NPC

Natural Product Communications

EDITOR-IN-CHIEF
DR. PAWAN K AGRAWAL
Natural Product Inc.
7963, Anderson Park Lane,
Westerville, Ohio 43081, USA

agrawal@naturalproduct.us
EDITORS
PROFESSOR ALEJANDRO F. BARRERO
Department of Organic Chemistry,
University of Granada,
Campus de Fuente Nueva, s/n, 18071, Granada, Spain
afbarre@ugr.es
PROFESSOR ALESSANDRA BRACA
Dipartimento di Chimica Bioorganicae Biofarmacia,
Universita di Pisa,
via Bonanno 33, 56126 Pisa, Italy
braca@farm.unipi.it
PROFESSOR DEAN GUO
State Key Laboratory of Natural and Biomimetic Drugs,
School of Pharmaceutical Sciences,
Peking University,
Beijing 100083, China
gda5958@163.com
PROFESSOR YOSHIHIRO MIMAKI
School of Pharmacy,
Tokyo University of Pharmacy and Life Sciences,
Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan
mimakiy@ps.toyaku.ac.jp
PROFESSOR STEPHEN G. PYNE
Department of Chemistry
University of Wollongong
Wollongong, New South Wales, 2522, Australia
spyne@uow.edu.au
PROFESSOR MANFRED G. REINECKE
Department of Chemistry,
Texas Christian University,
Forts Worth, TX 76129, USA
m.reinecke@tcu.edu
PROFESSOR WILLIAM N. SETZER
Department of Chemistry
The University of Alabama in Huntsville
Huntsville, AL 35809, USA
wsetzer@chemistry.uah.edu
PROFESSOR YASUHIRO TEZUKA
Institute of Natural Medicine
Institute of Natural Medicine, University of Toyama,
2630-Sugitani, Toyama 930-0194, Japan
tezuka@inm.u-toyama.ac.jp
PROFESSOR DAVID E. THURSTON
Department of Pharmaceutical and Biological Chemistry,
The School of Pharmacy,
University of London, 29-39 Brunswick Square,
London WC1N 1AX, UK
david.thurston@pharmacy.ac.uk

HONORARY EDITOR
PROFESSOR GERALD BLUNDEN
The School of Pharmacy & Biomedical Sciences,
University of Portsmouth,
Portsmouth, PO1 2DT U.K.
axuf64@dsl.pipex.com

ADVISORY BOARD
Prof. Berhanu M. Abegaz
Gaborone, Botswana
Prof. Viqar Uddin Ahmad
Karachi, Pakistan
Prof. yvind M. Andersen
Bergen, Norway
Prof. Giovanni Appendino
Novara, Italy
Prof. Yoshinori Asakawa
Tokushima, Japan
Prof. Lee Banting
Portsmouth, U.K.
Prof. Julie Banerji
Kolkata, India
Prof. Anna R. Bilia
Florence, Italy
Prof. Maurizio Bruno
Palermo, Italy
Prof. Csar A. N. Cataln
Tucumn, Argentina
Prof. Josep Coll
Barcelona, Spain
Prof. Geoffrey Cordell
Chicago, IL, USA
Prof. Ana Cristina Figueiredo
Lisbon, Portugal
Prof. Cristina Gracia-Viguera
Murcia, Spain
Prof. Duvvuru Gunasekar
Tirupati, India
Prof. Kurt Hostettmann
Lausanne, Switzerland
Prof. Martin A. Iglesias Arteaga
Mexico, D. F, Mexico
Prof. Leopold Jirovetz
Vienna, Austria
Prof. Vladimir I Kalinin
Vladivostok, Russia
Prof. Niel A. Koorbanally
Durban, South Africa

Prof. Karsten Krohn

Paderborn, Germany
Prof. Chiaki Kuroda
Tokyo, Japan
Prof. Hartmut Laatsch
Gottingen, Germany
Prof. Marie Lacaille-Dubois
Dijon, France
Prof. Shoei-Sheng Lee
Taipei, Taiwan
Prof. Francisco Macias
Cadiz, Spain
Prof. Imre Mathe
Szeged, Hungary
Prof. Ermino Murano
Trieste, Italy
Prof. M. Soledade C. Pedras
Saskatoon, Canada
Prof. Luc Pieters
Antwerp, Belgium
Prof. Peter Proksch
Dsseldorf, Germany
Prof. Phila Raharivelomanana
Tahiti, French Polynesia
Prof. Luca Rastrelli
Fisciano, Italy
Prof. Monique Simmonds
Richmond, UK
Dr. Bikram Singh
Palampur, India
Prof. John L. Sorensen
Manitoba, Canada
Prof. Valentin Stonik
Vladivostok, Russia
Prof. Winston F. Tinto
Barbados, West Indies
Prof. Sylvia Urban
Melbourne, Australia
Prof. Karen Valant-Vetschera
Vienna, Austria

INFORMATION FOR AUTHORS

Full details of how to submit a manuscript for publication in Natural Product Communications are given in Information for Authors on our Web site
http://www.naturalproduct.us.
Authors may reproduce/republish portions of their published contribution without seeking permission from NPC, provided that any such republication is
accompanied by an acknowledgment (original citation)-Reproduced by permission of Natural Product Communications. Any unauthorized reproduction,
transmission or storage may result in either civil or criminal liability.
The publication of each of the articles contained herein is protected by copyright. Except as allowed under national fair use laws, copying is not permitted by
any means or for any purpose, such as for distribution to any third party (whether by sale, loan, gift, or otherwise); as agent (express or implied) of any third
party; for purposes of advertising or promotion; or to create collective or derivative works. Such permission requests, or other inquiries, should be addressed
to the Natural Product Inc. (NPI). A photocopy license is available from the NPI for institutional subscribers that need to make multiple copies of single
articles for internal study or research purposes.
To Subscribe: Natural Product Communications is a journal published monthly. 2013 subscription price: US$2,395 (Print, ISSN# 1934-578X); US$2,395
(Web edition, ISSN# 1555-9475); US$2,795 (Print + single site online); US$595 (Personal online). Orders should be addressed to Subscription Department,
Natural Product Communications, Natural Product Inc., 7963 Anderson Park Lane, Westerville, Ohio 43081, USA. Subscriptions are renewed on an annual
basis. Claims for nonreceipt of issues will be honored if made within three months of publication of the issue. All issues are dispatched by airmail throughout
the world, excluding the USA and Canada.

