Pharmacological effects of Sapindus mukorossi

Abstract

Sapindus mukorossi is an extremely valuable medicinal plant, distributed in tropical and sub-tropical regions of Asia. The aim of present review is to form a short compilation of the phytochemical composition and pharmacological properties of this multipurpose tree. The main phytoconstituents isolated and identified from different parts of this plant are triterpenoidal saponins of oleanane, dammarane and tirucullane type. The structure and chemical names of all the types of triterpenoidal saponins reported in Sapindus mukorossi are included in this review. Many research studies have been conducted to prove the plant's potential as being spermicidal, contraceptive, hepatoprotective, emetic, anti-inflammatory and anti-protozoal. The present review highlights some of the salient pharmacological uses of Sapindus mukorossi.

Full text

Rev. Inst. Med. Trop. Sao Paulo
54(5):273-280, September-October, 2012
doi: 10.1590/S0036-46652012000500007
Malacology Laboratory, Department of Zoology, DDU Gorakhpur University, Gorakhpur, 273009, U.P. India.
Correspondence to: Prof. D.K. Singh, Malacology Laboratory, Department of Zoology, DDU Gorakhpur University, Gorakhpur, 273009, UP, India. Tel: +91 551 2202187(O)/0509(R).
E-mail: dksingh_gpu@yahoo.co.in
PHARMACOLOGICAL EFFECTS OF Sapindus mukorossi
Aparna UPADHYAY & D.K. SINGH
SUMMARY
Sapindus mukorossi is an extremely valuable medicinal plant, distributed in tropical and sub-tropical regions of Asia. The aim of
present review is to form a short compilation of the phytochemical composition and pharmacological properties of this multipurpose
tree. The main phytoconstituents isolated and identified from different parts of this plant are triterpenoidal saponins of oleanane,
dammarane and tirucullane type. The structure and chemical names of all the types of triterpenoidal saponins reported in Sapindus
mukorossi are included in this review. Many research studies have been conducted to prove the plant’s potential as being spermicidal,
contraceptive, hepatoprotective, emetic, anti-inflammatory and anti-protozoal. The present review highlights some of the salient
pharmacological uses of Sapindus mukorossi.
KEYWORDS: Sapindus mukorossi; Pharmacology; Saponins.
INTRODUCTION
Sapindus mukorossi Gaertn., a member of the family Sapindaceae, is
commonly known by several names such as soapnut, soapberry, washnut,
reetha, aritha, dodan and doadni. It is a deciduous tree widely grown in
upper reaches of Indo-Gangetic plains, Shivaliks and sub Himalayan
tracts at altitudes from 200 m to 1500 m. The Sapindus mukorossi is a
fairly large, deciduous tree with a straight trunk up to 12 meters in height,
sometimes attaining a height of 20 m and a girth of 1.8 m, with a globose
crown and rather fine leathery foliage. Bark is dark to pale yellow, fairly
smooth, with many vertical lines of lenticels and fine fissures exfoliating
in irregular wood scales. The blaze is 0.8-1.3 cm, hard, not fibrous, pale
orange brown, brittle and granular. Leaves are 30-50 cm long, alternate,
paripinnate; common petiole very narrowly bordered, glabrous; leaflets
5-10 pairs, opposite or alternate, 5-18 by 2.5-5 cm, lanceolate, acuminate,
entire, glabrous, often slightly falcate or oblique; petioles 2-5 m long.
Inflorescence is a compound terminal panicle, 30 cm or more in length,
with pubescent branches. Flowers are about 5 mm across, small, terminal,
polygamous, greenish white, subsessile, numerous, mostly bisexual.
Sepals 5, each with a woolly scale on either side above the claw. Fruits are
globose, fleshy, 1-seeded drupe, sometimes two drupels together, about
1.8-2.5 cm across. Seeds are 0.8-1.3 cm in diameter, globose, smooth,
black and loosely placed in dry fruit7.
The fruit is valued for the saponins (10.1%) present in the pericarp
and constitutes up to 56.5% of the drupe known for inhibiting tumor cell
growth37. In China and Japan it has been used as a remedy for centuries.
