuginosine
Lastourvilline
Latericine
Laudane
Laudanidine
Laudanine
Laudanosine
Laudanosoline
Lauforrnine
Launobine
Laureline
Laurelliptine
Laurepukine
Laurifoline
Lauroli tsine
Lauroscholtzine
Laurotetanine
Lauterine
Ledeborine
Ledecorine
Lernaireocereine
Leonticine
Leucoline
Leucoxine
Leucoxylonine
Leucoxylonine N-oxide
Lirnousarnine
Linaresine
Lincangenine
Lindcarpine
Linearisine
Liridinine
355
356
100
57
202
414
65
69
80
303
273
50
102
191
191
191
207
49
274
284
279
111
263
132
64
195
190
279
157
323
370
357
39
321
421
421
351
322
379
64
61
383
Liridine
Lirinidine
Lirinine
Lirinine N-oxide
Liriodendronine
Liriodenine
Lirioferine
Liriotulipiferine
Litsedine
Litseferine
Litsericine
Litsoeine
Longifolidine
Longifolonine
Longimammamine
Longimammatine
Longimammidine
Longimammosine
Lophocereine
Lophocerine
Lophophorine
Lophotine salt
Lotusine
Luteanine
Luteidine
Luxandrine
Lysicamine
Machigline
Machiline
Madeyine
Macrantaldehyde
Macrantaline
Macrantoridine
Magnococline
Magnocurarine
Magnoflorine
Magnoporphine
Majarine
Manibacanine
Marshaline
Mecambridine
Mecambrine
Trivial Name Index
19
396
92
374
374
47
257
204
72
295
290
274
190
370
100
45
42
45
41
91
91
444
444
62
192
159
49
170
289
97
329
451
449
449
358
104
129
218
297
175
324
450
275
20
The Simple Plant Isoquinolines
Mecambroline
Melosmidine
Melosmine
Menisperine
Mescalotam
a-N -Methopapaverberbine
Methoxyatherosperminine
Methoxyatherosperminine N-oxide
I-Methoxyberberine
10-Methoxycaaverine
3-Methoxyglaucine
3-Methoxyguattescidine
Methoxyhydrastine
10-Methoxyliriodenine
Il-Methoxyliriodenine
3-Methoxynordomesticine
3-Methoxynuciferine
3-Methoxyoxoputerine
13-Methoxy-8-oxyberberine
4-Methoxypalmatine
Methoxypolysignine
3-Methoxyputerine
8-Methoxyuvariopsine
N-Methylactinodaphnine
N-Methyladlumine
3-Methylallocryptopine
O-Methylanhalidine
N-Methylanhalidine quat
O-Methylanhalonidine
N-Methylanhalonidine
a-8-Methylanibacanine
N-Methylanolobine
O-Methylanolobine
N-Methylanonaine
N-Methylapocrotsparine
N-Methylarmepavine
o-Methylarmepavine
O-Methylarmepavine N-oxide
N-Methylasimilobine
N-Methylasimilobine-2-0-~-D-glucopyranoside
N-Methylasimilobine-2-o-a-L-rhamnopyranoside
O-Methylatheroline
276
399
387
197
442
448
395
395
447
105
402
412
452
279
273
390
395
414
305
403
217
412
282
287
242
328
440
432
441
434
94
263
266
248
103
181
185
185
55
55
561
220
Trivial NarneIndex
N-Methylboldine
Q-Methylbracteoline
N-Methylbulbocapnine
Q-Methylbulbocapnine
a-Q-Methylbulbocapnine N-oxide
~O-Methylbulbocapnine N-oxide
N-Methylbuxifoline
N-Methylcalifomine
N-Methylcalycinine
Q-Methy1calycinine
N-Methylcanadine
Q-Methy1capaurine
Q-Methylcaryachine
N-Methylcaryachinium quat
N-Methylcassyfiline
Q-Methylcassyfiline
N-Methylcassythine
Q-Methylcassythine
N-Methylcheilanthifoline quat
Q-Methylcinnamolaurine
N-Methylcoclaurine
Q-7-Methy1coclaurine
13-Methylcolumbarnine
3-Q-Methy1constrictosine
N-Methylcoreximine
Q-Methy1corledine
N-Methylcorydaldine
N-Methy1corydaline quat
N-Methylcorydalrnine quat
N-Methylcorydine
Q-Methy1corydine
Q-Methy1corydineNsoxide
N-Methylcorypalline
Q-Methylcorypalline
l-Methylcorypalline
2-Methylcorypallinium
N-Methylcorypalrnine
ll-Methylcorytuberine
N-Methylcrotonosine
N-Methylcrotsparine
N-Methylcrotsparinine
N-Methylcrychine
68
149
288
300
300
300
413
314
319
320
303
442
225,301
83,288
415
416
415
416
83
279
100
176
151
43
132
241
239
221
204
151
212
212
89
162
90
89
79
143
61
102
103
314
21
22 The Simple Plant Isoquinolines
O-Methylcularicine
N-Methylcularine
N-Methyldanguyelline
O-Methyldehydroisopiline
N-Methyldihydroberberine quat
0-Methyl-8,9-dihydroisoorientalinone
O-Methyldihydrosecoquettamine
O-Methyldomesticine
N-Methyldomesticinium
N-Methylduguevanine
N-Methylelmerrillicine
O-Methylelmerrillicine
6,7-Methylendioxy-1-<4-methoxybenzyD-IQ
6,7-Methylendioxy-1-<4-methoxybenzyD- THIQ
6,7-Methylendioxy-l-t 4-methoxy-a-hydroxybenzyD-3,4-DHIQ
2,3-Methylenedioxy-4,8,9-trimethoxy-N-methylpavinane
N-Methyl-10-epilitsericine
N-Methylescholtzine
0- Methylflavinantine
N-Methylfissoldine
7-Methyl-N-formyldehydroanonaine
O-Methylfumarophycine
O-Methylfumarophycinol
N-Methylglaucine
N-Methylheliamine
N-Methylhernangerine
N-Methylhernangerine /3-N-oxide
N-Methylhernovine
10-0-Methylhernovine
N-Methylhigenamine
N-Methylhigenamine, 7-O-~-D-glucopyranoside
N-Methylhigenamine N-oxide
N-Methylhydrasteine
N-Methylhydrasteine imide
N-Methylhydrastine
N-Methyl-~-hydrastine quat
O-Methylisoboldine
N-Methylisococlaurine
N-Methylisocorydine
N-Methylisocorypalmine quat
O-Methylisomoschatoline
O-Methylisoorientalinone
368
361
377
394
304
202
358
155
156
420
411
412
278
277
278
235,416
276
314
147
319
252
165
165
219
162
292
292
71
73
48
48
48
338
339
338
337
149
60
197
151
396
201
Trivial Name Index
0-Methylisopiline
N-Methylisopiline
N-Methylisosalsoline
1-0-Methylisothebaidine
N-Methylisothebaine
N-Methylisothebainium cation
0-Methylisovelucryptine
N-Methyllaudanidinium iodide
N-Methyllauformine
N-Methyllaunobine
N-Methyllaurelliptine
9-0-Methylla urolitsine
N-Methyllaurotetanine
N-Methyllaurotetanine N-oxide
O-Methylledecorine
N-Methyllindcarpine
0-Methyllirinine
N-Methyllitsericine
N-Methyllophophorine quat
N-Methylmecambridine
2-Methyl-1-(4-methoxybenzyD-
6,7-methylenedioxyisoquinolinium quat
N-Methyl-10-G-methylhernovine
O-Methylmoschatoline
N-Methylnandigerine
N-Methylnandigerine ~-N-oxide
N-Methylnantenine
N-Methyl-a-narcotine
O-Methylnarcotoline
N-Methylneocaryachine quat
D-Methylnorarmepa vine
9-0-Methylnorboldine
8-O-Methyloblongine
N-Methyloreophiline salt
D-Methylorientalinone
N-Methylovigerine
N-Methyloxoh ydrasteine
D-Methyloxopukateine
N-Methylpachycereine
N-Methylpachypodanthine
N-Methylpachypodanthine N-oxide
N-Methylpalaudium quat
278
76
396
292
292
228
454
452
288,369
184
73
371
450
201
310
339
273
457
256
256
197
23
394
385
90
175
96
96
189
197
276
286
124
73
195
196
324
66
395
276
444
450
24 The Simple Plant Isoquinolines
O-Methylpallidine
O-Methylpallidine N-oxide
O-Methylpallidinine
13-Methylpalmatine
N-Methylpapaveraldine
N-Methylpapaverine quat
N-Methylpavine
O-Methylpellotine
N-Methylpellotine quat
0-Methylpeyomvic acid
0-Methylpeyoxylic acid
0- Methylplatycerine
N-Methylplatycerinium quat
0-Methylprechilenine
0-Methylpreocoteine
0-Methyl przewalskiinone
8a- Methylpseudoanibacanine
8~-Methylpseudoanibacanine
N-Methylpseudolaudanine
0-Methylpukateine
N-Methylputerine
N-Methylsecoglaucine
0-Methylseverzine
N-Methylsinactine
N-Methylsparsiflorine
N-Methylstenantherine
N-Methylstepharine
0-Methylstepharinosine
N-Methylstylopinium quat
a-N-Methylstylopinium quat
~-N-Methylstylopinium quat
N-Methyltetrahydrocolumbamine
1-Methyl-1,2,3,4-tetrahydroisoquinoline
N-Methyltetrahydropalmatine
N-Methyltetrahydropapaverine
N-Methylthaicanine
0-Methylthaicanine
N-Methylthalbaicaline
0-Methylthalicmidine
N-Methylthalidaldine
0-Methylthalisopavine
N-Methyl-2,3,6-trimethoxymorphinandien-7 -one N-oxide
147
149
149
221
220
217
213
442
435
441
441
212,371
197,367
332
402
220
94
94
78
267
267
219
241
228
103
398
179
187
313
313
313
151
39
218
207
380
402
380
214
408
214
149
Trivial Name Index
25
N-Methylushinsunine
G-Methylvelucryptine
N-Methylviguine
N-Methylxylopine
N-Methylxylopine N-oxide
N-Methylzenkerine
Michelalbine
Michelanugine
Micheline A
Micheline B
Michepressine
Mil tanthaline
Milthanthine
Mocrispatine
Mollinedine
Moschatoline
Munitagine
Muramine
Nandazurine
Nandigerine
Nandinine
Nantenine
Narceimine
Narceine
Narceine imide
Narceinone
Narcosine
Narcotine
a-Narcotine
p-Narcotine
Narcotinediol
Narcotine hemiacetal
Narcotoline
Narcotolinol
Narlumicine
Narlurnidine
Neocaryachine
Neolitsine
Nigellimine
Nigellimine N-oxide
Nokoensine
Noramurine
255
186
245
268
268
106
253
270
254
257
276
436
179
50
307
383
117, 362
222
156
290
285
226
345
454
454
454
452
452
452
453
451
452
446
446
345
345
286, 368
312
164
164
437
153
26
The Simple Plant Isoquinolines
Noranicanine
Norannuradhapurine
Norargemonine
Norarmepavine
N-Norarmepavine
Noratherosperminine
Norboldine
Norbracteoline
Norbulbocapnine
Norcanelilline
Norcarnegine
Norcinnamolaurine
Norcoclaurine
Norcorydine
Norcorypalline
Norcularicine
Norcularidine
Nordelporphine
Nordicentrine
Nordomesticine
Norfissilandione
Norfumaritine
Norglaucine
Norgorchacoine
Norguattevaline
Norimeluteine
Norisoboldine
Norisocorydine
Norisocorydione
Norisocorytuberine
Norisocularine
Norisodomesticine
Norjusiphine
Norjuziphine
N-Norlaudanosine
Norlaureline
Norleucoxylonine
Norliridinine
Norlirioferine
Nornantenine
Nornarceine
Norneolitsine
174
280
147, 203
176
176
171
64
134
284
93
163
274
47
139
88
352
350
377
295
153
325
157
206
358
376
393
111
189
237
134
363
80
354
354
205
277
421
383
201
223
453
307
Nomuciferidine
Nomuciferine
Nomuciferine I
O-Nomuciferine
Noroconovine
Noroliveridine
Noroliverine
Noroliveroline
Nororientaline
Nororientinine
Noroxyhydrastinine
Norpachyconfine
Norpachystaudine
Norpallidine
Norphoebine
Norpredicentrine
Norpreocoteine
Norprotosinomenine
Norpurpureine
Norreframidine
Norreticuline
Norrufescine
Norsalutaridine
Norsarcocapnine
Norsarcocapnidine
Norsecocularidine
Norsecocularine
Norsecosarcocapnidine
Norsecosarcocapnine
Norsinoacutine
Norsonodione
Norstephalagine
Norstephanine
Nortehuanine
Northalicmine
Northalicthuberine
Northalifoline
Norushinsunine
Noruvariopsarnine
Norweberine
Noryuziphine
Noscapalin
Trivial Name Index 27
173
169
92
55
400
270
272
253
133
95
332
58
256
111
405
73
389
63
401
307
109
392
110
363
359
351
366
360
364
110
237
409
260
391
416
227
159
253
186
455
354
452
28
The Simple Plant Isoquinolines
Noscapine
u-Noscapine
Noscopine hemiacetal
Nuciferidine
Nuciferin
Nuciferine
Nuciferoline
Nudaurine
Nummularine
Oblongine
Obovanine
Ochotensidine
Ochotensimine
Ochotensine
Ocobotrine
Ocokryptine
Ocominarine
Ocominarone
Oconovine
Ocopodine
Ocoteine
Ocotominarine
Ocoxylonine
Oduocine
Oliveridine
Oliveridine N-oxide
Oliverine
Oliverine N-oxide
Oliveroline
Oliveroline P-N-oxide
Ophiocarpine
Ophiocarpinone
Opian
Opianine
Oreobeiline
Oreoline
Oreophiline
Oridine
Orientaline
Orientalinone
Orientidine
Orientine
452
452
452
174
170
170
181
155
53
356
262
327
238
87
120
423
325
422
401
323
417
422
420
418
270
270
272
272
254
254
305
306
452
452
124
99
450
99
135
135
183
184
Trivial Name Index
29
Orientinine
Oureguattidine
Ovigerine
Oxoanolobine
Oxoasimilobine
7-oxobaicaline
8-oxoberberrubine
Oxobuxifoline
8-0xocanadine
Oxocompostelline
8-0xocoptisine
Oxocrebanine
13-0xocryptopine
Oxocularidine
Oxocularicine
Oxocularine
7-0xodehydroasimilobine
Oxodicentrine
Oxoduocine
Oxoglaucine
Oxohydrastinine
Oxoisocalycinine
8-0xoisocorypalmine
Oxolaureline
Oxolaurenine '
Oxo-N -methylhydrasteine
13-0xomuramine
Oxonantenine
Oxonuciferine
Oxophoebine
8-0xopolyalthiaine
13-0xoprotopine
Oxopukateine
Oxopurpureine
Oxoputerine
Oxosarcocapnidine
Oxosarcocapnine
Oxosarcophylline
Oxostephanine
Oxostephanosine
8-0xotetrahydropalmatine
8-0xotetrahydrothalifendine
96
386
306
266
58
425
285
414
297
369
310
283
233
352
353
368
58
306
419
220
333
319
142
279
279
339
223
231
170
407
158
331
266
404
273
362
367
352
261
259
209
291
30
The Simple Plant Isoquinolines
8-0xothaicanine
Oxoushinsunine
Oxoxylopine
Oxyberberine
N-Oxycodamine
8-0xycoptisine
Oxydehydrocorybulbine
N-Oxyduguexine
N-Oxyguatterine
Oxyhydrastinine
N-Oxyoliveridine
Oxynarcotine
N-Oxypachyconfine
Oxypalmatine
13-0xyprotopine
N-Oxyspixianine
8-0xythalifendine
Pachycereine
Pachyconfine
Pachyconfine N-oxide
Pachypodanthine
Pachystaudine
Pacodine
Palaudine
Pallidine
Pallidinine'
Palmatine
Palmatrubine
Pancoridine
Pancorinine
Papaveraldine
Papaveraldinium quat
Papaverine
Papaveroxidine
Papaveroxine
Papaveroxinoline
Papracine
Papracinine
Paprafumine
Papraine
Papraline
Parfumidine
379
257
273
299
141
310
80
264
410
333
270
453
59
211
331
319
292
456
59
59
256
257
140
190
123
124
210
192
140
140
219
220
206
452
451
451
339
107
346
51
245
166
Parfumine
Pavine
Pectenine
Pellotine
Peruvianine
Peshawarine
Pessoine
Petaline
Petaline methine
Peyoglutam
Peyophorine
Peyorovic acid
Peyotine quat
Peyotline
Peyoxylic acid
Phanostenine
Phellodendrine
Phoebe base
Phoebe base II
Phoebine
Phyllocryptine
Phyllocryptonine
Pilocereine
Platycerine
Polyalthine
Polyberbine
Polycarpine
Polygospermine
Polysignine
Polysuavine
Prechilenine
Predicentrine
Preocoteine
Preocoteine N-oxide
Prepseudopalmanine
Proaporphine
Promucosine
Pronuciferine
Protopine
Protosinomenine
Protothalipine
Pseudoanibacanine
Trivial Name Index
107
205
164
434
176
345
109
358
357
438
445
434
435
434
434
293
132
66
62
406
288
289
240
192, 365
413
321
235
405
186
265
329
77
389
389
223
40
182
179
329
65
200
94
31
32
The Simple Plant Isoquinolines
Pseudoberberine
Pseudocheilanthifoline
Pseudocolumbamine
Pseudocoptisine
Pseudojatrorrhizine
Pseudolaudanine
Pseudomanibacanine
Pseudopalmatine
Pseudoprotopine
Pseudorine
Pseudoronine
Psilopine
Pterocereine
Pukateine
Pulchine
Purpureine
Puterine
Pycnarrhine
Quettamine
Raddeanamine
Raddeanidine
Raddeanine
Raddeanone
Refractamide
Reframidine
Reframine
Reframine methiodide
Reframoline
Rehybrine
Remerin
Remerine
Remerine N-oxide
Remeroline
Remrefidine
Remrefine
Reticuline
Reticuline N-oxide
Rhopalotine
Roefractine
Roehybrine
Roemecarine
Roemecarine N-oxide
300
154
146
311
76
73
175
213
331
78
78
411
372
263
106
402
266
88
357
232
232
231
232
307
311
226
228
83
135
248
248
249
263
250
228
111
114
145
62
135
74
74
Trivial Name Index
33
n-Roemehybrine
Roemeramine
Roemerialinone
Roemerine
Roemerine N-oxide
Roemerolidine
Roemeroline
Roemrefidine
Roemrefine
Rogersine
Romneine (also seeunder Escholinine)
Romucosine
Romucosine G
Romucosine H
Rotundine
Rufescine
Rugosinone
Rurrebanidine
Rurrebanine
Sal
Salsolidine
Salsoline
Salsolinol
Salutaridine
Salutaridine N-oxide
Salutarine
Sanjoinine Ia
Sanjoinine Ib
Sanjoinine E
Sanjoinine K
Sarcocapnidine
Sarcocapnidine N-oxide
Sarcocapnine
cis-Sarcocapinine N-oxide
Sarcophylline
Sauvagnine
Saxoguattine
Schefferine
Scoulerine
Sebiferine
Secocularidine
Secocularine
136
275
201
248
249
264
263
250
228
195
295
252
404
199
71, 122, 207
393
322
375
396
47
163
52
47
118
119
118
169
189
170
97
359
360
364
364
350
323
200
202
114
147
351
367
34
The Simple Plant Isoquinolines
Secoglaucine
Secophoebine
Secoquettamine
Secosarcocapnine
Secosarcocapnidine
Secoxanthoplanine
Sendaverine
Sendaverine N-oxide
Setigeridine
Setigerine
Sevanine
Severzine
Sewerzine
Siamine
SiaminineA
Siaminine B
Sibiricine
Sinactine
Sinacutine
Sinoacutine
Sinococuline
Sinomendine
Sinomenine
Sonodione
Sparsiflorine
Spermatheridine
Spiduxine
Spinosine
Spixianine
Spixianine N-oxide
Splendaboline
Splendidine
Srilankine
Stenantherine
Stephabinamine
Stephabine
Stephadiolamine 13-N-oxide
Stephalagine
Stephanine
Stepharanine
Stepharine
Stepharinosine
217
406
357
367
361
198
89
89
231
222
153
160
160
347
347
347
317
224
118
118
426
41
65
238
100
257
236
188
319
319
398
174
78
398
436
438
255
409
260
136
177
187
Trivial Name Index
35
Stephenanthrine
Stephenanthrine N-oxide
Stephodeline
Stepholidine
Steporphine
Stesakine
Stesakine-9-0-l3- D-glucopyranoside
Stipitatine
Stylophylline
Stylopine
Suavedol
Suaveoline
Subsessiline
Sukhodianine
Sukhodianine-~-N-oxide
Takatonine
Tannagine
Taxilamine
Tehuanine
Tehuanine N-oxide
Telazoline
Teliglazine
Telikovine
Telitoxine
Tembetarine
Tepenine
Tetradehydrocapaurine
Tetradehydrocheilanthifoline
Tetradehydroscoulerine
Tetrahydroberberine
Tetrahydroberberrubine
Tetrahydrocolumbarnine
Tetrahydrocoptisine
Tetrahydrocorysarnine
Tetrahydrojatrorrhizine
Tetrahydropalmatine
Tetrahydropalmatrubine
Tetrahydropapaverine
Tetrahydroprotoberberine
Tetrahydropseudoberberine
Tetrahydrosinacutine
Tetrahydrostephabine
251
251
429
136
249
280
280
372
337
307
102
188
398
282
282
400
429
234
391
392
92
386
174
167
127
371
437
81
117
296
285
141
307
315
74
207
191
205
40
300
120
438
36
The Simple Plant Isoquinolines
Thaicanine
Thailandine
Thaipetaline
Thalactamine
Thalbaicalidine
Thalbaicaline
Thalflavine
Thalicmidine
Thalicmidine methine
Thalicmidine N-oxide
Thalicmine
Thalicminine
Thalicsimidine
Thalicpureine
Thalicthuberine
Thalicthuberine N-oxide
Thalictricavine
Thalictricine
Thalictrimine
Thalictrine
Thalictrisine
Thalictuberine
Thalidastine
Thalidicine
Thalidine
Thalifaurine
Thalifendine
Thalifendlerine
Thalifoline
Thalihazine
Thalimicrinone
Thalimonine
Thalimonine N-oxide
Thaliporphine
Thaliporphine methine
Thalisopavine
Thalisopynine
Thaliphendine
Thalphenine
Thalprzewalskiinone
Trichoguattine
Triclisine
379
261
378
408
380
379
425
149
152
150
417
418
402
403
228
229
304
294
327
129
294
228
291
138
123
82
291
399
160
407
400
237, 424
237, 424
149
152
194
401
291
159
200
252
166
Trivial Name Index
Tridictyophylline
3,10,11-Trihydroxy-l,2-methylenedioxynoraporphine
Trilobinine
2,3,7-Trimethoxy-8,9-methylenedioxy-N -methyl pavinane
5,6,7-Trimethoxy-N-methylisoquinolinium quat
1,2,11-Trimethoxy-6a-noraporphine
2,3,6-Trimethoxy-N -normorphinandien-7 -one
1,2,3-Trimethoxy-5-oxonoraporphine
N,O,O- Trimethyllaurelliptine
N,O,O- Trimethylsparsiflorine
Tritopine
Tuduranine
Tuliferoline
Turcamine
Turcomanidine
Turcomanine
Uberine
Umbellatin
Ushinsunine
Ushinsunine l3-N-oxide
Uthongine
Uvariopsamine
Uvariopsamine N-oxide
Uvariopsine
Vaillantine
Velucryptine
Veronamine
Viguine
Weberidine
Weberine
Wilsonirine
Worenine
Xanthaline
Xanthopetaline
Xanthoplanine
Xanthopuccine
Xyloguyelline
Xylopine
Xylopinine
Xylopinine N-oxide
Yenhusomidine
Yenhusomine
438
382
158
235,416
392
183
139
394
214
185
191
178
396
354
188
109
46
297
254
254
283
187
187
268
51
106
399
245
44
456
139
316
219
292
198
296
384
266
212
213
234
234
37
38 TheSimplePlant Isoquinolines
Yuanhunine 205
Yuzirine 100
Yuziphine 355
Zanoxyline 185
Zanthoxyphylline 184
Zenkerine 105
Zijinlongine 449
Zippelianine 428
Zizyphusine 51
Structural Index - Unsubstituted
39
UNSUBSTITUTED ISOQUINOLINES
Isoquinoline
Leucoline
2-Benzazine
Cistanche salsa (Orobanchaceae) yh8, 522'88
Nicotiana tabacum cv (Solanaceae) abc 41, 377'77
Papaver somniferum (Papaveraceae) abf 21, 201'84
Spigelia anthelmia (Loganiaceae) pm 52, 378'86
OQ H
I-Methyl-l,2,3,4-tetrah ydroisoq uinoline
Pachycereus weberi (Cactaceae) ac 57, 109'85
I-Benzylisoquinoline
\ benzyl I
H IQ
Thalictrum spp. (Ranunculaceae) yfz 10,72 '90
40
The Simple Plant Isoquinolines
benzyl
Me THIQ
8,8a-Secoberbine
Not anatural product.