NPC

Natural Product Communications

Essential Oils from Five Species of Annonaceae from Vietnam

2013
Vol. 8
No. 2
239 - 242

Tran D. Thanga,*, Do N. Daib, Tran M. Hoib and Isiaka A. Ogunwandec, *

a

Department of Food Technology, Faculty of Chemistry, Vinh University, 182-Le Duan, Vinh City,
Nghe An Province, Vietnam
b
Institute of Ecology and Biological Resources, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet,
Cau Giay, Hanoi, Vietnam
c
Natural Products Research Unit, Department of Chemistry, Faculty of Science, Lagos State University,
Badagry Expressway, Ojo, P.M.B. 0001, Lasu Post office, Ojo, Lagos, Nigeria
thangtd@vinhuni.edu.vn; isiaka.ogunwande@lasu.edu.ng
Received: November 12th, 2012; Accepted: December 30th, 2012

The essential oils obtained by hydrodistillation from the leaves of five species of Annonaceace grown in Vietnam were analyzed by gas chromatography
(GC) coupled with mass spectrometry (GC/MS). The main constituents of Artabotrys hongkongensis Hance were the sesquiterpenes spathulenol (13.1%),
-caryophyllene (6.6%), -elemene (6.3%) and -cadinene (6.3%). -Caryophyllene (12.1%), bicycloelemene (11.2%) and bicyclogermacrene (11.6%) were
the predominant components of the oil of Melodorum fruticosum Lour, whereas the oil of Polyalthia longifolia var. pendula Hort was comprised mainly of
-caryophyllene (30.0%), -zingiberene (21.7%), aromadendrene (15.2%) and -selinene (9.1%). The main constituents of Fissistigma maclurei Merr. were
germacrene D (26.1%), -terpinene (8.2%), spathulenol (10.0%), and bicyclogermacrene (6.6%), while -santalene (14.3%), -caryophyllene (6.3%),
terpinen-4-ol (6.3%), caryophyllene oxide (5.7%), trans--bergamotene (5.3%) and allo-ocimene (5.3%) were identified in significant quantity from
Fissistigma rufinerve (Hook.f. & Thomson) Merr.
Keywords: Artabotrys hongkongensis, Melodorum fruticosum, Polyalthia longifolia var. pendula, Fissistigma maclurei, Fissistigma rufinerve.

Vietnam is blessed with many medicinal plants. Literature

information has shown that the essential oils of these plants have
received little chemical analysis. In view of this, we report herein
the essential oil constituents of five species of Annonanaceae from
Vietnam [1]. The genus Artabotrys has about 100 species in the
Paleotropics [2]. A. hongkongensis Hance, a shrub that grows up to
8 m tall, flowers between May and August. Little is known about
the chemistry of this plant, but other species of the genus are known
to contain biologically active compounds [3-5].
The genus Melodorum comprises about 55 species that are widely
distributed through Indo-China, Malaysia and Australia. White
Cheesewood, M. fruticosum Lour., is a plant native to South-East
Asia. This plant has a cream-colored flower with a single, alternate
leaf. It gives out a pleasant fragrance, especially in the evening. It
also has medical uses as a tonic and mild cardiac stimulant and
hematinic [6]. Several biologically active compounds have been
isolated from this species [7,8]. Many Melodorum species are
aromatic trees with a characteristic smell, but reports on their
volatile components are not readily available in the literature. A
handsome ornamental is the weeping form of the mast tree,
Polyalthia longifolia var. pendula Hort. It is a lofty evergreen tree,
commonly planted due to its effectiveness in alleviating noise
pollution. The tree is known to grow over 9 m in height. Extracts
and compounds isolated from the plant have been reported to
possess a number of biological activities [9-11], but there is only
one literature report on its volatile oil components [12].
Both Fissistigma rufinerve (Hook. f. et Thoms.) Merr. and F.
maclurei Merr. (syn. Meiogyne maclurei Sinclair) are climbers that
grow up to 6 m tall. Little is known about the chemistry of these
plants, but a number of biologically active compounds have been
characterized from other species in the genus [13,14].

The plant samples yielded low contents of essential oils: 0.10%,

v/w; A. hongkongensis; light yellow; 0.12%, v/w; M. fruticosum;
light yellow; 0.15%, v/w; P. longifolia var. pendula; light yellow,
0.15%, v/w; F. maclurei ; light blue, and 0.15%, v/w; F. rufinerve;
light yellow, calculated on a dry weight basis.
The chemical compositions of the oils are summarized in Table 1.
The major compounds identified from A. hongkongensis were
spathulenol (13.1%), -caryophyllene (6.6%), -cadinene (6.3%),
-elemene (6.3%) and benzyl benzoate (5.6%). The compositional
pattern of this oil differs from previous studies on other species in
the genus. Giang et al. [15] identified the main compounds of
Artabotrys hexapetalus as -caryophyllene (11.4%) and
caryophyllene oxide (31.5%) while Rang and Houng [16] reported
an abundance of caryophyllene oxide (36.2%), -copaene (10.9%),
-caryophyllene (7.8%) and -asarone (6.1%) in the same oil. On
the other hand, the oil of A. vinhensis [17] was found to be rich in
-pinene (16.7%), limonene (15.4%), germacrene D (14.4%),
benzyl benzoate (8.8%) and -pinene (7.5%). However, compounds
such as cyperene, cypernone and 1,5-epoxysavial-4(14)-ene, which
were the major components of other Artabotys species [18-20],
were conspicuously absent in this oil sample. From Table 2, the oil
of this species could be classified into a group whose chemical
constituents were dominated by sesquiterpenes.
The leaf oil of M. fruticosum was dominated by sesquiterpenoid
compounds (89.2%). The main constituents of the oil were
-caryophyllene (12.1%), bicyclogermacrene (11.6%) and
bicycloelemene (11.2%). Other significant components were benzyl
benzoate (6.1%), -cubebene (5.5%) and spathulenol (4.9%). The
main components of the flower oil of M. fruticosum from Thailand
[21] were 1-pheny butanone (20.5%), benzyl alcohol (8.7%) and
linalool (9.3%), while another author [22], by using three different
fibers in an SPME extraction method, identified -phellandrene

240 Natural Product Communications Vol. 8 (2) 2013

Thang et al.