In Japan its pericarp is called “enmei-hi”, which means “life prolonging
pericarp” and in China “wu-huan-zi”, the “non-illness fruit”37. The major
compounds isolated from Sapindus mukorossi are triterpenoidal saponins
of mainly three oleanane, dammarane and tirucullane types. Recently
many of the pharmacological actions of this plant have been explored
which includes the antimicrobial19, cytotoxic29, molluscicidal16,42,
insecticidal12,26, piscicidal44 and fungicidal37,41 activities. One of the most
talked about activities of this plant is the contraceptive activity of the
saponins extracted from the pericarp of the fruit11,27.
Sapindus mukorossi is well known for its folk medicinal values30.
Pericarps of Sapindus mukorossi have been traditionally used as an
expectorant as well as a source of natural surfactant20. Due to the presence
of saponins, soapnut is well known for its detergent and insecticidal
properties and it is traditionally used for removing lice from the scalp.
The fruits are of considerable importance for their medicinal value for
treating a number of diseases like excessive salivation, pimples, epilepsy,
chlorosis, migranes, eczema and psoriasis21. The powdered seeds are
employed in the treatment of dental caries, arthritis, common colds,
constipation and nausea8. The seeds of Sapindus mukorossi are used in
Ayurvedic medicine to remove tan and freckles from the skin. It cleanses
the skin of oily secretion and is even used as a cleanser for washing hair
as it forms a rich, natural lather. The leaves are used in baths to relieve
joint pain and the roots are used in the treatment of gout and rheumatism.
Since ancient times Sapindus mukorossi has been used as a detergent for
shawls and silks. The fruit of Sapindus mukorossi was utilized by Indian
jewelers for restoring the brightness of tarnished ornaments made of gold,
silver and other precious metals33.

UPADHYAY, A. & SINGH, D.K. - Pharmacological effects of Sapindus mukorossi. Rev. Inst. Med. Trop. Sao Paulo, 54(5): 273-80, 2012.
274
PHYTOCHEMICAL CONSTITUENTS
The major constituents of Sapindus mukorossi fruit are saponins
(10%-11.5%), sugars (10%) and mucilage10. Saponins are secondary plant
metabolites with divergent biological activities10. Sapindus saponins are
a mixture of six sapindosides (sapindosides A, B, C, D and mukorozi
saponins (E1 and Y1), with sapindoside B as one of the major constituents,
isolated by n-butanol extraction of the ethanolic extract of fruit pericarp
of Sapindus mukorossi and identified by liquid chromatography and
mass spectroscopy28. Saponins are a large family of structurally-related
compounds of steroid or triterpenoid aglycone (sapogenin) linked
to one or more oligosaccharide moieties by glycosidic linkage. The
aglycone, or sapogenin, may contain one or more unsaturated C-C
bonds. The oligosaccharide chain is normally attached at the C3 position
(monodesmosidic), but many saponins have an additional sugar moiety
at the C2,6 or C2,8 position (bidesmosidic)10. The great complexity of the
saponin structure arises from the variability of the aglycone structure, the
nature of the side chains and the position of attachment of these moieties
on the aglycone10. The carbohydrate moiety consists of pentoses, hexoses
or uronic acids. Due to this complexity, saponins are difficult to classify.
Because it is no longer customary to classify compounds based on their
physicochemical or biological properties, a state of the art classification
based on the biosynthesis of the saponin carbon skeletons was proposed
by VINCKEN et al.43.
Different types of triterpene, saponins of oleanane, dammarane and
tirucullane type were isolated from the galls, fruits and roots of Sapindus
mukorossi. Oleanane type triterpenoid saponins named Sapindoside A&B
(Fig. 34 & 35) were reported from the fruits of Sapindus mukorossi6.
Sapindoside C (Fig. 36)4, Sapindoside D (Fig. 37)5, which is a hexaoside
of hederagenin, and Sapindoside E (Fig. 38)3, a nonaoside of hederagenin,
was isolated and identified from the methanolic extract of the fruits of
Sapindus mukorossi.
Dammarane-type saponins, named Sapinmusaponins A & B (Fig. 11
& 12), C-E (Fig. 15, 16, 17), together with three known phenylpropanoid
glycosides, were isolated from the galls of Sapindus mukorossi45.
Tirucallane-type saponins, sapinmusaponins F-J (Fig. 18-22), were
isolated from the galls of Sapindus mukorossi as reported by HUANG
et al.17. The structures of these saponins were elucidated on the basis of
spectroscopic analysis including 1D and 2D NMR techniques.