syn 9, 887'92
Iwith a(2,N-Me) attack: I
Tetrahydroprotoberberine
Berbine
Berberis beaniana (Berberidaceae) tl25, 951'84
Fumaria officina lis (Papaveraceae) abs 4
4-HO-benzyl
Me THIQ
Compound unknown
Iwith a(1,8) attack: I
Proaporphine
Phoebe formosan a (Lauraceae) pptp 27, 65'93
Structural Index - Monosubstituted
5-SUBSTITUTED lSOQUINOLINES
Compound unknown
5-MeO
2,3-MeO,MeO-u,u- Me,HO-benzyl
H IQ
Iwith a (6,8) attack: I
Sinomendine
Sinomenium acutum (Menispermaceae)
jnp 57, 1033'94
6-SUBSTITUTED ISOQUINOLINES
6-HO
H
Me THIQ
H 0Yi(l
~N C H 3
Longimammosine
Dolichothele longimamma (Cactaceae) joe 41,319 '76
OH
H O~
~~C H 3
Iwith a4-hydroxy group: I
4,6-Dihydroxy-2-
methyltetrahydroisoquinoline
Theobroma cacao (Sterculiaceae) llyd 41, 130 '78
41
42 TheSimplePlant Isoquinolines
6-HO Compound unknown
4-HO-benzyl, HO
Me THIQ
with a(2,N-Me) attack
and loss of hydrogen:
H O
OH
5,6-Dihydroconstrictosine
Aristolochia constricta (Aristoloehiaeeae)
aa 13, 737'83
Iwith a3,4-ene: I H O
OH
Constrictosine
Aristolochia constricta (Aristolochiaceae)
aa 13, 737'83
6-MeO
H
H THIQ
Longimammatine
Dolichothele longimamma (Cactaceae) joe41, 319'76
Dolichothele uberiformis (Cactaceae) joe41, 319'76
Structural Index - Monosubstituted
Not anatural product.
tet 37, 3175'81
6-MeO
4-HO-benzyl, HO
Me THIQ
witha(2,N-Me) attack,
lossof hydrogen,
anda3,4-ene:
3-0-Methylconstrictosine
Aristolochia constricta (Aristolochiaceae) aa 13, 737'83
Not anatural product.
joc44, 3730'79
6-MeO
4-MeO-benzyl, HO
Me THIQ
witha(2,N-Me) attack
andlossof hydrogen:
5,6-Dihydro-3,5-di-O-meth ylconstrictosine
Aristolochia constricta (Aristolochiaceae) aa 13, 737'83
Ianda3,4-ene:I
3,5-Di-O-methylconstrictosine
Aristolochia constricta (Aristolochiaceae) aa 13, 737'83
43
OH
44
The Simple Plant Isoquinolines
7-SUBSTITUTED ISOQUINOLINES
7-HO
4-HO-benzyl
H THIQ
Compound unknown
with a1,2seco,
with an N-carbomethoxy:
Gusanlung C
Arcangelisia gusanlung (Menispermaceae)
phy 39, 439'95
H O
Weberidine 7-MeO
H
H THIQ
Pachycereus weberi (Cactaceae) ac 57, 109'85
Compound unknown 7-MeO
3,4-MeO,HO-benzyl
Me THIQ
Iwith a(6,3) attack: I
2,9-Dimethoxy-3-hydroxypavinane
C H
3
0
Argemone munita (Papaveraceae) joe38, 3701'73
also under: 6,7 MeO HO R Me THIQ
R= 4-MeO-benzyl (2,3) attack
Structural Index - Monosubstituted
8-SUBSTITUTED ISOQUINOLINES
Longimammidine
8-HO
H
Me THIQ
Dolichothele longimamma (Cactaeeae) joe41, 319'76
Dolichothele uberiformis (Cactaeeae) llyd 40, 173'77
Theobroma cacao (Sterculiaceae) llyd 41, 130'78
Iwitha4-hydroxy group: I
Longimammamine
Dolichothele longimamma (Cactaeeae) joe41, 319'76
Dolichothele uberiformis (Cactaeeae) llyd 40, 173'77
~N C H 3
OH
OH
q)
N C H
3
OH
45
46 The Simple Plant Isoquinolines
5,6-DISUBSTITUTED ISOQUINOLINES
5-MeO 6-MeO
4-HO-benzyl
Me,Me+ THIQ
5,6-Dimethoxy-2,2-dimethyl-l-(4-hydroxybenzy1)-l,2,3,4- THIQ quat
Desmos yunnanensis (Annonaceae) tcyyk 12, 1'00
5,7-DISUBSTITUTED ISOQUINOLINES
Uberine 5-MeO 7-HO
H
Me THIQ
Dolichothele uberiformis (Cactaceae) jnp 40, 173'77
5,8-DISUBSTITUTED ISOQUINOLINES
None found in plants
Structural Index - 6,7-HO,HO-Substituted
6,7-DIHYDROXYSUBSTITUTED ISOQUINOLINES
H 0: G Q
~ I S N H
H O
C H
3
6-HO 7-HO
Me
H THIQ
Salsolinol
Sal
Aconitum carmichaeli (Ranunculaceae) yx 17, 792'82
Musa paradisiaca (Musaceae) jafc 24, 189'76
Theobroma cacao (Sterculiaceae) jafc 24, 900'76
Compound unknown
6-HO 7-HO
a-keto-benzyl
H IQ
H O
Iwitha(2,8)attack: I Liriodendronine
H O
Liriodendron tulipifera (Magnoliaceae)
phy 16,2015'77
H O
Higenamine
Norcoc1aurine
Demethylcoc1aurine
6-HO 7-HO
4-HQ-benzyl
H THIQ
H O
H O
Aconitum carmichaelii (Ranunculaceae) kjp 29, 129'98
Aconitum japonicum (Ranunculaceae) jnp 44, 53'81
Aconitum koreanum (Ranunculaceae) kjp 29, 129'98
Aconitum kusnezoffii (Ranunculaceae) kjp 29, 129'98
47
48 The Simple Plant Isoquinolines
Aconitum napiforme (Ranunculaceae) kjp 29,129 '98
Annona reticulata (Annonaceae) tl28, 1251'87
Annona squamosa (Annonaceae) jnp 44, 53'81
Asiasarum heterotropoides (Aristolochiaceae) cpb 26, 2284'78
Asiasarum sieboldii (Aristolochiaceae) cpj 44, 211'92
Euodia rutaecarpa (Rutaceae) book 1
Gnetum parvifolium (Gnetaceae) jnp 62, 1025'99
Nelumbo nucifera (Nymphaeaceae) cpb 18,2564 '70
H O
6-HO 7-HO
4-HO-benzyl
Me THIQ
(d1)-N-Methylhigenamine
Gnetum parvifolium (Gnetaceae) jnp 62, 1025'99
Ithe N-oxide: I
(-)-N-Methylhigenamine N-Oxide
Gnetum parvifolium (Gnetaceae) jnp 62, 1025'99
with a(1,8) attack,
and reduction of adouble bond and of
the carbonyl group in the benzyl ring:
Discolorine
Croton discolor (Euphorbiaceae) rlq 1, 140'70
Croton plumieri (Euphorbiaceae) rlq 1, 140'70
Ithe glucoside at the 7-0H position: I
N-Methylhigenamine, 7-0-[3- D-glucopyranoside
Phellodendron amurense (Rutaceae) phy 35,209 '94
H O
H O
H O
H O
Structural Index - 6,7-HO,HO-Substituted
49
6-HO 7-HO
4-MeO-benzyl
Me,Me+ THIQ
H O
Luxandrine
H O
Pseudoxandra sclerocarpa (Annonaceae) phy 25,2693 '86
6-HO 7-HO
3,4-HO,HO-benzyl
Me THIQ
H O
H O
Laudanosoline
Papaver somniferum (Papaveraceae) book 4 H O
OH
6-HO 7-HO
3,4-HO,MeD-benzyl
H THIQ
Compound unknown
Iwitha(2,4a)attack: I
Croton bonplandianus (Euphorbiaceae)
phy20, 683'81
4,6-Dihydroxy-3-methoxymorphinandien-7-one
o
50
The Simple Plant Isoquinolines
Compound unknown 6-HO 7-HO
3,4-HO,MeO-benzyl
Me THIQ
Iwith a(2,4a) attack: I Mocrispatine
Monodora crispata (Annonaceae) aua 17, 105'81
o
Tetrahydroprotopapaverine
Not anatural product.
jcspt 2, 1696'80
6-HO 7-HO
3,4-MeO,MeO-benzyl
Me THIQ
with a(2,N-Me) attack
and aromatization of the c-ring:
H O
OC H 3
H O
Demethyleneberberine
OC H 3
Stephania venosa (Menispermaceae) zh 30, 250'99
Thalictrum javanicum (Ranunculaceae) jnp 46, 454'83
Iwith a(6,8) attack: I
Lastourvilline
Artabotrys lastourvillensis (Annonaceae)
jnp 48, 460'85
Fumaria indica (Papaveraceae)
phy 31, 2869'92
Glaucium leiocarpum (Papaveraceae)
pm 65, 492'99
Structural Index - 6,7-HO,HO-Substituted
Compound unknown 6-HO 7-HO
3,4-MeO,MeO-benzyl
Me,Me+ THIQ
Iwitha(2,8)attack I
Zizyphusine
Nandina domestica (Berberidaceae)
nmt 50, 427'96
Ziziphus fructus (Rhamnaceae)
apr10,208'87
Ziziphus jujuba (Rhamnaceae)
apr 12,263'89
Ziziphus spinosa (Rhamnaceae) kjp 16,44 '85
H O
6-HO 7-HO
6',7'-MOO-isobenzofuranone, 3'-yl
Me THIQ
Papraine
Fumaria indica (Papaveraceae) het 29,1091'89
H O
6-HO 7-HO
3,4-MeO,MeO-benzyl, HO
Me,Me+THIQ
Compound unknown
Iwitha(2,N-Me) attack I
Vaillantine
Fumaria vaillantii (Papaveraceae) kps 476'74
Theassigned structure of this compound has been
challenged:jnp 45,241'82
H O
H O
51
52
The Simple Plant Isoquinolines
6,7-HO-MeO-ISOQUINOLINES
Isocorypalline 6-HO 7-MeO
H
Me THIQ
Berberis oblonga (Berberidaceae) cnc11,563'75
Corydalis stricta (Papaveraceae) kps 19,461'83
Stephania cepharantha (Menisperrnaceae) nrn52,541'98
Isopycnarrhine
H Om
I +
: : : : : : ..... / : N C H
a
C H aO
6-HO 7-MeO
H
Me+ DHIQ
Popowia pisocarpa (Annonaceae) jnp49,1028'86
H Om
I N
C H aO : : : : : : .....
6-HO 7-MeO
H
4-MeO-benzyl THIQ
Isosendaverine
Corydalis sp. (Papaveraceae) phy 36,241'94
Ceratocapnos heterocarpa (Papaveraceae) phy 36,241'94 OC H
a
Salsoline
H 0x: Q
I N H
C H aO: : : : : : "' " S
C H
a
6-HO 7-MeO
Me
H THIQ
Alangium lamarckii (Alangiaceae) prns 5'80
Corispermum leptopyrum (Chenopodiaceae) app 34,421'77
Desmodium tiliaefolium (Fabaceae) phy 12,193'73
Structural Index - 6,7-HO,MeO-Substituted
Echinocereus merkerii (Cactaceae) jps 58, 1413'69
Genista purgens (Fabaceae) nr
Pachycereus pecten-aboriginum (Cactaceae) aps 15, 127'78
Salsola arbuscula (Chenopodiaceae) ber 67, 878'34
Salsola kali (Chenopodiaceae) book 6
Salsola pestifera (Chenopodiaceae) iant 2, 86'85
Salsola richteri (Chenopodiaceae) rr 16, 86'80
6-HO 7-MeO
Me
3,4-HO,MeO-benzyl THIQ
Nummularine
Berberis nummularia (Berberidaceae) cnc 33,70 '97
6-HO 7-MeO
Me
3,4-MeO,MeO-benzyl THIQ
Bemumicine
Berberis nummularia (Berberidaceae) kps 3, 397'93
6-HO 7-MeO
Me
3,4-MDO-benzyl THIQ
Bemumine
Berberis nummularia (Berberidaceae) kps 3, 394'93
53
54
The Simple Plant Isoquinolines
Not anatural product.
joc49,581'84
6-HO 7-MeO
benzyl
H THIQ
Iwith a(2,8) attack: I
(-)-Asimilobine
Anaxagorea spp. (Annonaceae) pm 41, 48'81
Annona cherimolia (Annonaceae) jccs44, 313'97
Annona squamosa (Annonaceae) cpj 46, 439'94
Annona spp. (Annonaceae) fit 65,87 '94
Anomianthus spp. (Annonaceae) bs&e 26, 139'98
Artabotrys spp. (Annonaceae) jbas 15,59 '91
Asimina spp. (Annonaceae) yz 85, 77'65
Cananga odorata (Annonaceae) jccs46, 607'99
Cardiopetalum spp. (Annonaceae) pm 57, 581'91
Cymbopetalum spp. (Annonaceae) pm 50,517'84
Desmos spp. (Annonaceae) jnp 45, 617'82
Disepalum spp. (Annonaceae) phy 29, 3845'90
Fissistigma spp. (Annonaceae) abs 3
Glossocalyx spp. (Monimiaceae) jnp 48, 833'85
Goniothalamus spp. (Annonaceae) abs 3
Guatteria spp. (Annonaceae) jnp 46, 335'83
Hexalobus spp. (Annonaceae) lac 1982,1623'82
Laurelia philippiana (Monimiaceae) phy 21, 773'82
Liriodendron spp. (Magnoliaceae) cnc 13, 602'77
Magnolia spp. (Magnoliaceae) phy 23, 188'84
Meiogyne spp. (Annonaceae) phy 26, 537'87
Melodorum spp. (Annonaceae) ajc24, 2187'71
Monocyclanthus spp. (Annonaceae) jnp 54, 1331'91
Nelumbo spp. (Nymphaeaceae) jnp 50, 773'87
Ocotea spp. (Lauraceae) fes 30, 479'75
Oncodostigma spp. (Annonaceae) pmp 20, 251'86
Orophea spp. (Annonaceae) bs&e 27, 111'99
Phoebe spp. (Lauraceae) jccs40, 209'93
Polyalthia suberosa (Annonaceae) jbas 16, 99'92
Popowia spp. (Annonaceae) jnp 49, 1028'86
Rollinia spp. (Annonaceae) jnp 49,1028 '86
H O
C H
3
0
Structural Index - 6,7-HO,MeO-Substituted
Siparuna spp. (Monimiaceae) pm 59,100 '93
Stephania spp. (Menispermaceae) yhhp 21, 223 '86
Talauma spp. (Magnoliaceae) apf 43, 189 '85
Uvaria spp. (Annonaceae) nm51, 272 '97
Xylopia spp. (Annonaceae) pmp 16,253 '82
Ziziphus spp. (Rhamnaceae) pjsr 3D, 81'78
Iglucosideat the 6-HO position: I
(-)-Asimilobine- 2-0-/3-D-gI ucoside
Stephania pierrei (Menispermaceae) jnp 56, 1468 '93
6-HO 7-MeO
benzyl
Me THlQ
Not anatural product.