Table 1: Compounds identified in the studied oil samples.

Compounds *
Tricyclene
Artemesia triene
-Pinene
Camphene
Sabinene
-Pinene
-Myrcene
-Phellandrene
-3-Carene
-Terpinene
-Cymene
-Phellandrene
Limonene
1, 8-Cineole
(Z)--Ocimene
(E)--Ocimene
-Terpinene
-Terpinolene
Linalool
cis-Verbenol
neo allo-Ocimene
Borneol
-Terpineol
Verbenone
n-Tridecane
Bicycloelemene
-Elemene
-Cubebene
-Longipinene
Neryl acetate
-Ylangene
Isoledene
-Copaene
-Elemene
-Bourbonene
-Cubebene
-Elemene
(Z)-Jasmone
Longifolene
-Cedrene
-Santalene
-Caryophyllene
-Gurjunene
trans--Bergamotene
-Elemene
-Guaiene
Aromadendrene
epi--Santalene
-Himachalene
-Humulene
(E)--Farnesene
-Patchuolene
allo-Aromadendrene
-Gurjunene
ar-Curcumene
-Curcumene
-Amorphene
Germacrene D
(E)--Ionone
-Selinene
-Selinene
Ledene (Viridiflorene)
-Zingiberene
Valencene
Cadina-1,4-diene
-Selinene
Bicyclogermacrene
-Muurolene
Epizonarene
trans--Guaiene
-Bisabolene
(E,E)--Farnesene
-Cadinene
trans--Bisabolene
cis-(Z)--Bisabolene
epoxide c
-Sesquiphellandrene
-Cadinene
cis-Calamenene
-Calacorene
Elemol
Germacrene B
Spathulenol
Caryophyllene oxide
Globulol
Viridiflorol
Widdrol
Rosifoliol
Ledol
-Oplopenone

RI a
926
930
939
953
976
980
990
1006
1011
1017
1026
1028
1032
1034
1043
1052
1061
1089
1100
1141
1144
1169
1189
1205
1300
1327
1337
1351
1353
1362
1375
1376
1377
1381
1387
1388
1391
1393
1408
1412
1418
1419
1434
1435
1437
1440
1441
1447
1451
1454
1457
1457
1461
1477
1481
1483
1485
1486
1489
1490
1493
1494
1494
1496
1496
1498
1500
1501
1502
1503
1506
1506
1513
1514
1515

RI b
921
923
932
946
969
974
988
1002
1008
1014
1020
1025
1024
1026
1032
1044
1054
1086
1095
1137
1140
1165
1186
1204
1300
1338+
1335
1345
1350
1359
1373
1374
1374
1381+
1387
1387
1389
1392
1407
1410
1416
1417
1431
1432
1434
1437
1439
1445
1449
1452
1454
1455
1458
1475
1479
1481
1483
1484
1487
1489
1492
1492
1493
1496
1495
1498
1500
1500
1501
1502
1505
1505
1514
1514
-

1
1.6
0.4
0.4
0.7
1.5
2.5
0.4
0.5
0.4
0.4
0.4
0.8
0.6
1.9
0.4
0.8
0.6
0.4
1.8
6.6
6.3
1.0
1.4
1.5
4.7
1.7
0.7
0.5
1.6
0.8
2.0
0.5
1.6
1.0
0.7

2
3.0
2.7
2.8
3.2
11.2
2.8
5.5
4.0
12.1
3.8
2.8
3.7
3.4
2.8
4.0
2.0
11.6
-

1523
1525
1530
1546
1550
1561
1576
1583
1585
1593
1599
1605
1608
1608

1521
1522
1528
1544
1548
1559
1577
1582
1590
1592
1599
1600
1602
1607

2.9
6.3
0.3
13.1
0.6
1.3

4.9
3.1
-

3
tr
1.6
0.7
tr
tr
0.5
tr
tr
0.1
tr
1.1
tr
tr
tr
0.1
0.2
Tr
0.1
1.2
0.1
0.7
0.2
30.0
0.2
1.9
0.2
15.2
2.7
0.3
1.1
2.0
0.9
9.1
21.7
0.1
0.1
3.3
0.1
0.1
0.2
0.5

4
0.6
0.1
0.3
0.2
0.5
8.2
0.1
0.7
0.2
0.3
0.1
0.2
0.1
0.1
0.1
0.3
0.1
0.5
4.2
6.5
4.6
0.2
3.0
0.4
0.4
0.7
26.1
0.7
0.1
6.6
1.0
0.1
1.1
1.0

5
1.9
0.8
1.0
0.6
0.8
1.5
0.7
0.8
0.6
0.9
0.8
0.6
0.6
0.6
5.8
0.7
0.5
0.4
0.8
0.6
0.6
0.6
0.7
14.8
6.8
5.8
1.3
3.8
3.6
3.4
0.5
1.0
1.0
1.6
1.5
2.0
0.8
3.5
0.7
0.7
2.4

1.0
0.1
0.8
0.4
0.6
-

4.2
0.3
0.1
0.3
0.6
10.0
2.4
-

1.0
2.2
6.2
0.9
0.2
-

allo-Aromadendrene
1641
1639
4.7
epoxide
-Muurolol
1644
1644
2.6
3.5
5.9
Valerianol
1675
1656
3.1
2.8
0.1
(E,Z)-Farnesol
1718
1714
0.7
Benzyl benzoate
1760
1759
5.5
6.1
Guaizulene
1781
1779
1.2
Phytol
1946
1942
0.8
Eicosane
2000
2000
0.7
n-Heneicosane c
2100
0.6
Total
94.4
99.8
99.2
93.3
90.1
Monoterpene hydrocarbons
8.4
11.7
4.1
10.9
16.2
Oxygenated monoterpenes
2.1
2.8
0.2
3.7
Sesquiterpene hydrocarbons
49.6
64.9
92.6
62.7
55.8
Oxygenated sesquiterpenes
26.7
14.3
2.3
19.7
12.6
Diterpenes
0.8
Others
5.5
6.1
1.0
*
Compounds identified by RI from column, co-injection, literature MS pattern and literature retention
indices (RIb), except where stated; a Retention indices on HP-5MS capillary column; b Literature
Retention indices (Adams [30]); + Found in Joulain and Koenig [32]; - Not present; tr, trace < 0.1%;
c
identified by column RI, co-injection, MS pattern and comparison with authentic MS data collection
in our library; 1. A. hongkongensis; 2. M. fruticosum; 3. P. longifolia var. pendula; 4. F. maclurei ; 5.
F. rufinerve

Table 2: Chemical forms of the oils of Artabotrys species.

