D
Journal of Pharmacy and Pharmacology 2 (2014) 1-18
DAVID
PUBLISHING
An Overview of Entada phaseoloides: Current Research
and Future Prospects
Chandana Choudhury Barua1, Mousumi Hazorika1 and Jyoti Misri2
1. Department of Pharmacology and Toxicology, Assam Agricultural University, Guwahati, Assam 781022, India
2. Department of Animal Health, ICAR, Krishi Anusandhan Bhavan (Pusa), New Delhi 110001, India
Received: September 22, 2013 / Accepted: November 25, 2013 / Published: February 28, 2014.
Abstract: In recent times, focus on plant research and herbal products has increased tremendously in the western world as well as in
developed and developing countries. Entada phaseoloides, a well-known creeper widely used therapeutically in the orient and has
become increasingly popular as an important medicinal plant. Many studies have been carried out on this medicinal plant and have
generated immense data about the morphology, chemical composition, corresponding to biological activity of extracts and isolated
secondary metabolites. Biological studies and traditional clinical practice demonstrated that Entada phaseoloides and its bioactive
compounds possess various pharmacological properties. The plant has been traditionally used in Ayurvedic medicine for centuries as
an anti-inflammatory, analgesic, antipyretic, antiarthritis, antidiabetic, antioxidant, cytotoxic, antimicrobial and molluscidal agent.
The present review summarizes current knowledge on morphology, major bioactive(s) constituents and its chemistry, reported
medicinal properties, pharmacological actions, folklore uses and the possibility of interactions of the herb with the conventional
drugs. Despite this, further investigations are required to explore Entada phaseoloides and to evaluate the different biological
activities of either its extracts or the isolated compounds with probable modes of action.
Key words: Entada phaseoloides, morphology, bioactive constituents, folklore uses.
1. Introduction
Throughout the ages, humans have traditionally
relied on plants, animals and minerals for their basic
needs, such as food, protection against enemies,
hunting, and healing of infections and health disorders.
A number of traditional medicinal systems have
evolved that have been used for centuries and today,
are still a source of interesting drugs for
phytotherapy [1]. Nature always stands as a gold
mark to exemplify the outstanding phenomenon of
symbiosis [2, 3]. Interest in the use of herbal products
has grown dramatically in the western world [4] as
well as in developed countries [5]. The herbal vendors
are the mobile men seen on the busy streets of many
Indian cities selling crude medicinal plants and its
Corresponding author: Chandana Choudhury Barua, Ph.D.,
professor, research fields: Pharmacology and toxicology.
E-mail: chanaicn@gmail.com.
products. They prescribe herbal treatment for several
diseases, a skill they inherited from their forefathers
through several generations of experience [6]. One of
the important medicinal plants, widely used
therapeutically in the orient and becoming
increasingly popular is Entada phaseoloides, a creeper,
of genus Entada which consists of 30 species of trees,
shrubs and tropical lianas. About 21 species are
known from Africa, six from Asia, two from the
American tropics and one with a pan tropical
distribution [7]. Entada phaseoloides is a very large
woody climber belonging to Order Fabales, Family
Fabaceae or Leguminosae, Subfamily Mimosoideae
and Tribe of Mimoseae. Botanical name is Entada
phaseoloides (L.) Merril [8]. Synonyms of Entada
phaseoloides is Entada scadens (L.) [9], Lens
phaseoloides L. [10] and is commonly known as
Matchbox Bean, Vine, Gogo, Elva Climber, etc. [11].
2
An Overview of Entada phaseoloides: Current Research and Future Prospects
In India, the species is widely distributed in the
eastern Himalayas, East Bengal, Tirupati (Andhra
Pradesh) etc. [12]. In the folklore of Indian medicine,
the herb has been used traditionally in various
diseases as analgesic, counter irritant, hair growth
stimulant, emetic and remedy for cerebral
haemorrhage. This comprehensive review summarizes
our current knowledge of the major bioactivities and
clinical efficacy of Entada phaseoloides as one of the
currently used popular herbal plant. The popularity of
Entada phaseoloides as a medicinal plant can be best
determined by the number of papers published per
year over a period of time which is presented in Fig. 1
[13-41]. We aim to derive an impressive and
convenient review; scientifically beneficial for both
investigators and readers who are interested in the
pharmaceutical aspects of medicinally active herbs.
However, it was not the intention of this review to go
beyond the field of phytochemistry and ethnobotany.
2. Morphology
The woody creeper Entada phaseoloides with all its
parts stem, leaves, leaves with flowers, flowers, fruits
and fruit with seed are presented in Figs. 2a-2f,
respectively [8].
Stem diameters measures up to 18 cm, laterally
compressed or flattened and twisted like a corkscrew.
Vessels are large, readily visible to the naked eye in
transverse sections. Pith is located eccentrically much
closer to one margin than the other in stem cross sections.
Leaves are bipinnate with about 8-16 leaflets, (two
to four leaflets on each secondary axis) main rhachis
projecting as a branched tendril beyond the leaf.
Leaflet blades measure about (4-11) × 2.5-5.5 cm,
while leaflet stalks are of about 0.1-0.7 cm long and are
transversely wrinkled.
y= 0.021 x + 0.3907
R2 = 0.0166
y = 0.013 x - 0.1886
R2 = 0.1437
Fig. 1 Popularity of Entada phaseoloides over time.
Plots of numbers of papers mentioning Entada phaseoloides (filled column histogram and left hand axis scale) and line of best fit,
1926 to 2006 (complete line, with equation and % variation accounted for, in box on the left hand side); plots of a proportional micro
index, derived from numbers of papers mentioning Entada phaseoloides as a proportion (scaled by multiplying by one million) of the
total number of papers published for that year (broken line frequency polygon and right hand scale) and line of best fit, 1926 to 2006
(broken line, with equation and % variation accounted for, in broken line box on the right hand side).
An Overview of Entada phaseoloides: Current Research and Future Prospects
(a)
(c)
(e)
3
(b)
(d)
(f)
Fig. 2 (a) Stem bark & stem transverse section; (b) Entada leave (10 mm); (c) Entada leaves & flowers; (d) Entada fruit; (e)
Entada seed; (f) Entada fruit & seeds.
4
An Overview of Entada phaseoloides: Current Research and Future Prospects
Stipules are linear and falcate which measures 2-4 ×
2 mm. Scattered large clear glands are visible to the
naked eye in the leaflet blades, whereas numerous
smaller glands can be visible with a lens.
Flowers are more or less cup-shaped, about 1.5 mm
in diameter at the apex. Corolla is pink to red in colour
and cream or translucent in colour on the inner surface.
Petals are about 3 × (1-1.5) mm. Staminal filaments
crumpled in the bud which are of about 6-7 mm long at
anthesis. Style crumpled in the bud.
Fruits are flattened, about (88-100) × (9-12) cm,
constricted at intervals and divided into about 12
segments, each segment measures about 7 × (9-10) cm,
surrounded by endocarp and falling from the pod
leaving only the sutures of the pod attached to the vine.
Exocarp shed by rolling up into rolls of tissue.
Endocarp is not hard but more or less leathery or like
parchment.
Seeds are laterally compressed, about 5-6 cm in
diameter and 1-1.5 cm thick. Testa is hard. Cotyledons
are hard, about (4.5-5.5) × (4.5-5) cm in diameter
which fused around the margin. Radicle measures
about 4 mm long [11].
3. Distribution and Ecology
It is distributed in the altitudinal range from near
sea-level to 100 m. The plant grows in beach forest,
gallery forest, monsoon forest and lowland rain forest
and also occurs in New Guinea and other parts of
Malaysia, Asia and the Pacific islands [11]. The plant
occurs throughout the sub-Himalayan tract, from
Nepal eastwards ascending to 4,000 ft. in Sikkim, in
Assam, Bihar and Orissa, and in the monsoon forest of
western and eastern ghats; it is abundant in Andaman
Islands [42]. Also found in forests at low and medium
altitudes, from Northern Luzon (Cagayan) to
Mindanao and Palawan [43].