Triterpene saponins of oleanane type like, Sapinmusaponin K-N (Fig.
25-28), Mukorozisaponin G & E1 (Fig. 29-30), Sapindoside A & B along
with dammarane types like Sapinmusaponin O and P (Fig. 13 & 14) were
isolated from fruits and the galls of Sapindus mukorossi as per HUANG
et al.15. In another study by NAKAYAMA et al.23, Mukorozisaponin Y1
(Fig. 31), Y2 (Fig. 32), X (Fig. 33) were isolated from the pericarp of
Sapindus mukorossi.
Fractionation of an ethanolic extract of the galls of Sapindus mukorossi
has resulted in the isolation of two tirucallane type triterpenoid saponins,
sapinmusaponin Q and R (Fig. 23-24), along with three known oleanane
type triterpenoid saponins: sapindoside A, sapindoside B, and hederagenin-
3-O-[β-D-xylopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)+-α-L
arabinopyranoside14. The roots of Sapindus mukorossi contain tirucallane-
type triterpenoid saponins like Sapimukoside A & B38, Sapimukoside C
&D25. Further investigation of the roots of Sapindus mukorossi by NI
et al.24 reported the presence of Sapimukosides E-J24. The structures of
Sapimukosides A-J are shown in Fig. 1 to Fig. 10 respectively. Table 1
shows whole view of all the saponins isolated from Sapindus mukorossi.
BIOLOGICAL EFFECTS
1. Anti-bacterial activity: IBRAHIM et al.19 evaluated that
ethanolic and chloroform extracts of Sapindus mukorossi inhibited
the growth of Helicobacter pylori (both sensitive and resistant), at
very low concentrations, when given orally for seven days to male
wister rats. In the in vitro study, the isolates show a considerable zone
of inhibition at very low concentration (10 µg/mL) and in the in vivo
Fig R1 R2
1
3-Ara
Glc
2-Rha
H
2 Glc6-Rha H
3
3-Ara
Glc
2-Rha
Et
4
3-Ara
Glc
2-Rha
Me
5
3-Ara
Glc
2-Rha3-Ara
Et
6
3-Ara
Glc
2-Rha3-Xyl
Et
7
3-Ara
Glc
2-Rha3-Xyl
Me
8 3-Ara
Glc
2-Rha3-Ara
Et
9 3-Rha
Glc
2-Rha3-Ara
Me
10 Glc6-Rha Et
Abbreviations
Glc:β-D-Glucopyranosyl
Rha:α-L-hamnopyranosyl
Ara:α-L-rabinopyranosyl
Xyl:β-D-Xylopyranosyl

UPADHYAY, A. & SINGH, D.K. - Pharmacological effects of Sapindus mukorossi. Rev. Inst. Med. Trop. Sao Paulo, 54(5): 273-80, 2012.
275
Table 1
List of Saponins isolated from Sapindus mukorossi
Saponins Chemical name Tirucullane/oleanane/
dammarane type
Structure Reference
Sapindoside
A Hederagenin-3-O-α-L-arabinosyl-(2→1)-α-L-
rhamnopyranoside
Oleanane 34 Chirva et al., 1970 a
B Hederagenin-3-O-α-L-arabinosyl-(2→1)-O-α-L-
rhamnopyranosyl-(3→1)-β-D-xylanopyranoside
Oleanane 35 Chirva et al., 1970 a
C Hederagenin-3-O-β-D-glucosyl(1→4)-β-D-xylosyl
(1→3)-α-L-rhamnosyl(1→2)- α-L-arabinoside
Oleanane 36 Chirva et al., 1970 b
Sapinmusaponin
A 3,7,20(S),22-tetrahydroxydammar-24-ene-3-O-α-L-
rhamnopyranosyl-(1→2)-D-glucopyranoside
Dammarane 11 Yao et al., 2005
B 3,7,20(S),22,23-pentahydroxydammar-24-ene-3-O-α-L-
rhamnopyranosyl-(1→2)-D-glucopyranoside
Dammarane 12 Yao et al., 2005
C 3,7,20(S),22,25-pentahydroxydammar-23-ene-3-O-α-L-
rhamnopyranosyl-(1→2)-D-glucopyranoside
Dammarane 15 Yao et al., 2005