Chemical forms
Oils dominated by
sesquiterpenes

Species a
A. odoratissimus

A. hexapetalus b
A. hexapetalus b

A. lastoursvillensis
A. insignis, A.
pierreanus, A. rufus,
A. thomsoni, A.
venustus
A. hongkongensis

Oils rich in both

monoterpenes and
sesquiterpenes
a

A. vinhensis

Major components
-caryophyllene (14.717.3%), -copaene (6.49.3%), caryophyllene oxide
(3.2-16.8%)
-caryophyllene (11.4%),
caryophyllene oxide (31.5%)
caryophyllene oxide
(36.2%), -copaene (10.9%),
-caryophyllene (7.8%), asarone (6.1%)
cyperene (25.9%),
cyperenone (11.1%)
cyperenone , 1,5epoxysavial-4(14)-ene

Origin
India

Ref
[18]

Vietnam

[15]

Vietnam

[16]

Gabon

[19]

[20]

spathulenol (13.7%), caryophyllene (6.6%) and elemene (6.3%), -cadinene

(6.3%)
-pinene (16.7%), limonene
(15.4%), germacrene D
(14.4%), -pinene (7.5%)

Vietnam

This
study

Vietnam

[17]

Leaf samples; b Flower sample; - origin unknown

(7.2-17.2%), (Z)--ocimene (9.1-10.4%), p-methylanisole (7.018.0%), linalool (4.5-7.4%) and -cadinene (4.1-4.3%) as
prominent compounds. From Table 3, a noteworthy observation is
the fact that bicyclogermacrene, caryophyllene and spathulenol
have featured prominently among the volatiles of other species,
such as Melodorum sp. (Claudie River B.P), Melodorum sp. (Topaz
G. Sankowsky), Melodorum sp. (Font Hills G. Sankowsky), M.
leichhardtii and M. uhrii from Australia [23].
Sesquiterpenes, represented by -caryophyllene (30.0%), zingiberene (21.7%), aromadendrene (15.2%) and -selinene
(9.1%), are the dominant class of compound in P. longifolia var.
pendula. Nguyen et al. [12] have reported high quantities of cadinene (24.5%), zingiberene (19.6%) and aromadendrene (19.1%)
in the oil. However, -cadinene was conspicuously absent in our
result, while caryophyllene was identified in low quantity in a
previous study [12].
From Table 4, four chemical forms of the oils of Polyalthia species
may be proposed. These are oils with an abundance of
sesquiterpene hydrocarbons, such as P. longifolia var. pendula [12],
P. longifolia [24], P. suaveolens [25] and P. nitidissima [26]; oils
with relative large amounts of hydrocarbon and oxygenated
sesquiterpenes, as exemplified by P. australis and Polyalthia sp.
(Wyvuri B.P.) [26]; oils dominated by oxygenated sesquiterpenes,
as seen in P. michaelii [26]; and oils consisting of monoterpene
hydrocarbons, as found in the fruit of P. suaveolens [25] and
P. nitidissima [26].

Essential oils from the leaves of five species of Annonaceace grown in Vietnam

Table 3: Chemical forms of Melodorum species.

Chemical forms
Oils with large
amounts of
sesquiterpenes
hydrocarbons

Species
Melodorum sp.
(Claudie River B.P)
Melodorum sp.
(Topaz G.
Sankowsky)
M. uhrii
M. leichhardtii

Major components
bicyclogermacrene (29.3%), caryophyllene (26.7%)
bicyclogermacrene (34-50%),
-caryophyllene (11-16%)

Origin
Australia

Ref
[23]

Australia

[23]

bicyclogermacrene (45%),
Australia
[23]
germacrene D (6-10%),
Australia
[23]
bicyclogermacrene (15-19%)
M. fruticosum
-caryophyllene (12.1%),
Vietnam
This
bicyclogermacrene (11.6%),
study
bicycloelemene (11.2%),
(6.1%), -cubebene (5.5%)
-eudesmol (9-5%), Australia
[23]
Oils containing
Melodorum sp.
eudesmol (7-11%), monoterpene- and (Font Hills G.
Sankowsky)
caryophyllene (10-16%),
sesquiterpenes
bicyclogermacrene (1-9%), pinene (14-15%)
Oils rich in
Melodorum sp L.W. benzyl benzoate (20%), benzyl
Australia
[23]
benzenoid
Jessup)
salicylate (2.7%)
compounds
M. fruticosum *, a
1-pheny butanone (20.52),
Thailand
[21]
benzyl alchol (8.75), linalool
(9.27%), -cadinol (5.04%),
globulol (4.25%)
a
Flower sample while others are from the leaves; * contain appreciable amount of monoterpenes and
sesquiterpenes.

Table 4: Chemical forms of P. longifolia var. pendula species.