4. Natural History
Entada phaseoloides is a food plant for the larval
stages of the tailed green-banded blue butterfly [44].
This species may have medicinal properties and has
been used as a fish poison. The species has been used
medicinally in Malaysia, the Philippines and Java. The
seed are considered as tonic, emetic and anthelmintic [42].
5. Properties
The seeds of Entada phaseoloides are slightly
bitter-acrid in taste and mildly cooling in nature. It
was
reported
as
antirheumatic,
relieving
gastrointestinal disorders and aids circulation. The
juice extracted from the bark was reportedly found to
be irritating to the eyes, causing conjunctivitis. Entada
phaseoloides was also found to exhibit detectable
genotoxicity [11].
6. Utility and Edibility
Bark, seeds and vines were usually the utilized parts
of Entada phaseoloides. The vines may be collected
during any time of the year, rinse, section into slices,
steamed and lastly sundried. The seeds may be
collected from January to April. Seed coats are
removed and roasted in a frying pan, sun-dried and
pulverized. In the Dutch Indies, young leaves are
eaten, raw or cooked. In Bali and Sumatra, the seeds
are eaten while in South Africa, pod and seeds are
used as coffee substitute [11]. The white kernels of the
seeds are eaten by the poor, after soaking in water and
roasting to remove toxic principles. Roasted pods are
occasionally used as substitute for calabar bean. The
seeds, stems and barks are poisonous. The leaves are
reported to be free from the toxic saponins which are
present in other parts of the plant. They are eaten by
elephants [42].
7. Folkloric Uses
Dried vine materials of about 15 g to 30 g in
decoction are reported to be effective in rheumatic
lumbar, leg pains, sprains and contusions. Powdered
seeds of about 3 g to 9 g when taken orally with water
can cure jaundice and edema due to malnutrition. In
abdominal pains and colic, the pound kernels of seeds
An Overview of Entada phaseoloides: Current Research and Future Prospects
after mixing with oil can be applied as poultice onto
affected area. The paste of seed is used as
counterirritant and applied to glandular swellings in
the axilla, loins and joints, and swollen hands and feet.
It is also used as hair growth stimulant. Seeds are used
as emetic. It is used as febrifuge. In South Africa,
seeds are used by infants to bite on during their
teething period. Also, used as remedy for cerebral
hemorrhage. As a treatment of skin itches, the affected
part is washed with a decoction of the bark of Entada
phaseoloides. Stem macerated in cold water used as
cleansing soap and also used as an emetic [11].
8. Local Application
The seeds of Entada phaseoloides used extensively
in the Philippines and other oriental countries for
washing the hair. Also it is an ingredient of hair tonics.
The bark is soaked in water until soft, the fibers are
spread, the juice is expressed by rubbing the fibers
against each other until it lathers, which is then used
to cleanse the scalp. Bark is used as cordage. In
Europe, it is used for tinder and for making match
boxes. Large pods and seeds were used by children as
playthings. In Sunda Islands, a fatty oil extracted from
the seeds is used as an illuminant. In Europe, seeds
were reportedly used for snuff [11]. The saponins
have a strong haemolytic action on human red blood
5
cut. The bark fibre, which is coarse but durable, is used
for cordage and nets. The hard and smooth-shelled
seeds are used for burnishing pottery, polishing
hand-made paper and crimpling linen. The seeds are
hollowed out and employed in making trinkets and
small receptacles e.g., snuff and tinder boxes [42].
9. Constituents and Chemistry
9.1 Saponin
Entada phaseoloides yields saponin which is
reported to be abundant in the bark, less so in the
wood, plentiful in the seeds, and absent from the leave [43],
a crystalline saponin isolated from seed kernels of
Entada phaseoloides, which have the tentative
empirical formula C45H82O27. Acid hydrolysis yields a
crystalline sapogenin C30H48O5 which appears to be
identical with entagenic acid, together with arabinose
and xylose [33], the chemical formula of saponin [46],
sapogenin [47], entagenic acid, arabinose and xylose
are presented in Figs. 3a-3e, respectively [48].
9.2 Phaseoloidin
The structure of phaseoloidin isolated from the
seeds of Entada phaseoloides has been determined as
homogentisic acid 2-O-β-D-glucopyranoside by
chemical and spectral means [34], whose chemical
formula is presented in Fig. 4 [48].
cells. A sharp fall in blood pressure was observed in
experimental animals after doses of saponins varying
9.3 Amides
from 0.0005-0.002 g/kg of body weight; the fall was
Entadamide A [35] and Entadamide B [36], the two
new sulfur-containing amides, isolated from the seeds
of Entada phaseoloides which were synthesized by
the addition reaction of methanethiol to propiolic acid
followed by condensation with ethanolamine by the
use of dicyclohexylcarbodiimide. These compounds
inhibited the 5-lipoxygenase activity of RBL-1 cells at
10-4 g/mL. This finding suggests that entadamides A
and B may be examples of a new type of
anti-inflammatory drug [37]. Entadamide B was
characterized by spectroscopic methods as
N-(2-hydroxyethyl)-3,3-bis(methylthio) propaneamide
associated with an increase in the volume of the
intestines and, to a lesser extent, of the kidneys; there
was no fall in blood pressure in animals which had
received atropine [42, 45]. The saponins are reported
to have a depressant effect on the respiratory system
and inhibit the movements of unstriped muscles of the
intestines and the uterus. Entagenic acid has antifungal
activity against phytopathogenic fungi. A glycoside of
entagenic acid possesses antineoplastic activity. The
oil is used in lamps for illuminating purposes. A
potable watery fluid exudes from the fresh stem when
6
An Overview of Entada phaseoloides: Current Research and Future Prospects
(a)
(b)
(c)
(d)
(e)
Fig. 3 (a) Chemical structure of the saponinl; (b) Chemical structure of the sapogenin; (c) Chemical structure of the
entagenic acid; (d) Chemical structure of the arabinose; (e) Chemical structure of the xylose.
phaseoloides together with entadamide A. Entadamide
C, the sulphoxide form of entadamide A, is called as
(R)-(+)-trans-N-(2-hydroxyethyl)-3-methylsulphinylpr
openamide. Chemical synthesis of (±)-entadamide C
was achieved in three steps from propiolic acid [21].
The chemical formula of Entadamide C is presented
Fig. 4
Chemical structure of phaseoloidin.
and was synthesized in two steps from propiolic acid [37].
The chemical formula of Entadamide A [49] and
Entadamide B [50] are presented in Figs. 5a and 5b,
respectively.
Entadamide C, a third new sulphur-containing
amide, has been isolated from the leaves of Entada
in Fig. 5c [51]. Again four sulfur-containing amide
compounds were isolated from the n-BuOH-soluble
fraction
and
identified
as
entadamide
A-β-D-glucopyranosyl-(1→3)-β-D-glucopyranoside
(Compound 1), which is a new compound along with
and entadamide A (Compound 2), entadamide
A-β-D-glucopyranoside (Compound 3) and clinacoside
An Overview of Entada phaseoloides: Current Research and Future Prospects
7
(a)
(b)
(c)
Fig. 5 (a) Chemical structure of entadamide A; (b) Chemical structure of entadamide B; (c) Chemical structure of the
entadamide C.
C (Compound 4). Compound 4 is isolated from the
genus Entada for the first time. The chemical formula
of Compound 1, Compound 2, Compound 3 and
Compound 4 are presented in Figs. 6a-6d, respectively
[52].
