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HONORARY EDITOR
DR. PAWAN K AGRAWAL
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ADVISORY BOARD
PROFESSOR ALEJANDRO F. BARRERO
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University of Granada,
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Gaborone, Botswana Gottingen, Germany
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Universita di Pisa, Bergen, Norway
via Bonanno 33, 56126 Pisa, Italy
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Horinouchi 1432-1, Hachioji, Tokyo 192-0392, Japan
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London WC1N 1AX, UK
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NPC Natural Product Communications
Secondary Metabolites of Eichhornia crassipes (Waterhyacinth): A
Review (1949 to 2011)
Pottail Lalitha, Shubashini.K.Sripathi and Ponnusamy Jayanthi
Department of Chemistry, Avinashilingam Institute for Home Science and Higher Education for Women
University (Estd. u/s.3 of UGC Act 1956), Coimbatore, Tamilnadu, India-641043
jayanthijns@gmail.com
Received: April 25th, 2012; Accepted: July 20th, 2012
Eichhornia crassipes (Mart.) Solms (Waterhyacinth), an aquatic perennial herb present throughout the world, has a myriad of metabolites. Phenalenone
compounds and sterols have been isolated from this plant. Extracts, as well as pure compounds isolated from this plant, have been demonstrated to possess
pharmacological activities. An account of the phytochemistry, pharmacological activities and several applications of waterhyacinth are included in this review.
Keywords: Phytochemicals, Waterhyacinth, Flavonoids, Alkaloids, Phenalenones, Eichhornia crassipes.
Mankind through observation and experience developed knowledge
of the properties of plants as a source of food and medicines [1].
Phytochemicals are as important as synthetic medicines since in
some regions it is the only source of medicine. In the history of
ancient civilizations, the use of medicinal herbs for curing diseases
has been documented. Drugs were used in crude forms as
decoctions, infusions, tinctures and poultices [2]. Phytochemicals
play an important role in the pharmaceutical industry as raw
materials or as a particular drug. Waterhyacinth {Eichhornia
crassipes (Mart.) Solms} is an herbal product [3] rich in
phytochemicals [4-7].
Taxonomy: The English common names of E. crassipes (family
Pontederiaceae; sub-family Trollioideae; tribe Eichhornieae [8])
are waterhyacinth, water hyacinth and water-hyacinth.
Waterhyacinth is the standardized spelling adopted by the Weed
Science Society of America [9] to denote that it is not an aquatic
relative of true “hyacinth” (Hyacinthus spp.), as the two-word
spelling suggests.
Origin, geographical distribution, growth and reproduction of
the plant: Waterhyacinth, a member of the pickerelweed family
(Pontederiaceae) [10], is indigenous to South America, particularly
to the Amazonian basin [11]. Waterhyacinth has invaded freshwater
systems in over 50 countries on five continents and, according to
recent climate change models, its distribution may expand into
higher latitudes as temperatures rise. Waterhyacinth is especially
pervasive throughout Southeast Asia, the South Eastern United
States, Central and Western Africa and Central America [12].
Waterhyacinth grows in all types of freshwater, lentic and lotic. The
plant might be exceptionally productive since it is a warm water
species with submerged roots and aerial leaves like emergent
macrophytes [13]. Plant growth is described in two ways either by
reporting the percentage of water surface covered in a period of
time or by reporting the plant density in units of wet plant mass per
unit of surface area [14]. So, under normal conditions, loosely
packed waterhyacinth can cover the water surface at relatively low
plant density (10 kg/m2 wet weight) and can reach maximum
density of 50 kg/m2 wet weight before growth ceases [15].
2012
Vol. 7
No. 9
1249 - 1256
Growth of waterhyacinth depends on various ecological factors.
The chief limiting factors for regular plant growth and development
are the ability of the plant to use solar energy, the nutrient
composition of the water, cultural methods, environmental factors
[16], salinity, temperature, nutrients, disturbance, natural enemies
[17], and pH levels [18]. Waterhyacinth can tolerate salinity up to
1.3-1.9 ppt and even below 1ppt [19]. The plant grows fast at
temperatures from 20 to 30C, but growth fully stops at
temperatures from 8 to 15C [20]. It can withstand near freezing
temperature (<5C) for a limited period, but exhibits a steady
decline in regrowth potential [21]. Efficient intake of calcium,
magnesium, sulfur, iron, manganese, aluminum, boron, copper,
molybdenum, zinc, nitrogen, phosphorus and potassium favors its
growth over other aquatic species [22]. Nitrogen and phosphorus
levels are the most important limiting factors.
Waterhyacinth reproduces in both a generative and vegetative way.
Seeds generally germinate within six months, with dry conditions
promoting germination. It commonly forms dense, interlocking
mats due to its rapid reproductive rate and complex root structure
[23].
Contemporary scenario of waterhyacinth: The rapid spread of
the plant leads to the formation of mat-like coverage of fresh
waterways. The effect of waterhyacinth on phytoplankton,
zooplankton, macroinvertebrates, fish and birds is deleterious [12].
Skin rash, cough, malaria, encephalitis, bilharzia, gastro intestinal
disorders and schistosomiasis are common among the people near
water bodies infested by waterhyacinth. Socio-economic impacts of
waterhyacinth are multi-faceted. Fishing, boating, irrigation,
municipal water supply [24], and navigation [18] are greatly
affected. Control measures taken to prevent the growth of
waterhyacinth are difficult and hence measures are taken to
minimize the plant density to the extent that economic and
environmental effects are reduced. The mechanical, physical and
chemical methods used to control waterhyacinth have their own
advantages and constraints and even more long term results are not
obtained in any of the methods. The cost incurred with these control
measures is also enormous. In contrast, waterhyacinth can be
harvested mechanically and used in a way beneficial to society.
1250 Natural Product Communications Vol. 7 (9) 2012
However, although waterhyacinth is considered as the world’s
worst aquatic weed, there are areas where this plant finds uses and
in some areas it still remains unexplored.
Phytochemicals in waterhyacinth: Waterhyacinth possesses
nutritionally important compounds like phenolics, flavonoids,
glutathione [18] and many other metabolites. The chemical
composition of waterhyacinth from different geographic regions is
found to vary [19]. The protein [19], hemicellulose, cellulose,
lignin, and magnesium contents have been documented [25].