jhc 4, 417 '67
Iwitha(2,8)attack: I
N-Methylasimilobine
O-Nomuciferine
Annona cherimolia (Annonaceae) jccs44, 313 '97
Annona spp. (Annonaceae) phy 49, 2015 '98
Colubrina spp. (Rhamnaceae) pm 27, 304 '75
Duguetia spp. (Annonaceae) jnp 50, 664 '87
Monocyclanthus spp. (Annonaceae) jnp 54, 1331'91
Nelumbo spp. (Nymphaeaceae) jps 66, 1627 '77
Oxymitra spp. (Annonaceae) phy 3D, 1265 '91
Papaver spp. (Papaveraceae) dsa 7, 93 '83
Stephania cepharantha (Menispermaceae) jnp 63, 477 'DO
Xylopia spp. (Annonaceae) jnp 44, 551'81
Ziziphusspp. (Rhamnaceae) apr 12, 263 '89
Iglucosideat the6-HO position: I
()N-Methylasimilobine-2-0-~-D-glucopyranoside
Stephania cepharantha (Menispermaceae) jnp 63, 477 'DO
H O
55
56
The Simple Plant Isoquinolines
Irhamnoside at the 6-HO position: I
Floripavidine
N-Methylasimilobine-2-0-a- L-rhamnopyranoside
Papaver armeniacum (Papaveraceae) dsa 7, 93'83
Papaver fugax (Papaveraceae) dsa 7, 93'83
Papaver tauricolum (Papaveraceae) dsa 7, 93'83
Compound unknown 6-HO 7-MeO
benzyl
Me,Me+ THIQ
with a(2,8) attack
and a1,2seco:
HO
Argentinine
Annona montana (Annonaceae)
pnsc 3, 63'79
Aristolochia argentina (Aristolochiaceae) aaqa 60, 309'72
Enantia chlorantha (Annonaceae) pm 9, 296'75
Guatteria discolor (Annonaceae) jnp 47, 353'84
Guatteria foliosa (Annonaceae) jnp 57, 890'94
Guatteria goudotiana (Annonaceae) phy 30, 2781'91
Monocyclanthus vignei (Annonaceae) jnp 57, 1033'94
Phaeanthus vietnam ens is(Annonaceae) fit 62, 315'91
Popowia pisocarpa (Annonaceae) jnp 49,1028 '86
I the N-oxide: I
Argentinine N-Oxide
Monocyclanthus vignei (Annonaceae) jnp 57, 1033'94
Structural Index - 6,7-HO,MeO-Substituted
Compound unknown 6-HO 7-MeO
benzyl
Ac THIQ
Iwitha(2/8)attack I
(-)-N-Acetylasimilobine
Liriodendron tulipifera (Magnoliaceae)
phy 15/547'76
Zanthoxylum simulans (Rutaceae)
phy 36/237/94
6-HO 7-MeO
benzyl
CONH
2
THIQ
Compound unknown
Iwitha(2/8)attack I
N-Carbamoylasimilobine
Hexalobus crispiflorus (Annonaceae)
jnp46/761/83
H O
C
H
30
6-HO 7-MeO
benzyl
C0
2
Et THIQ
Compound unknown
witha(2/8)attack,
glucosideat the 6-HO position:
Kamaline
Stephania venosa (Menispermaceae)
phy36/1053/94
G lu-O
C H 30
57
58 The SimplePlant Isoquinolines
6-HO 7-MeO Compound unknown
a-keto-benzyl
H IQ
Iwith a(2,8) attack: I HO
Oxoasimilobine
7-0xodehydroasimilobine
Annona cherimolia (Annonaceae) jccs46, 77'99
Dasymaschalon rostra tum (Annonaceae) zzz 26, 39'01
Monocyclanthus vignei (Annonaceae) jnp 57, 1033'94
6-HO 7-MeO
a-Me-benzyl
CHO THIQ
Compound unknown
with a(2,8) attack
and an a,l-ene:
HO
Duguespixine
Duguetia spixiana (Annonaceae) jnp 51, 389'88
Guatteria sagotiana (Annonaceae) jnp 51, 389'88
6-HO 7-MeO
a-HO-benzyl
H THIQ
Compound unknown
Norpachyconfine
Iwith a(2,8)attack: I
Duguetia spixiana (Annonaceae) jnp 50, 664'87
Structural Index - 6,7-HO,MeO-Substituted
(-)-Anaxagoreine
Anaxagorea sp. (Annonaceae) pm41,48 '81
Cananga odorata (Annonaceae) jccs46, 607'99
C H 30
H O
6-HO 7-MeO
a-HO-benzyl
Me THIQ
Compound unknown
Iwith a(2,8)attack: I
Pachyconfine
H O
Duguetia spixiana (Annonaceae) jnp 50, 664'87
Guatteria sagotiana (Annonaceae) jnp 49, 1078'86
Pachypodanthium confine (Annonaceae) apf 35, 65'77
ItheN-oxide: I
N-Oxypachyconfine
Pachyconfine N-oxide
Duguetia spixiana (Annonaceae) jnp 50, 664'87
6-HO 7-MeO
4-HO-benzyl
H THIQ
(+)-Isocodaurine
Desmos yunnanensis (Annonaceae) tcyyk 12, 1'00
59
60
The Simple Plant Isoquinolines
Iwith a(1,8) attack: I
H O
Crotonosine
C H
3
0
Croton cumingii (Euphorbiaceae) llyd 32, 1'69
Croton discolor (Euphorbiaceae) llyd 32, 1'69
Croton linearis (Euphorbiaceae) llyd 32, 1'69
0
Croton plumieri (Euphorbiaceae) phy 8, 777'69
and reduction of the 2,3double bond
H O
and of the carbonyl group
in the benzyl ring:
C H
3
0
jaculadine
Croton discolor (Euphorbiaceae) rlq 1, 140'70
H O
Croton plumieri (Euphorbiaceae) rlq 1, 140'70
H O
Iwith a(2,8) attack: I
Apocrotonosine
C H
3
0
Croton sp. (Euphorbiaceae) jnp 38, 275'75
H O
N-Methylisococlaurine
6-HO 7-MeO
4-HO-benzyl
Me THIQ
(+)-isomer:
Desmoe yunnanensis (Annonaceae) tcyyk 12,1'00
Structural Index - 6,7-HO,MeO-Substituted
(-)-isomer:
Phoebe minutiflora (Lauraceae) cpj 49, 217'97
isomernot specified:
Nelumbo nucifera (Nymphaeaceae) phy 12, 699'73
Iwitha(l,8) attack: I
H O
N-Methylcrotonosine
(-)-isomer:
Croton discolor (Euphorbiaceae) rlq 1, 140'70
Croton plumieri (Euphorbiaceae) phy 8,777 '69
Meconopsis cambrica (Papaveraceae) jnp 44,67 '81
Papaver triniaefolium (Papaveraceae) pm 63, 575'97
o
isomernot specified:
Anomianthus dulcis (Annonaceae) bs&e 26, 139'98
Croton cumingii (Euphorbiaceae) llyd 32, 1'69
Croton linearis (Euphorbiaceae) llyd 32, 1'69
Orophea hexandra (Annonaceae) bs&e 27, 111'99
Papaver fugax (Papaveraceae) pm 41, 105'81
Theearliestisolation of this base from the Croton species (pes 261'64)
wasamixtureof alkaloids that was given the name Homolinearisine.
Subsequentpurification showed it to be N-Methylcrotonosine
(jcs 1676'66).
andreduction of adouble
bondinthebenzyl ring:
H O
Linearisine
Croton discolor (Euphorbiaceae) rlq 1, 140'70
Croton linearis (Euphorbiaceae) llyd 32,1'69 0
Croton plumieri (Euphorbiaceae) phy 8,777 '69
61
62
The Simple Plant Isoquinolines
H O
Lotusine 6-HO 7-MeO
4-HO-benzyl
Me,Me+ THIQ
C H sO
Nelumbo nucifera (Nymphaeaceae)
zzz 16, 673'91
Tiliacora racemosa (Menispermaceae)
jics57, 773'80
H O
H O
(+)-Roefractine 6-HO 7-MeO
4-MeO-benzyl
Me THIQ
C H sO
Roemeria refracta (Papaveraceae)
jnp 53, 666'90
C H sO
Iwith a(2,8) attack: I
H O
Phoebe base II C H sO
Phoebe sp. (Lauraceae) jnp 38, 275'75
C H sO
6-HO 7-MeO Isovelucryptine
4-MeO-a-keto-benzyl
H DHIQ
Cryptocarya velutinosa (Lauraceae)
jnp 52, 516'89
Structural Index - 6,7-HO,MeO-Substituted
6-HO 7-MeO Compound unknown
3,4-HO,HO-benzyl
Me THIQ
HO
Iwith a(2,8) attack: I Glaufine
Glaucium fimbrilligerum (Papaveraceae)
kps 4, 493'83
C H sO
HO
HO
HO
Iwith a(6,N-Me) attack: I
(-)-Artavenustine
C H sO
Artabotrys venustus (Annonaceae)
jnp 49, 602'86
OH
andaglucoside on the 3-HO
of theoriginal benzyl group:
Dauricoside
Menispermum dauricum (Menispermaceae) cpb 41, 1866 '93
HO
6-HO 7-MeO
3,4-HO,MeQ-benzyl
H THIQ
(+)- Norprotosinomenine
C H sO
HO
Erythrina lithosperma (Fabaceae) ajc 24, 2733 '71
63
64 TheSimplePlant Isoquinolines
Iwith a(2,8) attack I H O
Lindcarpine
Hernandia voyronii (Hernandiaceae)
pm64,58'98
Illigera pentaphylla (Hernandiaceae)
jnp 48, 835'85
Lindera pipericarpa (Lauraceae) het 9, 903'78
Lindera reflexa (Lauraceae) cty 25, 565'94
Litsea acuminata (Lauraceae) cpj 46, 299'94
Phoebe grandis (Lauraceae) phy 45, 1543'97
Stephania sp. (Menispermaceae) jnp 38, 275'75
I with a(6,8) attack I
H O
Laurolitsine
Norboldine
Cryptocarya longifolia (Lauraceae)
ajc34, 195'81
Dehaasia kurzii (Lauraceae)
fit 62,261'91
Illigera pentaphylla (Hernandiaceae)
jnp 48, 835'85
Lindera reflexa (Lauraceae) cty 25,565 '94
Litsea rotundifolia (Lauraceae) ryz 8,324 '00
Litsea spp. (Lauraceae) pm48, 52'83
Machilus duthei (Lauraceae) jcp 2, 157'80
Monimia roiundiiolia (Monimiaceae) apf 38,537 '80
Nectandra saliciiolia (Lauraceae) jnp 59, 576'96
Neolitsea aurata (Lauraceae) jccs22, 349'75
Neolitsea buisanensis (Lauraceae) jccs22, 349'75
Peumus boldus (Monimiaceae) phy 32, 897'93
Phoebe clemensii (Lauraceae) jnp 46,913 '83
Phoebe formosana (Lauraceae) jnp 46,913 '83
Phoebe grandis (Lauraceae) phy 45,1543 '97
Phoebe minutiflora (Lauraceae) cpj 49, 217'97
Retanilla ephedra (Rhamnaceae) rlq 5, 158'74
OH
Structural Index - 6,7-HO,MeO-Substituted
H O
6-HO 7-MeO
3,4-HO,MeQ-benzyl
Me THIQ
C H sO
Protosinomenine
Erythrina lithosperma (Fabaceae)
ajc24, 2733'71
Litsea glutinosa (Lauraceae)
jcsptI, 1477'88
Polyalthia nitidissima (Annonaceae) pm49, 20'83
Stephania cepharantha (Menispermaceae) cpb 45, 470'97
C H sO
I witha(2,N-Me) attack: I
H O
Isoscoulerine
C H sO
(-)-isomer:
Corydalis ambigua (Papaveraceae)
daib45, 2160'85
isomernot specified:
Stephania hainanensis (Menispermaceae) cty 18, 146'87
Iwitha(2,4a)attack: I
C H sO
thel,8atrans isomer:
Sinomenine
Cucoline
Kukoline
Stephania cepharantha (Menispermaceae)
cpb45, 470'97
Stephania epigaea (Menispermaceae)
nyx 5,203'85
Stephania micrantha (Menispermaceae)
nyx 7,13 '87
OH
OH
OC H s
H O
o
OC H
s
65
66 The SimplePlant Isoquinolines
the 1,8acis isomer: C H sO
14-Episinomenine
H O
Ocotea brachybotra (Lauraceae)
fes 32, 767'77
Stephania cepharantha (Menispermaceae)
cpb 45, 470'97
o
OC H
s
H O
Iwith a(2,8)attack: I
N-Methyllindcarpine
Phoebe base
C H sO
H O
Dehaasia triandra (Lauraceae)
tet 52, 6561'96
Glaucium paucilobum (Papaveraceae)
jsiri 10, 229'99
Glaucium spp. (Papaveraceae) jnp 61, 1564'98
Illigera pentaphylla (Hernandiaceae) jnp 48, 835'85
Litsea cubeba (Lauraceae) jccs39, 453'92
Magnolia acuminata (Magnoliaceae) daib 32, 2312'71
Menispermum canadense (Menispermaceae) llyd 34, 292'71
Phoebe clemensii (Lauraceae) jnp 46,913 '83
Strychnopsis thouarsii (Menispermaceae) pm58, 540'92
C H sO
I with a(6,N-Me) attack: I H O
OC H
s
C H sO
(S)(-)-Isocoreximine
ll-O-Demethyldiscretine
Toddalia asiatica (Rutaceae) phy 48, 1377'98
Xylopia vieillardi (Annonaceae) jnp 54,466 '91
OH
Structural Index - 6,7-HO,MeO-Substituted
Iwitha(6,8)attack: I HO
Boldine
CHsO
Actinodaphne spp. (Lauraceae)
ajc22, 2257'69
Artabotrys lastouroillensis (Annonaceae) CHsO
jnp48, 460'85 OH
Cocculus spp. (Menispermaceae)
jics56, 1020'79
Dehaasia kurzii (Lauraceae) fit 58, 430'87
Desmos tieoaghiensis (Annonaceae) jnp 45, 617'82
Hedycarya angustifolia (Monimiaceae) het 26, 447'87
Illigera pentaphylla (Hernandiaceae) jnp 48, 835'85
Laurelia novae-zelandiae (Monimiaceae) hca 50, 1583'67
Laurus nobilis (Lauraceae) jnp 45, 560'82
Lindera spp. (Lauraceae) jnp 48, 160'85
Litsea spp. (Lauraceae) cpj 46, 299'94
Machilus duihei (Lauraceae) jcp 2, 157'80
Monimia rotundifolia (Monimiaceae) apf 38, 537'80
Nectandra grandiflora (Lauraceae) ijp 31, 189'93
Neolitsea spp. (Lauraceae) jccs45, 103'98
Peumus spp. (Monimiaceae) jc612, 315'93
Phoebe grand is(Lauraceae) phy 45,1543 '97
Polyalthia cauliflora var. beccarii (Annonaceae) jnp 47, 504'84
Retanilla ephedra (Rhamnaceae) rlq 5, 158'74
Sassafras albidum (Lauraceae) llyd 39, 473a'76
Trivalvaria macrophylla (Annonaceae) jnp 53, 862'90
landana,l-ene:1
HO
Dehydroboldine
CHsO
Peumus boldus (Monimiaceae)
jnp51,389'88
CHsO
OH
67
68
The Simple Plant Isoquinolines
Compound unknown
6-HO 7-MeO
3,4-HO,MeO-benzyl
Me,Me+ THIQ
H O
Iwith a(2,8) attack: I
N,N-Dimethyllindcarpine
Aristolochia triangularis (Aristolochiaceae)
jcps 6, 8'97
Caltha leptosepala (Ranunculaceae)
phy 16, 500'77
Coscinium fenestratum (Menispermaceae) pm 38, 24'80
Magnolia spp. (Magnoliaceae) jnp 38, 275'75
C H sO
H O
Iwith a(6,8) attack: I
N-Methylboldine
Boldine methiodide
C H sO
Cocculus sp. (Menispermaceae)
jnp 46, 761'83
C H sO
OH
Compound unknown
6-HO 7-MeO
3,4-HO,MeO-benzyl
Ac THIQ
H O
Iwith a(6,8) attack: I
N-Acetyllaurolitsine
C H sO
Litsea rotundifolia (Lauraceae)
ryz 8, 324'00
Litsea sp. (Lauraceae) ajc 22, 2259'69
C H sO
OH
Structural Index - 6,7-HO,MeO-Substituted
6-HO 7-MeO
3,4-MeO,HO-benzyl
H THIQ
Not anatural product.
jcspt I, 1531'75
Iwitha(2,8)attack: I (+)-Hemovine
Croton linearis (Euphorbiaceae)
llyd32, 1'69
Croton wilsonii (Euphorbiaceae)
rlq1, 140'70
Hernandia guianensis (Hemandiaceae)
pm50, 20'84
Hernandia nymphaeifolia (Hemandiaceae) pm63,154 '97
Hernandia ovigera (Hemandiaceae) apf 42,317 '84
Illigera luzonensis (Hemandiaceae) jnp 60, 645'97
Illigera parviflora (Hemandiaceae) cty 22, 393'91
Lindera myrrha (Lauraceae) phy 35, 1363'94
Neolitsea variabillima (Lauraceae) het 9, 903'78
Ocotea teleiandra (Lauraceae) rlq 23,18 '92
H O
H O
(ThenameHemovine isused as asynonym for Ovigerine. Seepg. 306)
lwitha(6,8)attack: I Laetanine
Hernandia voyronii (Hernandiaceae)
pm64,58'98
Litsea leata (Lauraceae) phy 18, 910'79
Ocotea teleiandra (Lauraceae) rlq 23, 18'92 HO
H O
OC H
s
6-HO 7-MeO
3,4-MeO,HO-benzyl
Me THIQ
Not anatural product.
dmd 14,703 '86
69
70
The Simple Plant Isoquinolines
I with a(2,N-Me) attack: I
H O
(S)(-)Discretamine
Aequaline C H sO
Annona cherimolia (Annonaceae) pmp 23, 159'89
Annona reticulata (Annonaceae) zzz 17,295 '92
Anomianthus dulcis (Annonaceae) bs&e 26,139 '98
Artabotrys maingayi (Annonaceae) jnp 53, 503'90
Artabotrys venustus (Annonaceae) jnp 49, 602'86
Desmos longiflorus (Annonaceae) fit 66, 463'95
Desmos tiebaghiensis (Annonaceae) jnp 45, 617'82
Duguetia calycina (Annonaceae) pmp 12, 259'78
Fissistigma glaucescens (Annonaceae) phy 24, 1829'85
Fissistigma oldhamii (Annonaceae) abs 3
Goniothalamus amuyon (Annonaceae) abs 3
Guatteria discolor (Annonaceae) jnp 47, 353'84
Meiogyne virgata (Annonaceae) phy 26, 537'87
Nandina domestica (Berberidaceae) phy 27, 2143'88
Oncodostigma monosperma (Annonaceae) jnp 52, 273'89
Polyalthia stenopetala (Annonaceae) phy 29, 3845'90
Rollinia leptopetala (Annonaceae) pb138, 318'00
Saccopetalum prolificum (Annonaceae) ccl Tl, 129'00
Schefferomitra subaequalis (Annonaceae) joe42, 3588'77
Stephania intermedia (Menispermaceae) yhtp 16, 1'85
Stephania succifera (Menispermaceae) zx 31, 544'89
Uvaria lucida (Annonaceae) nm51, 272'97
Xylopia buxifolia (Annonaceae) jnp 44, 551'81
Xylopia discreta (Annonaceae) bull I
H O
Iand aromatization of the c-ring: I
Dehydrodiscretamine C H sO
Fissistigma balansae (Annonaceae) phy 48, 367'98
Nandina domestica (Berberidaceae) phy 27, 2143'88
Stephania intermedia (Menispermaceae) yhtp 16, 1'85
Thalictrum foliolosum (Ranunculaceae) daib 45, 520'84
Tinospora capillipes (Menispermaceae) pm 50, 88'84
OC H s
OH
OC H s
OH
Structural Index - 6,7-HO,MeO-Substituted
Iwitha(2,8)attack: I N-Methylhemovine HO
Croton linearis (Euphorbiaceae)
llyd32,1'69
Croton wilsonii (Euphorbiaceae)
llyd32,1'69
Hernandia guianensis (Hernandiaceae)
pm50, 20'84
Hernandia nymphaeifolia (Hernandiaceae) pm 63,154 '97
Hernandia peltata (Hernandiaceae) pm 46, 119'82
Lindera megaphylla (Lauraceae) j np 57, 689'94
Lindera oldhamii (Lauraceae) het 9, 903'78
Neolitsea variabillima (Lauraceae) het 9, 903'78
OH
Iwitha(6,N-Me) attack: I
HO
lO-O-Demethyldiscretine
Artabotrys venustus (Annonaceae)
jnp49,602'86
Caryomene olivascens (Menispermaceae) afb 6, 163'87
Guatteria discolor (Annonaceae) j np 47, 353'84
Xylopia vieillardi (Annonaceae) j np 54, 466'91
OH
OCH
s
OH
Iwitha(6,3)attack: I
HO
OCHs
Bisnorargemonine
Dinorargemonine
Rotundine
CHsO
Argemone spp. (Papaveraceae) j np 46,293 '83
Chasmanthera dependens (Menispermaceae) pm 49,17 '83
Cocculus laurifolius (Menispermaceae) tet 40, 1591'84
Corydalis decumbens (Papaveraceae) jca6691/2,225 '94
Cryptocarya longifolia (Lauraceae) j np 46, 293'83
Eschscholzia spp. (Papaveraceae) j np 46,293 '83
71
72
The Simple Plant Isoquinolines
Fumaria bastardii (Papaveraceae) nps 4, 257'98
Thalictrum dasycarpum (Ranunculaceae) jnp 46, 293'83
also under: 6,7 MeO HO R Me THIQ
R= 3,4-HO,MeO-benzyl (6,3) attack
(Thename Rotundine has been used for two unrelated alkaloids; the one
in this section, and one which is asynonym for Tetrahydropalmatine.