9.4 Glycosides
Three
new
compounds,
2-hydroxy-5-butoxyphenylacetic
acid,
2-β-D
glucopyranosyloxy-5-butoxyphenylacetic acid, and
entadamide A-β-D-glucopyranoside, in addition to the
new natural product 2,5-dihydroxyphenylacetic acid
methyl ester isolated and characterized from seeds of
Entada phaseoloides collected in Indonesia. None of
these compounds was found to demonstrate
significant cytotoxicity for cultured human cancer
cells, but 2-hydroxy-5-butoxyphenylacetic acid and
2,5-dihydroxyphenylacetic acid methyl ester gave
ED50 values of 1.01.7 μg mL-1 and 1.7 μg mL-1,
respectively, with cultured P-388 cell [39].
9.5 Chalcone Glycosides
Two
new
chalcone
glycosides4'-O-(6″-O-galloyl-β-D-glucopyranosyl)-2',
4
dihydroxychalcone
(1)
and
4'-O-(6″-O-galloyl-β-D-glucopyranosyl)-2'-hydroxy-4
methoxychalcone (2) together with one known
chalcone
glycoside
4'-O-β-d-glucopyranosyl-2'-hydroxy-4-methoxychalco
ne (3) isolated from the stems of Entada phaseoloides.
The structures of the new compounds were elucidated
on the basis of extensive spectroscopic analysis,
including HSQC (heteronuclear single quantum
correlation spectroscopy), HMBC (heteronuclear
multiple bond correlation spectroscopy), 1H-1H COSY
(1H-1H correlation spectroscopy), and chemical
evidences. This was the first report of chalcone-type
compounds isolated from the genus Entada. The
chemical structure of three isolated compounds, i.e.,
Compound 1, Compound 2 and Compound 3 are
presented in Fig. 7 [53].
9.6 Glucosides
The phytochemical investigation of the defatted
seeds of Entada phaseoloides Merill. (Mimosaceae) led
to the isolation of three new phenolic acid glucosides,
Fig. 6 The chemical structures of four sulphur containing amides, i.e., Compound 1, Compound 2, Compound 3 and
Compound 4.
An Overview of Entada phaseoloides: Current Research and Future Prospects
8
Fig. 7
The chemical structures of three chalcone glycosides, i.e., Compound 1, Compound 2 and Compound 3 .
which
were
characterized
as 2-hydroxy-5methylbenzoyl-β-L-glucopyranoside[p-cresotyl
glucoside, 1(first phenolic acid glucosides)],
2-hydroxy-5-methylbenzoy
l-β-L-glucopyranosyl
(2→1)-β-glucopyranosyl(2→1)-β-L-glucopyranoside
[p-cresotyltriglucoside, 2( second phenolic acid
glucosides)],
and
2-hydroxybenzoyl-β-Lglucopyranosyl(2→1)-β-L-gluc
opyranosyl(2→1)-β-L-glucopyranosyl(2→1)-β-L-gluc
opyranoside (salicylic acid tetraglucoside, 5( fifth
phenolic acid glucosides)], along with sucrose and
triglucoside. The structures of these phytoconstituents
have been established on the basis of spectral data
analysis and chemical reactions [54].
9.7 Sulphur-Containing Glucoside
One new and one known sulphur-containing
glucoside from a MeOH extract, along with four new
triterpene saponins containing N-acetylglucosamine in
their sugar chains were isolated from the
1-BuOH-soluble fraction of a H2O extract of kernel
nuts of Entada phaseoloides (L.) Merrill [55].
9.8 Flavonoids
The
compound
5,6,7,5'-Tetramethoxy-3',
4'-methylene dioxy flavones monohydrate (systematic
name:
5,6,7-trimethoxy-2-(7-methoxy-1,3-dihydro-2-benzof
uran-5-yl)-4H-chromen-4-onemonohydrate),
was
isolated from the popular Chinese medicinal plant
Entada phaseoloides. In the crystal, inversion-related
molecules are joined by pairs of weak C-H O
hydrogen bonds. The dimers are further
interconnected by a bridging water molecule via weak
C-H Owater and pairs of (O-H)water O hydrogen
bonds into a linear tape running parallel to the b axis [56].
9.9 Antioxidants
The EtOH extract of the stems of Entada
phaseoloides displayed potent antioxidant activity
when
assessed
by
the
1,1-diphenyl-2-picrylhydrazyl(DPPH)
and
2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)
(ABTS)
radical-scavenging,
reducing
power,
β-carotene-bleaching
and
superoxide
radical-scavenging assays. Fractionation of the ethanol
(EtOH) extracts showed that the ethyl acetate (AcOEt)
fraction is the most active, which inhibited the linoleic
acid oxidant to the greatest extent, had the strongest
DPPH and ABTS radical-scavenging abilities, and
possessed significant reducing power over other
fractions followed by the H2O fraction, while BuOH
(butanol) fraction was least active. Further
activity-guided fractionation studies on the active
An Overview of Entada phaseoloides: Current Research and Future Prospects
fractions resulted in the isolation of 22 compounds,
i.e.,
3,4‟,7-trimethylquercetin
(1),
5-hydroxy-3,4‟,7-trimethoxyflavone
(2)
[57],
quercetin (3), (þ)-3,3‟,5‟,5,7-pentahydroxyflavanone
(4) [58], luteolin (5), (þ)-dihydrokaempferol (6) [58],
dehydrodicatechin A (7) [59], apigenin (8),
(_)-epicatechin
(9), (þ)-catechin
(10)
[60],
3-deoxysappanchalcone (11) [61], naringenin (12),
rhamnocitrin (13), 4‟,7-dihydroxyflavone (14) [62],
protocatechuic acid (15), vanillic acid (16),
4‟,5,7-trihydroxy-3‟-methoxyflavonol
(17)
[63],
galangin
(18),
rutin
(19),
3‟,5,5‟,7-tetrahydroxyflavanone
(20)
[64],
2‟,5,5‟-trihydroxy-3,4‟,7-trimethoxyflavone-2‟-O-b-dglucoside (21) [65] and (_)-epigallocatechin (22) [60]
were confirmed by comparing their HPLC, HPTLC,
and characteristic spectroscopic data with those of the
standards or with those reported in the literature. The
Fig. 8
9
chemical structures of the isolated compounds are
presented in Fig. 8. The identities of these compounds
were established based on extensive spectroscopic
studies. Furthermore, the antioxidant activities of the
isolated compounds were evaluated by using the
above-mentioned
five
assays.
The
results
demonstrated that the EtOH extract of E. phaseoloides
stems exhibit an excellent antioxidant activity and
thus presents a great potential as a source of natural
antioxidants. The antioxidant activity of EtOH extract
and three fractions from stem of E. phaseoloides are
presented graphically in Fig. 9. This is claimed to be
the first extensive study of all compounds from E.
phaseoloides and genus Entada by the author [66].
9.10 Crude and Processed Products
The chemical constituents of the Entada
phaseoloides (L.) Merrill were studied by extracting it
Chemical structures of isolated compounds 1-22 from the stems of Entada phaseoloides.
An Overview of Entada phaseoloides: Current Research and Future Prospects
Scavenging ratio (%)
ANT (%)
Equivalent Trolox Amount (mg/mg)
EC50 (µg/mL)
10
Fig. 9 The antioxidant activity of EtOH extract and three fractions from the stems of Entada phaseoloides. (a) DPPH and
ABTS radical-scavenging assays; (b) Reducing power; (c) β-carotene-linoleate and superoxide radical-scavenging assays.
with 70% ethanol at room temperature. Isolation and
purification were performed by silica gel,
reversed-phase silica gel column chromatography and
semi-preparative HPLC. Structures of the pure
compounds were established on the basis of spectral
analysis [46]. A novel method established and the
results were compared for HPLC fingerprint
determination of crude and processed products of E.
phaseoloides (L.) Merrill. HPLC-ESI-MS was
introduced to analyze the common peaks in each batch
of crude E. phaseoloides (L.) Merrill. Sixteen
characteristic peaks were found in crude E.