Phenolic compounds: Phenolic compounds are a large and diverse
group of molecules, which include many different families of
aromatic secondary metabolites in plants. Specialised phenol cells
[26] contain p-hydroxybenzoic, ferulic, chlorogenic, protocatechuic,
vanillic, p-coumaric [27] and o-hydroxy phenols [28]. Phenolic
compounds are detected in the leaves [29, 30], methanol extract
[22, 31], aqueous extract [32] and ethyl acetate extract [33] of
waterhyacinth. 4-Methylresorcinol, 2-methylresorcinol, catechol,
pyrogallol, and genetisic, p-hydroxybenzoic, syringic, vanillic and
salicylic acids have been detected by TLC in the ethanolic shoot
extract, whereas 4-methylresorcinol, 2-methylresorcinol, resorcinol,
catechol, and genetisic and salicylic acids were present in rhizomes
[34]. 1(2,4-Dihydroxyphenyl)2(4-methoxy-3-nitrophenyl)ethanone
was identified in the ethanol extract by GC-MS [35]. A
benzoindonic compound, 2,5-dimethoxy-4-phenyl-benzoindenone
(1), a red oily metabolite isolated from waterhyacinth, inhibits the
growth of the fungus Candida albicans [6]. Phenalene metabolites
(2-5) [7] and permethylated derivatives of ten aromatic metabolites
with the phenalene skeleton (2-11) [36] were isolated from the ethyl
acetate extract of waterhyacinth. Compounds 2-5 inhibited the
growth of the freshwater alga Porphyridium aerugineum [7].
2-Hydroxy-8-(4-hydroxyphenyl)-phenalen-1-one (12) and 2-
hydroxy-8-(3,4-dihydroxyphenyl)-phenalen-1-one (13) have been
isolated from the acetone extract of roots and leaves of
waterhyacinth [37]. The structures of certain compounds isolated
from waterhyacinth by Greca et al were revised based on 2D-NMR
analysis and found to be 4,8,9-trimethoxy-1-phenyl-2,3-dihydro-
1H-phenalene, 4,8,9-trimethoxy-1-(4΄ methoxyphenyl)-2,3-dihydro-
1H-phenalene, 4,4΄΄,8,8΄΄,9,9΄΄-hexamethoxy-1,1΄΄-diphenyl-2,2΄΄,
3,3 -tetrahydro-7,7 -bi(1H-phenalene), and 6,6΄΄,8,8΄΄,9,9΄΄,4΄,4΄΄΄-
΄΄ ΄΄
octamethoxy-1,1΄΄ diphenyl-2,2΄΄,3,3΄΄-tetrahydro-7,7΄΄-bi(1H-phena-
lene) (14-18) [38]. Compounds 2, 19-21 were isolated from the
ethyl acetate extract by column chromatography [39].
Six new phenylphenalenes (22-27) and several known compounds
(28-31) were isolated from the ethyl acetate fraction of the methanol
extract of waterhyacinth [40]. The phenalenes, sterols and
dimethylesters isolated are listed in Figure 1.
Flavonoids: The presence of flavonoids in waterhyacinth [32,41]
makes it an attractive source of antioxidants. Flavonoids are present
in the light petroleum and aqueous extracts [33]. The presence of
apigenin, tricin, chrysoeiol, azaeleatin, gossypetin and luteolin in
the shoot and rhizome of the plant was confirmed by paper
chromatography [42] and TLC [43], whereas kaempferol, orientin
[42], quercetin, isovitexin, and kaya flavone [43] are also present in
the shoot and rhizome. The ethanol extract contains 4H-pyran4-
one,2,3-dihydro-3,5-dihydroxy-6-methyl [35]. The aqueous extract
showed the presence of anthocyanins [33]. From the purple flowers,
[6-m-O-{delphinidin 3-O-(6 m-O-(β-D-glucopyranosyl)-β-D-
glucopyranosyl)}], and [6-m-O-{apigenin 7-O-(β-D-gluco-
pyranosyl)}] malonate were extracted with 5% acetic acid [44].
Lalitha et al.
Tannins: Tannins are present in the methanol and aqueous extracts
of waterhyacinth [31,32,41]. The plant detritus and decayed
materials after cutting or herbicide application release tannin-like
compounds [26].
Alkaloids: Phytochemical investigation of the plant showed the
presence of alkaloids in waterhyacinth [31,32,33,45]. Qualitative
separation of alkaloids by TLC revealed that cytisine and tomatine
are present both in the shoot and rhizome, whereas codeine,
thebaine and quinine are present in the shoot, and the rhizome
contains nicotine [46]. GC-MS analysis of the methanol extract of
waterhyacinth showed the presence of 18,19-secoyohimban-19-oic
acid, and 16,17,20,21-tetradehydro-16-(hydroxymethyl)-methyl
ester [22,47], whereas pipradrol, and 1H-pyrrole,1-phenyl were
detected in the ethanol extract [35].
Terpenoids: Terpenoids were detected in various extracts of
waterhyacinth [22,31,32,33]. 3,7,11,15-Tetramethyl-2-hexadecen-1-
ol and phytol were identified in the ethanol extract by GC-MS [35].
Growth regulating substances, indole compounds and gibberellins
were separated from the roots of the plant [48, 49]. Carotene was
extracted from waterhyacinth by different methods. A maximum
yield of 85.3% was attainable when extractions were made by direct
heating over a water bath employing high-boiling petroleum [50],
but a much more economic and environmentally benign method
was developed giving a better yield by a simple process [51].
Sterols: Sterols are present in various extracts of waterhyacinth
[31-33]. From the ethyl acetate extract, 4-methyl-5-ergosta-
8,14,24(28)-triene-3,4-diol (32), 4-methyl-5-ergosta-8,24(28)-
diene-3,4-diol (33), and 4-methyl-5-ergosta-7,24(28)-diene-
3,4-diol (34) were isolated [52], whereas campesterol,
stigmasterol and -sitosterol were detected in the sterol mixture
isolated from the acetone extract [53]. 6-Hydroxystigmata-4, 22-
dien-3-one (35), a novel steroid, has also been isolated [54].
Glycosides: Glycosides [45], in particular cardiac glycosides [32],
were reported in the chloroform and aqueous extracts of the shoot,
respectively. Monogalactosyldiglycerides and digalactosyl-
diglycerides are the major glycolipids. Phospholipids found in the
roots, leaf stalks and flowers are respectively phosphatidylcholine,
phosphatidylglycerol and phosphatidylethanolamine. The major
fatty acids in the roots, leaf stalks, leaves and flowers are palmitic
and linoleic, linoleic, palmitic, linolenic and linoleic, respectively
[55]. Stigmatic exudates of waterhyacinth contain the soluble
sugars, fructose, sucrose, and free fatty acids [56]. Analysis of the
polysaccharide revealed that the heteropolysaccharide of
waterhyacinth is composed of D-xylose, L-galactose and L-
arabinose [57].
A galactomannan and a branched (13)--D-glucan were isolated
from waterhyacinth. The galactomannan, purified from the cold
water extract, is composed of D-galactose and D-mannose in a ratio
of 1.0:2.8. It has a (14)-linked D-mannose backbone, with one
out of three D-mannose residues being substituted with a single -
D-galactosyl unit. The branched (13)-β-D-glucan isolated from
the hot water extract has a main chain composed of β-(13)-linked
D-glucopyranosyl residues, and two single β (16)-D-glucopy-
ranosyl groups attached as side chains to, on average, every 5 sugar
units of the main chain. In addition, the branching of the β-glucan
occurs regularly at O-6 of the β-(13)-linked backbone [58]. In
the water soluble sugars isolated from water hyacinth, the predomi-
nant ones were galactose, glucose, xylose and arabinose [59].
Review on some aspects of Waterhyacinth Natural Product Communications Vol. 7 (9) 2012 1251