The literature shows that (-)-Rotundine (Tetrahydropalmatine) comes
from Stephania sp., whereas this Rotundine comes fromArgemone sp.)
Iwith a(6,8) attack: I
HO
Liriotulipiferine
Artabotrys lastourvillensis (Annonaceae)
jnp 48, 460'85
Liriodendron tulipifera (Magnoliaceae)
jnp 42, 325'79
Litsea cubeba (Lauraceae) jca667, 322'94
Strychnopsis thouarsii (Menispermaceae) pm 58, 540'92
HO
6-HO 7-MeO
3,4-MeO,HO-a- Me-benzyl
Me THIQ
Compound unknown
HO
Iwith a(2,N-Me) attack: I
Corydalidzine
Corydalis caucasica (Papaveraceae)
ijcd27, 161'89 OH
Corydalis koidzumiana (Papaveraceae) cpb 23, 313'75
Corydalis nobilis (Papaveraceae) ecce54, 2009'89
Corydalis solida ssp. brachyloba (Papaveraceae) jcsp 13, 63'91
Structural Index - 6,7-HO,MeO-Substituted
6-HO 7-MeO
3,4-MeO,MeO-benzyl
H THIQ
Not anatural product.
sh 17,49 '86
Iwitha(2,8)attack: I lO-O-Methylhernovine
Croton wilsonii (Euphorbiaceae) rlq 1, 140'70
Iwitha(6,8)attack: I
Norpredicentrine
9-0- Methyllaurolitsine
9-0-Methylnorboldine
Guatteria scandens (Annonaceae)
jnp46, 335'83
Hernandia voyronii (Hemandiaceae)
pm64, 58'98
Isopacodine
H O
6-HO 7-MeO
3,4-MeO,MeO-benzyl
H IQ
Papaver somniferum var. noordster (Papaveraceae)
jcsptI, 1531'75 CH
3
0
(+)-Pseudolaudanine HO 6-HO 7-MeO
3,4-MeO,MeO-benzyl
Me THIQ
Arctomecon merriami (Papaveraceae)
bse18,45'90
Roemeria refracta (Papaveraceae)
jnp53, 666'90
73
74
The Simple Plant Isoquinolines
Iand a(+)-trans 4-hydroxy group: I
OH
Roemecarine
Roemeria carica (Papaveraceae)
het 24, 1227'86
Roemeria refracta (Papaveraceae)
jnp 53, 666'90
Ithe N-oxide: I
Roemecarine N-Oxide
Roemeria carica (Papaveraceae) het 24, 1227'86
Iwith a(2,N-Me) attack: I
(-)-Corypaimine
(+Tetrahydrojatrorrhizine
3-Hydroxy-2,9,lO-trimethoxy-
tetrahydroprotoberberine
Annona cherimolia (Annonaceae) pmp 23,159 '89
Argemone grandiflora (Papaveraceae) phy 11,461'72
Berberis julianae (Berberidaceae) cz 29, 265'75
Coptis teeta (Ranunculaceae) ijcs28, 97'51
Corydalis lutea (Papaveraceae) phy 33, 943'93
Corydalis nobilis (Papaveraceae) ecce54, 2009'89
Duguetia stelichantha (Annonaceae) rlq 16,107 '85
Enantia chlorantha (Annonaceae) pmp 9, 296'75
Fibraurea chloroleuca (Menispermaceae) pw 113, 1153'78
Glaucium grandiflorum (Papaveraceae) jnp 49,1166 '86
Guatteria discolor (Annonaceae) jnp 47, 353'84
Hydrastis canadensis (Ranunculaceae) gci 110, 539'80
Pachypodanthium confine (Annonaceae) apf 35,65 '77
Pachypodanthium staudtii (Annonaceae) pw 113, 1153'78
Rollinia leptopetala (Annonaceae) pbI 38, 318'00
Stephania mashanica (Menispermaceae) cty 14, 249'83
Stephania micrantha (Menispermaceae) yhhp 16,557 '81
Structural Index - 6,7-HO,MeO-Substituted
Stephania succifera (Menispermaceae) zx 31, 544'89
Xylopia vieillardii (Annonaceae) jnp 54, 466'91
landaromatization of the c-ring: I HO
J atrorrhizine
Arcangelisia flava (Menispermaceae) jnp 45, 582'82
Berberis erataegina (Berberidaceae) kps 106, '96
Berberis spp. (Berberidaceae) jnp 58, 1100'95
Burasaia australis (Menispermaceae) bse 19, 433'91
Burasaia congesta (Menispermaceae) bse 19, 433'91
Burasaia gracilis (Menispermaceae) bse 19, 433'91
Chasmanthera dependens (Menispermaceae) pm 46, 228'82
Coptis spp. (Ranunculaceae) phy 21,1419 '82
Corydalis spp. (Papaveraceae) jca6691/2, 225'94
Coscinium fenestratum (Menispermaceae) pm 38, 24'80
Dioscoreophyllum cumminsii (Menispermaceae) phy 22, 1671'83
Enantia chlorantha (Annonaceae) pmp 9, 296'75
Fagara chalybea (Rutaceae) kdr 23, 153'90
Fibraurea chloroleuca (Menispermaceae) pw 113, 1153'78
Fibraurea recisa (Menispermaceae) ncyh 2, 77'82
Glaucium arabicum (Papaveraceae) duj 17, 185'90
Hydrastis canadensis (Ranunculaceae) sz 46, 42'92
Jatrorrhiza palmata (Menispermaceae) llyd 28, 73'65
Jeffersonia dubia (Berberidaceae) pm 51,52 '85
Mahonia aquifolium (Berberidaceae) pm 61, 372'95
Mahonia spp. (Berberidaceae) pm 57, 505'91
Nandina domestica (Berberidaceae) phy 27, 2143'88
Penianthus zenkeri (Menispermaceae) phy 30,1957 '91
Phellodendron spp. (Rutaceae) pm 59,557 '93
Sphenocentrum jollyanum (Menispermaceae) phy 15, 2027'76
Stephania glabra (Menispermaceae) jnp 45, 407'82
Stephania intermedia (Menispermaceae) yhtp 16, 1'85
Stephania miyiensis (Menispermaceae) zh 30, 250'99
Stephania viridiflavens (Menispermaceae) cty 12, 1'81
Thalictrum spp. (Ranunculaceae) jnp 43, 372'80
Tinospora spp. (Menispermaceae) pm 48, 275'83
Xanthorhiza simplicissima (Ranunculaceae) llyd 26, 254'63
Zanthoxylum chalybeum (Rutaceae) jnp 59, 316'96
75
76 The Simple Plant Isoquinolines
Iwith a(2,8) attack: I HO
N,O-Dimethylhernovine
N-Methyl-lO-O-methylhernovine
Croton linearis (Euphorbiaceae)
llyd 32,1'69
Croton wilsonii (Euphorbiaceae)
rlq 1,140 '70
Iwith a(6,N-Me) attack: I
H O
Discretine
Caryomene olivascens (Menispermaceae) afb 6,163 '87
Duguetia obovata (Annonaceae) jnp 46, 862'83
Guatteria discolor (Annonaceae) jnp 46, 862'83
Guatteria scandens (Annonaceae) jnp 46, 335'83
Pachypodanthium staudtii (Annonaceae) pmp 11, 315'77
Stephania suberosa (Menispermaceae) phy 26, 547'87
Xylopia discreta (Annonaceae) bull 1
Xylopia vieillardi (Annonaceae) jnp 54, 466'91
Iand aromatization of the c-ring: I
H O
Dehydrodiscretine
Pseudojatrorrhizine
Fibraurea chloroleuca (Menispermaceae) pw 113, 1153'78
Heptacyclum zenkeri (Menispermaceae) phy 22, 321'83
Penianthus zenkeri (Menispermaceae) phy 22, 321'83
Sinomenium acutum (Menispermaceae) nm 48, 287'94
Thalictrum [auriei (Ranunculaceae) jps 69, 1061'80
Xylopia vieillardii (Annonaceae) jnp 54, 466'91
Structural Index - 6,7-HO,MeO-Substituted
I witha(6,3)attack: I
Isonorargemonine
Argemone gracilenta (Papaveraceae) jnp 46, 293'83
Argemone munita (Papaveraceae) jnp 46, 293'83
Eschscholzia californica (Papaveraceae) ecce51, 1743'86
Eschscholzia douglasii (Papaveraceae) ecce51,1743 '86
Eschscholzia glauca (Papaveraceae) ecce51, 1743'86
Thalictrum minus (Ranunculaceae) pm 63, 533'97
Thalictrum revolutum (Ranunculaceae) jnp 46, 293'83
alsounder: 6,7 MeO MeO R Me THIQ
R= 3,4-HO,MeO-benzyl (6,3) attack
H O
Iwitha(6,8) attack: I
(+)- Predicentrine
Annona purpurea (Annonaceae)
jnp 61,1457'98
Aromadendron elegans (Magnoliaceae) C H
3
0
phy31,2495'92 OCH
3
Beilschmiedia podagrica (Lauraceae)
het 9,903 '78
Cassytha [iliformis (Lauraceae) prs 12, 39'98
Corydalis cava (Papaveraceae) zpn 69, 99'85
Corydalis spp. (Papaveraceae) pm 50,136 '84
Dicentra peregrina (Papaveraceae) cnc 20, 74'84
Glaucium leiocarpum (Papaveraceae) pm 65, 492'99
Glaucium spp. (Papaveraceae) cnc 19, 714'83
Liriodendron tulipifera (Magnoliaceae) cnc 13, 602'77
Litsea trif/ora (Lauraceae) aqsc 76, 171'80
Dcotea spp. (Lauraceae) fes 32, 767'77
Platycapnos spicata (Papaveraceae) phy 32, 1055'93
PolyaIthia caulif/ora var. beccarii (Annonaceae) jnp 47, 504'84
Strychnopsis thouarsii (Menispermaceae) pm 58, 540'92
77
78 The Simple Plant Isoquinolines
land an a,1-ene: I
Dehydropredicentrine
Polyalthia cauliflora (Annonaceae)
jnp 51, 389'88
OH
Iwith a4-hydroxy group: I
Srilankine
Alseodaphne semicarpifolia (Lauraceae)
jnp 42, 325'79
HO
6-HO 7-MeO
3,4-MeO,MeO-benzyl
Me,Me+ THIQ
Pseudorine
N-Methylpseudolaudanine
C H
3
0
Fagara mayu (Rutaceae) pm48, 77'83 OC H 3
Papaver pseudo-orientale (Papaveraceae) ecce51, 1752'86
Popowia pisocarpa (Annonaceae) jnp 49,1028 '86
the seco-compound was also isolated from this plant,
the substitution positions were not determined:
Pseudoronine
Papaver pseudo-orientale (Papaveraceae) ecce51, 1752'86
Structural Index - 6,7-HO,MeO-Substituted
I witha(2,N-Me) attack: I
H O
N-Methylcorypalmine
n-Hainanine
Berberis iliensis (Berberidaceae) cnc 29,69 '93
Cyclea hainanensis (Menispermaceae) cwhp 23, 216'81
6-HO 7-MeO Compound unknown
3,4-MeO,MeO-a-Me-benzyl
Me THIQ
I witha(2,N-Me) attack: I HO
Corybulbine
GJrydalis ambigua (Papaveraceae)
5Z 42,214'88
Corydalis cava (Papaveraceae) sz 40, 61'86
Corydalis koidzumiana (Papaveraceae) yz 94, 844'74
GJrydalis platycarpa (Papaveraceae) jnp 51, 262'88
GJrydalis nobilis (Papaveraceae) ecce54, 2009'89
GJrydalis nokoensis (Papaveraceae) yz 96, 527'76
GJrydalis remota (Papaveraceae) jnp 51, 262'88
GJrydalis tuberosa (Papaveraceae) book 2
GJrydalis turtschaninovii (Papaveraceae) yx 21, 447 '86
landaromatization of the c-ring: I HO,
Dehydrocorybulbine
C H
3
0
Berberis baluchistanica (Berberidaceae)
daib38,686'77 H3C
GJrydalis ambigua (Papaveraceae)
daib45,2160'85
GJrydalis nokoensis (Papaveraceae) yz 96, 527'76
79
80
The Simple Plant Isoquinolines
Iand acarbonyl on the original N-Me group: I
H O
Oxydehydrocorybulbine
Corydalis ambigua (Papaveraceae)
daib 45, 2160'85
6-HO 7-MeO
3,4-MOO-benzyl
H THIQ
Not anatural product.
cpb 16, 953'68
Iwith a (2,8)attack: I
Laetine
Hernandia peltata (Hernandiaceae) cjc64, 123'86
Litsea laeta (Lauraceae) phy 19, 998'80
Ocotea teleiandra (Lauraceae) rlq 23, 18'92
Iwith a(6,8) attack: I
Norisodomesticine
Glossoealyx brevipes (Monimiaceae) jnp 48, 833'85
Guatteria goudotiana (Annonaceae) phy 30, 2781'91
Laurus nobilis (Lauraceae) jnp 45, 560'82
Xylopia danguyella (Annonaceae) jnp 44, 551'81
H O
6-HO 7-MeO
3A-MOO-benzyl
Me THIQ
Not anatural product.
het 1, 223'73
Structural Index - 6,7-HO,MeO-Substituted
Iwitha(2,N-Me) attack: I
H O
Cheilanthifoline
(5)(-)-isomer:
Argemone grandiflora (Papaveraceae) phy 11,461'72
Argemone mexicana (Papaveraceae) ecce40, 1576'75
Argemone ochroleuca (Papaveraceae) ecce38, 2307'73
Corydalis koidzumiana (Papaveraceae) yz 94, 844'74
Corydalis spp. (Papaveraceae) phy 13,2620 '74
Fumaria bella (Papaveraceae) jnp 49,178 '86
Fumaria capreolata (Papaveraceae) jnp 49, 178'86
Fumaria parviflora (Papaveraceae) jnp 44, 475'81
Fumaria uaillantii (Papaveraceae) phy 22, 2073'83
Papaver commutatum (Papaveraceae) pm 62, 483'96
(d1):
Dactylicapnos torulosa (Papaveraceae) phy 36,519 '94
Eschscholzia californica (Papaveraceae) pm 62, 188'96
isomernot specified:
Argemone hybrida (Papaveraceae) cnc 22, 189'86
Corydalis ochotensis (Papaveraceae) jccs34, 157'87
Dicentra epeciabilis (Papaveraceae) cnc 20,74 '84
Fumaria densiflora (Papaveraceae) jnp 49, 370'86
Menispermum dauricum (Menispermaceae) yz 91, 684'71
Papaver arenarium (Papaveraceae) cnc 20,71'84
Papaver cylindricum (Papaveraceae) pm 46, 175'82
Papaver fugax (Papaveraceae) cnc 24, 475'89
Papaver triniaefolium (Papaveraceae) pm 49, 43'83
land aromatization of the c-ring: I HO
Dehydrocheilanthifoline*
Groenlandicine C H
3
0
Tetradehydrocheilanthifoline
Coptis chinensis (Ranunculaceae) sz 37, 195'83
Coptis deltoides (Ranunculaceae) sz 37, 195'83
Coptisgroenlandica (Ranunculaceae) pm21, 313'72
81
o
)
o
o
)
o
82
The Simple Plant Isoquinolines
Copt is japonica (Ranunculaceae) jnp 47, 189'84
Coptis quinquefolia (Ranunculaceae) sz 46, 42'92
Coptis trifolia (Ranunculaceae) phy 31,717 '92
Corydalis humosa (Papaveraceae) jcpu 20, 261'89
Corydalis ochotensis (Papaveraceae) jcspt I, 63'76
Corydalis ophiocarpa (Papaveraceae) yz 98, 1658'78
Fumaria capreolata (Papaveraceae) per 4, 96'85
Fumaria indica (Papaveraceae) phy 15, 545'76
Menispermum canadense (Menispermaceae) llyd 34, 292'71
Nandina domestica (Berberidaceae) phy 27, 2143'88
Thalictrum glandulosissimum (Ranunculaceae) pm 53, 498'87
"This name has also been given to the 6-MeO 7-HO isomer.