An Overview of Entada phaseoloides: Current Research and Future Prospects
phaseoloides samples and twenty-one common peaks
existed in processed E.phaseoloides samples. Nine
characteristic peaks of which were identified by
comparison of the retention time and their molecular
weights of chemical standards, most of which were
identified belong to triterpenoid saponins and
glucosides. After processing, the chemical composition
of the extraction with solution of 60% methanol from
crude E. phaseoloides are found to be less or more
similar to that of processed E. phaseoloides, and the
changes in the main peaks of fingerprint
chromatography suggest that HPLC can be used to
reflect the difference of chemical composition of E.
phaseoloides and their processed products. As per their
report, it would be an efficient way for qualitative
control of E. phaseoloides [67].
11
83% of the total fatty acid recovered. The kernel
exhibited high trypsin and chymotrypsin inhibitor
activities (96.65 mg TI g−1 and 30.02 CIU mg-1 sample
respectively) in addition to containing phenolics,
phytic acid, lectins and oligosaccharides. Another
major toxic constituent was identified as a group of
triterpenoid saponins (3.21%), which had high HeU
(haemolytic activity) against cattle erythrocytes and
caused high mortality in fish. The in vitro digestibility
of the kernel protein was low (67%) [40].
10. Pharmacological Activity
10.1 Anti-inflammatory and Analgesic Activities
On the basis of various previous study models,
saponins obtained from Entada phaseoloides, was
reported to have significant anti-inflammatory activity
9.11 Nutrients
and specifically the saponin from seed kernels of
The physical characteristics of pods and seeds,
proximate composition, different protein fractionation,
SDS-PAGE analysis of proteins, amino acid
Entada phaseoloides, was reported to have significant
activity against Walker 256 carcinosarcoma in rats [33].
Anti-inflammatory
activity
of
saponin
was
composition, starch content, fatty acid profiles and
explained in the study of methanolic extract of Entada
various
Entada
phaseoloides seeds in animal models of inflammation
phaseoloides Merrill were also studied. The pod length
where the LD50 was found to be more than 5,000
and the number of seeds per pod ranged from 55 cm to
mg/kg in acute oral toxicity testing. Pre-treatment with
90 cm and from 5 to 11 respectively. The kernel was
the extract (400 mg/kg) reduced carrageenan induced
rat paw edema at 3rd hour compared to control group
anti
metabolic
substances
of
found to be comprised of 66.1% of the seed weight
(18.41 ± 1.14 g). The seed kernels contained 256.7 g
kg
−1
crude protein, 108.1 g·kg
−1
−1
lipid, 27.3 g·kg
of rats. Dose dependent (100, 200 and 400 mg/kg)
ash
reduction in inhibition of granuloma formation of
and a high content of carbohydrate (585.7 g·kg ). The
cotton pellet granuloma, exudate volume, and total
levels of potassium, phosphorus, zinc and iron were
similar to those in conventional pulses. Among the
leukocyte count was observed with the extract. The
−1
different protein fractions of seed kernels, albumins
extract inhibited acetic acid induced writhing dose
dependently (40, 80 and 120 mg/kg) but was found
constituted the major storage proteins (69.7%). The
inactive in reducing the pain produced by thermal
kernel proteins were rich in essential amino acids,
injury. C-reactive proteins were absent in extract
particularly sulphur-containing amino acids, and their
treated group. The results indicated that extract
possesses weaker acute but strong sub-acute
values appeared to be higher than the FAO/WHO
(1990) reference protein for a 2-5-year-old growing
child and soybean, and comparable to hen egg. Seed
anti-inflammatory activity and strong peripheral
kernel lipids contained high levels of unsaturated fatty
analgesic activity. The results also suggested that the
extract may act on the “proliferative phases of
acids, oleic and linoleic acids, which accounted for
inflammation” [68].
An Overview of Entada phaseoloides: Current Research and Future Prospects
12
In another study of anti-inflammatory effect of
topical application of different formulations of seed
pulp
of
EP
(Entada
phaseoloides),
localized
inflammatory reaction were developed in all the rats in
24 h. In control group, there was no resolution of
swelling even in 21 days. Both EP formulations
showed significant (P < 0.001) anti-inflammatory
activity as compared to that of control. Entada
phaseoloides ointment was equi-effective to that of
diclofenac sodium on 12th day. Its paste was
significantly (P < 0.05) found to be more effective
than diclofenac sodium on 21st day. Both the
formulations of Entada phaseoloides were found to
Drug treatment was given topically according to
groups for 14 days. Animals were observed for joint
inflammation and gait. Joint histopathology was
studied and scored. Swelling and redness of left knee
was seen in all rats within 24 h which subsided
gradually. Lame to gait and thickening of the joint
capsule was seen only in control rats.
Histopathologically, osteoarthritic changes were
significantly less in drug-treated groups compared to
control. As a result, both the formulations of EP were
found be effective in preventing the damage to the
joint [70].
10.3 Antidiabetic and Hypolipidemic Activities
have anti-inflammatory activity, but the paste was
significantly more effective than Diclofenac
[69].
sodium
On the basis of previous study, the TSEP (Total
Saponin from Entada phaseoloides) was reported to
dramatically reduce the fasting blood glucose and
10.2 Anti Arthritic Activity
serum insulin levels and alleviated hyperglycemia
The effect of two formulations of Entada
phaseoloides seeds after topical application in
“monoiodoacetate-induced osteoarthritis” in rats was
studied since arthritis is a very common clinical
condition affecting both sexes and all ages. Most
common forms of arthritis are osteoarthritis and
rheumatoid arthritis. In all types of arthritis pain,
inflammation and functional restriction are the
presenting manifestation. Anti-inflammatory drugs like
NSAIDs, corticosteroids and disease-modifying
antirheumatic drugs, etc. are used for symptomatic
relief, but many times they are associated with adverse
effects that can often be as difficult to manage as the
disease itself. Therefore, a need exists for new ways to
treat these patients. The effect of topical application of
two formulations of EP (Entada phaseoloides) seeds
was studied in the MIA (monoiodoacetate-induced
osteoarthritis) model in rats. Both the paste and
ointment formulations of EP were tested on 32 Wistar
rats weighing 150-200 g, divided into four groups as (I)
vehicle, (II) EP paste, (III) EP ointment and (IV)
diclofenac ointment. Osteoarthritis was induced by
intra articular injection of 50 μL of MIA solution.
associated oxidative stress in T2DM (type 2 Diabetes
mellitus) rats. Moreover, a significantly hypolipidemic
effect and an improvement in tissue steatosis were
observed
after
TSEP
administration.
Further
investigations revealed a possible anti-inflammation
effect of TSEP by examining serum levels of IL-6
(interleukin-6), TNF-α (tumor necrosis factor-alpha)
and CRP (C-reactive protein). The effects of TSEP
exhibited a dose-dependent manner and were
comparable to metformin. Both hypoglycemic and
hypolipidemic activities of TSEP in T2DM rats
supported its anti-diabetic property. TSEP exerted its
therapeutic
effect
through
repressing
chronic
inflammation responses [71].