OMe OMe OMe

O OMe OMe OMe
OMe O
OMe OMe OMe OMe OMe
OMe OMe OMe OMe
MeO OMe
OMe OMe
OMe MeO MeO MeO
OMe OMe OMe MeO
(1) (2) (3) (4) (5) (6) (7)

MeO MeO MeO MeO

OH
OMe
O
MeO OMe
OMe MeO MeO OMe
OMe OMe
OMe OMe OMe OMe OMe
OMe
OMe MeO OMe

MeO MeO MeO MeO MeO MeO MeO MeO

HO
(8) (9) (10) (11) (12)
MeO OMe

MeO OMe MeO OMe OMe

OH
O MeO MeO MeO OMe
OMe
MeO MeO OMe
MeO

MeO OMe MeO OMe

HO MeO OMe MeO OMe MeO

HO MeO MeO MeO MeO

(13) (14) (15) (16) (17) (18)

OMe

CO2Me MeO
CO2Me
O HO O HO
CO2Me OMe H HO

HO OH OH OH OMe

MeO OMe MeO MeO MeO MeO

(19) (20) (21) (22) (23) (24)
O O
OMe O OMe
OH
O OH O
HO HO OMe HO O
Ph
OMe OMe
OH OMe
MeO
MeO OMe OH HO OH
(25) (26) (27) (28) (29) (30) (31)
C10H19
OMe