D 25-methoxy-3,7,20(S),22-tetrahydroxydammar-23-ene-3-O-α-
L-rhamnopyranosyl-(1→2)-D-glucopyranoside,
Dammarane 16 Yao et al., 2005
E 25-methoxy-3,7,20(R)-trihydroxydammar-23-ene-3-O-α-L-
rhamnopyranosyl-(1→2)-D-glucopyranoside
Dammarane 17 Yao et al., 2005
F 21 β-methoxy-3-β-21(S), 23I-epoxy tirucall-7,24-diene-3-O-
α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl
Tirucullane 18 Huang et al., 2006
G 21α-methoxy-3-β-21(S), 23I-epoxy tirucall-7,24-diene-3-O-α-
L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl
Tirucullane 19 Huang et al., 2006
H 21α-methoxy-3-β-21(S), 23I-epoxy tirucall-7,24-diene-3-O-
α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl
Tirucullane 20 Huang et al., 2006
I 21β-methoxy-3-β-21(S), 23I-epoxy tirucall-7,24-diene-3-O-
α-L-dirhamnopyranosyl-(1→2,6)-β-D-glucopyranosyl
Tirucullane 21 Huang et al., 2006
J 21α-methoxy-3-β-21(S), 23I-epoxy tirucall-7,24-diene-3-O-
α-L-dirhamnopyranosyl-(1→2,6)-β-D-glucopyranosyl
Tirucullane 22 Huang et al., 2006
K hederagenin-3-O-(3-O-acetyl-alpha-L-arabinopyranosyl)-
(1→3)-alpha-L-rhamnopyranosyl-(1→2)-alpha-L-
arabinopyranoside
Oleanane 25 Huang et al., 2008
L hederagenin-3-O-(4-O-acetyl-alpha-L-arabinopyranosyl)-
(1→3)-alpha-L-rhamnopyranosyl-(1→2)-alpha-L-arabino-
pyranoside,
Oleanane 26 Huang et al., 2008
M hederagenin-3-O-(2,3-O-diacetyl-beta-D-xylopyranosyl)-
(1→3)-alpha-L-rhamnopyranosyl-(1→2)-alpha-L-
arabinopyranoside
Oleanane 27 Huang et al., 2008
N hederagenin-3-O-(2,4-O-diacetyl-beta-D-xylopyranosyl)-
(1→3)-alpha-L-rhamnopyranosyl-(1→2)-alpha-L-
arabinopyranoside
Oleanane 28 Huang et al., 2008
O 3,7,20(S)-trihydroxydammar-24-ene-3-O-alpha-L-
rhamnopyranosyl-(1→2)-beta-D-glucopyranoside
Dammarane 13 Huang et al., 2008
P 3,7,20(R)-trihydroxydammar-24-ene-3-O-alpha-L-
rhamnopyranosyl-(1→2)-beta-d-glucopyranoside
Dammarane 14 Huang et al., 2007
Q 21α-methoxy-3β, 21I, 23(S)-epoxytirucall-7,24-diene-3-O-β-
D-glucopyranosyl-(1→2)-β-D-glucopyranoside
Tirucullane 23 Huang et al., 2007
R 21α-methoxy-3β, 21I, 23(S)-epoxytirucall-7,24-diene-3-O-α-
L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-(1→2)-β-D-
glucopyranoside
Tirucullane 24 Huang et al., 2007

UPADHYAY, A. & SINGH, D.K. - Pharmacological effects of Sapindus mukorossi. Rev. Inst. Med. Trop. Sao Paulo, 54(5): 273-80, 2012.
276
Sapinmukoside
A 3-O-α-L-rhamnopyranosyl-(1→2)-*α-L-
arabinopyranosyl-(1→3)+ – β-D-glucopyranosyl-21,
23R-epoxyl tirucall-7, 24R-diene-3 β, 2-diol
Tirucullane 1 Teng et al., 2003
B 3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl-21,
23R-epoxyl tirucall-7, 24R-diene-3 β, 21-diol
Tirucullane 2 Teng et al., 2003
C 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-arabinopyranosyl-
(1→3)]-β-D-glucopyranosyl (21,23R)-epoxyl tirucalla-7,24-
diene-(21S)-ethoxyl-3β-ol
Tirucullane 3 Teng et al., 2004
D 3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-arabinopyranosyl-
(1→3)]-β-D-glucopyranosyl (21,23R)-epoxyl tirucall-7,
24-diene-(21S)-methoxyl-3β-ol .