In another experimental model, the anti-diabetic
effects of AcOEt (Ethyl acetate), Pet ether
(Petroleum-ether) and Chloroform fractions were
investigated from the methanolic extract of seeds of
Entada phaseoloides in AIDM (alloxan induced
diabetic mice). The effect of these fractions (200 mg/kg
body weight i.p) was observed on FBG (fasting blood
glucose) level and active fraction was further
investigated for its dose dependent activity (250 mg/kg
An Overview of Entada phaseoloides: Current Research and Future Prospects
and 350 mg/kg body weight) on fasting blood glucose
level and also on TC (total cholesterol), TG
(triglyceride), SGOT (serum glutamate oxaloacetate
transaminases) and SGPT (serum glutamate pyruvate
transaminases) level in AIDM which showed
significant effects. The most significant reduction of
FBG level of around 72.02% was observed for Et-Ac
fraction in AIDM. A significant reduction (*p < 0.05) in
serum TC and TG level of 53.00% and 57.25%
respectively was also found for Et-Ac fraction of E.
Phaseoloides. The hypoglycemic and hypolipidemic
activities were comparable to metformin HCl (150
mg/kg). In diabetic mice, SGOT and SGPT levels were
significantly elevated that were further reduced after
intraperitoneal administration of this fraction. These
results indicated AcOEt fraction of E. Phaseoloides
have favourable effects in bringing down the severity of
diabetes together with hepatoprotectivity [72].
In another study, to observe the effect of TSEP
(total saponins from Entada phaseoloides) on islet
morphology and skeletal muscle PI3K pathway-related
protein expression of type 2 diabetic rats, the type 2
diabetic rats were induced by high-fat diet and
low-dose streptozotocin and then randomly divided
into 5 groups, i.e., the normal control, the model group,
the positive control drug (200 mg·kg-1 metformin), the
low-dose TSEP (25 mg·kg-1) group and the high-dose
TSEP (50 mg·kg-1. Three weeks later, the islet
morphology of rat pancreas were observed by HE
(Hematoxylin and Eosin) staining, and protein
expressions of IRS-1 (insulin receptor substrate-1),
PI3K (phosphatidyl inositol 3-kinase), PTP-1 B
(protein tyrosine phosphatase-1B) and GLUT4
(glucose transporter 4) in rat skeletal muscle were
detected by Western blot. When compared with the
model group, TSEP administered groups showed
relatively normal structures, clear pancreatic cells and
intact capsula structures in pancreatic tissue
pathological sections, with the number of pancreatic
islets close to the normal control group. Meanwhile,
above TSEP administered groups showed increased
13
IRS-1, PI3K and GLUT4 protein expressions in their
skeletal muscle tissues and decreased PTP-1B protein
expression compared with the model group. TSEP has
an effect on protecting pancreatic tissues of type 2
diabetic rats and intervening in abnormal expression of
proteins in skeletal muscle tissues [73].
10.4 Anti-Toxicity Activities
Entada africana, a widely used African medicinal
plant of the same genus Entada, has been reported for
various medicinal properties. When the acute toxicity
of the methanolic stem bark and leaf extracts of
Entada africana Guill. and Perr., (Mimosaceae) was
assessed on mice, it revealed an average toxicity with a
LD50 of 146.7 mg·kg-1 and 249.9 mg·kg-1 body weight
for stem barks and leaves, respectively. The extracts
showed no cytotoxicity against Human epidermoid
carcinoma (KB) and African green monkey (Vero)
cells. Sub-chronic toxicity was assessed in rabbits,
which received orally, daily for a month, a dose
corresponding to 10% of the LD50. Compared to the
control group, this dose caused no significant (p > 0.05)
modification of haematological and biochemical
parameters, total cholesterol, urea, creatinine and AST
(aspartate amino-transferase). The extracts lowered
serum glucose significantly (p < 0.05) by 52% at first
two weeks of treatment. The stem bark and leaf
extracts showed temporary decrease (p < 0.05) of ALT
(alanine amino transferase) by 26.1 % and 39.1%,
respectively. The stem bark extracts increased
triglycerides significantly (p < 0.01) by 108% at the
end of last week of treatment. These investigations
seemed to indicate the safety of sub-chronic oral
administration (up to 14.67 mg·kg-1 and 24.9 mg·kg-1
body weight) of the methanolic extracts of Entada
africana in rabbits [74].
The impact of the crude and processed products of
Entada phaseoloides on gastrointestinal movement in
mice was studied with the methods of charcoal
propulsion of small intestine and methyl orange
colorimetry of gastric emptying to observe
14
An Overview of Entada phaseoloides: Current Research and Future Prospects
acute-toxicity. The oral LD50 of crude Entada
phaseoloides, and two processed products of Entada
phaseoloides in mice were 27.17 g/kg, 35.13 g/kg and
42.18 g/kg body weight respectively. Crude and
processed products of Entada phaseoloides can
significantly promote the enteric propulsion of normal
mice, and can significantly counteract the depressing
status induced by atropine, but have no influence on the
overactive status induced by neostigmine. The high,
middle and low-dose of groups showed significant
inhibition of the gastric emptying in normal mice.
Processed Entada phaseoloides showed effects on the
enteric propulsion of normal and depressing mice, can
restrain the gastric emptying under normal mice, but its
safety was better than crude Entada phaseoloides [75].
10.5 Antiulcer Activities
The ethanol extract of the seeds of Entada
phaseoloides was assessed for its antiulcer activity
against aspirin plus pylorus ligation induced gastric
ulcers in rats, HCl- ethanol induced ulcer in mice and
water immersion stress-induced ulcers in rats. A
significant (P < 0.001) antiulcer activity was observed
in all the models. The parameters taken to assess
antiulcer activity were volume of gastric secretion, free
acidity, total acidity and ulcer index. Preliminary
phytochemical screening of the Entada Phaseoloides
gave positive test for steroids, saponins and alkaloids.
The results indicate that Entada phaseoloides
possessed antiulcer activity [2].
10.6 Anticomplement and Antimicrobial Activities
Seventeen flavonoids isolated from the extracts of
the stem of Entada phaseoloides, which were
investigated for their anticomplement (both classic and
alternative pathways) and antimicrobial activities
against Gram-positive bacteria MSSA (Methicillin
sensitive Staphylococcus aureus), MRSA (Methicillin
resistant
Staphylococcus
aureus),
Standard
Enterococcus and Bacillus subtilis], Gram-negative
bacteria (Escherichia coli, Pseudomonas aeuroginosa)
and the yeast-like pathogenic fungus Candida albicans.
The
anti-complement
studies
revealed
a
dose-dependent activity among isolated quercetin,
luteolin,
apigenin,
galangin,
5,2',5'-trihydroxy-3,7,4'-trimethoxyflavone-2'-O-β-D-g
lucoside(+)-3,3',5',5,7-pentahydroflavanone,
(+)-dihydrokaempferol, (-)-epicatechin, (+)-catechin,
naringenin, and 5,7,3',5'-tetrahydroxyflavanone, and
the antimicrobial results indicated that quercetin,
5,7,4'-trihydroxy-3'-methoxyflavonol and galangin
produced the inhibitory activities against MRSA,
MSSA, and Standard Enterococcus, while luteolin and
rhamnocitrin displayed inhibition against only MRSA
and MSSA [76].
10.7 Antioxidant and Cytotoxic Activities
The methanolic crude extract of the bark and seed of
Entada phaseoloides (L.) Merrill and its different
organic soluble partitionates were screened for
antioxidant, cytotoxic, membrane stabilizing and
antimicrobial activities. The crude extract, carbon
tetrachloride and aqueous soluble fractions of both
bark and seed showed higher level of total phenolic
content (TPC, 245.59, 240.22, 240.03 and 117.0 mg of
Gallic acid equivalent (GAE)/gm of dried extract). In
the DPPH (1,1-diphenyl-2-picrylhydrazyl) assay, the
crude extract of bark and its chloroform and aqueous
soluble fractions demonstrated strong antioxidant
property with the IC50 of 3.24, 1.55 and 3.6 μg/mL,
respectively, whereas, all the fractions of seed extract
revealed mild antioxidant activity. The petroleum ether
soluble fraction of both seed and bark exhibited
significant cytotoxicity (LC50 = 1.54 mg/mL and 5.4
mg/mL) which confers the presence of bioactive
metabolites in this plant. On the other hand, the crude
extract of seed and petroleum ether soluble fraction of
bark inhibited the hemolysis of RBC of rat‟s blood by
78.89% and 57.43%, respectively, as compared to
84.44% exerted by acetyl salicylic acid (0.10 mg/mL).