with a(6,N-Me) attack,
and aromatization of the c-ring:
H O
Thalifaurine
Copt is quinquefolia (Ranunculaceae) sz 43, 81'89
Thalictrum fauriei (Ranunculaceae) jps 69, 1061'80
Iwith a(6,N) attack: I
H O
Cryptowolidine C H
3
0
Cryptocarya phyllostemon (Lauraceae)
cjc67, 947'89
OH
o
>
o
I with a(6,3) attack: I
(-)-Caryachine C H 30
Cryptocarya chinensis (Lauraceae) jnp 53, 1267'90
Eschscholzia californica (Papaveraceae) ecce51, 1743'86
Eschscholzia douglasii (Papaveraceae) ecce51, 1743'86
Eschscholzia glauca (Papaveraceae) ecce51, 1743'86
also under: 6,7 MDO R Me THIQ
R= 3,4-HO,MeO-benzyl (6,3) attack
Structural Index - 6,7-HO,MeO-Substituted
Iwith a (6,4) attack: I
Reframoline
Meconopsis speciosa (Papaveraceae) zh 27, 459 '96
Roemeria refracta (Papaveraceae) jnp 46, 293 '83
Iwitha(6,8) attack: I
H O
Guatteria goudotiana (Annonaceae) phy 30, 2781'91
Laurus nobilis (Laraceae) jnp 45, 560 '82
Litsea spp. (Laraceae) jccs 39, 453 '92
Nandina domestica (Berberidaceae) jnp 38, 275 '75
Neolitsea villosa (Laraceae) cpj 47, 69 '95
Platycapnos spicata (Papaveraceae) phy 32, 1055 '93
Isodomesticine C H
3
0
6-HO 7-MeO
3,4-MDQ-benzyl
Me,Me+THIQ
Compound unknown
H O
Iwith a(2,N-Me) attack: I
C H
3
0
N-Methylcheilanthifoline quat
Dicentra spectabilis (Papaveraceae) sz 46, 109 '92
Iwith a(6,3) attack: I
OH
Caryachine methiodide
N-Methylcaryachinium quat
C H
3
0
Cryptocarya chinensis (Lauraceae) jnp 42, 163 '79
Eschscholzia californica (Papaveraceae) ecce 51, 1743 '86
83
o
>
o
o
)
o
84 The Simple Plant Isoquinolines
Eschscholzia douglasii (Papaveraceae) ecce51, 1743'86
Eschscholzia glauca (Papaveraceae) ecce51, 1743'86
also under: 6,7 MOO R Me,Me+ THIQ
R= 3,4-HO,MeO-benzyl (6,3) attack
H O
with a(6,8) attack
and a1,2seco:
C H 30
3-0-Demethylthalicthuberine
Ocotea insularis (Lauraceae) jnp 57, 1033'94
6-HO 7-MeO
3,4-MOO-a-Me-benzyl
Me THIQ
Compound unknown
Isoapocavidine
o
>
o
Iwith a(2,N-Me) attack: I
Dactylicapnos torulosa (Papaveraceae)
phy 36,519 '94
6-HO 7-MeO
2,3,4-MDO,MeO-benzyl
Me THIQ
Compound unknown
H O
OC H
3
(-)-9-Demethylthalimonine
I with a(6,3)attack: I
Thalictrum simplex (Ranunculaceae) pm 59, 262'93
also under: 5,6,7 MOO MeO R Me THIQ
R= 3,4-HO,MeQ-benzyl (6,3) attack
Structural Index - 6,7-HO,MeO-Substituted
6-HO 7-MeO Compound unknown
3,4,5-MeO,MeO,MeO-benzyl
Me THIQ
Iwitha(2,8)attack: I Acutifolidine
C H 30
C H
3
0
Thalicrum acutifolium (Ranunculaceae)
jnp 57,1033'94 CH
3
0
H O
OC H 3
6-HO 7-MeO
~-(4-Ho-phenyl)ethyl
Me THIQ
(S)-Colchiethanamine
Colchicum szavitsii (Liliaceae) jnp 53,634 '90
C H
3
0
H O
OH
H O
6-HO 7-MeO
13-(4-MeO-phenyl)ethyl
Me THIQ
(S)-Colchiethine
Colchicum szavitsii (Liliaceae) jnp 53,634 '90
C H
3
0
OC H 3
85
86
The Simple Plant Isoquinolines
H O
6-HO 7-MeO
~-(3,4,5-HO,MeO,MeO-phenyl)ethyl
Me THIQ
C H
3
0
(-)-Isoautumnaline
Colchicum ritchii (Liliaceae) jnp 50,684 '87
OH
OC H
3
H O
6-HO 7-MeO
6',7'-MDG-isobenzofuranone,3'-yl
Me THIQ
C H
3
0
Corledine
6-0-Demethy ladlumine
Corydalis ledebouriana (Papaveraceae) jnp 45, 105'82
Fumaria parviflora (Papaveraceae) ojc 14, 217'98
Fumaria oaillaniii (Papaveraceae) tet 39, 577'83
Corlumidine
C H
3
0
(+)-isomer:
Corydalis decumbens (Papaveraceae) jcps 4, 57'95
Corydalis linarioides (Papaveraceae) yhhp 16, 798'81
Corydalis scouleri (Papaveraceae) jnp 45, 105'82
Fumaria parviflora (Papaveraceae) ojc 14,217 '98
H O
6-HO 7-MeO Compound unknown
3,4-MDO-a-(=CH
z
)-benzyl, Me
Me THIQ
Structural Index - 6,7-HO,MeO-Substituted
HO
[witha(2,I-Me) attack: I
(+)-Ochotensine
C H
3
0
Corydalis ochotensis (Papaveraceae) jccs34, 157'87
Corydalis solida (Papaveraceae) cjc56, 383'78
Corydalis stewartii (Papaveraceae) jnp 51, 1136'88
Corydalis thyrsiflora (Papaveraceae) yx 26, 303'91
Compound unknown 6-HO 7-MeO
3,4-MDO-benzyl, HO
Me,Me+ THIQ
HO
Iwitha(2,N-Me) attack: I
Izmirine
C H
3
0
Fumaria parviflora (Papaveraceae) jnp 46,934 '83
87
o
>
o
88 The Simple Plant Isoquinolines
6,7-MeO,HO-ISOQUINOLINES
Norcorypalline
CH30m
~ I NH
H O
6-MeO 7-HO
H
H THIQ
Ziziphus rugosa (Rhamnaeeae) phy 27, 1915'88
CH30~
HO~NCH3
6-MeO
H
Me
Corypalline 7-HO
THIQ
Berberis nummularia (Berberidaeeae) cne33, 70'97
Berberis tureomanniea (Berberidaeeae) cne29, 63'93
Berberis valdiviana (Berberidaeeae) fit 64, 378'93
Corydalis ophioearpa (Papaveraceae) yz 98, 1658'78
Corydalis speeiosa (Papaveraeeae) yz 95, 838'75
Corydalis strieta (Papaveraeeae) kps 19,461'83
Doryphora sassafras (Monimiaeeae) llyd 37,493 '74
Islaya minor (Cactaeeae) je189, 79'80
Menispermum daurieum (Menispermaeeae) tcyyk 5,30 '93
Papaver brae tea tum (Papaveraeeae) phy 22, 247'83
Stephania eepharantha (Menispermaeeae) nm52, 541'98
Thalietrum dasyearpum (Ranunculaeeae) joe34, 1062'69
Thalietrum rugosum (Ranunculaeeae) jnp 43,143 '80
Thalietrum uehiyamai (Ranunculaeeae) kjp 13, 132'82
Xylopia vieillardii (Annonaeeae) jnp 54, 466'91
CH30ro
I +
~ ~ N C H 3
H O
6-MeO 7-HO
H
Me DHIQ
(+J -Pycnarrhine
Dehydrocorypalline
Areangelisia flava (Menispermaeeae) jnp 45, 582'82
Corydalis ophioearpa (Papaveraeeae) yz 98, 1658'78
Structural Index - 6,7-MeO,HO-Substituted
Corydalis stricta (Papaveraceae) kps 4, 490'83
Pycnarrhena longifolia (Menispermaceae) phy 20, 323'81
6-MeO 7-HO
H
Me,Me+ THIQ
2-Methylcorypallinium
N-Methylcorypalline
Corydalis stricta (Papaveraceae) kps 4, 490'83
CH30m
I N
H O ~
6-MeO 7-HO
H
4-HO-benzyl THIQ
Corgoine
Ceratocapnos sp. (Papaveraceae) kps 7, 211'70
Corydalis sp. (Papaveraceae) kps 6, 638'70
CH30m
I N
H O ~
6-MeO 7-HO
H
4-MeQ-benzyl THIQ
Sendaverine
Corydalis gortschakovii (Papaveraceae) kps 6, 438'70
Ceratocapnos heterocarpa (Papaveraceae) phy 36, 241'94
Corydalis impatiens (Papaveraceae) patent 3
Corydalis tashiroi (Papaveraceae) pm 41, 403'81
OCH3
ItheN-oxide: I
Sendaverine N-oxide
Corydalis gortschakovii (Papaveraceae) kps 6, 834'77
89
OH
90 The Simple Plant Isoquinolines
6-MeO 7-HO
H
3,4-HO,MeO-benzyl THIQ
Capnosine
Ceratocapnos heterocarpa (Papaveraceae)
phy 36, 241'94
Corydalis sp. (Papaveraceae) phy 36, 241'94
CH30m
I N
H O ~
H O
6-MeO
Me
H
Isosalsoline
OC H 3
7-HO
THIQ
CH30:cy
I NH
H O ~
C H
3
Hammada articulata (Chenopodiaceae) apf 48,219 '90
Pachycereus pecten-aboriginum (Cactaceae) aps 15, 127'78
6-MeO 7-HO
Me
H IQ
7-0-Desmethylisosalsolidine
CH30:cQ""::::::
I N
H O: : : : : : "' " ~
C H 3
Hernandia nymphaeifolia (Hernandiaceae) phy 42,1479 '96
7-HO
6-MeO
Me
Me
I-Methylcorypalline
N-Methylisosalsoline
THIQ
C H
3
0Y(J
HO~NCH,
C H
3 (R)(+)-isomer:
Corydalis ambigua (Papaveraceae) phy 12, 3008'73
(S)(-)-isomer:
Arthrocnemum glaucum(Chenopodiaceae) phy 31,1023 '92
isomer not specified:
Haloxylon articulatum (Chenopodiaceae) book 6
Structural Index - 6,7-MeO,HO-Substituted
7-HO 6-MeO
i-Bu
Me
Lophocereine
Lophocerine
THIQ
iopnocereus schottii (Cactaceae) phy 8,1481'69
Pachycereus marginatus (Cactaceae) book 6
7-HO Not anatural product.
joc41,443 '76
6-MeO
benzyl
H THIQ
IWitha(2,8)attack: I
C H
3
0
Caaverine
Isolona pilosa (Annonaceae) pm 50, 23'84
Liriodendron tulipifera (Magnoliaceae) cnc 23, 521'88
Liriodendron sp. (Magnoliaceae) jnp 38, 275'75
Neostenanthera gabonensis (Annonaceae) jnp 51, 973'88
Ocotea glaziovii (Lauraceae) fes 30, 479'75
Ocotea sp. (Lauraceae) jnp 38, 275'75
Papaver pseudo-orientale (Papaveraceae) paz 13, 50'77
Polyalthia acuminata (Annonaceae) jnp 45, 471'82
Symplocos celastrinea (Symplocaceae) llyd 33s, 1'70
Symplocos sp. (Symplocaceae) jnp 38, 275'75
Ziziphus jujuba (Rhamnaceae) apr 12, 263'89
Ziziphus spinosus (Rhamnaceae) sh 16, 233'86
H O
7-HO Not anatural product.
jhc 4, 417'67
6-MeO
benzyl
Me THIQ
lwitha(2,N-Me)attack: I
Bharatamine
H O
Alangium lamarckii (Alangiaceae) tl24, 291'83
91
92 TheSimplePlant Isoquinolines
Iwith a(2,8) attack: I C H
3
0
Lirinidine
Nomuciferine I
H O
Lirinidine:
Annona purpurea (Annonaceae) phy 49, 2015'98
Artabotrys venustus (Annonaceae) jnp 49,602 '86
Guatteria sagotiana (Annonaceae) jnp 49,1078 '86
Isolona zenkeri (Annonaceae) pm 50, 23'84
Liriodendron tulipifera (Magnoliaceae) cnc 23, 521'88
Nelumbo nucifera (Nymphaeaceae) jnp 50, 773'87
Neostenanthera gabonensis (Annonaceae) jnp 51,973 '88
Ocotea macrophylla (Lauraceae) pptp 27, 65'93
Papaver spp. (Papaveraceae) pm41,105 '81
Nornuciferine I:
Croton bonplandianus (Euphorbiaceae) abs 10
Croton sparsiflorus (Euphorbiaceae) tet 35, 2323'79
Dehydrolirinidine H O
Iand an a.,1-ene: I
Annona purpurea (Annonaceae) jnp 61,1457 '98
6-MeO 7-HO
a.-NH
2
-benzyl
H IQ
Compound unknown
with a(2,8)attack
aromatization and oxidation:
Telazoline
Telitoxicum peruvianum (Menispermaceae)
jnp 44, 320'81
Structural Index - 6,7-MeO,HO-Substituted
Compound unknown
6-MeO 7-HO
a-keto-benzyl
Me+ IQ
Iwith a (2,8) attack: I
O,N-Dimethylliriodendronine
HO
Guatteria chrysopetala (Annonaceae) pmp 18, 165'84
Stephania dinklagei (Menispermaceae) pm 66,478 '00
6-MeO 7-HO
3-HO-benzyl
H THIQ
(-)-Norcanelilline
Aniba canelilla (Lauraceae) cjc 71, 1128'93
6-MeO 7-HO
3-HO-benzyl
Me THIQ
Canelilline
OH
Aniba canelilla (Lauraceae) cjc 71, 1128'93
Iwitha(2,N-Me) attack: I
Anibacanine
Aniba canelilla (Lauraceae)
cjc 71,1128'93
OH
93
OH
94
The Simple Plant Isoquinolines
land amethyl group on the original N-Me group: I
(-)-a-8-Methylanibacanine
Aniba canelilla (Lauraceae)
cjc71, 1128'93
Iwith a(2,8) attack: I
Isothebaidine
Papaver orientale (Papaveraceae)
cnc 14, 402'78
I with a(6,N-Me) attack: I
(-)-Pseudoanibacanine
Aniba canelilla (Lauraceae) cjc71, 1128'93
H O
H O
land amethyl group on the original N-Me group: I
the cis isomer:
(-)-8a-Methylpseudoanibacanine
Aniba canelilla (Lauraceae)
cjc71,1128 '93
the trans isomer:
(-)-8~-Methylpseudoanibacanine
Aniba canelilla (Lauraceae)
cjc71, 1128'93
OH
OH
Structural Index - 6,7-MeO,HO-Substituted
6-MeO 7-HO
3-MeO-benzyl
H THIQ
Compound unknown
Iwitha(6,8)attack: I Nororientinine
Ocotea caesia (Lauraceae) jnp 57, 1033'94
C H 30
H O
OC H
3
6-MeO 7-HO
3-MeO-benzyl
Me THIQ
Not anatural product.
cpb 29, 1083'81
Iwitha(2,8)attack: I
C H 30
Isothebaine
H O
C H 30
Discaria serratifolia (Rhamnaceae)
jnp47, 1040'84
Papaver atlanticum (Papaveraceae)
ecce 51,2232'86
Papaver bracteatum (Papaveraceae) pm 32, 60'77
Papaver nudicaule (Papaveraceae) zpf 114, 361'84
Papaver orientale (Papaveraceae) jps 66, 1050'77
Papaver pseudo-orientale (Papaveraceae) paz 13, 50'77
Papaver setigerum (Papaveraceae) zpf 114,361'84
Papaver somniferum (Papaveraceae) zpf 114,361'84
IandanCJ .,1-ene: I
Dehydroisothebaine
H O
C H 30 Papaver orientale (Papaveraceae)
jnp51,389'88
95
96 The Simple Plant Isoquinolines
I with a(6,8) attack: I
Orientinine
Papaver orientale (Papaveraceae) jnp 51, 389'88
OC H
3
6-MeO 7-HO Compound unknown
3-MeO-benzyl
Me,Me+ THIQ
Iwith a(2,8) attack: I C H
3
0
N-Methylisothebainium cation
N-Methylisothebaine
H O
C H 30
Papaver bracteatum (Papaveraceae)
jnp 51, 389'88
Papaver pseudo-orientale (Papaveraceae)
ecce51, 1752'86
Compound unknown 6-MeO 7-HO
3-MeO-a-keto-benzyl
Me IQ
Iwith a(2,8)attack: I
Alkaloid PO-3
H O
C H
3
0
Papaver orientale (Papaveraceae)
jnp 38, 275'75
Structural Index - 6,7-MeO,HO-Substituted
C H 30
6-MeO 7-HO
4-HQ-benzyl
H THIQ
Coclaurine
Machiline
Sanjoinine K
(S)(-)-isomerof Coclaurine
Machiline:
Alseodaphne archboldiana (Lauraceae) het 9,903 '78
Aniba canelilla (Lauraceae) cjc71,1128 '93
Annona montana (Annonaceae) pmp 16, 169'82
Annona reticulata (Annonaceae) jcspt I, 1515, '79
Cocculus hirsutus (Menispermaceae) npl 2, 105'93
Cocculus pendulus (Menispermaceae) jpic 32, 250'60
Corydalis gortschakovii (Papaveraceae) kps 6, 638'70
Corydalis paniculigera (Papaveraceae) cnc 18, 689'82
Corydalis pseudoadunca (Papaveraceae) cnc 21, 807'86
Cryptocarya longifolia (Lauraceae) ajc34, 195'81
Fumaria parviflora (Papaveraceae) cnc 18, 608'82
Fumaria vaillantii (Papaveraceae) cnc 17, 437'81
Litseaglutinosa (Lauraceae) abs 10
Litsea lecardii (Lauraceae) pm 52, 74'86
Machilus acuminatissima (Lauraceae) het 9,903 '78
Machilus kusanoi (Lauraceae) het 9,903 '78
Magnolia salicifolia (Magnoliaceae) pm 48, 43'83
Mezilaurus synandra (Lauraceae) phy 22, 772'83
Nymphaea stellata (Nymphaeaceae) jics 63, 530'86
Pachygone ovata (Menispermaceae) daib 45, 567'84
Peumus boldus (Monimiaceae) fit 64, 455'93
Phoebe minutiflora (Lauraceae) cpj 49,217 '97
Polyalthia macropoda (Annonaceae) phy 29, 3845'90
Retanilla ephedra (Rhamnaceae) rlq 5, 158'74
Stephania pierrei (Menispermaceae) jnp 52,846 '89
Xylopia papuana (Annonaceae) npl6, 57'95
Ziziphus jujuba (Rhamnaceae) apr 12, 263'89
Ziziphus spinosus (Rhamnaceae) kjp 16, 44'85
Ziziphus vulgaris (Rhamnaceae) apr 10, 203'87
(R)(+}-isomer of Coclaurine
SanjoinineK:
Abuta pahni (Menispermaceae) phy 26, 2136'87
HO
HO
97
98
The Simple Plant Isoquinolines
Alseodaphne archboldiana (Lauraceae) het 9, 903'78
Annona muricata (Annonaceae) pm42, 37'81
Bongardia chrysogonum (Berberidaceae) jnp 52,818 '89
Caryomene olivascens (Menispermaceae) afb 6, 163'87
Cassytha racemosa (Lauraceae) het 9, 903'78
Cocculus laurifolius (Menispermaceae) tet 36, 3107'80
Colubrina faralaotra ssp. sinuata (Rhamnaceael pm30, 201'76
Corydalis severtzovii (Papaveraceae) cnc 11, 826'75
Cyclea barbata (Menispermaceae) jnp 56, 1989'93
Cyclea peltata (Menispermaceae) jnp 56,1989 '93
Discaria pubescens (Rhamnaceae) pm50, 454'84
Litsea triflora (Lauraceae) aqsc 76,171'80
Magnolia fargesii (Magnoliaceae) pm48, 43'83
Magnolia liliflora (Magnoliaceae) yhtp 20, 522'85
Magnolia salicifolia (Magnoliaceae) pm48, 43'83
Nectandra salicifolia (Lauraceae) jnp 59, 576'96
Neolitsea villosa (Lauraceae) cpj 47, 69'95
Peumus boldus (Monimiaceae) fit 64, 455'93
Polyalthia acuminata (Annonaceae) jnp 45,471'82
Popowia pisocarpa (Annonaceae) jnp 49, 1028'86
Roemeria refracta (Papaveraceae) hca 75, 260'92
Sciadotenia eichleriana (Menispermaceae) jnp 48, 69'85
Sparattanthelium uncigerum (Hernandiaceae) jnp 48,333 '85
Stephania cepharantha (Menispermaceae) cpb 45, 470'97
Stephania excentrica (Menispermaceae) jnp 60, 294'97
Ziziphus jujuba (Rhamnaceae) apr 12, 263'89
Ziziphus vulgaris (Rhamnaceae) apr 12, 263'89
(d1)-Codaurine:
Cocculus hirsutus (Menispermaceae) ijc 14b, 62'76
Cryptocarya konishii (Lauraceae) het 9, 903'78
Machilus acuminatissima (Lauraceae) het 9, 903'78
Machilus macrantha (Lauraceae) het 9,903 '78
Peumus boldus (Monimiaceae) fit 64, 455'93
Polyalthia acuminata (Annonaceae) jnp 45,471'82
Retanilla ephedra (Rhamnaceae) rlq 5, 158'74
Talguenea quinquenervis (Rhamnaceae) aaqa 62, 361'74
Xylopia papuana (Annonaceae) llyd 33s, 1'70
Ziziphus jujuba (Rhamnaceae) kps 13,239 '77
Structural Index - 6,7-MeO,HO-Substituted
Iwitha(l,8) attack: I
Crotsparine
Crotoflorine
Alphonsea sclerocarpa (Annonaceae) jnp 50, 518'87
Croton bonplandianus (Euphorbiaceae) jcspt 1659'75
Croton flavens (Euphorbiaceae) llyd 32, 1'69