O
HO HO HO COOMe
OH OH OH OH MeOOC
(32) (33) (34) (35) (36)
OMe
OMe

OMe OMe
MeO
OMe OMe
OMe

COOMe COOMe COOMe COOMe

MeO MeOOC MeOOC MeOOC MeOOC
(37) (38) (39) (40)
Figure 1: 1, 2,5-dimethoxy-4-phenyl-benzoindenone; 2, 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one (lachnanthtocarpone red dimethyl ether); 3, 4,9-dimethoxy-7-phenyl-2,3-dihydrophenalen-1-
olo-O-methyl ether; 4, 4,9-dimethoxy-7-(4’-methoxy-phenyl)-2,3-dihydro-phenalen-l-olo-O-methyl ether; 5 4,5-dimethoxy-9-phenyl-2,3-dihydro-phenalen-1-ol-O-methyl ether; 6, dimer of
phenalene; 7, dimer of phenalene; 8, dimer of phenalene; 9 dimer of phenalene; 10, dimer of phenalene; 11, dimer of phenalene; 12, 2-hydroxy-8-(4-hydroxyphenyl)-phenalen-1-one; 13, 2-
hydroxy-8-(3,4-dihydroxyphenyl)-phenalen-1-one; 14, 4,8,9-trimethoxy-1-phenyl-2,3-dihydro-1H-phenalene; 15, 4,8,9-trimethoxy-1-(4΄ methoxyphenyl)-2,3-dihydro-1H-phenalene; 16,
4,4΄΄,8,8΄΄,9,9΄΄-hexamethoxy-1,1΄΄-diphenyl-2,2΄΄,3,3΄΄-tetrahydro-7,7΄΄-bi(1H-phenalene); 17, 4,4΄΄,8,8΄΄,9,9΄΄,4΄,4΄΄΄- octamethoxy-1,1΄΄-diphenyl-2,2΄΄,3,3΄΄-tetrahydro-7,7΄΄-bi(1H-phenalene); 18,
6,6΄΄,8,8΄΄,9,9΄΄,4΄,4΄΄΄-octamethoxy-1,1΄΄ diphenyl-2,2΄΄,3,3΄΄-tetrahydro-7,7΄΄-bi(1H-phenalene); 19, dimethyl 3-(4 -methoxyphenyl)naphthalene-1,8-dicarboxylate; 20, methyl 5-methoxy-2-phenyl-8-
(3,7,10-trimethoxy-6-phenyl-5,6-dihydro-4H-phenaleno[2,1-b]furan-9-yl)-1-naphthoate; 21, 2,3-dihydro-4,9- dihydroxy-8-methoxy-1-phenylphenalene; 22, 2,3-dihydro-3,9-dihydroxy-5-methoxy-
4-phenyl-1H-phenalen-1-one; 23, 2,3-dihydro-8-methoxy-9-phenyl-1H-phenalene-1,4-diol; 24, 2,3-dihydro-4,8-dimethoxy-9-phenyl-1H-phenalen-1-ol; 25, 2,3-dihydro-9-(4-hydroxyphenyl)-8-
methoxy-1H-phenalene-1,4-diol; 26, 2,6-dimethoxy-9-phenyl-1H-phenalen-1-one; 27, 7-(4-hydroxyphenyl)-5,6-dimethoxy-1H-phenalen-1-one; 28, 2-hydroxy-9-(4-hydroxyphenyl)-1H-phenalen-
1-one; 29, 5,6-dimethoxy-7-phenyl-1H-phenalen-1-one; 30, 2-hydroxy-8-(4-hydroxyphenyl)-1H-phenalen-1-one; 31, methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (methyl ferulate); 32,
4-methyl-5-ergosta-8,14,24(28)-triene-3,4-diol; 33, 4-methyl-5-ergosta-8,24(28)-diene-3,4-diol; 34, 4-methyl-5-ergosta-7,24(28)-diene-3,4-diol; 35, 6-hydroxystigmata-4,22-
dien-3-one; 36, 2-phenyl-5-methoxy-1,8-naphthalenedicarboxylic acid dimethyl ester; 37, 2-(p-methoxyphenyl)- 5-methoxy-1,8 naphthalenedicarboxylic acid dimethyl ester; 38, 2-phenyl-6-
methoxy-1,8-naphthalenedicarboxylic acid dimethyl ester; 39, 2-phenyl-1,8-naphthalene dicarboxylic acid dimethyl ester linked at C-5 to a phenalenol; 40, 1,8-naphthalene dicarboxylic acid
dimethyl ester linked at C-5 to a phenalenol.
1252 Natural Product Communications Vol. 7 (9) 2012
α-Cellulose present in waterhyacinth [60-62] was etherified with
chloroacetic acid in a solvent medium giving carboxymethyl
cellulose [63]. Enzymatic hydrolysis of waterhyacinth yielded 10.7
mg of reducing sugars per 100 mg pretreated biomass in a 24 h
reaction. Although roots contain large amounts of polysaccharides,
such as cellulose and hemicellulose, they generated less
monosaccharides than the leaves [64].
Treatment of shoot and root biomass of waterhyacinth with NaOH
and CS2 yielded alkali-treated straw and cellulose xanthogenate,
respectively. Alkali treatment removes most of the lignin and
hemicellulose from the raw plant material, whereas the formation of
cellulose xanthogenate introduces new CS and O–CS–S functional
groups [65].
Other Metabolites: Resins [41] are present in waterhyacinth.
Saponin in chloroform and methanol extracts [45,31], and
anthroquinone in the chloroform extract [55] of waterhyacinth were
observed. The aqueous extract of waterhyacinth shoot contains
phlobatannin, quinone, anthraquinone and cardiac glycosides,
whereas phlobatannin and cardiac glycosides are absent in the
rhizome [32].
Cyclic voltammetric and titration methods show the presence of
ascorbic acid in waterhyacinth. By the cyclic voltammetric method
the yield was 10.2%, and by the titrometric method, 16.3 mg/100 g
[66]. Ascorbic acid (AA), iso-ascorbic acid and dehydroascorbic
acid was detected in the ethanol and light petroleum extracts of the
shoot, whereas only dehydroascorbic acid was present in the
rhizome. Quinones, such as 7-methyljuglone, rhein and aloe-emodin
were found in the shoot, whereas aloe-emodin was present in the
rhizome [67].
Acid extracts of waterhyacinth contain carbohydrates, and aqueous
extracts show the presence of proteins. Quinones and anthocyanins
have been noted in the acid extract. Anthraquinones are present in
all extracts except the light petroleum. The ethanol fraction of the
aqueous extract contained proteins [33].
Pectin was prepared from waterhyacinth in high yield by extracting
dried waterhyacinth with water, then ammonium oxalate and
subsequently with HCl followed by NaOH to give pectin yields of
25.1%, 39.4% and 10.7%, respectively vs 12.5%, 11.7% and 7.6%,
respectively using undried waterhyacinth [68].
The tissues of waterhyacinth contain many air-filled intercellular
spaces, which soak up water, but are also tough as a result of fibers,
which contains sharp needles of calcium oxalate [69].
Surface waxes from the chloroform extract of waterhyacinth leaves
yield olefins. The alkanes separated from the waxes through column
chromatography were identified by means of gas chromatography
[70].
Five 1,8-naphthalenedicarboxylic acid dimethyl esters (36-40) were
isolated from the acidic portion of the ethylacetate extract. An
oxidative process might transform phenylphenalenones into
phenylnapthalic acid and a subsequent hydrolysis of these
compounds might give phenyl-1,8-naphthalene dicarboxylic acid
[71].
Crushing, and alkaline treatment at high temperature, enzymatic