In antimicrobial screening, the carbon tetrachloride
soluble fraction of bark showed significant
An Overview of Entada phaseoloides: Current Research and Future Prospects
antimicrobial activity against Staphylococcus aureus
(zone of inhibition = 17.0 mm) with MIC (minimum
inhibitory concentration) and MBC (minimum
bactericidal concentration) values of 7.81 mg/mL and
125 mg/mL, respectively [77].
Apart from the above, the bark of Entada
phaseoloides exhibits potent molluscidal activity
against Oncomelenia quadrasi, the snail intermediate
host of Schistosoma japonicum with LC50 of 3.6-5.8
ppm since Entada phaseoloides remained stable over a
wide range of pH values, in the presence of minerals
and yeast cells and after ultraviolet irradiation of
solutions. Under field conditions, the Gogo bark at a
dose rate of ≥ 40 g/m2 was sufficient to produce a
satisfactory molluscicidal effect [41] or commercial
gogo bark at a dose rate of 2 g/L of water with
Oncomelenia quadrasi can kill 100% of snail within
24 h. Thus the molluscidal effect of Entada
phaseoloides is very much effective in controlling
Schistosomiasis, a snail transmitting debilitating and
fatal endemic disease which is of major public health
concern [78].
11. Current Finding and Future Prospects
Natural products are promising candidates for drug
discovery and they still continue to play an important
role in future small organic compound drug
development
programs
[79].
Reports
on
pharmacological effects of medicinal plants are
growing almost exponentially. However, it was found
to be very difficult to attribute the pharmacological
activity in a multi-component mixture to only a single
compound of an extract, as plant extracts consist of a
diversity of secondary metabolites [80]. From the
above review of literature, it is evident that Entada
phaseoloides has been one of the most thoroughly
studied interesting plants as reported during the last 2
decades. The body of knowledge about plants, herbs
and spices, and their respective and collective roles in
promoting health is modest [81, 82]. Though modern
synthetic drugs are very effective in curing diseases
15
but also cause a number of side effects; although crude
drugs are less efficient in curing diseases but are
relatively free from side effects [83]. Herbs have been
used as food and for medicinal purpose for centuries [82].
In recent times, the use of herbal products has
increased enormously in the western world as well as
in developed countries [84]. But the traditional herbal
medicine has simple solution which is both easier and
economical. Nature keeps ready in her vast green
reservoir some of those herbal remedies which can
cure all human ailments and diseases that take place
on this earth. The need is only to locate those
miraculous herbs through trained eyes which could
alleviate the pains and sufferings of mankind.
12. Prospects
Since the use of medicinal plants is a widely
accepted therapeutic strategy for millions of people,
further attention should be focused on the discovery of
the exact modes of action of their extracts as well as
the isolated pure compounds and potential
combinations, so as to exploit them commercially.
However, because of the diverse molecular
pharmacological data, the spectrum of interpretation
and speculations seem to be endless. Therefore, in
future studies there is a need for thorough
phytochemical, clinical and possible studies on
molecular mechanism of action along with preclinical
trials that are required for an integration and
acceptance of many Entada phaseoloides extracts in
conventional medicine. At the same time efforts
should be made to standardise the plant extracts and
formulate best alternative herbal preparations to
replace or complement the synthetic drugs which are
currently in use.
13. Conclusions
Entada phaseoloides offers a wide range of
ethnobotanical utilizations, which are based on the
diverse patterns of secondary metabolites of which
most abundant are saponins, diterpenes, triterpenes and
An Overview of Entada phaseoloides: Current Research and Future Prospects
16
phenolics compounds. Phenolic compounds, saponins,
diterpenes as well as triterpenes were reported to
contribute the pharmacological properties of Entada
phaseoloides such as anti-inflammatory, antidiabetic,
antitumour and analgesic activity (saponin);
anticomplement, antimicrobial and antioxidants
(phenolics); as antiulcer, anti toxic in addition to
molluscicidal activities (crude and processed product
of Entada phaseoloides).
[16]
[17]
[18]
References
[19]
[1]
[2]
[3]
[4]
[5]
[6]
[7]
[8]
[9]
[10]
[11]
[12]
[13]
[14]
[15]
B.E. VanWyk, M. Wink, Medicinal Plants of the World:
An Illustrated Scientific Guide to Important Medicinal
Plants and Their Uses, OR: Timber Press, Portland, 2004.
D. Ramakrishna, K. Pawan kumar, K. Mukkanti, K.
Abdulla Khan, Antiulcer activity of the seeds of Entada
Phaseoloides, Pharmacologyonline 3 (2008) 93-99.
K. M. Madkarri‟s, A.K. Nadkarni, Indian Material Medica,
Vol. 2, Popular Prakashan II, 1976, PP. 394-395.
A. Sparreboom, M.C. Cox, M. R. Acharya, W. D. Figg,
Herbal remedies in the United States: potential adverse
interactions with anticancer agents, Journal of Clinical
Oncology 22 (2004) 2489-2503.
K.J. Gohil, J.A. Patel, A review on Bacopa monniera:
Current research and future prospects, International
Journal of Green Pharmacy 4 (2010) 1-9.
R. A. Singha, Herbal remedies of street vendors for some
urino-genital diseases, Ancient Science Life 1 (1992)
187-192.
"Entada Adans", Germplasm Resources Information
Network, United States: Department of Agriculture, 2007.
E. D. Merrill, Entada phaseoloides (L.)Merr. Philippine
Journal Science Section C Botany 9 (1914) 86.
Benth, Entada scandens (L.) Benth. Hooker‟s Journal of
Botany 4 (1841) 332.
O. Stickman, Lens phaseoloides L. Herb. Amoin 18 (1754),
National
tropical
botanical
garden,
http://ntbg.org/plants/plant_details.php?plantid=4612,2011
Entada phaseoloides, Australian Tropical Rainforest
Plant.
K.M. Madkarri‟s, A.K. Nadkarni, Indian Material Medica,
Vol. 1, 1976, PP. 485-486.
Australian
new
crops
wensite:
http://newcrops.com.au/index.php?option=com_content&
view=article&id=22&Itemid=54
T. Acamovic, C.S. Stewart, T. W. Pennycott, Poisonous
Plants and Related Toxins, CABI, 2004, pp. 377-386.
A. Agarwal, A carbonized fossil seed, viz.Entada
palaeoscandens (Awasthi & Prasad) Antal & Awasthi,
[20]
[21]
[22]
[23]
[24]
[25]
[26]
[27]
[28]
[29]
from lignite deposits of Kalviwadi, Sindhudurg district,
Maharashtra, India, Phytomorphology 53 (2003)
133-139.
N. Bluthgen, K. Fiedler, Interactions between weaver ants
Oecophylla smaragdina, homopterans, trees and lianas in
an Australian rain forest canopy, Journal of Animal
Ecology 71 (2002) 793-801.
J.V.S. Rao, K.S.V. Priya, In vitro response of embryo axis
of Entada phaseoloides Merrill, Phytomorphology 52
(2002) 97-102.
Y. Zheng, K. Ben, S. Jin, Anti-human immunodeficiency
virus activity of proteins from 17 species of plants,
Virologica Sinica 13 (1998) 312-321.
G. Grant, L.J. More, N.H. McKenzie, P.M. Dorward, W.C.
Buchan,
L.