Croton ruizianus (Euphorbiaceae) bse 24, 463'96
Croton sparsiilorus (Euphorbiaceae) llyd 32, 1'69
Monodora brevipes (Annonaceae) phy 28,2489 '89
Ocotea glaziovii (Lauraceae) het 9, 903'78
withreduction of the
benzyl 2,3double-bond:
(lS-cis)(+)-Crotsparinine
Croton bonplandianus (Euphorbiaceae) jcspt 1659'75
(l R-trans) (-)-J acularine
Croton discolor (Euphorbiaceae) rlq I, 140'70
Croton echinocarpus (Euphorbiaceae) llyd 32, 1'69
Croton linearis (Euphorbiaceae) llyd 32, 1'69
Croton plumieri (Euphorbiaceae) rlq I, 140'70
Croton ruizianus (Euphorbiaceae) bse 24, 463'96
Croton sparsiflorus (Euphorbiaceae) exp 25, 354'69
withreduction of both double bonds
andof thecarbonyl group in the benzyl ring:
Oridine
Oreoline
(-)-isomer:
Papaver lisae (Papaveraceae) cnc 14, 228'78
Papaver oreophilum (Papaveraceae) frm29, 23'80
C H sO
H O
C H sO
H O
R,S is C rotsparinine
R,R is J acularine
C H sO
H O
H O
99
100
The Simple Plant Isoquinolines
Sparsiflorine
Apocrotsparine
Iwith a(2,8) attack: I
(-I-Isomer:
Monodora tenuifolia (Annonaceae) pm 50, 455'84
isomer not specified:
Alphonsea sclerocarpa (Annonaceae) jnp 50,518 '87
Croton bonplandianus (Euphorbiaceae) jcspt 1,1659 '75
Croton flavens (Euphorbiaceae) llyd 32, 1'69
Thalicirum foliolosum (Ranunculaceae) jnp 45,252 '82
6-MeO 7-HO
4-HO-benzyl
H IQ
J uzirine
Yuzirine
H O
Ziziphus jujuba (Rhamnaceae) iant 4,48 '87
Magnolia fargesii (Magnoliaceae) pm48, 43'83
Magnolia salicifolia (Magnoliaceae) ws 14, 101'81 H O
6-MeO 7-HO
4-HO-a-keto-benzyl
H DHIQ
Longifolonine
Cryptocarya velutinosa (Lauraceae) ajc 34, 195'81
6-MeO 7-HO N-Methylcoclaurine
4-HO-benzyl
Me THIQ
H O
(S)(+)-isomer:
Aniba canelilla (Lauraceae) cjc71, 1128'93 H O
Desmos tiebaghiensis (Annonaceae) jnp 45,617 '82
Stephania cepharantha (Menispermaceae) cpb 45, 470'97
Structural Index - 6,7-MeO,HO-Substituted 101
Stephania pierrei (Menisperrnaceae) jnp 52, 846'89
Thalictrum revolutum (Ranunculaceae) llyd 40, 593'77
(R)(-)-isomer:
Aniba burchellii (Lauraceae) bse 8, 51'80
Aniba cylindriflora (Lauraceae) bse 8, 51'80
Aniba simulans (Lauraceae) bse 8, 51'80
Berberis lycium (Berberidaceae) daib 44, 1458'83
Ceratocapnos palaestinus (Papaveraceae) jnp 53, 1006'90
Cryptocarya longifolia (Lauraceae) ajc34,195 '81
Cyclea peltata (Menispermaceae) jnp 56, 1989'93
Discaria serratifolia var. discolor (Rhamnaceae) jnp 42, 430'79
Discaria toumatou (Rhamnaceae) jnp 45,777 '82
Glaucium fimbrilligerum (Papaveraceae) cnc 16, 177'80
Glaucium leiocarpum (Papaveraceae) pm 65, 492'99
Cuaiteria sagotiana (Annonaceae) jnp 49, 1078'86
Litsea triflora (Lauraceae) aqsc 76,171'80
Magnolia fargesii (Magnoliaceae) pm 48, 43'83
Magnolia salicifolia (Magnoliaceae) pm48, 43'83
Thalictrum dioicum (Ranunculaceae) llyd 41, 169'78
Xylopia pancheri (Annonaceae) pm 30, 48'76
Xylopia vieillardii (Annonaceae) jnp 54, 466'91
Ziziphus mucronata (Rhamnaceae) phy 13, 2328'74
(dl):
Berberis actinacantha (Berberidaceae) daib 45,2160 '85
Berberis boliviana (Berberidaceae) jnp 52, 81'89
Bongardia chrysogonum (Berberidaceae) jnp 52, 818'89
Polyalthia acuminata (Annonaceae) jnp 45, 471'82
Roemeria refracta (Papaveraceae) hca 75, 260'92
Tiliacora racemosa (Menispermaceae) cc226'78
isomer notspecified:
Aniba muca (Lauraceae) rbq 13, 19'96
Annona squamosa (Annonaceae) cpj 46, 439'94
Artabotrys odoratissimus (Annonaceae) fit 65, 92'94
Berberis iliensis (Berberidaceae) cnc 29, 69'93
Berberisnummularia (Berberidaceae) cnc 29, 335'93
Berberisvaldiviana (Berberidaceae) fit 64, 378'93
Cocculus laurifolius (Menispermaceae) ijc26b, 24'87
Corydalis gortschakovii (Papaveraceae) cnc 20, 245'84
Discariacrenata (Rhamnaceae) phy 12, 954'73
102
The Simple Plant Isoquinolines
Fumaria capreolata (Papaveraceae) per 4, 96'85
Glaucium oxylobum (Papaveraceae) cnc 20, 244'84
Gyrocarpus american us (Hernandiaceae) jnp 49,101'86
Litsea acuminata (Lauraceae) cpj 46, 299'94
Nectandra salicifolia (Lauraceae) jnp 59, 576'96
Retanilla ephedra (Rhamnaceae) rlq 5, 158'74
Stephania excentrica (Menispermaceae) zh 27, 586'96
Thalictrum longistylum (Ranunculaceae) jnp 62, 1410'99
!xyloside at the 7-HO position: I
Latericine
Papaver californicum (Papaveraceae) svs 55, 23'93
C H
3
0
Iwith a(1,8) attack: I
N-Methylcrotsparine
Glaziovine
Suavedol
H O
(R)(+)-isomer:
N-Methylcrotsparine
Glaziovine: 0
Annona cherimolia (Annonaceae) pmp 23,159 '89
(5)(-)-isomer:
N-Methylcrotsparine
Glaziovine
Suavedol:
Aniba canelilla (Lauraceae) cjc71, 1128'93
Annona purpurea (Annonaceae) jnp 61, 1457'98
Aristolochia chilensis (Aristolochiaceae) fit 61, 190'90
Berberis lycium (Berberidaceae) daib 44, 1458'83
Corydalis claviculata (Papaveraceae) jnp 53, 1280'90
Croton bonplandianus (Euphorbiaceae) tet 37,3175 '81
Desmos tiebaghiensis (Annonaceae) jnp 45, 617'82
Guatteria sagotiana (Annonaceae) jnp 49, 1078'86
Isolona zenkeri (Annonaceae) pm 50, 23'84
Liriodendron tulipifera (Magnoliaceae) cnc 11, 829'75
Litsea cubeba (Lauraceae) jca667, 322'94
Structural Index - 6,7-MeO,HO-Substituted
Litsea laurifolia (Lauraceae) pmp 13, 262'79
Meeanopsis cambrica (Papaveraceae) jpps 27, 84p '75
Neetandra membranacea (Lauraceae) pptp 27, 65'93
Neetandra salicifolia (Lauraceae) jnp 59, 576'96
Neostenanthera gabonensis (Annonaceae) jnp 51, 973'88
Ocotea brachybotra (Lauraceae) pptp 27, 65'93
Deotea glaziovii (Lauraceae) het 9,903 '78
Deotea variabilis (Lauraceae) pptp 27, 65'93
Paehygone ovata (Menispermaceae) jnp 42, 399'79
Papaver caucasicum (Papaveraceae) phzi 23, 267'68
Stephania eepharantha (Menispermaceae) cpb 45, 470'97
Uvaria ehamae (Annonaceae) pmp 14, 143'80
isomernot specified:
Neolitsea konishii (Lauraceae) phzi 45, 442'90
C H
3
0
Iwiththereduction of adouble bond: I
N-Methylcrotsparinine H O
Croton bonplandianus (Euphorbiaceae)
jcsptI, 1659'75
Iwitha(2,8)attack: I C H
3
0
Apoglaziovine
N-Methylsparsiflorine
N-Methylapocrotsparine
H O
(5)(+l-isorner:
Aniba canelilla (Lauraceae) cjc71, 1128'93 HO
Berberis brandisiana (Berberidaceae) jnp 49, 538'86
Croton bonplandianus (Euphorbiaceae) jnp 38, 275'75
Croton sparsiflorus (Euphorbiaceae) tet 37, 3175'81
Liriodendron tulipifera (Magnoliaceae) cnc 27,516 '92
Deotea sp_(Lauraceae) jnp 38, 275'75
(R)(-)-isomer(Apoglaziovine only):
Neetandra membranacea (Lauraceae) fit 60, 474'89
Stephania venosa (Menispermaceae) jnp 50, 1113'87
103
104
The Simple Plant Isoquinolines
6-MeO 7-HO
4-HO-benzyl
Me,Me+ THIQ
Magnocurarine
C H
3
0
H O
(5)(+)-isomer:
Euodia trichotoma (Rutaeeae) pm 59, 290'93
Lindera oldhamii (Lauraeeae) jnp 49, 726'86
Litsea cubeba (Lauraeeae) het 9, 903'78
H O
(R)(-)-isomer:
Colletia hystix (Rhamnaeeae) aaqa 59, 343'71
Colletia spinosissima (Rhamnaeeae) llyd 335, 1'70
Dicentra spectabilis (Papaveraeeae) sz 46, 109'92
Leontice leontopetalum (Berberidaeeae) jnp 49, 726'86
Litsea cubeba (Lauraeeae) jnp 56, 1971'93
Magnolia acuminata (Magnoliaeeae) llyd 335, 1'70
Magnolia obovata (Magnoliaeeae) pm 58, 137'92
Magnolia officinalis var. biloba (Magnoliaeeae) nm50, 413'96
Magnolia rostrata (Magnoliaeeae) ety 12, 10'81
Tiliacora racemosa (Menispermaeeae) jic57, 773'80
isomer not specified:
Magnolia anglietia (Magnoliaeeae) yhhp 23, 383'88
Magnolia sprengeri (Magnoliaeeae) yhhp 23, 383'88
Magnolia szechuanica (Magnoliaeeae) yhhp 23, 383'88
Magnolia wilsonii (Magnoliaeeae) yfz 2, 95'82
Manglietia chingii (Magnoliaeeae) yhhp 24, 295'89
Manglietia duclouxii (Magnoliaeeae) yhhp 24, 295'89
Manglietia insignis (Magnoliaeeae) yhhp 24, 295'89
Manglietia szechuanica (Magnoliaeeae) yhhp 24, 295'89
Manglietia yuyuanensis (Magnoliaceae) yhhp 24, 295'89
6-MeO 7-HO
4-HO-a-HD-benzyl
H IQ
Annocherine A
C H 30
H O
Annona cherimolia (Annonaeeae) phy 56,753 '01
H O
Structural Index - 6,7-MeO,HO-Substituted
6-MeO 7-HO Annocherine B
4-HO-a-MeO-benzyl
H IQ
Annona cherimolia (Annonaceae) phy 56, 753'01
C H
3
0
H O
H O
6-MeO 7-HO
4-HO-a-HO-benzyl
Me,Me+ THIQ
(+)-la-Hydroxymagnocurarine
Cryptocarya konishii (Lauraceae)
jnp56,1971'93
6-MeO 7-HO
4-MeO-benzyl
H THIQ
Not anatural product.
Is30, 1747'82
Iwitha(2,8)attack: I Zenkerine
lO-Methoxycaaverine
(-)-isomer:
Dcotea caesia (Lauraceae) jnp 42, 325'79
isomernot specified:
Iso/ana pi/osa (Annonaceae) era 285, 447'77
Iso/ana zenkeri (Annonaceae) pm 50, 23'84
C H
3
0
H O
C H
3
0
6-MeO 7-HO N-DemethyIcoIIetine
4-MeO-benzyl
Me THIQ
(R)-isomer:
Aconitum /eucostomum (Ranunculaceae)
kps6,805'80
C H
3
0
C H
3
0
H O
105
106
The Simple Plant Isoquinolines
Discaria serratifolia (Rhamnaceae) jnp 42, 430'79
Xylopia pancheri (Annonaceae) pm 30, 48'76
C H 30
Iwith a(2,3) attack: I
2,9-Dimethoxy-3-hydroxypavinane H O
Argemone munita (Papaveraceae) joe38, 3701'73
also under: 7 MeO R Me THIQ
R= 3,4-MeO,HO-benzyl (6,3) attack
C H 30
I with a(2,8) attack: I
N-MethyIzenkerine
Pulchine
H O
Ocotea caesia (Lauraceae) jnp 42, 325'79
C H 30
6-MeO 7-HO
4-MeO-benzyl
Me,Me+ THIQ
Colletine
H O
Colchicum luteum (Liliaceae) kpr 12, 359'76
Colletia spinosissima (Rhamnaceae)
llyd 335, 1'70
Cymbopetalum brasiliense (Annonaceae) pm 50,517 '84
Zanthoxylum sarasinii (Rutaceae) pm54, 189'88
C H 30
6-MeO 7-HO
4-MeO-a-keto-benzyl
H DHIQ
VeIucryptine
C H 30
H O
Cryptocarya velutinosa (Lauraceae) jnp 52, 516'89
C H 30
Structural Index - 6,7-MeO,HO-Substituted
6-MeO 7-HO Compound unknown
2,3-MeO,MeO-a-keto-benzyl
H IQ
Iwitha(6,8)attack: I Annolatine
Annona montana (Annonaceae) phy 33, 497'93
C H
3
0
H O
6-MeO 7-HO Compound unknown
2,3-MOO-benzyl,Me
Me THIQ
witha(6,1-Me)attack,
theN-oxide:
(+)-Papracinine
Fumaria indica (Papaveraceae) phy 31,2869 '92
H O
6-MeO 7-HO Compound unknown
2,3-MOO-a-keto-benzyl,Me
Me THIQ
lwitha(6,1-Me)attack: I (+)-Parfumine
Corydalis rutifolia (Papaveraceae) ijcdr 26, 155'88
Corydalis solida (Papaveraceae) guefd 5, 9'88
Fumaria densiflora (Papaveraceae) cccc61, 1064'96
Fumaria indica (Papaveraceae) phy 31, 2869'92
Fumaria mural is (Papaveraceae) jpps 33, 16'81
H O
107
108
The Simple Plant Isoquinolines
Fumaria officina lis (Papaveraceae) jnp 46, 433'83
Fumaria parviflora (Papaveraceae) pm45,120 '82
Fumaria rostellata (Papaveraceae) dban 25, 345'72
Compound unknown 6-MeO 7-HO
2,3-MDO-a-HO-benzyl, Me
Me THIQ
C H
3
0
Iwith a(6,I-Me) attack: I Fumaritine
Fumarophycinol
(+)-isomer:
Corydalis caucasica (Papaveraceae) ijcdr 27, 161'89
Corydalis solida (Papaveraceae) jcsp 13, 63'91
(-)-isomer:
Corydalis rutifolia (Papaveraceae) ijcdr 26, 155'88
Fumaria bastardii (Papaveraceae) nps 4, 257'98
Fumaria densiflora (Papaveraceae) ecce61, 1064'96
Fumaria macrosepala (Papaveraceae) aqse 83, 119'87
Fumaria muralis (Papaveraceae) jpps 33, 16'81
Fumaria officina lis (Papaveraceae) jnp 46, 433'83
Fumaria spp. (Papaveraceae) nps 4, 257'98
I the N-oxide: I
Fumaritine N-oxide
Alkaloid Fk-5
Fumaria indica (Papaveraceae) phy 31, 2869'92
Fumaria kralikii (Papaveraceae) cjc57, 53'79
H O
C H
3
0
6-MeO 7-HO
2,5-MeO,HO-benzyl
Me THIQ
Dehassiline
Dehassia kurzii (Lauraceae) fit 62, 261'91
H O
H O
Structural Index - 6,7-MeO,HO-Substituted
C H
3
0
6-MeO 7-HO
3,4-HO,HO-benzyl
H IQ
H O
Turcomanine
Berberis turcomanica (Berberidaceae) cnc 32, 59'96
H O
OH
6-MeO 7-HO Compound unknown
3,4-HO,HO-benzyl
Me THIQ
Iwitha(6,N-Me) attack: I
H O
(-)-Pessoine
Annona spinescens (Annonaceae) jnp 59, 438'96
OH
6-MeO 7-HO Norreticuline
3,4-HO,MeO-benzyl
H THIQ
(R)( +)-isomer:
Ficus pachyrrachis (Moraceae) pm59, 286'93
(S)(-)-isomer: OH
Annona reticulata (Annonaceae) phy 26, 3235'87
Argemone platyceras (Papaveraceae) phy 26, 3235'87
Berberis aggregata (Berberidaceae) phy 26,3235 '87
Berberis aristata (Berberidaceae) phy 26, 3235'87
Berberis beaniana (Berberidaceae) phy 26, 3235'87
Berberis koetineana (Berberidaceae) phy 29,3491'90
Berberis stolonifera (Berberidaceae) phy 26,3235 '87
Berberiswilsoniae var. subcaulialata (Berberidaceae) phy 26, 3235'87
109
OH
110
The Simple Plant Isoquinolines
Chelidonium majus (Papaveraceae) phy 26, 3235'87
Cissampelos pareira (Menispermaceae) phy 26, 3235'87
Corydalis cava (Papaveraceae) phy 26, 3235'87
Corydalis meifolia (Papaveraceae) tet 42,675 '86
Eschscholzia californica (Papaveraceae) phy 26,3235 '87
Eschscholzia lobbii (Papaveraceae) phy 26, 3235'87
Fumaria parviflora (Papaveraceae) phy 26,3235 '87
Papaver somniferum (Papaveraceae) phy 26,3235 '87
Thalictrum dipterocarpum (Ranunculaceae) phy 26, 3235'87
Thalictrum flavum (Ranunculaceae) phy 26, 3235'87
Thalictrum foetidum (Ranunculaceae) phy 26, 3235'87
Thalictrum rugosum (Ranunculaceae) phy 26, 3235'87
Iwith a(2,4a) attack: I
Norsinoacutine
HO
Croton balsamifera (Euphorbiaceae) llyd 32, 1'69
Croton bonplandianus (Euphorbiaceae) phy 20,683 '81
Croton flavens (Euphorbiaceae) rlq 1, 140'70
Croton linearis (Euphorbiaceae) llyd 32, 1'69 CH
3
0
Croton plumieri (Euphorbiaceae) phy 8, 777'69 0
Norsalutaridine
C H
3
0
(+)-isomer:
Papaver pseudo-orientale (Papaveraceae) HO
jnp 51, 802'88
isomer not specified:
Croton hemiargyreus (Euphorbiaceae)
C H
3
0
phy 47, 1445'98 0
and ahydrogenated double bond
C H 30
at the 8,8a-position :
8/14-Dihydronorsalutaridine
HO
Croton echinocarpus (Euphorbiaceae) llyd 32, 1'69
Croton linearis (Euphorbiaceae) llyd 32, 1'69
C H
3
0
Croton plumieri (Euphorbiaceae) phy 8, 777'69
0
Structural Index - 6,7-MeO,HO-Substituted
OH
Iwitha(6,4a)attack I C H
3
0
H-Norpallidine
Fumaria vaillantii (Papaveraceae) phy 15, 1802'76
C H 30
o
Iwitha(6,8)attackl
C H 30
Norisoboldine
Laurelli ptine
HO
Annona salzmanii (Annonaceae) je36,39 '92
Artabotrys monteiroae (Annonaceae) pa 4, 72'93
Beilschmiedia spp. (Lauraceae) het 9,903 '78
Cassytha pubescens (Lauraceae) het 9,903 '78 C H 30
Cassytha racemosa (Lauraceae) het 9, 903'78 OH
Cocculus laurifolius (Menispermaceae) cnc 27, 73'91
Illigera pentaphylla (Hemandiaceae) jnp 48,835 '85
Litsea acuminata (Lauraceae) cpj 46, 299'94
Litsea triflora (Lauraceae) aqsc 76, 171'80
Litsea spp. (Lauraceae) ajc22, 2259'69
Monodora tenuifolia (Annonaceae) daib 45, 520'84
Nectandra rigida (Lauraceae) jnp 43,353 '80
Neolitsea zeylanica (Lauraceae) het 9,903 '78
Ocotea caesia (Lauraceae) phy 28, 3577'89
Ziziphus jujuba (Rhamnaceae) kps 13,239 '77
C H 30 6-MeO 7-HO
3,4-HO,MeD-benzyl
Me THIQ
HO
Reticuline
W~ CH~
Argemonegracilenta (Papaveraceae) joe34, 555'69 OH
Machi/us duthei (Lauraceae) jcp 2, 157'80
Ocoteavelloziana (Lauraceae) phy 39,815 '95
Papaverbradeatum (Papaveraceae) phy 16, 1939'77
111
112 The Simple Plant Isoquinolines
(+)(S)-isomer:
Alseodaphne archboldiana (Lauraceae) het 9, 903'78
Aniba canelilla (Lauraceae) cjc71, 1128'93
Annona cherimolia (Annonaceae) jnp 48, 151'85
Annona spp. (Annonaceae) jnp 48, 151'85
Argemone spp. (Papaveraceae) joe34, 555'69
Artabotrys monteiroae (Annonaceae) pa 4, 72'93
Artabotrys venustus (Annonaceae) jnp 49, 602'86
Berberis spp. (Berberidaceae) phy 29, 3505'90