hydrolysis and fermentation of waterhyacinth yields 2,3-butanediol.
Prefermentation hydrolysis followed by combined hydrolysis and
fermentation has been found to be more efficient than combined
Lalitha et al.
hydrofermentation and separate hydrolysis fermentation, yielding
15g of 2,3-butanediol per 100 g of plant [72]. Roots of
waterhyacinth extracted successively with solvents of increasing
polarity viz. diethyl ether, acetone and ethyl acetate showed the best
antialgal activity. -D-dehydrated pyranose, pelargonic acid,
isocyanoethyl acetate, 2,2-dimethyl cyclo pentanone, and propane
amide isolated from the acetone extract by column chromatography
showed inhibitory activity against algae [73].
Leaves, stems and roots of the plant contains humic acids, which
play an important role in water retention, metal and organic solute
binding functions, and texture/workability in soils [74]. Acid-
catalyzed hydrolysis of waterhyacinth yields levulinic acid at higher
sulfuric acid concentrations, but propionic acid at lower
concentrations [75].
Waterhyacinth oil contains both phenethyl alcohol and benzyl
alcohol. These substances are found in many essential oils and have
a variety of uses [76]. The presence of N1-acetyl-N2-formyl-5-
methoxykynuramine and its precursor melatonin [77], which are
potent free radical scavengers, assist plants in coping with harsh
environmental insults [78]. The S- and R-enantiomer of fipronil in
waterhyacinth was detected by HPLC. Fipronil-sulfone and
fipronil-sulfide, the metabolites of fipronil, were detected by GC–
MS to show the main metabolic pathway of fipronil in
waterhyacinth [79]. The acetone extract yielded N-phenyl-2-
naphthylamine, linoleic acid and glycerol-1,9-12 (ZZ)-
octadecadienoic ester. These compounds possess antialgal and
antialgal activities, with that of N-phenyl-2-naphthylamine being
greater than that of the common algicide CuSO4 [80].
Pharmacological aspects
Antimicrobial activity: Many researchers have evaluated the
antimicrobial activity of various extracts of the plant. The methanol
extract and its fractions showed antimicrobial (bacterial and fungal)
and anti-algal activities (green microalgae and cyanobacteria) using
the paper disc diffusion bioassay. The crude extract, as well as all
five TLC fractions, exhibited antibacterial activity against both the
Gram-positive: Bacillus subtilis and Streptococcus faecalis; and
Gram-negative bacteria: Escherichia coli and Staphylococcus
aureus. Growth of Aspergillus flavus and A. niger were not
inhibited by either waterhyacinth crude extract or its five fractions.
In contrast, Candida albicans (yeast) was inhibited by all. Anti-
algal activity of the crude extract and its fractions manifested
against the green microalgae Chlorella vulgaris and
Dictyochloropsis splendid, as well as the cyanobacteria Spirulina
platensis and Nostoc piscinale. High anti-algal activity was only
recorded against Chlorella vulgaris. Analyses showed the presence
of an alkaloid and four phthalate derivatives that exhibited the
antimicrobial and anti-algal activities [22].
The methanolic extract of waterhyacinth showed significant
reduction in the growth of Aspergillus niger [81], whereas it did not
show any inhibition of the growth of the fungus Colletotrichum
graminicola [82]. Significant antimicrobial activity was reported of
the ethanol, methanol and aqueous extracts of the roots and leaves
of waterhyacinth tested against different bacterial and fungal stains.
Among the extracts, the aqueous extract showed better activity, that
of the leaves being higher than that of the roots [83].
Antimicrobial assay was performed against 11 different human
pathogenic bacteria and 7 phytopathogenic fungi. The methanolic
fraction showed the greater antibacterial activity, while the water
fraction obtained by cold percolation showed comparably better
results against different fungi [84].
Review on some aspects of Waterhyacinth
Waterhyacinth extract showed activity against Staphylococcus
aureus, Escherichia coli, Penicillium and Aspergillus niger, but the
activity depended on pH, concentration and action time [85]. The
pharmacognostical details of the root and rhizome viz. macro and
microscopical studies, along with preliminary phytochemical tests
and fluorescence analysis have been reported [86]. The methanolic
extract of waterhyacinth showed activity against Alternaria
alternata, Aspergillus flavus, Fusarium oxysporum, Rhizoctonia
solani, and Xanthomonas compestries [87].
Antioxidant activity: Waterhyacinth displays effective antioxidant
activity and the glutathione content of the plant was 32 ± 1.6 nmol
per gram of dry hyacinth leaves, which corresponds to ca. 3.2 nmol
per gram of fresh leaves [88]. The ethanol extract contains higher
amounts of polyphenols [6.68 mg gallic acid equivalents (GAE)/g]
in the leaf than in the stem (4.37 mg GAE/g). Waterhyacinth also
contains higher contents of flavonoids [1524 and 453 mg rutin
equivalents per gram of leaf and stem, respectively]. Accordingly,
both the leaf and stem have high reducing power [118.3 and 47.2
10μg ascorbic acid equivalents per gram, respectively] and DPPH
radical scavenging capability (74.6% for leaf and 62.7% for stem)
[89].
Eichhornia crassipes exposed to various concentrations of Ag, Cd,
Cr, Cu, Hg, Ni, Pb and Zn hydroponically for 21 days showed
increases in the activity of catalase, peroxidase and superoxide
dismutase, and there was differential inducement among the metals.
Overall, Zn had the least inducement of the antioxidant enzymes in
Eichhornia crassipes and Pistia stratiotes, while Hg had the highest
inducement [90].
Waterhyacinth at a dose of 50% ethanol extract was observed to be