Chemical forms
Oils with abundant
sesquiterpene
hydrocarbons

Species
P. longifolia
var. pendula

Major components
-caryophyllene (30.0%),
zingiberene (21.7%),
aromadendrene (15.2%) and
-selinene (9.1%)
P. longifolia
-cadinene (24.5%), zingiberene
var. pendula
aromadendrene (19.1%)
P. longifolia
allo-aromadendrene (19.7%),
caryophyllene oxide (14.4%),
and -caryophyllene (13.0%)
P. longifolia a
-copaene/ -muurolol (ca. 8.7%)
(8.6%), viridiflorene (8.1%),
-guaiene (7.8%) and
allo-aromadendrene/-cadinene
(ca.7.4%)
P. suaveolens
-caryophyllene and humulene
(both 34%)
#
P. nitidissima
-caryophyllene, aromadendrene,
D, bicyclogermacrene,
-cadinene, and spathulenol
Oils with relatively P. australis #
-caryophyllene, germacrene D,
large amounts of
bicyclogermacrene,
hydrocarbon and
caryophyllene oxide and
oxygenated
spathulenol
sesquiterpenes
Polalthia sp. (Wyvu -elemene, germacrene D,
bicyclogermacrene,
germacrene B, ledol, globulol
and spathulenol.
Oils dominated by o P. michaelii #
spathulenol
sesquiterpenes
#
Oils consisting of P. nitidissima
-pinene, limonene and
hydrocarbons
()--ocimene
#, b
P. suaveolens
myrcene, -pinene and limonene

Origin
Vietnam

Ref
This
study

Vietnam

[12]

Nigeria

[24]

Nigeria

[24]

Gabon

[25]

Australia

[26]

Australia

[26]

Australia

[26]

Australia

[26]

Gabon

[25]

Stem bark sample ; b Fruit sample; Others are from the leaves; # Quantitative data not
available.

The major compounds of the oil of F. maclurei were germacrene D

(26.1%), spathulenol (10.0%) and -terpinene (8.2%), but
there were also significant quantities of bicyclogermacrene (6.6%),
-caryophyllene (6.5%) and -muurolol (5.9%). On the other hand,
-santalene (14.8%), -caryophyllene (6.3%), terpinen-4-ol (6.3%),
caryophyllene oxide (5.7%), trans--bergamotene (5.8%) and
allo-ocimene (5.8%) were present in higher amounts in F. rufinerve.
The authors have found no literature information on the volatile oil
content of these species and, as such, this may represent the first of
its kind. However, the volatile constituents of some Fissistigma
species from Vietnam have been reported. The oil of F. thorelii
[27] was dominated by -terpinene (22.0%), -phellandrene
(7.3%), bicyclogermacrene (7.2%) and (Z)--ocimene (6.4%), while
F. bracteolatum was characterized by a high content of
myrcene (83.0%). On the other hand, (E)--ocimene (10.2%),
-caryophyllene (23.7%) and -cadinene (27.2%) were the major
components of F. oldhamii, while F. polyanthoides was rich in

Natural Product Communications Vol. 8 (2) 2013 241

-phellandrene (8.3%), -phellandrene (14.3%) and (E)--ocimene

(43.4%).
Fissistigma rubigirosa [28] produced an oil in which the main
components were (E)--ocimene (21.4%) and -cadinene (13.3%).
Therefore, the volatile oils of Fissistigma growing in Vietnam are
thought to exist in three chemical forms namely; oils dominated by
sesquiterpenoid compounds (F. maclurei, F. rufinerve and F.
oldhamii); oils rich in monoterpenoid compounds (F. bracteolatum
and F. polyanthoides), and oils with relatively large amounts of
monoterpenes and sesquiterpenes (F. thorelii and F. rubigirosa).
Sabinene, bicycloelemene, -caryophyllene, bicyclogermacrene and
aromadendrene were the five compounds common to the oil
samples. The content and composition of essential oils depends on
the origin, environmental conditions, phenological stage, plant parts
analyzed, harvesting time and processing methods [1]. Some of
these factors may have been responsible for the observed variations
in the oil contents when compared with other species from other
parts of the world.
Experimental
Plant collection: Leaves of A. hongkongensis, M. fruticosum and F.
rufinerve were collected from Bch M National Park, Tha Thin Hu Province Bach, Vietnam, in August 2011, while those of
P. longifolia var. pendula were obtained from Thanh Ha Province,
Vietnam, in September 2011. The leaves of F. maclurei were
harvested from V Quang, National Park, H Tnh Province,
Vietnam, in September 2011. Voucher specimens DND 805, DND
808, DND 089, DND 195 and DND 199, respectively have been
deposited at the Botany Museum, Vinh University, Vietnam. Plant
samples were air-dried prior to extraction.
Extraction of the oils: About 0.5 kg of air-dried sample of each
species was shredded and their oils obtained by hydrodistillation for
3h at normal pressure, according to the Vietnamese Pharmacopoeia
[29].
Analysis of the oils: About 15 mg of each oil sample, which was
dried with anhydrous sodium sulfate, was dissolved in 1 mL of nhexane (for spectroscopy or chromatography). Gas chromatography
(GC) analysis was performed on an Agilent Technologies HP 6890
Plus Gas chromatograph equipped with a FID and fitted with HPWax and HP-5MS columns (both 30 m x 0.25 mm, film thickness
0.25 m, Agilent Technology). The analytical conditions were:
carrier gas H2 (2 mL/min), injector temperature (PTV) 250oC,
detector temperature 260oC, column temperature programmed from
60oC (2 min hold) to 220oC (10 min hold) at 4oC/min. Samples
were injected by splitting and the split ratio was 10:1. The volume
injected was 1.0 L. Inlet pressure was 6.1 kPa. Each sample was
analyzed thrice.
An Agilent Technologies HP 6890N Plus Chromatograph fitted
with a fused silica capillary HP-5 MS column (30 m x 0.25 mm,
film thickness 0.25 m) and interfaced with a mass spectrometer
HP 5973 MSD was used for the GC/MS analysis, under the same
conditions as those used for GC analysis. The conditions were the
same as described above with He (2 mL/min) as carrier gas. The
MS conditions were as follows: ionization voltage 70eV; emission
current 40 mA; acquisitions scan mass range of 35-350 amu at a
sampling rate of 1.0 scan/s. The MS fragmentation patterns were
checked with those of other essential oils of known composition
with Wiley (Wiley 9th Version), NIST 08 Libraries (on
ChemStation HP), with those in the literature, and also with

242 Natural Product Communications Vol. 8 (2) 2013

standard substances. The identification of constituents was

performed on the basis of retention indices (RI) determined with
reference to a homologous series of n-alkanes, under identical
experimental conditions, co-injection with standards (SigmaAldrich, St. Louis, MO, USA) or known essential oil constituents,
MS library search (NIST 08 and Wiley 9th Version), and by
comparing with MS literature data [30-32]. The relative amounts of

Thang et al.

individual components were calculated based on the GC peak area

(FID response) without using correction factors.
Acknowledgments - The authors wish to thank the NAFOSTED
(Vietnam) for the financial support of this study through the Project
Nr. 104.01-2010.27.