Bongardia chrysogonum (Berberidaceae) jnp 52,818 '89
Cananga odorata (Annonaceae) jccs46, 607'99
Ceratocapnos palaestinus (Papaveraceae) jnp 53, 1006'90
Cinnamomum spp. (Lauraceae) het 9, 903'78
Corydalis spp. (Papaveraceae) ijcdr 26, 155'88
Cryptocarya spp. (Lauraceae) het 9, 903'78
Cymbopetalum brasiliense (Annonaceae) pm 50, 517'84
Desmos tiebaghiensis (Annonaceae) jnp 45,617 '82
Eschscholzia californica (Papaveraceae) lac 6, 555'90
Fumaria capreolata (Papaveraceae) per 4, 96'85
Glaucium grandiflorum (Papaveraceae) apt 43, 89'01
Glaucium fimbrilligerum (Papaveraceae) cnc 16, 177'80
Glossocalyx brevipes (Monimiaceae) jnp 48, 833'85
Guatteria goudotiana (Annonaceae) phy 30,2781'91
Hernandia spp. (Hernandiaceae) bmnh 2, 387'80
Illigera parviflora (Hernandiaceae) cty 22, 393'91
Laurus nobilis (Lauraceae) jnp 45, 560'82
Leontice leontopetalum (Berberidaceae) jnp 49, 726'86
Lindera spp. (Lauraceae) jnp 47, 1066'84
Litsea spp. (Lauraceae) ajc43, 1949'90
Magnolia spp. (Magnoliaceae) pm 48, 43'83
Monocyclanthus vignei (Annonaceae) jnp 54,1331'91
Nectandra salicifolia (Lauraceae) jnp 59, 576'96
Neolitsea spp. (Lauraceae) jnp 47, 1062'84
Papaver somniferum (Papaveraceae) kps 12, 750'76
Papaver spp. (Papaveraceae) phy 25, 2639'86
Peumus boldus (Monimiaceae) jps 57,1023 '68
Phoebe minutiflora (Lauraceae) cpj 49, 217'97
Polyalthia acuminata (Annonaceae) jnp 45, 471'82
Rollinia emarginata (Annonaceae) jnp 49,717 '86
Siparuna tonduziana (Monimiaceae) pm 56, 492'90
Sparattanthelium uncigerum (Hernandiaceae) jnp 48, 333'85
Stephania spp. (Menispermaceae) cpb 45, 470'97
Structural Index - 6,7-MeO,HO-Substituted
Thalictrum minus chemovar b (Ranunculaceae) llyd 41, 257'78
Thalictrum spp. (Ranuneulaeeae) jnp 45, 252'82
Uvaria spp. (Annonaeeae) nm51, 272'97
Xylopia spp. (Annonaeeae) pm30, 48'76
(-)(R)-isomer:
Aniba spp. (Lauraceae) bse 8, 51'80
Anomianthus dulcis (Annonaeeae) bse 26, 139'98
Croton celtidifolius (Euphorbiaeeae) pm 63, 485'97
Ficus pachyrrachis (Moraceae) pm 59, 286'93
Papaver spp. (Papaveraceae) phy 25, 2639'86
isomernot specified:
Aconitum zeravschanicum (Ranuneulaeeae) ene20, 760'84
Aniba muca (Lauraeeae) rbq 13, 19'96
Annona squamosa (Annonaceae) epj 46, 439'94
Anomianthus dulcis (Annonaceae) bse 26, 139'98
Arctomecon humile (Papaveraceae) bse 18, 45'90
Chelidonium majus (Papaveraceae) jcspt I, 1140'75
Cinnamomum camphora (Lauraeeae) het 9, 903'78
Cocculus laurifolius (Menispermaeeae) tet 36, 3107'80
Corydalis spp. (Papaveraceae) ene20, 245'84
Croton hemiargyreus var. gymnodiscus (Euphorbiaceae) pa 10, 254'99
Cryptocarya longifolia (Lauraeeae) abs 11
Dicentra peregrina (Papaveraceae) ene20, 74'84
Doryphora sassafras (Monimiaeeae) llyd 37, 493'74
Erythrina arborescens (Fabaeeae) yz 93,1617 '73
Fumaria vaillantii (Papaveraceae) ene 17, 437'81
Glaucium spp. (Papaveraceae) cne 19, 714'83
Guatteria spp. (Annonaeeae) pmp 18, 165'84
Gyrocarpus american us (Hernandiaceae) jnp 49, 101'86
Hernandia guianensis (Hemandiaeeae) pm 50, 20'84
Hydrastis canadensis (Ranuneulaeeae) llyd 33s, 1'70
LAureliaphilippiana (Monimiaeeae) phy 21,773 '82
LAurobasidium lauri (Exobasidiaeeae) jpp 40, 801'88
Litsea spp. (Lauraeeae) epj 46, 299'94
Machilus thunbergii (Lauraeeae) het 9, 903'78
Magnolia salicifolia (Magnoliaceae) pm 51, 291'85
Ocoteaspp. (Lauraeeae) rlq 11, 110'80
Oropheahexandra (Annonaeeae) bse 27, 111'99
Oxandra major (Annonaeeae) phy 26, 2093'87
Pachygone ovata (Menispermaeeae) jnp 42, 399'79
113
114 The Simple Plant Isoquinolines
Papaver spp. (Papaveraceae) cnc 24, 475'89
Phoebe spp. (Lauraceae) jca667, 322'94
Phylica rogersii (Rhamnaceae) llyd 33s, 1'70
Polyalthia nitidissima (Annonaceae) pm49,20 '83
Sassafras albidum (Lauraceae) llyd 39, 473a'76
Thalictrum pedunculatum (Ranunculaceae) izk 21, 246'88
Xylopia frutescens (Annonaceae) pmp 16, 253'82
Xylopia papuana (Annonaceae) npl 6, 57'95
(Beware of the spelling without the final "e." Reticulin is aconnective
tissue protein.)
Ithe N-oxide:1 Reticuline N-oxide
(+)-isomer:
Corydalis pseudoadunca (Papaveraceae) cnc 21, 807'86
Magnolia saliciiolia (Magnoliaceae) pm 48, 43'83
isomer not specified:
Pachygone ovata (Menispermaceae) jnp 42, 399'79
I with a3,4-ene: I
C H
3
0
a-Dehydroreticuline
H O
Croton hemiargyreus (Euphorbiaceae) pa 10, 254'99
Licaria armeniaca (Lauraceae) bps 8, 28'85
C H
3
0
OH
I with a(2,N-Me) attack: I
C H
3
0
Scoulerine
Aurotensine
H O
OH
(d1)-Scoulerine
Aurotensine:
Giaucium oxylobum (Papaveraceae) llyd 33s, 1'70
OC H s
Structural Index - 6,7-MeO,HO-Substituted 115
(R)(+)-Scoulerine:
Corydalis bulleyana (Papaveraceae) pm 52, 193'83
Corydalis caucasica (Papaveraceae) ijcd27, 161'89
Corydalis incisa (Papaveraceae) cpb 24, 2859'76
Corydalis rutifolia (Papaveraceae) ijcdr 26, 155'88
Corydalis scouleri (Papaveraceae) bull 1
Corydalis solida ssp. brachyloba (Papaveraceae) jcsp 13, 63'91
(5)(- )-Scoulerine:
Argemone albiflora (Papaveraceae) ecce38, 3312'73
Argemone polyanthemos (Papaveraceae) ecce39, 2491'74
Corydalis claviculata (Papaveraceae) phy 24, 585'85
Corydalis decumbens (Papaveraceae) jcps 4, 57'95
Corydalis gigantea (Papaveraceae) kps 12, 754'76
Corydalis hsuchowensis (Papaveraceae) pm 57, 156'91
Corydalis incisa (Papaveraceae) phy 13, 2620'74
Corydalis intermedia (Papaveraceae) ecce54,2009 '89
Corydalis koidzumiana (Papaveraceae) yz 94, 844'74
Corydalis majori (Papaveraceae) pmp 22, 219'88
Corydalis nobilis (Papaveraceae) ecce54, 2009'89
Corydalis ochroleuca (Papaveraceae) cjc47, 1103'69
Corydalis omeiensis (Papaveraceae) tcyyk 4, 7'92
Corydalis saxicola (Papaveraceae) zx 24, 289'82
Corydalis severtzovii (Papaveraceae) cnc 11, 826'75
Corydalis stewartii (Papaveraceae) pm 58, 108'92
Corydalis vaginans (Papaveraceae) cnc 12, 118'76
Disepalum pulchrum (Annonaceae) phy 29, 3845'90
Eschscholzia californica strain bb (Papaveraceae) tet 47, 5945'91
Eschscholzia lobbii (Papaveraceae) ecce41,2429 '76
Eschscholzia oregana (Papaveraceae) ecce40, 1095'75
Fumaria asepala (Papaveraceae) ijcdr 24, 105'86
Fumaria bella (Papaveraceae) jnp 49, 178'86
Fumaria capreolata (Papaveraceae) jnp 48, 670'85
Fumaria judaica (Papaveraceae) guefd 1, 15'84
Fumaria kralikii (Papaveraceae) ijcdr 26, 61'88
Fumaria petteri ssp. thuretii (Papaveraceae) ijcdr 26, 61'88
Fumaria vaillantii (Papaveraceae) phy 22, 2073'83
Glaucium fimbrilligerum (Papaveraceae) cnc 16, 177'80
Hunnemannia fumariaefolia (Papaveraceae) ecce45, 914'79
Hypecoum procumbens (Papaveraceae) jnp 46, 414'83
Sarcocapnos crassifolia speciosa (Papaveraceae) phy 28,251'88
Sarcocapnos enneaphylla (Papaveraceae) phy 30, 1005'91
116
The Simple Plant Isoquinolines
Sarcocapnos saetabensis (Papaveraceae) phy 30,2071'91
Stephania cepharantha (Menispermaceae) cpb 45, 470'97
isomer not specified:
Annona paludosa (Annonaceae) pmp 22, 159'88
Argemone alba (Papaveraceae) cnc 22, 189'86
Argemone albiflora (Papaveraceae) cnc 22,742 '87
Argemone hybrida (Papaveraceae) cnc 22, 189'86
Argemone mexicana (Papaveraceae) cnc 22, 189'86
Argemone orchroleuca (Papaveraceae) kps 6, 798'86
Berberis valdiviana (Berberidaceae) fit 64, 378'93
Chelidonium majus (Papaveraceae) pm 60,380 '94
Cop tis japonica (Ranunculaceae) phy 32, 659'93
Corydalis bungeana (Papaveraceae) pm 53,418 '87
Corydalis gortschakovii (Papaveraceae) cnc 20, 245'84
Corydalis impatiens (Papaveraceae) patent 3
Corydalis ochotensis (Papaveraceae) jcspt I, 390'77
Corydalis pseudoadunca (Papaveraceae) cnc 21, 807'86
Corydalis repens (Papaveraceae) yhtp 17, 3'82
Corydalis soiida (Papaveraceae) guefd 5, 9'88
Corydalis stricia (Papaveraceae) kps 19, 461'83
Corydalis tashiroi (Papaveraceae) pm 67, 423'01
Cryptocarya longifolia (Lauraceae) abs 11
Dicentra peregrina (Papaveraceae) cnc 20,74 '84
Dicentra speciabilis (Papaveraceae) cnc 20,74 '84
Fumaria capreolata (Papaveraceae) ijcd23, 161'85
Fumaria densiflora (Papaveraceae) ecce61, 1064'96
Fumaria [udaica (Papaveraceae) ijcd22, 181'84
Fumaria officinalis (Papaveraceae) cjc47, 1103'69
Fumaria parviflora (Papaveraceae) cnc 18, 608'82
Fumaria oaillantii (Papaveraceae) cnc 17,437 '81
Fumaria spp. (Papaveraceae) jnp 48, 670'85
Glaucium fimbrilligerum (Papaveraceae) cnc 19,464 '83
Glaucium oxylobum (Papaveraceae) ecce50, 854'84
Glaucium squamigerum (Papaveraceae) ecce49, 1318'84
Glaucium spp. (Papaveraceae) ecce50,854 '84
Mahonia aquiiolium (Berberidaceae) cp 39,537 '85
Nandina domestica (Berberidaceae) patent 1
Papaver argemone (Papaveraceae) ecce53,1845 '88
Papaver atlanticum Ball (Papaveraceae) ecce51, 2232'86
Papaver bracteatum (Papaveraceae) IT 24, 400'88
Papaver confine (Papaveraceae) ecce54, 1118'89
Structural Index - 6,7-MeO,HO-Substituted
Papaver cylindricum (Papaveraceae) pm 46,175 '82
Papaver fugax (Papaveraceae) kps 4, 559 '88
Papaver lecoquii (Papaveraceae) ecce46, 2587 '81
Papaver litwinowii (Papaveraceae) ecce46, 1534 '81
Papaver orientale (Papaveraceae) ecce56, 1534 '91
Papaver pinnatifidum (Papaveraceae) ecce59, 1879 '94
Papaver rhoeas var. chelidonioides (Papaveraceae) ecce54,1118 '89
Papaver setigerum (Papaveraceae) ecce61, 1047 '96
Papaver stevenianum (Papaveraceae) ecce55, 1812 '90
Papaver tauricolum (Papaveraceae) phy 19, 2189 '80
Papaver triniaejolium (Papaveraceae) pm 49, 43 '83
Stylophorum lasiocarpum (Papaveraceae) ecce56, 1116 '91
Stylophorum diphyllum (Papaveraceae) ecce49, 704 '84
Thalictrum tuberosum (Ranunculaceae) phy 33,1431 '93
landaromatization of the c-ring: I C H sO
Tetradehydroscoulerine
HO
Pseuduvaria indochinensis (Annonaceae)
phy 27, 4004 '88
Thalictrum tuberosum (Ranunculaceae)
phy 33,1431 '93
OH
!witha(2,3) attack: I
C H sO
Munitagine
HO
Argemone hybrida (Papaveraceae) cnc 22, 189 '86
Argemone gracilenta (Papaveraceae) jnp 46, 293 '83
Argemone munita (Papaveraceae) jnp 46, 293 '83
Argemone platyceras (Papaveraceae) kfz 22, 580 '88
Argemone pleiacantha (Papaveraceae) phy 8, 611'69
alsounder: 7,8 MeO HO R Me THIQ
R=3,4-MeO,Ho-benzyl (6,3) attack
OH
OC H s
OC H
s
117
(-)-Salutaridine
(-)-Sinoacutine
Sinacutine:
Artabotrys uncinatus (Annonaceae) jnp 64, 1157'01 HO
Berberis buxifolia (Berberidaceae) daib 44,1458 '83
Berberis ilieifolia (Berberidaceae) het 43,949 '96
Cassytha pubescens (Lauraceae) het 9, 903'78
Ceraiocapnos palaestinus (Papaveraceae)
jnp 53, 1006'90
Cocculus carolinus (Menispermaceae) jps 61, 1825'72
Corydalis koidzumiana (Papaveraceae) yz 94,844 '74
Corydalis majori (Papaveraceae) pmp 22, 219'88
Corydalis ochotensis var. raddeana (Papaveraceae) jcspt I, 390'77
Corydalis stewartii (Papaveraceae) pm 58, 108'92
Croton flavens (Euphorbiaceae) llyd 32, 1'69
Croton lechleri (Euphorbiaceae) pm 62, 90'96
118 The Simple Plant Isoquinolines
Iwith a(2,4a) attack: I Salutaridine
Floripavine
Salutarine
Sinoacutine
Sinacutine
C H sO
(+)-Salutaridine
Floripavine:
Croton balsamifera (Euphorbiaceae) rlq 1,140 '70
Croton plumieri (Euphorbiaceae) rlq 1,140 '70
Croton spp. (Euphorbiaceae) llyd 32, 1'69
Glaucium fimbrilligerum (Papaveraceae)
jnp 61, 1564'98
Glaueium flavum (Papaveraceae) phy 27, 1021'88
Glaucium spp. (Papaveraceae) jnp 61, 1564'98
Papaver bracteatum (Papaveraceae) ecce50, 1215'85
Papaver fugax (Papaveraceae) jsiri 7, 263'96
Papaver orientale (Papaveraceae) book 4
Papaver pseudo-orientale (Papaveraceae) ecce51, 1752'86
Papaver somniferum (Papaveraceae) book 4
Papaver triniifolium (Papaveraceae) pm49, 43'83
Papaver spp. (Papaveraceae) dsa 7, 93'83
Sarcocapnos crassifolia (Papaveraceae) phy 30, 1175'91
Sarcocapnos saetabensis (Papaveraceae) phy 30,1175 '91
C H sO
C H sO
C H sO
H O
o
o
Structural Index - 6,7-MeO,HO-Substituted
Glaucium contortuplicatum (Papaveraceae) jps 65, 755'76
Nandina domestica (Berberidaceae) yz 94, 1149'74
Ocotea brachybotra (Lauraceae) tl1631'76
Peumus boldus (Monimiaceae) fit 54, 175'83
Platycapnos saxicola (Papaveraceae) phy 30,3315 '91
Stephania brachyandra (Menispermaceae) tcyyk 4, 11'92
Stephania cepharaniha (Menispermaceae) bpb 22, 268'99
Stephania dicentzinifeza (Menispermaceae) zh 15, 8'84
Stephania dielsiana (Menispermaceae) zh 14, 57'83
Stephania elegans (Menispermaceae) ijnp 42, 147'80
Stephania epigaea (Menispermaceae) nyx 5,203 '85
Stephania graciienia (Menispermaceae) ijnp 3,8 '87
Stephania micrantha (Menispermaceae) yx 16, 557'81
Stephania officinarum (Menispermaceae) zx 32, 368'90
Stephania pierrei (Menispermaceae) jnp 56, 1468'93
Stephania yunnanensis (Menispermaceae) zx 31, 296'89
Strychnopsis thouarsii (Menispermaceae) bse 23, 679'95
(dll-Salutaridine
(dll-Salutarine: (structure the same as (+)-Salutaridine)
Croton salutaris (Euphorbiaceae) phy 20, 543'81
isomernot specified:
Antizoma angustifolia (Menispermaceae) jnp 51, 584'88
Croton linearis (Euphorbiaceae) rlq 1, 140'70
Sinomenium acutum (Menispermaceae) llyd 33s, 1'70
Thalictrum foetidum (Ranunculaceae) pm 56,337 '90
(theN-oxide:I (+)-Salutaridine N-oxide
Papaver bracteatum (Papaveraceae) pm 58, 368'92
andahydrogenated double bond
atthe8,8a-position:
CHsO
(-)-8,14-Dihydrosal utaridine
H O
Crotondiscolor (Euphorbiaceae) llyd 32, 1'69 CHsO
Crotonechinocarpus (Euphorbiaceae) llyd 32, 1'69 0
Crotonlinearis (Euphorbiaceae) llyd 32, 1'69
119
120
The Simple Plant Isoquinolines
Croton plumieri (Euphorbiaceae) phy 8, 777 '69
Croton stenophyllus (Euphorbiaceae) ref 16, 45 '82
Sinomenium acutum (Menispermaceae) bydx 23, 235 '91
Stephania brachyandra (Menispermaceae) cty 13, 1'82
C H 30
Hernandia voyronii (Hernandiaceae) pm 64, 58 '98
Ocotea brachybotra (Lauraceae) tl 1631'76
Thalictrum [auriei (Ranunculaceae)
jnp 62, 803 '99
H O
(-)-Ocobotrine
C H 30
o
Iand hydrogenated double bonds: I
C H 30
H O
Tetrahydrosinacutine
Ocotea brachybotra (Lauraceae) fes 32, 767 '77
o
Iwith a (2,8) attack: I C H 30
Corytuberine
H O
H O Aconitum spp. (Ranunculaceae)
ecce 60, 1034 '95
Actaea spicaia (Ranunculaceae)
ecce 60, 1034 '95
Adonis spp. (Ranunculaceae) ecce 52, 804 '87
Annona cherimolia (Annonaceae) jnp 48, 151'85
Aquilegia spp. (Ranunculaceae) ecce 52, 804 '87
Aristolochia clematitis (Aristolochiaceae) ecce 52, 804 '87
Caltha palustris (Ranunculaceae) ecce 52, 804 '87
Chelidonium majus (Papaveraceae) pm 60, 380 '94
Cissampelos pareira (Menispermaceae) fit 63, 282 '92
Clematis recta (Ranunculaceae) ecce 52, 804 '87
Consolida regalis (Ranunculaceae) ecce 52, 804 '87
Corydalis dasyptera (Papaveraceae) tcyyk 9, 37 '97
Corydalis gortschakovii (Papaveraceae) cnc 13, 702 '77
Corydalis nobilis (Papaveraceae) ecce 54, 2009 '89
C H
3
0
616
CODE
aa
aabc
aajps
aaqa
abb
abc
abf
abs
ac
acc
accc
acr
acre
acs
acssb
acv
adq
afb
aim
ajb
ajc
ajps
akz
al
ap
apf
apj
apn
app
apr
aps
apt
apw
aq
aqsc
The Simple Plant Isoquinolines
J ournal Names Appendix
J OURNAL NAME
Acta Amazonica
Anales Acad. Brasil Cienc.