most effective in the treated rats and reduced the arsenic
accumulation in liver, spleen, kidney, intestine, lungs and skin.
Besides, it reduced the oxidative stress caused by arsenic as is
evident by decreased levels of malondialdehyde (MDA) in the
above organs [3].
The reducing power of light petroleum, ethyl acetate, acetone and
hydrolyzed extracts of waterhyacinth determined by the ferricyanide
method showed that the extracts possess good antioxidant activity
[91]. The aqueous and methanol fractions assessed for their
reducing power showed an increase in absorbance with increase in
concentration of the extract [92]. The reducing power of the
aqueous extract by the ferricyanide method revealed the potential
antioxidant activity of the extract [93]. The reducing power of the
aqueous extract and fractions – ethanol, aqueous, methanol and
aqueous- of waterhyacinth evaluated for their reducing power
capability at five different concentrations showed increasing
absorbance and this was related to their high antioxidant capacity
[94]. The DPPH scavenging assay of the light petroleum, acetone,
ethyl acetate, aqueous, and hydrolyzed extracts, and fractions
showed that the hydrolyzed extract has good DPPH scavenging
activity [95].
The antioxidant activity of n-hexane, ethyl acetate and methanol
extracts by both DPPH and ABTS methods revealed that the
activity is concentration dependent. In the DPPH assay, the ethyl
acetate extract showed greater activity than the methanol and n-
hexane extracts, whereas in the ABTS assay the methanol extract
recorded the higher activity. The crude methanolic extract showed
higher activity than its fractions [47]. The antioxidant activity of
waterhyacinth by the DPPH scavenging method showed appreciable
activities and this was attributed to the presence of hydroxyl groups
and unsaturated bonds in the structure of the compounds [96].
Natural Product Communications Vol. 7 (9) 2012 1253
Wound healing activity: The methanolic extract of waterhyacinth
leaves in the form of an ointment, at two different concentrations
(10% and 15%, w/w of leaf extract in a simple ointment base) were
investigated for their wound healing potential in an excision
experimental model of wounds in rats. The treatments showed better
wound contraction ability that was significantly greater than that of
the control [97]. Incision wound healing carried out on the ethyl
acetate and aqueous extracts also showed good activity, as
confirmed by studies in our laboratory.
Antitumor activity: A methanolic leaf extract of waterhyacinth
(50%) at different doses (200 mg/kg body weight to 500 mg/kg
body weight) showed good response against B16F10 in vivo
melanoma tumor bearing hybrid mice models (from Swiss albino
female and C57BL male) [98]. The crude extract compared with all
isolated compounds showed better activity against several tumor
types. Some fractions exhibited selective anticancer activity against
a liver cancer cell line, while other fractions exhibited high
anticancer activity against hormone dependent tumor types (cervix
and breast cancers). The potency of the crude extract compared to
its fractions has been attributed to the auto-synergistic effect of
these fractions within the same extract [96].
Larvicidal activity: Chironomus ramosus Chaudhuri eggs and
larvae subjected to varying concentrations of crude root extracts of
E. crassipes (final concentrations 0.25–2.5%) showed 100%
efficiency [99]. The acetone extract had moderate feeding deterrent
and toxic activities towards third instar larvae of two lepidopteran
pests, the tobacco cut worm, Spodoptera litura Fab. and the castor
semilooper, Achaea janata L. (Noctuidae: Lepidoptera) [100].
Putative cytokinin glucoside-like activity was detected only in
leaves and flowers. The cytokinin complements of the leaves and
the roots were qualitatively different. Cytokinins supplied by the
roots are metabolized in the leaves, and certain cytokinins are
synthesized in the leaves themselves [101]. Larvicidal, pupicidal
and repellent activity carried out on the light petroleum, ethyl
acetate, and aqueous extracts, and methanol and ethanol fractions
against Culex quinquefasciatus in our laboratory showed good
activity.
Waterhyacinth as adsorbate: Waterhyacinth efficiently removes a
vast range of pollutants, from suspended materials, nutrients and
organic matter to heavy metals [102,103] and pathogens [16].
Other potential uses of waterhyacinth: Waterhyacinth can be
effectively used to improve the livelihood of many people either for
harvesting the plant or in other ways where it can be effectively
utilized. Waterhyacinth can be used in agriculture as a fertilizer,
feed [104], biomanure [105], a protein source for animal and
possibly human nutrition, and as fiber for ruminants [69], and for
energy production [29]. It is also used for the preparation of high
caloric fuel (HCF) [106], cogeneration of H2 and CH4 [107], and
liquid fuels [108]. Waterhyacinth fiber is also used as a filler in the
manufacture of natural rubber (STR20), where it increases the
hardness and modulus of the products [109].
The elaboration of a wide variety of phytochemicals from
waterhyacinth, their significant pharmacological activity, and the
large scale harvesting for other utilities render the plant of potential
importance. Phytochemicals present in the plant indicates relevance
to large scale harvesting, chemical modification, and utilization. If
some useful compounds could be isolated from waterhyacinth,
which is considered a threat to the environment and economy, it
could be harvested and constructively used. Though there are many
1254 Natural Product Communications Vol. 7 (9) 2012 Lalitha et al.