Telek,
et
al.,
Nutritional
and
haemagglutination properties of several tropical seeds,
Journal of Agricultural Science 124 (1995) 437-445.
E. Bergstrom, O. Hernal, L.A. Person, Dietary changes in
Swedish adolescents, Acta Paediatrica 82 (1993) 472-480.
V.R. Mohan, K. Janardhanan, Chemical and nutritional
evaluation of raw seeds of the tribal pulses Parkia
roxburghii G. Don. and Entada phaseoloides (L.) Merr,
International Journal of Food Science and Technology 44
(1993) 47-53.
Y. Okada, S. Shibata, O. Kamo, T. Okuyama,
Carbon-13 NMR spectral studies of entagenic acid to
establish its structure, Chemical and Pharmaceutical
Bulletin 36 (1988) 5028-5030.
Y. Okada, S. Shibata, A.M.J. Javellana, O. Kamo, Entada
Saponins Es II and IV from the bark of Entada
phaseoloides, Chemical and Pharmaceutical Bulletin 36
(1988) 1264-1269.
Y. Okada, S. Shibata, T. Ikekawa, A.M.J. Javellana, O.
Kamo, Entada Saponin III a saponin isolated from the
bark of Entada-phaseoloides, Phytochemistry 26 (1987)
2789-2796.
F.C. Ho, Notes on the Genus Entada of Taiwan, Journal
of Taiwan Museum 38 (1985) 75-80.
C.Y. Lim-Sylianco and W.T. Shier, Mutagenic and
antimutagenic activities in Philippine medicinal and food
plants, Journal of Toxicology Toxin Reviews 4 (1985)
71-105.
G. Panigrahi, Proposal to amend the type citation of
Entada conserved name and of Gigalobium rejected name
Fabaceae. Taxon 34 (1985) 714-715.
K. Yasuraok, A.T.J. Santos, M.J. Santos, K. Takamura, Y.
Hosaka, Laboratory trials of 2 new molluscicides, the bark
of “Gogo” (Entada-Phaseoloides) and Polynactin, against
Oncomelania snails: a preliminary report, Southeast Asian
Journal of Tropical Medicine and Public Health 7 (1976)
346-347.
A.K. Barua, A. Basak, Chemical examination of the seeds
An Overview of Entada phaseoloides: Current Research and Future Prospects
[30]
[31]
[32]
[33]
[34]
[35]
[36]
[37]
[38]
[39]
[40]
[41]
[42]
of Entada-Phaseoloides, Journal of Indian Chemical
Society 49 (1972) 1199
A.K. Barua, Triterpenoids: XXV. The constitution of
entagenic acid: A new triterpenoid sapogenin from Entada
phaseoloides Merrill, Tetrahedron 23 (1967) 1499-1503.
A.K. Barua, P. Chakraborty, B.C. Das, Triterpenoids:
XXVI. The constitution of entagenic acid, Tetrahedron 23
(1967) 1505-1508.
J.P.M. Brenan, Notes on Mimosoideae: I, Kew Bulletin
1(1955) 161-192.
W.C. Liu, M, kugelman, R.A. Wilson, K.V. Roa, A
crystalline saponin with antitumor activity from Entada
phaseoloides, The John L. Smith Memorial for Cancer
Research 11 (1972) 171–173.
A.K. Barua, M. Chakraborty, P.K. Dutta, S. Ray,
Phaseoloidin, a homogentisic acid glucoside from Entada
phaseoloides, Phytochemistry 27 (1988) 3259–3261.
F. Ikegami, S. Ohmiya, N. Ruangrungsi, S.I. Sakai, I.
Murakoshi, Entadamide A, a new sulphur-containing
amide from Entada phaseoloides seeds, Chemical and
Pharmaceutical Bulletin 33 (1985) 5153−5154.
F. Ikegami, S. Ohmiya, N. Ruangrungsi, S.I. Sakai, I.
Murakoshi,
Entadamide
B,
a
second
new
sulphur-containing amide from Entada phaseoloides,
Phytochemistry 26 (1987) 1525−1526.
F. Ikegami, T. Sekine, M. Aburada, Y. Fujii, Y. Komatsu,
I. Murakoshi, Synthesis of entadamide A and entadamide
B isolated from Entada phaseoloides and their inhibitory
effects on 5-lipoxygenase, Chemical and Pharmaceutical
Bulletin 37 (1989) 1932-1933.
F. Ikegami T. Sekine, S. Duangteraprecha, N. Matsushita,
N. Matsuda, N. Ruangrungsi, I. Murakoshi,
Entadamide C, a sulphur-containing amide from Entada
phaseoloides, Phytochemistry 28 (1989) 881−882.
J.R. Dai, L.B.S. Kardono, S. Tsauri, K. Padmawinata, J.M.
Pezzuto, A.D. Kinghorn, Phenylacetic acid derivatives
and a thioamide glycoside from Entada phaseoloides,
Phytochemistry 30 (1991) 3749−3752.
P. Siddhuraju, K. Becker, H.P.S. Makkar, Chemical
composition, protein fractionation, essential amino acid
potential and antimetabolic constituents of an
unconventional legume, Gila bean (Entada phaseoloides
Merrill) seed kernel, Journal of the Science of Food and
Agriculture 82 (2002) 192–202.
K. Yasuraoka, Y. Irie, K. Takamura, H. Shimomura, J.
Hashiguchi, M.J. Santos, et al., Laboratory and field
assessment of the molluscicidal activity of gogo (Entada
phaseoloides) against the amphibious snail intermediate
host of Schistosoma japonicum, Journal of Experimental
Medicine 47 (1977) 483-487.
A. Kumar, Entada phaseoloides (Linn.) Merrill. syn. E.
scandens: A glycoside of entagenic acid possesses anti-
17
neoplastic activity, Science 2.0 Join the revolution 2009.
[43] Gogo, Entada phaseoloides, St Thomas Bean, Philippine
Medicinal Plants.
[44] I.F.B. Common, D.F. Waterhouse, Butterflies of Australia,
Angus and Robertson Publishers 2 (1981) 682.
[45] R.C. Cambie, A.A. Brewis, Anti-fertility Plants of the
Pacific, CSIRO Pub., 1997, P. 115.
[46] K. Hostettmann, A. Marston, Saponins, Cambridge:
Cambridge University Press, 1995.
[47] R.
Hardman,
E.A.
Sofowora,
Isolation
and
characterization of yamogenin from Balanites aegyptiaca,
Phytochemistry 9 (1970) 645–649.
[48] Royal Society of Chemistry, available at internet site:
www. Chem Spider. Com, 2013 (Accessed 4 November
2013).
[49] Chemical Book, 2008. Chem Spider ID: 24606073, 2013.
[50] U.S. National Library of Medicine. National Institutes of
Health. Department of Health & Human Services. 8600
Rockville Pike, Bethesda, MD 20894, 2013.
[51] Available at internet site: www.ichemistry.cn 2009-2013.
[52] H. Xiong, E. Xiao, Y.H. Zhao, G.Z. Yang, Z.N. Mei,
Sulfur-containing amides from Entada phaseoloides, Acta
Pharmaceutica sinnnica 45 (2010) 624-626.
[53] Z.X. Zhao, J. Jin, C.Z. Lin, C.C. Zhu, Y.M. Liu, A.H. Lin,
et al., Two new chalcone glycosides from the stems of
Entada phaseoloides, Fitoterapia 82 (2011) 1102-1105.
[54] O. Singh, M. Ali, N. Ahktar, Phenolic acid glucosides
from the seeds of Entada phaseoloides Merill, Journal of
Asian Natural Products Research 13 (2011) 682-687.
[55] Y. Iwamoto, S. Sugimoto, L. Harinantenaina, K.