Al-Azhar J ournal of Pharm. Sci.
An. Asoc. Quimica Argentina
Arch. Biochem. Biophys.
Agr. Biol, Chern.
Ann. Bot. Fenn.
(seeABSTRACTS below)
Anal. Chern.
Acta Crystallog., Commun.
Acta Crystallog., Sec. C Commun.
Anticancer Research
Acgc Chern. Res. Commun.
Acta Chimica Scandinav.
Acta Chimica Scandinav., Ser. B
Acta Gent. Venze.
Anales DeQuimica
Acta Farm. Bonaerense
Annals of Internal Medicine
American J ournal of Botany
Australian J ournal of Chemistry
Alexandria J ournal of Pharm. Sci.
Arm. Khim. Zh.
Acta Leidensia
Arch. Pharm. (Germany)
Ann. Pharm. France
Acta Pharm. J ugosl.
Acta Pharm. Nord.
Acta Pol. Pharm. (Poland)
Archives of Pharm. Res.
Acta Pharm. Suecica
Acta Pharm. Turc.
Arch Pharm. (Weinheim)
An.Quim.
An. Quim. Ser. C
arch
aua
aup
babf
bbb
be
bemm
besj
ber
bfs
bgac
bio
bkcs
bmel
bmnh
book
bp
bpb
bps
br
bs
bscq
bs&e
bscf
bscq
bsp
bsrs
bull
bydx
CA
cb
cc
cccc
cel
cct
cf
chern
chim
chr
chy
ci
cjc
cjr
J ournal Names Appendix
Arch. Androl.
Ann. Univ. Abidjan Ser. C
Acta Univ. Palacki. Olomuc., Fac. Rerum Nat., Chern.
Bol. Assoc. Brasil Farm.
Biosci. Biotech. Biosci.
Biomed. Chromatography
Bull. Chinese Materia Medica
Bull. Chern. Soc. J apan
Chemische Berichte
Bull. Fac. Sci., Assiut University
Bulletin Georgian Acad. Sci.
Biokhimiya
Bulletin Korean Chern. Soc.
Bioorg. Med. Chern. Letters
Bull. Mus. Natl. Hist. Nat. Sect. B
(seeBOOKSbelow)
Biochem. Pharmacology
BioI. Pharm. Bulletin
Bull. Pharm. Sci. Assiut Univ.
Brain Res.
Biosciences
Biol, Soc. Chil. Quim.
Biochem. Systematics &Ecol.
Bull. Soc. Chim. Fr.
Bull. de laSoc. Chilena de Quimica
Bull. Sci. Pharmacology
Bull. Soc. R. Sci. Leige
(seeBULLETINS below)
BeijingYikeDaxue Xuebao
Chemical Abstracts
Chern. Ber.
Chern. Communications
Coll, Czee. Chern. Comm.
Chinese Chern. Letters
Contrib. Gent. Teenol. (Univ, Tee. Estado, Santiago)
Cesk. Farm.
Chemica
Chimia
Chromatographia
Chung-Hua YaoHsueh TsaChili
Chern. Ind. (London)
Canadian J ournal of Chemistry
Canadian J ournal of Research
617
618
cl
cnc
cp
cpb
cpj
cra
crab
crhs
crt
ct
cty
cwf
cwhp
cytp
cz
daib
dant
dban
diss
dmd
dsa
duj
eb
ejcp
ejps
exp
fes
ffbd
fit
fm
frm
fzs
gci
go
gp
guefd
hca
het
hh
hhhp
hkkuc
hue
hx
The Simple Plant Isoquinolines
Chern. Letters
Chern. Nat. Compo
Chern. Pap.
Chern. Pharm. Bulletin
Chinese Pharmaceut. J ournal
c. R. Acad. Sei., Ser. C
C. R. Acad. Bulg. Sci.
C. R. Hebd. Seances Acad. Sci., Ser. C
Chern. Res. Toxicol.
Clinical Toxicology
Chung Ts'ao Yao
Chih Wu Fen Lei Hsueh Pao
Chih Wu Hsueh Pao
Chung YaoTung Pao
Chern. Zvesti
Dissertation Abstracts Int. b
001<1.Akad. Nauk Tadzh. SSR
001<1.Boig. Akad. Nauk
(see DISSERTATIONSbelow)
Drug Metab. Dispos.
DogaSeriA
Dirasat-Univ; J ordan Ser. b
Economic Botany
Eur. J . Clin. Pharmacology
Egypt J ournal of Pharm. Sci.
Experientia
Farmaco Ed. Sci.
Fabad. Farm. Bilimler Derg.
Fitoterapia
Folia Med.
Farmatsiya (Moscow)
Faming Zhuanli Shenqing Gongkai Shoumingshu
Gazetta Chimica Italiana
Garcia Orta
General Pharmacology
Gazi. Univ. Eczacilik Fak. Derg.
Helvetica Chimica Acta
Heterocycles
HerbaHung
Hua Hsueh Hsueh Pao
Hwahak Kwa Kongop Ui Chinbo
Hacettepe Univ. Eczacilik Fak. Derg.
Huaxue Xuebao
J ournal Names Appendix
hyz
iang
ians
iant
Huaxi Yaoxue Zazhi
Izv. Akad. Nauk Gruz., Ser. Khim.
Izv. Akad. Nauk SSSRSer. Khim.
Izv. Akad. Nauk Tadzh. SSROtd. Fiz. Mat. Khirn. Geol.
Nauk
Indian Drugs
Indian J ournal of Chern. Sec. B
Int. J ournal of Crude Drug Res.
Indian J ournal of Chern. Soc.
Indian J ournal of Exp. Biol.
Indian J ournal of Heterocycl. Chern.
Indian J ournal of Natural Products
Int. J ournal of Pharmacognosy
Indian J ournal Pharm. Sci.
Iyakuhin Kenkyu
Izv. Khim.
J ournal of American Chemical Society
J ournal of Agric. &Food Chern.
J ournal of Amer. Pharm. Ass. Sci. Ed.
J ournal of Bangladesh Acad. Sci.
J ournal of Chromatography
J ournal of Chromatography A
J ournal of Chern. Crystal.
J ournal of Chin. Chern. Soc. (Taipei)
J ournal of the Chern. Soc. of Pakistan
J ournal of Chinese Pharm. Science
J ournal of Chinese Pharm. University
J ournal of Chemical Research
J ournal of Chemical Research Synop.
J ournal of the Chemical Society-C
J ournal of the Chemical Society-Chern. Communications
J ournal of Chern. Soc. Pakistan
J ournal of the Chemical Society-Perkins Transactions
J ournal of Crystallographic &Spectroscopic Res.
J ournal of Ethnopharmacology
J ournal of Fac, Pharm. Istanbul Univ.
J ournal of Heterocyclic Chern.
J ournal of Inst. Chern. (Calcutta)
J ournal of the Indian Chern. Soc.
J ournal of Natural Products
J ournal of Neuroscience Research
J ournal of Natl. Sci. Council Sri Lanka
J ournal of Organic Chemistry
id
ijc
ijcdr
ijcs
ijeb
ijhc
ijnp
ijp
ijps
ik
izk
jacs
jafc
jap
jbas
jc
jca
jcc
jccs
jcp
jcps
jcpu
jcr
jcrs
jcsc
jcscc
jcsp
jcspt
jcsr
je
jfp
jhc
jic
jics
jnp
jnr
jnsc
joe
619
620
joe
jp
jpic
jpp
jpps
ips
jpsj
jrim
jscs
jsiri
kdr
kfz
kjp
kps
lac
llyd
lr
Is
mjps
mjs
nasb
nat
ncyh
nei
nl
nm
nmt
npl
nps
nr
nyx
oiz
ojc
ornr
pa
patent
paz
pb
pbl
pebr
pci
pel
The Simple Plant Isoquinolines
J ournal of Ethnopharmacology
J ournal of Pharm.
J ournal of Proc. Inst. Chern. (India)
J ournal of Pharm. Pharmacol.
J ournal of Pharm. Pharmacol. Suppl.
J ournal of Pharmaceutical Science
J ournal of Pharm. Society J apan
J ournal of Res. Indian Med, YogaHomeopathy
J ournal of Serb. Chern. Soc.
J ournal of Sci. Islamic Repub. Iran
Kagoshima Daigaku Rigakubu Kiyo Sugaku
Butsurigaku Kagaku
Khim. Farm. Zh.
Korean J ournal of Pharmacognosy
Khimiya Prirodnykh Soedinenii
Liebigs Ann. Chern.
Lloydia
Lekarstv. Rasteniya
LifeScience
Mansoura J ournal of Pharm Sci.
Malaysian J ournal of Science
National Applied Science Bulletin
Nature
Nan-Ching YaoHsueh Yuan Hsueh Pao
Neirokhimiya
Neuroscience Letters
Natural Medicine
Natural Medicine, Tokyo
Natural Products Letters
Natural Products of Science
no reference
Nanjing Yixueyuan Xuebao
Okayama Igakkai Zasshi
Orient. J ournal of Chemistry
Org. Magn. Reson.
Phytochemical Analysis
(seePATENTSbelow)
Pazhoohandeh(Tehran)
Pharm. Bull.
Pharm. Biol, (Netherlands)
Prog. CIin. BioI. Res.
Pharm. Chern. J ournal
Pharmacologist
pcr
pes
pet&oc
pert
phy
phymed
phzi
pjps
pjsr
pm
pmj
pmp
pms
pnsc
pp
pptp
pr
prs
psj
ptn
pw
qn
rbf
rbp
rbq
ref
rcq
rlq
IT
ryz
san
sci
sh
sp
svs
sy
syn
syx
sz
taxon
tcdh
tcyyk
tet
J ournal Names Appendix
Plant Cell Rep.
Proceedings of the Chemical Society
Plant Cell Tissue & Organ Culture
Pertanika
Phytochemistry
Phytomedicine
Pharmazie
Pakistan J ournal of Pharm. Sci.
Pakistan J ournal of Sci. Res.
Planta Medica
Pahlavi Med. J ournal
Planta Medica Phytother.
Planta Medica Supp.
Proceedeings of the National Sci. Council, Rep. China
Plant Physiology
Phytochem. Potential Trop. Plants
Phytotherapy Research
Phytotherapy Research Supp.
Pharm. Soc. J apan
Phyton (Horn, Austria)
Pharm Weekbl. (Sci. Ed.)
Quim.Nova
Rev. Brasil Farm
Rev. Brasil Plant Med.
Rev. Boliv. Quimica
Rev. Cubana Farm.
Rev. Colomb. Quimica
Rev. Latinoam. Quimica
Rastit. Resur.
Redai Yaredai Zhiwu Xuebao
Soobshch. Akad. Nauk Gruz. SSR
Science
Saengyak Hakhoechi
Sci. Pharm.
Sb. Vys. Sk. Zemed. Praze, Fak. Agron., Rada A
Synth. Commun.
Synthesis
Shenyang Yaoxueyuan Xuebao
Shoyakugaku Zasshi
Taxon
Tap Chi Duoc Hoc
Tianran Chanwu YanjiuYuKaifa
Tetrahedron
621
622
teta
tjc
tl
tox
tyhtc
ws
yfz
yg
yh
yhc
yhhp
yhtp
yt
yx
yz
zh
zk
zpf
zpn
zx
zydx
zyhz
zyz
zzz
ABSTRACTS
abs 1
abs2
abs3
abs4
abs 5
The Simple Plant Isoquinolines
Tetrahedron-Asymmetry
Turkish J ournal of Chemistry
Tetrahedron letters
Toxicon
Taiwan YaoHsueh TsaChih
Wakanyaku Shinpojumu
Yaowu Fenxi Zazhi
Yiyao Gongye
Youji Huaxue
Yakhak Hoe Chi
YaoHsueh Hsueh Pao
YaoHsueh Tung Pao
Yaoxue Tongbao
YaoxueXuebao
Yakugaku Zasshi
Zhongcaoyao
Zhongyaocao Keji
ZPflanzenphysiol
Zb. Prir. Nauke
Zhiwu Xuebao
Zhonggou YaokeDaxue Xuebao
Zhonggou Yaowu Huaxue Zazhi
Zhonghua Yaoxue Zazhi
Zhongguo Zhongyao Zazhi
Abstr 23rd Annual Meeting American Society of
Pharmacognosy, Aug. 1-5(1982) Pittsburgh, PA: Abstr-26
Abstr J oint Meeting American Society of Pharmacognosy
and Society for Economic Botany, J uly 13-17(1981)
Boston, MA :31-
Abstr Intemat Res Cong Nat Prod ColI Pharm UNC
Chapel Hill, NC, J uly 7-12(1985):Abstr-19
Proc 1st Int Coni Chern Biotechnol Biol Act Nat Prod
(1981) BAtanasova(Ed) Bulgarian Acad Sci Sofia, 31:74-
Proceedings of the 38th Asms Conference 'on Mass
Spectrometry and Allied Topics: (1990)
abs 6
abs 7
abs8
abs9
abs 10
abs 11
abs 12
abs 13
abs 14
abs 15
abs 16
BOOKS
book 1
J ournal Names Appendix
623
Int Conf Chern Biotechnol Biol Act Nat Prod (Proc)
1st 31:95-97 (1981)
Plant Tissue Cult Proc Int Congr Plant Tissue Cell Cult
5th (1982) :315-316
Tezisy Dokl Molodezhnaya Konf Org Sint Bioorg Khim
(1976):59-60
Abstr Internat Res Cong Nat Prod Coll Pharm, UNC
Chapel Hill, NC, J uly 7-12(1985):Abstr-61
Proc Fifth Asian Symposium on Medicinal Plants and
Spices, Seoul, Korea, Aug. 20-24(1984)
BhHan Os Han Yn Han and Ws Woo(Eds) 5:509-518
Abstr 4th Asian Symp Med Plants Spices, Bangkok,
Thailand, Sept. 15-19(1980):170-
Proc Int Symp Recent Adv Nat Prod Res, Seoul, Korea,
Dec. 14-16(1979):18-23
Proc 25th Symp on the Chern of Nat Prod, Tokyo (1982)
25:353-360
Biochem. Physiol. Alkaloide, Int. Symposium, 4th, (1972)
Meeting Date 1969, 275-8. Publisher: Akad.-Verlag,
Berlin, E. Germany.
Revista de laFacultad de Ciencias Quimicas
Universidad Nacional de laPlata 6, 75(1930)
Abstr 27th Annual Meeting American Society of
Pharmacognosy, J uly 27-30(1986), Ann Arbor, MI:
Abstr-49
Scientific Basis of Traditional Chinese Medicine, Y.Lau &
J .P.Fowler (Eds) p. 45(1982)
624
book 2
book 3
book 4
book 5
book 6
BULLETINS
The Simple Plant Isoquinolines
Chinese Herbal Medicine. US Dept. of Health, Education
and Welfare, Publ. No. (NIH) 75-732, Washington,DC
Li,Cp: Book (1974)
Adv Nat Prod Chern-Extraction &Isolation of
Biologically Active Compounds. S. Natori, N. Ikekawa,
M. Suzuki (Eds.), Wiley, NY.:240-248(1981)
Opium Poppy. Botany, Chemistry, and Pharmacology.
Kapoor, L.D., Hayworth Press (1995)
Sacred Cacti. K. Trout, Better Days Publication (1999)
Cactus Alkaloids. K. Trout, Better Days Publication,
in press
buIll Ars, Usda, TechBull 1234, Supt Documents,
Govt Print Office, Washington DC (1961)
DISSERTATIONS
diss 1 Dissertation-Ph.D.-Univ Illinois Medical Center (1979):
pp 171-
PATENTS
patent 1
patent 2
patent 3
patent 4
Patent-J apan Kokai Tokkyo Koho-08 208,651: 7pp-.(1996)
Ca 125:257165y
Patent-USSR-721,101:1pp-(1980) Gindarine
Faming Zhuanli Shenqing Gongkai Shoumingshu (2001)
CA 135:142208
Faming Zhuanli Shenqing Gongkai Shoumingshu (2000)
CA 134:120918