works citing the use of this plant in bioremediation and energy
production, the plant has been exploited only to a certain extent in
terms of its phytochemicals. Based on this review, the economic
impact of waterhyacinth is huge as it involves both the control of
growth and the problem caused by the plant on the ecosystem. So,
harvesting of waterhyacinth could be effectively utilized by either
extracting the compounds from the plant or by producing fortified
products enriched with the extracts, or by use in the pharmaceutical
industry. The wound healing property of the plant extract could be
examined so that the plant can be exploited based on its medicinal
properties. The project sanctioned by DRDO-LSRB, Ministry of
Defence, Government of India aims at the isolation of compounds
of commercial importance from waterhyacinth.
Acknowledgments - The financial support of DRDO-LSRB is
acknowledged and the authors thank Avinashilingam Institute for
Home Science and Higher Education for Women University, Estd.
u/s UGC Act of 1956, Coimbatore, Tamil Nadu, India for providing
necessary facilities to carry out this work.

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 Natural Product Communications Vol. 7 (9) 2012
Published online (www.naturalproduct.us)

Plant Growth Inhibitor from the Malaysian Medicinal Plant Goniothalamus andersonii and Related Species
Tomoko Takemura, Tsunashi Kamo, Raihan Ismil, Baki Bakar, Naoya Wasano, Syuntaro Hiradate and Yoshiharu Fujii 1197
Furanone Derivatives from Terrestrial Streptomyces spp.
Muhammad Arfan, Khaled A. Shaaban, Anja Schüffler and Hartmut Laatsch 1199
Cytotoxicity Analysis of Active Components in Bitter Melon (Momordica charantia) Seed Extracts Using
Human Embryonic Kidney and Colon Tumor Cells
Elizabeth S. Chipps, Renuka Jayini, Shoko Ando, April D. Protzman, M. Zubayed Muhi, M. Abdul Mottaleb, Ahmed Malkawi
and M. Rafiq Islam 1203
Phytochemical and Biological Studies on Some Egyptian Seaweeds
Khaled N. M. Elsayed, Mohamed M. Radwan, Sherif H. M. Hassan, Mohamed S. Abdelhameed, Ibraheem B. Ibraheem, and Samir A. Ross 1209
Electrochemical Characterization of the Marine Antioxidant Gadusol
Ernesto Maximiliano Arbeloa, Cristina Luján Ramírez, Raúl Ariel Procaccini and María Sandra Churio 1211
Insecticidal Properties of Annonaceous Acetogenins and Their Analogues. Interaction with Lipid Membranes
Lilian Di Toto Blessing, Juan Ramos, Sonia Diaz, Aída Ben Altabef, Alicia Bardón, Margarita Brovetto, Gustavo Seoane and
Adriana Neske 1215
Activity of Alkanediol Alkanoates against Pathogenic Plant Fungi Rhizoctonia solani and Sclerotium rolfsii
Paraj Shukla, Suresh Walia, Vivek Ahluwalia, Balraj S. Parmar and Muraleedharan G. Nair 1219
A Somaclonal Variant of Rose-Scented Geranium (Pelargonium spp.) with Moderately High Content of
Isomenthone in its Essential Oil
Swaroop S Kulkarni, Nagawara S Ravindra, Kalavagunta V N S Srinivas and Raghavendra N Kulkarni 1223
Comparative Study of the Chemical Composition of Essential Oils of Five Tagetes Species Collected in Venezuela
Kaylin Armas, Janne Roja, Luis Rojas and Antonio Morales 1225
Chemical Composition and Antiphytoviral Activity of Essential Oil of Micromeria graeca
Elma Vuko, Valerija Dunkić, Nada Bezić, Mirko Ruščić and Dario Kremer 1227
Chemical Composition and Biological Activity of the Essential Oil from Jamaican Cleome serrata
Megil J. McNeil, Roy B. R. Porter and Lawrence A. D. Williams 1231
Chemical Compositions and Biological Activities of Amomum subulatum Essential Oils from Nepal
Prabodh Satyal, Noura S. Dosoky, Brittany L. Kincer and William N. Setzer 1233
Chemical Composition and Antimicrobial Activity of Salvia x jamensis Essential Oil
Daniele Fraternale, Guido Flamini, Angela Bisio, Maria Cristina Albertini and Donata Ricci 1237
Antimicrobial and Antioxidant Activities of Stachys lavandulifolia subsp. lavandulifolia Essential Oil and its Infusion
Gökalp İşcan, Betül Demirci, Fatih Demirci, Fatih Göger, Neşe Kırımer, Yavuz B. Köse and Kemal Hüsnü Can Başer 1241
Composition, Anticancer, and Antimicrobial Activities in vitro of the Heartwood Essential Oil of Cunninghamia lanceolata
var. konishii from Taiwan
Yu-Chang Su, Kuan-Ping Hsu, Eugene I-Chen Wang and Chen-Lung Ho 1245

Review/Account
Secondary Metabolites of Eichhornia crassipes (Waterhyacinth): A Review (1949 to 2011)
Pottail Lalitha, Shubashini.K.Sripathi and Ponnusamy Jayanthi 1249
 Natural Product Communications
2012
Volume 7, Number 9
Contents
Original Paper Page