Tirucullane 4 Teng et al., 2004
E 3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-
(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucopyranosyl
(21,23R)-epoxyl tirucalla-7,24-diene-21β-ethoxyl-3β-ol}
Tirucullane 5 Ni et al., 2006
F {3-O-β-D-xylanopyranosyl-(1→3)-α-L-rhamnopyranosyl-
(1→2)-[β-L-arabinopyranosyl-(1→3)]-β-D-glucopyranosyl
21,23R-epoxyl tirucalla-7,24-diene-21β-ethoxyl-3β-ol}
Tirucullane 6 Ni et al., 2006
G {3-O-β-D-xylanopyranosyl-(1→3)-α-L-rhamnopyranosyl-
(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucopyranosyl
(21,23R)-epoxyl tirucalla-7,24-diene-21β-methoxy-3β-ol}
Tirucullane 7 Ni et al., 2006
H {3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-
(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl
21,23R-epoxyl tirucalla-7,24-diene-21β-ethoxy-3β-ol}
Tirucullane 8 Ni et al., 2006
I {3-O-α-L-arabinopyranosyl-(1→3)-α-L-rhamnopyranosyl-
(1→2)-[α-L-rhamnopyranosyl-(1→3)]-β-D-glucopyranosyl
21,23R-epoxyl tirucalla-7,24-diene-21β-methoxy-3β-ol}
Tirucullane 9 Ni et al., 2006
J {3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyl
21,23R-epoxyl tirucalla-7,24-diene-21β-ethoxyl-3β-ol}
Tirucullane 10 Ni et al., 2006
Mukorozi-saponin
G Hederagenin-3-O-(2-O-acetyl-β-D-xylanopyranosyl)-(1→3)-
α-L-rhamnopyranosyl-(1→2)-α-L-arabinoside.
Oleanane 29 Huang et al., 2008
E1 Hederagenin-3-O-α-L-arabinosyl-(1→3)-α-L-
rhamnopyranosyl-(1→2)-α-L-arabinoside.
Oleanane 30 Huang et al., 2008
Table 1
List of Saponins isolated from Sapindus mukorossi (cont.)
study the Helicobacter pylori infection was cleared with minimal dose
extracts of 2.5 mg/mL.
2. Insecticidal activity: Saponins possess insecticidal activity,
causing mortality and/or growth inhibition in the insects tested, the
cotton leafworm Spodoptera littoralis caterpillars and the pea aphid
Acyrthosiphon pisum. In the experiments with Acyrthosiphon pisum,
0.1% saponin killed all aphids, whereas with Spodoptera some
caterpillars were still able to develop into apparently normal adults on
food containing 7% saponin12. Saponins can be employed as novel natural
tactics in integrated pest management (IPM) to control pest insects, which
fit in modern agriculture and horticulture13. Ethanolic extract of Sapindus
mukorossi was investigated for repellency and insecticidal activity against
Sitophilus oryzae and Pediculus humanus. Average mortality percentage
indicated that the extracts caused significant mortality and repellency on
the target insects and bioassays indicated that toxic and repellent effect
was proportional to the concentration26.
3. Spermicidal activity: Saponins from Sapindus mukorossi are
known to be spermicidal11,27. Morphological changes in human ejaculated
spermatozoa after exposure to this saponin were evaluated under scanning
electron microscopy. The minimum effective concentration (0.05% in spot
test) did not affect the surface topography after exposure for one minute.
However, incubation of spermatozoa for 10 minutes resulted in extensive
vesiculation and a disruption of the plasma membrane in the head region.
Higher concentrations (0.1%, 1.25%, 2.5% and 5.0%) caused more or less
similar changes which included vesiculation, vacuolation, disruption or
erosion of membranes in the head region. These findings suggest that the
morphological changes observed are due to alterations in the glycoproteins
associated with the lipid bilayer of the plasma membrane of spermatozoa8.
This spermicidal property has been used in contraceptive cream9.