Matsunami, H. Otsuka, Entadosides A–D, triterpene
saponins and a glucoside of the sulphur-containing amide
from the kernel nuts of Entada phaseoloides (L.) Merrill,
Journal of Natural Medicine 66 (2012) 321-328.
[56] H.J. Li, D.L. Zhou, T.J. Xu, C.K. Lam, W.L. Lan,
5,6,7,5'-Tetramethoxy-3',4'methylenedioxyflavone
monohydrate, Acta Crystallographica 68 (2012) 1390.
[57] K. Sutthanut, B. Sripanidkulchai, C. Yenjai, M. Jay,
Simultaneous identification and quantitation of 11
flavonoid constituents in Kaempferia parvifloraby gas
chromatography, Journal of Chromatography A 1143
(2007) 227–233.
[58] L.S. Ding, Q.L. Liang, Y.F. Teng, Study on flavonoids in
seeds of Hovenia dulcis, Acta Pharmaceutica Sinica 32
(1997) 600-602.
[59] S. Sang, S. Tian, H. Wang, R.E. Stark, R.T. Rosen, C.S.
Yang, et al., Chemical studies of the antioxidant
mechanism of tea catechins: Radical reaction products of
epicatechin with peroxyl radicals, Bioorganic Medical
chemistry 11 (2003) 3371-3378.
[60] L.Y. Foo, Y. Lu, W.C. McNabb, G. Waghorn, M.J. Ulyatt,
Proanthocyanidins
from
Lotus
pedunculatus,
18
An Overview of Entada phaseoloides: Current Research and Future Prospects
Phytochemistry 45 (1997) 1689.
[61] Y.P. Chen, L. Liu, Y.H. Zhou, J. Wen, Y. Jiang, P.F. Tu,
Chemical constituents from Sappan lignum, Journal of
Chinese Pharmaceutical Sciences 17 (2008) 82–86.
[62] W. Herath, J.R. Mikell, A.L. Hale, D. Ferreira, I.A. Khan,
Microbial metabolism. Matabolites of 3- and
7-hydroxyflavones, Chemical and Pharmaceutical Bulletin
54 (2006) 320.
[63] E. Lee, B.H. Moon, Y. Park, S. Hong, S. Lee, Y. Lee, Y.
Lim, Effects of hydroxy and methoxy substituents on
NMR Data in flavonols, Bulletin Korean Chemical
Society 29 (2008) 507-510.
[64] F. Nessa, Z. Ismail, N. Mohamed, M.R.H.M. Haris, Free
radical-scavenging activity of organic extracts and of pure
flavonoids of Blumea balsamifera DC leaves, Food
Chemistry 88 (2004) 243-252.
[65] F.W. Collins, V. Deluca, R.K. Ibrahim, B. Voirin, M. Jay,
Polymethylated flavonols of Chrysosplenium americanum.
I. Identification and enzymatic synthesis, Zeitschrift fur.
Naturforschung C 36 (1981) 730-736.
[66] D Y. Dong, H. Shi, H. Yang , Y. Peng, M. Wang, X. Li,
Antioxidant phenolic compounds from the stems of
Entada phaseoloides, Chemical Biodiversity 9 (2012)
68-79.
[67] E. Xiao, H. Xiong, X. Chen, Y. Zhao, Z. Mei, Study on
HPLC fingerprint of crude and processed products of
Entada phaseoloides, Zhongguo Zhong Yao Za Zhi 35
(2010) 3140-3143.
[68] R. Gupta, B.S. Rathi, P.A. Thakurdesai, S.L. Bodhankar,
Anti-inflammatory and analgesic effects of methanolic
extract of Entada phaseoloides seeds, Journal of Cell
Tissue Research 6 (2006) 609-613.
[69] J.S. Dawane, V.A. Pandit, B.D. Rajopadhye,
Experimental evaluation of anti-inflammatory effect of
topical application of Entada phaseoloides seeds as paste
and ointment, North American Journal of Medical
Sciences 3 (2011) 513-517.
[70] J.S. Dawane, V.A. Pandit, B.D. Rajopadhye, M.
Karandikar, The effect of two formulations of Entada
phaseoloides seeds after topical application in
„monoiodoacetate-induced osteoarthritis‟ in rats, Journal
of Experimental and Integrative Medicine 3 (2013) 37-41.
[71] T. Zheng, G. Shu, Z. Yang, S. Mo, Y. Zhao, Z. Mei,
Antidiabetic effect of total saponins from Entada
phaseoloides (L.)Merr. in type 2 diabetic rats, Journal of
Ethnopharmacology 39 (2012) 814-821.
[72] M. Ikram, Z.M. Babar, A.M.T. Islam, M.A.U. Chowdhury,
M.E. Uddin, M.R. Islam, et al., Antidiabetic and
hypolipidemic effects of the different fractions of
[73]
[74]
[75]
[76]
[77]
[78]
[79]
[80]
[81]
[82]
[83]
[84]
methanolic extracts of Entada phaseoloides (L.) Merr. in
alloxan induced diabetic mice, International Journal of
Pharmaceutical Sciences and Research 2 (2011)
3160-3165.
T. Zheng, G. Shu, Z. Yang, S. Mo, Y. Zhao, Z. Mei,
Preliminary study on mechanisms of total saponins from
Entada phaseoloides against diabetes, Zhongguo Zhong
Yao Za Zhi 37 (2012) 615-619.
A. Tibiri, J.T. Banzouzi, A. Traore, G.O. Nacoulma, I.P.
Guissou, B. Mbatchi, Toxicological assessment of
methanolic stem bark and leaf extracts of Entada africana
Guill. and Perr., Mimosaceae, International Journal
Pharmacology 3 (2007) 393-399.
E. Xiao, H. Xiong, Y.H. Zhao, X.K. Deng, Z.N. Mei,
Study on acute toxicity and animal gastrointestinal
activity of crude and processed products of Entada
phaseoloides, Zhong Yao Cai 33 (2010) 1704-1707.
K. Li, S. Xing, M. Wang, Y. Peng, Y. Dong, X. Li,
Anticomplement and antimicrobial activities of flavonoids
from
Entada
phaseoloides,
Natural
Product
Communications 7 (2012) 867-871.
F. Aktar, M.R. Kuddus, O.S. Faruque, F. Rumi, M.A.
Quadir, M.A. Rashi, Antioxidant, cytotoxic, membrane
stabilizing and antimicrobial activities of bark and seed of
Entada phaseoloides (L.) Merrill: A medicinal plant from
Chittagong Hill Tracts, Journal of Pharmacy and Nutrition
Sciences 1 (2011) 171-176.
E.C. Garcia, B.D. Cabrera, A.V. Castilla, Studies on
Schistosoma japonica and Saponins, Science Diliman 1
(1981) 47-79.
D.J. Newman, G.M. Cragg, K.M. Snader, Natural
products as sources of new drugs over the period
1981-2002, Journal of Natural Product 66 (2003)
1022-1037.
M. Wink, Evolutionary advantage and molecular modes
of action of multicomponent mixtures used in
phytomedicine, Current Drug Metabolism 9 (2008)
996-1009.
A.D. Ballatine, M.C. Albano, M.G. Nair, Role of
medicinal plants, herbs and spices in protecting human
health, Nutritional Review 57 (1999) 41-45.
A.A. Adedapo, O.O. Shabi, O.A. Adedokun, Anthelmintic
efficacy of the aqueous crude extract of Euphorbia hirta
Linn in Nigerian dogs, Veterinary Arhiv 75 (2005)39-47.
R.G. Mali, A.A. Mehta, A review on anthelminthic plants,
Natural Product Radiance 7 (2008) 466-475.
D. Sudharani, K.L. Krishna, K. Deval, A.K. Safia, Priya,
Pharmacological profiles of Bacopa monnieri: A review,
International Journal of Pharmacy 1 (2011) 15-23.