References
[1]
[2]
[3]
[4]
[5]
[6]
[7]
[8]
[9]
[10]
[11]
[12]
[13]
[14]
[15]
[16]
[17]
[18]
[19]
[20]
[21]
[22]
[23]
[24]
[25]
[26]
[27]
[28]
[29]
[30]
[31]
[32]

Dai DN, Hoi TM, Thang TD, Ogunwande IA. (2012) The leaf essential oils of five Vietnamese Desmos species (Annonaceae). Natural Product
Communications, 7, 231-234.
Kessler PJA. (1993) Annonaceae. In The Families and Genera of Vascular Plants. Kubitzki K, Rohwerand JG, Bittrich V (Eds). Springer-Verlag,
Berlin/Heidelberg, Germany, 102-105.
Sichaem J, Ruksilp T, Worawalai W, Siripong P, Khumkratok S, Tip-pyang S. (2011) A new dimeric aporphine from the roots of Artabotrys
spinosus. Fitoterapia, 82, 422-425
Somanawat J, Talangsri N, Deepolngam S, Kaewamatawong R. (2012) Flavonoid and megastigmane glycosides from Artabotrys hexapetalus.
Biochemical Systematics and Ecology, 44, 124-127.
Bordoloi PK, Bhuyan PD, Boruah P, Bordoloi M, Rao PG. (2009) A long chain alkylated -methylene--butyrolactone from Artabotrys
odoratissimus fruit. Phytochemistry Letters, 2, 22-24.
Nguyen TB. (2000) Flora of Vietnam. Vol. 1. Science and Technology Publishing House, Hanoi, Vietnam.
Chaichantipyuth C, Tiyaworanan S, Mekaroonreung S, Ngamrojnavanich N, Roengsumran S, Puthong S, Petsom A, Ishikawa T. (2001) Oxidized
heptenes from flowers of Melodorum fruticosum. Phytochemistry, 58, 1311-1315.
Tuchinda P, Udchachon J, Reutrakul V, Santisuk T, Taylor WC, Farnsworth NR, Pezzuto JM, Kinghorn AD. (1991) Bioactive butenolides from
Melodorum fruticosum. Phytochemistry, 30, 2685-2689.
Sashidhara KV, Singh SP, Kant R, Maulik PR, Sarkar J, Kanojiya S, Kumar, KR. (2010) Cytotoxic cycloartane triterpene and rare isomeric
bisclerodane diterpenes from the leaves of Polyalthia longifolia var. pendula. Bioorganic and Medicinal Chemistry Letter, 20, 5767-5771.
Sashidhara KV, Singh SP, Shukla PK. (2009) Antimicrobial evaluation of clerodane diterpenes from Polyalthia longifolia var. pendula. Natural
Product Communications, 4, 327-330.
Chung-Yi C, Fang-Rong C, Yao-Ching S, Tian-Jye H, Yi-Chen C, Huang-Yi T, Hua-Chien C, Shu-Jen C, Ming-Chu H, Yang-Chang W. (2000)
Cytotoxic constituents of Polyalthia longifolia var. pendula. Journal of Natural Products, 63, 14751478.
Nguyen TC, Thuy LT, Nguyen HD, Thang TD, Dai DN. (2009) Chemical composition of the leaf essential oil of Polyalthia longifolia var. pendula
Hort. from Nghean. Proceedings of the 3rd National Scientific Conference on Ecology and Biological Resources. Agricultural Publishing House,
Hanoi, Vietnam, 930-932.
Porzel A, Lien TP, Schmidt J, Drosihn S, Wagner C, Merzweiler K, Sung TV, Adam G. (2000) Fissistigmatins AD: Novel type natural products
with flavonoid-sesquiterpene hybrid structure from Fissistigma bracteolatum. Tetrahedron, 56, 865-872.
Xu-Dong H, Xiang-Gen Z, Xiang-Hua Z, Yi-Nan Z, Zong-Ping Z, Yu, Z, Wei T, Yang Y, Yi-Fu Y, Li-Hong H, Jian-Ping Z. (2007) 7-(3,4dihydroxyphenyl)-N-[(4-methoxyphenyl)ethyl]propenamide (Z23), an effective compound from the Chinese herb medicine Fissistigma oldhamii
(Hemsl.) Merr, suppresses T cell-mediated immunity in vitro and in vivo. Life Sciences, 81, 1677-1684.
Giang PM, Son PT, Knig WA. (2007) Chemical composition of the flower essential oil of Artabotrys hexapetalus (L. f.) Bhandare of Vietnam.
Journal of Essential Oil Research, 19, 523-524.
Rang DD, Huong HH. (2004) The primary study of the chemical composition of the Artabotrys hexapetalus flower in Ninh Binh Province. Journal
of Science University of Hanoi, Vietnam, 4, 70-73.
Dai DN, Thang TD, Hoi TM, Dung NX. (2010) Chemical constituents of essential oil from Artabotrys vinhensis of Vietnam. Journal of Science
and Technology, Vietnam, 48, 946-950.
Jirovetz L, Buchbauer G, Puschmann Ch, Fleischhacker W, Shafi PM, Abraham GT. (1998) Analysis of the essential oils of Artabotrys
odoratissimus fruits and leaves from South India. Journal of Essential Oil Bearing Plants, 1, 94-103.
Menut C, Bessiere JM, Mve-Mba CE, Affane-Nguema JP. (1992) Aromatic plants of tropical central Africa.VI. The essential oil of Artabotrys
lastourvillensis Pell. from Gabon. Journal of Essential Oil Research, 4, 305-307.
Fournier G, Leboeuf M, Cave A. (1999) Annonaceae essential oils: a review. Journal of Essential Oil Research, 11, 131-142.
Pripdeevech P, Chukeatirote E. (2010) Chemical compositions, antifungal and antioxidant activities of essential oil and various extracts of
Melodorum fruticosum flowers. Food Chemistry and Toxicology, 48, 2754-2758.
Pripdeevech P. (2011) Analysis of the odor constituents of Melodorum fruticosum flower by solid-phase microextraction-gas chromatography-mass
spectrometry. Chemistry of Natural Compounds, 47, 292-294.
Brophy JJ, Goldsack RJ, Forster PI. (2004) The leaf oils of the Queensland species of Melodorum (Annonaceae). Journal of Essential Oil Research,
16, 483-486.
Ogunbinu AO, Ogunwande IA, Essien E, Cioni PL, Flamini G. (2007) Sesquiterpenes-rich essential oils of Polyalthia longifolia Thw.
(Annonaceae) from Nigeria. Journal of Essential Oil Research, 19, 419-421.
Cravo L, Perineau F, Delmas M, Bessiere J.-M. (1991) Chemical composition of the leaf and fruit oil of Polyalthia suaveolens Eng. et Diels.
Journal of Essential Oil Research, 3, 459-461.
Brophy JJ, Goldsack RJ, Forster PI. (2001) Leaf oils of the Australian species of Polyalthia (Annonaceae). Journal of Essential Oil Research, 12, 5-7.
Dai DN, Thang TD, Hoi TM, Nguyen XD. (2009) Chemical composition of the stems essential oil of Fissistigma thorelii (Pierre ex Fin. &
Gagnep.) Merr. from Hatinh. Proceedings of the 3rd National Scientific Conference on Ecology and Biological Resources, Agricultural Publishing
House, Hanoi, Vietnam, 933-937.
Thang TD, Dung NX. (2007) Progress in the study of some Fissistigma species from Vietnam. In Aromatic Plants from Asia their Chemistry and
Application in Food and Therapy, Jirovetz L, Nguyen XD, Varshney VK. (Eds). Har Krishan Bhalla & Sons, Dehradun, India, 119-126.
Vietnamese Pharmacopoeia (1997) Medical Publishing House, Hanoi, Vietnam, 1-134.
Adams RP. (2007) Identification of Essential Oil Components by Gas Chromatography/Quadrupole Mass Spectrometry. Allured Publishing, Carol
Stream. IL, 1-502.
Heller SR, Milne GWA. (1978, 1980, 1983) EPA/NIH Mass Spectral Data Base. U.S. Government Printing Office, Washington, USA.
Joulain D, Koenig WA. (1989) The Atlas of Spectral Data of Sesquiterpene Hydrocarbons. E. B. Verlag, Hamburg, Germany, 1-234.