4. Anti-Trichomonas activity: TIWARI et al.39 demonstrated
that the Sapindus saponin mixture shows anti-Trichomonas activity
at a 10-fold lower concentration (0.005%) than its minimal effective

UPADHYAY, A. & SINGH, D.K. - Pharmacological effects of Sapindus mukorossi. Rev. Inst. Med. Trop. Sao Paulo, 54(5): 273-80, 2012.
277
spermicidal concentration against human spermatozoa (0.05%)11.
Saponin concentration dependently inhibited the ability of parasites
to adhere to HeLa cells and decreased the proteolytic activity of the
parasite’s cysteine proteinases. This was associated with the decreased
expression of adhesin AP65 and membrane-expressed cysteine proteinase
TvCP2 genes. Saponins produced no adverse effect on host cells in the
mitochondrial reduction potential measurement assay. Saponin disrupts
the actin cytoskeleton network beneath the cell membrane and affects
membrane-mediated adherence of Trichomonas to the host cells.
5. Anti-cancer activity: Due to the great variability in saponin
structure, saponins always display anti-tumorigenic effect through
varieties of anti-tumor pathways. There are more than 11 distinguished
classes of saponins including dammaranes, tirucallanes, lupanes,
hopanes, oleananes, taraxasteranes, ursanes, cycloartanes, lanostanes,
cucurbitanes and steroids. Ginsenosides, belonging to dammaranes,
have been found beneficial in the inhibition of tumor angiogenesis by
suppressing its inducer in the endothelial cells of blood vessels, and then
in the prevention of adhering, invasion and metastasis of tumor cells22.
Dioscin, one of the steroidal saponins, and its aglycone diosgenin also
has an extensive anti-tumor effect by cell cycle arrest and apoptosis22.
The preliminary bioassay data revealed that saponins [39,4]-43] showed
moderate cytotoxic activity (ED50~9-18µg/mL) against human tumor cell
lines (Hepa59T/VGH, NCL, HeLa and Med)29. Strychnopentamine was
the reference compound used in the study. All saponins were reported to
be at least five times less active than the reference compound36.
6. Hepatoprotective activity: IBRAHIM et al.18 reported that the
extracts of Sapindus mukorossi (2.5 mg/L) and Rheum emodi (3.0 mg/L)
have a protective capacity both in vitro on primary hepatocytes cultures
and in vivo in a rat model of tetrachloride carbon (CCl4) mediated liver
injury as judged from serum marker enzyme activities. These cultures
were treated with CCl4 and extracts of Sapindus mukorossi & Rheum
emodi. A protective activity could be demonstrated in the CCl4 damaged
primary monolayer culture. For the in vivo study, the hepatoprotective
capacity of the extract of the fruit pericarp of S. mukorossi and the
rhizomes of Rheum emodi was analyzed in liver injured CCl4- treated
male rats. Extracts of the fruit pericarp of Sapindus mukorossi (2.5 mg/
mL) and rhizomes of Rheum emodi (3.0 mg/mL) were found to have
protective properties in rats with CCl4 induced liver damage as judged
from serum marker enzyme activities. Thus, it was concluded that the
extracts of Sapindus mukorossi and Rheum emodi do have a protective
capacity both in vitro on primary hepatocytes cultures and in in vivo in
a rat model of CCl4 mediated liver injury.
7. Anxiolytic activity: Methanolic extracts of Sapindus mukorossi
(200 and 40 mg/L) show significant anxiolytic activity as compared to
standard anxiolytics Diazepam (2 mg/Kg) and Fluoxetine (10 mg/Kg)1.
Fig R1 R2 R3 R4 R5
11 Glc2-Rha H OH OH H
12 Glc2-Rha H OH OH OH
13 Glc2-Rha OH CH3 H H
14 Glc2-Rha CH3 OH H H
Fig R1 R2 R3
15 Glc2-Rha OH OH
16 Glc2-Rha OH OCH3
17 Glc2-Rha H OCH3
Fig R1R2
18 Glc6-Rha β-OCH3
19 Glc6-Rha α-OCH3
20 Glc2-Rha α-OCH3
2-Rha
21 Glc β-OCH3
6-Rha
2-Rha
22 Glc α-OCH3
6-Rha
23 Glc2-Glc α-OCH3
2-Glc
24 Glc α-OCH3
6-Rha

UPADHYAY, A. & SINGH, D.K. - Pharmacological effects of Sapindus mukorossi. Rev. Inst. Med. Trop. Sao Paulo, 54(5): 273-80, 2012.