Catalytic and Molecular Properties of Rabbit Liver Carboxylesterase Acting on 1,8-Cineole Derivatives
María del H. Loandos, Ana C. Muro, Margarita B. Villecco, Marcelo F. Masman, Paul G.M. Luiten, Sebastian A. Andujar,
Fernando D. Suvire and Ricardo D. Enriz 1117
Antiparasitic and Anticancer Carvotacetone Derivatives of Sphaeranthus bullatus
Francis Machumi, Abiy Yenesew, Jacob O. Midiwo, Matthias Heydenreich, Erich Kleinpeter, Babu L. Tekwani, Shabana I. Khan,
Larry A. Walker and Ilias Muhammad 1123
Naturally Occurring Limonene to Cinnamyl-type γ-Butyrolactone Substituted Aldol Condensation Derivatives as
Antioxidant Compounds
Pushpinder Kaur, Pralay Das, Abha Chaudhary and Bikram Singh 1127
Sesquiterpenes from Onopordum illyricum and their Antifeedant Activity
Sergio Rosselli, Antonella Maria Maggio, Marisa Canzoneri, Monique S. J. Simmonds and Maurizio Bruno 1131
Three New Lactarane Sesquiterpenoids from the Mushroom Russula sanguinea
Yasunori Yaoita, Moe Hirao, Masao Kikuchi and Koichi Machida 1133
Royleanumin, a New Phytotoxic neo-Clarodane Diterpenoid from Teucrium royleanum
Shabir Ahmad, Muhammad Arfan, Naheed Riaz, Riaz Ullah, Ziarat Shah and Azhar Ul-Haq Ali Shah 1137
Bioactive-guided Identification of Labdane Diterpenoids from Aerial Parts of Aristeguietia glutinosa as
anti-Trypanosoma cruzi agents
Javier Varela, María L. Lavaggi, Mauricio Cabrera, Alejandra Rodríguez, Patricio Miño, Ximena Chiriboga, Hugo Cerecetto and
Mercedes González 1139
Characterization of Yew Tree (Taxus) Varieties by Fingerprint and Principal Component Analyses
Kalle Truus, Merike Vaher, Maria Borissova, Marju Robal, Tuuli Levandi, Rando Tuvikene, Peeter Toomik and Mihkel Kaljurand 1143
Identification of Triterpenes from Milkweed (Asclepias syriaca)
Erzsébet Háznagy-Radnai, Edit Wéber, Szilvia Czigle and Imre Máthé 1147
Evaluation of the Anti-angiogenic Activity of Saponins from Maesa lanceolata by Different Assays
Kenn Foubert, Annelies Breynaert, Mart Theunis, Rita Van Den Bossche, Guido R. Y De Meyer, André Van Daele,
Ahmad Faizal, Alain Goossens, Danny Geelen, Edward M. Conway, Arnold Vlietinck, Luc Pieters and Sandra Apers 1149
Conversion of Protopanaxadiol Type Saponins to Ginsenoside Rg3 by Lemon
Cheng-Peng Sun, Wei-Ping Gao, Bao-Zhong Zhao and Le-Qin Cheng 1155
Triterpene Glycosides from the Sea Cucumber Eupentacta fraudatrix. Structure and Biological Activity of
Cucumariosides B1 and B2,Two New Minor Non-Sulfated Unprecedented Triosides
Alexandra S. Silchenko, Anatoly I. Kalinovsky, Sergey A. Avilov, Pelageya V. Andryjaschenko, Pavel S. Dmitrenok,
Ekaterina A. Martyyas and Vladimir I. Kalinin 1157
Osteoclastogenesis Inhibitory Effect of Ergosterol Peroxide Isolated from Pleurotus eryngii
Satoru Yokoyama, Tran Hai Bang, Kuniyoshi Shimizu and Ryuichiro Kondo 1163
A Novel Sterol Sulfate and New Oligosaccharide Polyester from the Aerial Parts of Polygala sibirica
Yue Lin Song, Si Xiang Zhou, He Lin Wei, Yong Jiang and Peng Fei Tu 1165
Angustinine – A New Benzopyridoquinolizine Alkaloid from Alangium lamarckii
Mumu Chakraborty and Sibabrata Mukhopadhyay 1169
Antifungal Activity of Hydrochloride Salts of Tylophorinidine and Tylophorinine
Mini Dhiman, Rajashri R. Parab, Sreedharannair L. Manju, Dattatraya C. Desai and Girish B. Mahajan 1171
Evaluation of Antibacterial and Anti-biofilm Activities of Cinchona Alkaloid Derivatives against Staphylococcus aureus
Malena E. Skogman, Janni Kujala, Igor Busygin, Reko Leino, Pia M. Vuorela and Adyary Fallarero 1173
Simultaneous Determination of Alkaloids and Flavonoids from Aerial Parts of Passiflora Species and
Dietary Supplements using UPLC-UV-MS and HPTLC
Bharathi Avula, Yan-Hong Wang, Chidananda Swamy Rumalla, Troy J. Smillie and Ikhlas A. Khan 1177
Chemical Fingerprinting by RP-RRLC-DAD and Principal Component Analysis of Ziziphora clinopodioides from
Different Locations
Shuge Tian, Qian Yu, Lude Xin, Zhaohui Sunny Zhou and Halmuart·Upur 1181
Simultaneous Determination of Four Major Constituents of Semen Vaccariae Using HPLC-DAD
Haijiang Zhang, Wei Yao, Yunyun Chen, Peipei He, Yao Chen, Peipei Chen, Jia Han and Xiaoyu Li 1185
Biological Activity of Isoflavonoids from Azorella madreporica
Luisa Quesada, Carlos Areche, Luis Astudillo, Margarita Gutiérrez, Beatriz Sepúlveda and Aurelio San-Martín 1187
Analysis of Homoisoflavonoids in Caesalpinia digyna by HPLC-ESI-MS, HPLC and Method Validation
Somendu K. Roy, Amit Srivastava and Sanjay M. Jachak 1189
Oligonol-induced Degradation of Perilipin 1 is Regulated through Lysosomal Degradation Machinery
Junetsu Ogasawara, Kentaro Kitadate, Hiroshi Nishioka, Hajime Fujii, Takuya Sakurai, Takako Kizaki, Tetsuya Izawa,
Hitoshi Ishida and Hideki Ohno 1193
Continued inside backcover