Natural Product Communications Vol. 8 (2) 2013

Published online (www.naturalproduct.us)

Essential Oil of Flowers of Anaphalis contorta, an Aromatic and Medicinal Plant from India
Rajesh K. Joshi
Composition of Essential Oils from Seeds of Abies koreana
Anna Wajs-Bonikowska, Karol Olejnik, Radosaw Bonikowski and Piotr Banaszczak
Chemical Composition of Hypericum richeri subsp. grisebachii Essential Oil from Croatia
Igor Jerkovi, Maja Marasovi, Zvonimir Marijanovi, Kroata Hazler Pilepi, eljan Male and Mladen Milo
Chemical Composition of the Essential Oils from Two Vietnamese Asarum Species: A. glabrum and A. cordifolium
Tran Huy Thai, Ophlie Bazzali, Tran Minh Hoi, Nguyen Anh Tuan, Flix Tomi, Joseph Casanova and Ange Bighelli
Essential Oils from Five Species of Annonaceae from Vietnam
Tran D. Thang, Do N. Dai, Tran M. Hoi and Isiaka A. Ogunwande
Essential Oils from the Leaves of Six Medicinal Plants of Nigeria
Isiaka A. Ogunwande, Nudewhenu O. Avoseh, Guido Flamini, Alimot-Sadiat O. Hassan, AbdulRazaq O. Ogunmoye,
Akindele O. Ogunsanwo, Kamorudeen O. Yusuf, Atuonwu O. Kelechi, Zainab A. Tiamiyu and Godgift O. Tabowei
Comparative Study on In Vitro Activities of Citral, Limonene and Essential Oils from Lippia citriodora and L. alba on
Yellow Fever Virus
Luz Angela Gmez, Elena Stashenko and Raquel Elvira Ocazionez
TLC-Bioautographic Evaluation of In Vitro Anti-tyrosinase and Anti-cholinesterase Potentials of Sandalwood Oil
Biswapriya B. Misra and Satyahari Dey
Composition, Mosquito Larvicidal, Biting Deterrent and Antifungal Activity of Essential Oils of Different Plant Parts of
Cupressus arizonica var. glabra (Carolina Sapphire)
Abbas Ali, Nurhayat Tabanca, Betul Demirci, K. Husnu Can Baser, Jane Ellis, Sandra Gray, Brett R. Lackey, Christine Murphy,
Ikhlas A. Khan and David E. Wedge
Composition of Cassia fistula Oil and its Antifungal Activity by Disrupting Ergosterol Biosynthesis
Md. Irshad, Aijaz Ahmad, Md. Zafaryab, Farah Ahmad, Nikhat Manzoor, Man Singh and M. Moshahid A. Rizvi
Chemical Composition and Biological Activity of the Essential Oil of Amomum biflorum
Chakkrapat Singtothong, Michel J. Gagnon and Jean Legault
Chemical Composition and Antibacterial Activity of Essential Oils from Myrcia alagoensis (Myrtaceae)
Aline do N. Silva, Ana Paula T. Uetanabaro and Anglica M. Lucchese
Composition, in-vitro Anticancer, and Antimicrobial Activities of the Leaf Essential Oil of Machilus mushaensis from Taiwan
Yu-Chang Su, and Chen-Lung Ho
Chemical Constituents and Cytotoxic Evaluation of Essential Oils from Leaves of Porcelia macrocarpa (Annonaceae)
Erica Biolcati P. da Silva, Alisson L. Matsuo, Carlos R. Figueiredo, Mariana H. Chaves, Patricia Sartorelli and Joo Henrique G. Lago

225
227
231
235
239

243

249
253

257
261
265
269
273
277

Book Review
Medicinal Plants of China, Korea, and Japan: Bioresources for Tomorrows Drugs and Cosmetics by Chritophe Wiart, PharmD, PhD
Stephen Pyne