278
8. Molluscicidal activity: Extracts of Sapindus mukorossi showed
molluscicidal effect against the golden apple snail, Pomacea canaliculata
Lamarck. (Ampullariidae) with LC50 values of 85, 22 and 17 ppm
at 24, 48 and 72h exposure period, respectively16. Bioassay-directed
fractionation of Sapindus mukorossi resulted in the isolation of one
new hederagenin-based acetylated saponin, hederagenin 3-O-(2,4-O-di-
acetyl-α-l-arabinopyranoside)-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-
L-arabinopyranoside [1], along with six known hederagenin saponins,
hederagenin 3-O-(3,4-O-di-acetyl-α-L-arabinopyranoside)-(1→3)-α-L-
rhamnopyranosyl-(1→2)-α-L-arabinopyranoside [2], hederagenin 3-O-(3-
O-acetyl-β-D-xylopyranosyl)-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-
arabinopyranoside [3], hederagenin 3-O-(4-O-acetyl-β-D-xylopyranosyl)-
(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside [4],
hederagenin 3-O-(3,4-O-di-acetyl-β-D-xylopyranosyl)-(1→3)-α-L-
rhamnopyranosyl-(1→2)-α-L-arabinopyranoside [5], hederagenin
3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-
arabinopyranoside [6], and hederagenin 3-O-α-L-arabinopyranoside [7].
The bioassay data revealed that 1-7 were molluscicidal, causing 70-100%
mortality at 10 ppm against the golden apple snail16.
UPADHYAY & SINGH42 reported that Sapindus mukorossi fruit
pericarp is a potential source of botanical molluscicides against Lymnaea
acuminata. These snails are the intermediate host of liver fluke Fasciola
gigantica, which causes 94% fascioliasis in the buffalo population
of northern India32. The active molluscicidal component of Sapindus
mukorossi fruit is soluble in chloroform, ether, acetone and ethanol.
The toxicity of ethanolic extract of Sapindus mukorossi fruit powder
is higher than other extracts which indicates that the molluscicidal
component present is more soluble in ethanol than other organic solvents.
UPADHYAY & SINGH42 characterized that saponin is the active
component present in Sapindus mukorossi fruit by High Performance
Liquid Chromatography. A comparison of the molluscicidal activity of
the column-purified fraction of Sapindus mukorossi fruit powder with
synthetic molluscicides clearly demonstrates that the purified fraction
of Sapindus mukorossi is more potent. The LC50 at 96 h of the column–
purified fraction of Sapindus mukorossi fruit powder (5.43 mg/L) against
Lymnaea acuminata is lower than those of synthetic molluscicides-
carbaryl (14.40 mg/L), phorate (15.0 mg/L), formothion (8.56 mg/L) and
niclosamide (11.8 mg/L)32. LC50 at 96 h of crude powder of Sapindus
mukorossi (119.57 mg/L) against Lymnaea acuminata is lower than the
crude powder of Canna indica root (359.02 mg/L)40, Thuja orientalis
leaf powder (250.55 mg/L), Thuja orientalis fruit powder (255.12
mg/L)31, Zingiber officinale rhizome (273.80 mg/L), Allium cepa bulb
(253.27 mg/L)34.
9. Tyrosinase inhibition and free radical scavenging: CHEN
et al.2 first evaluated that the extracts of Sapindus mukorossi seeds
using methanol (MeOH), ethyl acetate (EA) or hexane as solvents
show tyrosinase inhibition, free radical scavenging, antimicrobial and
anticancer properties. Sapindus mukorossi extracts showed strong specific
inhibition activities on the proliferation of human melanoma and lung
cell lines. The data exhibited the high potential of applying Sapindus
mukorossi extracts in medical cosmetology, food supplementation,
antibiotics and chemotherapy.