281

Natural Product Communications

2013
Volume 8, Number 2
Contents
Original Paper

Page

Drimendiol, A Drimane Sesquiterpene with Quorum Sensing Inhibition Activity

Cristian Paz, Gerardo Crcamo, Mario Silva, Jos Becerra, Homero Urrutia and Katherine Sossa
Microbial Transformation of Curcumol by Aspergillus niger
Chen Li-Xia, Zhang Hui, Zhao Qian, Yin Shi-Yu, Zhang Zhong, Li Tian-Xian and Qiu Feng
Chemopreventive Effect of Sarcophine-diol on NOR-1-Induced TPA-Promoted Skin Carcinogenesis in Female HOS:HR-1 Mice
Pawel T. Szymanski, Safwat A. Ahmed, Sherief Khalifa, Harukuni Tokuda, Eiichiro Ichiishi, Akira Iida, Nobutaka Suzuki and
Hesham Fahmy
Carmichaeline A: A New C20-diterpenoid Alkaloid from Aconitum carmichaeli
Shu-hua Li, Jun-ruXiong, Yuan-qin Zhang, Qing-xiang Xiang and Feng-zheng Chen
Steroidal Saponins from Dracaena marginata
Abdelmalek Rezgui, Anne-Claire Mitaine-Offer, David Pertuit, Tomofumi Miyamoto, Chiaki Tanaka, Stphanie Delemasure,
Patrick Dutartre and Marie-Aleth Lacaille-Dubois
Zephgrabetaine: A New Betaine-type Amaryllidaceae Alkaloid from Zephyranthes grandiflora
Deepali Katoch, Dharmesh Kumar, Upendra Sharma, Neeraj Kumar, Yogendra S. Padwad, Brij Lal and Bikram Singh
Antioxidant and Anti-inflammatory Compounds in the Popular Landscape Plant Berberis thunbergii var. atropurpurea
Chuan-Rui Zhang, Robert E. Schutzki and Muraleedharan G. Nair
Two New Amides from Streptomyces michiganensis
Jinghua Xue, Liangxiong Xu, Zi-Hua Jiang and Xiaoyi Wei
Determination of Bioactive Compounds in the Juice of Pummelo (Citrus grandis Osbeck)
Marina Russo, Ivana Bonaccorsi, Germana Torre, Antonella Cotroneo, Paola Dugo and Luigi Mondello
Antiplasmodial Activity of Compounds from the Surface Exudates of Senecio roseiflorus
Leonidah Omosa Kerubo, Jacob Ogweno Midiwo, Solomon Derese, Moses K. Langat, Hosea M. Akala, Norman C. Waters,
Martin Peter and Matthias Heydenreich
Anti-inflammatory, Antioxidant and Cytotoxicity Activities of Methanolic Extract and Prenylated Flavanones Isolated from
Leaves of Eysehardtia platycarpa
Valeri Domnguez-Villegas, Vanessa Domnguez-Villegas, Mara Luisa Garca, Ana Calpena, Beatriz Clares-Naveros and
Mara Luisa Garduo-Ramrez
Phenolic Glycosides from Lindera obtusiloba and their Anti-allergic Inflammatory Activities
Hyun Gyu Choi, Hwa Dong Lee, Sang Hyun Kim, MinKyun Na, Jeong Ah Kim and Seung Ho Lee
Antiproliferative Effects of an Analog of Curcumin in Hep-2 cells: A Comparative Study with Curcumin
Mohankumar Kumaravel, Pajaniradje Sankar, Periyasamy Latha, Chellakan S Benson and Rajagopalan Rukkumani
Antiproliferative Activity of epi-Cercosporin in Human Solid Tumor Cell Lines
ngel Trigos, Csar Espinoza, Maricela Martnez, Olivia Mrquez, Leticia G. Len, Jos M. Padrn, Manuel Norte and Jos J. Fernndez
New Anthraquinone Derivatives from Geosmithia lavendula
Lourin G. Malak, Daoud W. Bishay, Afaf M. Abdel-Baky, Ahmed M. Moharram, Stephen J. Cutler and Samir A. Ross
Pancreatic Lipase Inhibitory Activity of Cassiamin A, a Bianthraquinone from Cassia siamea
Dilip Kumar, Aniket Karmase, Sneha Jagtap, Ruchi Shekhar and Kamlesh K. Bhutani
Antifeedant Activity of Spin-Labeled Derivatives of Deoxypodophyllotoxin against Brontispa longissima Larvae
Gang Feng, Jing Zhang, Liu Yang, Ying-Qian Liu, Zhi-Wei Zhang, Xuan Tian, Qi-An Jin and Zheng-Qiang Peng
Determination of Organic Acids in Salicornia herbacea by Solid-phase Extraction Combined with Liquid Chromatography
Dandan Han, Minglei Tian, Dong Wha Park and Kyung Ho Row
Hypoglycemic Effect of Bumelia sartorum Polyphenolic Rich Extracts
Halliny S. Ruela, Katia C. C. Sabino, Ivana C. R. Leal, Ana M. Landeira-Fernandez, Michelle R. A. de Almeida,
Talita S. M. Rocha and Ricardo M. Kuster
Protoanemonin Content Variation between Clematis spp.: Leaf, Stem and Root
Fangming Jin, Christian Narkowicz and Glenn A Jacobson
Methanolic Extract of Nigella sativa Seed Inhibits SiHa Human Cervical Cancer Cell Proliferation Through Apoptosis
Tarique N. Hasan, Gowhar Shafi, Naveed A Syed, Muhammad A Alfawaz, Mohammed A. Alsaif, Anjana Munshi, Kai Y. Lei and
Ali A. Alshatwi
Glucosinolate Biosynthesis in Hairy Root Cultures of Broccoli (Brassica oleracea var. italica)
Sun-Ju Kim, Woo Tae Park, Md. Romij Uddin, Yeon Bok Kim, Sang-Yong Nam, Kwang Hyun Jho and Sang Un Park
Characterization of Volatile Components of Zingiber roseum Essential Oil Using Capillary GC on Modified Cyclodextrins
VPPalayam S Pragadheesh, Anju Yadav, Manju Singh and Chandan S Chanotiya

Continued inside backcover

147
149

153
155

157
161
165
169
171

175

177
181
183
187
191
195
199
203

207
211

213
217
221