10. Fungicidal activity: The crude extract of Sapindus mukorossi
exhibits a strong growth inhibition against the pathogenic yeast Candida
albicans, which causes cutaneous candidiasis. Extracts from the dried
pericarp of Sapindus L. (Sapindaceae) fruits were investigated for their
antifungal activity against clinical isolates of yeasts Candida albicans
and Candida non-albicans from vaginal secretions of women with
Vulvovaginal Candidiasis. Four clinical isolates of C. albicans, a single
clinical isolate of each of the species C. parapsilosis, C. glabrata, C.
tropicalis, and the strain of C. albicans ATCC 90028 were used. The
hydroalcoholic extract was bioactivity-directed against a clinical isolate
of C. parapsilosis, and showed strong activity. The n-BuOH extract and
one fraction showed strong activity against all isolates tested41. The
saponin fraction inhibited the dermatophytic fungi Trichophyton rubrum,
Trichophyton mentagrophytes, Sabouraudites canis and Epidermophyton
floccosum37.
Fig R1R2
25 Ara2-Rha3-Ara3-OAC H
26 Ara2-Rha3-Rha4-OAC H
2-OAC
27 Ara2-Rha3-Xyl H
3-OAC
2-OAC
28 Ara2-Rha3-Xyl H
4-OAC
3-OAC
29 Ara2-Rha3-Xy H
4-OAC
30 Ara2-Rha3-Xyl4-OAC H
31 Ara2-Rha3-Xyl Glc2-Glc
32 Ara2-Rha3-Xyl Glc2-Glc
33 Ara2-Rha Glc2-Glc
34 Ara2-Rha H
35 Ara2-Rha3-Xyl H
36 Ara2-Rha3-Xyl4-Glc H
6-Rha
37 Ara2-Rha3-Xyl4-Glc H
2-Glc
6-Rha
38 Ara2-Rha3-Xyl Ara2-Rha3-Xyl4-Glc
2-Glc

UPADHYAY, A. & SINGH, D.K. - Pharmacological effects of Sapindus mukorossi. Rev. Inst. Med. Trop. Sao Paulo, 54(5): 273-80, 2012.
279
11. Anti-inflammatory activity: TAKAGI et al.35 reported that crude
saponin and hederagenin isolated from Sapindus mukorossi inhibited
the development of carrageen-induced edema in the rat hind paw as
well as on granuloma and exudates formations induced by croton oil
in rats. The effects of these agents on vascular permeability and acetic
acid induced writhing in mice were also examined. Anti-inflammatory
activity on carrageenin edema was observed after intraperitoneal and
oral administration of crude saponin, whilst hederagenin and the other
agents showed activity only when administered.
12. Piscicidal activity: Effects of Sapindus mukorossi have been
studied on fish. Pericarp of Sapindus mukorossi is the most toxic parts
yielding 100% mortality within 12 hours and mean survival time was
found to be 1.18 hours. LD10, LD50, LD100 ranging between 3.5 ppm and
10 ppm at 48 hrs and possess high potential for fish eradication. Sapindus
mukorossi fruit pericarp can be used as a selective eradicant for horny
fish like Heteropneustes fossils and channa punctuate44.
13 Anti-platelet aggregation activity: HUANG and co workers
demonstrated that five new tirucallane type saponins, sapinmusasaponins
from the galls of Sapindus mukorossi, showed moderate activity in a
12-0-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein-Barr virus
early antigen (EBV-EA) activation assay25.
DISCUSSION
Sapindus mukorossi is a versatile and exceptionally valuable
medicinal plant. It is known by such regional names as soapnut,
soapberry, washnut, reetha and dodan. The phytochemical screening of
the plant extract showed the presence of saponins (10.1%) present in the
pericarp of the fruit. The use of Sapindus mukorossi in folk medicine
worldwide30 is validated by scientific studies that have demonstrated the
efficacy of the extracts in various experimental models. Pharmacological
effects of Sapindus mukorossi have been reported like anti-bacterial19,
insecticidal12,13,26, spermicidal11,27, anti-trichomonas11,39, anti-tumor22,29,36,
hepatoprotective18, anxiolytic1, molluscicidal16,42, fungicidal37,41, anti-
inflammatory35 and piscicidal44 activities and are being employed for
the treatment of different ailments in the indigenous system of medicine.
Although a number of phytochemicals present in Sapindus mukorossi
have been isolated and identified by researchers working in different
laboratories, their pharmacological/biological studies in human welfare
has not been studied so far.
Most of the scientific study is confined to the elaboration of traditional
practices of Sapindus mukorossi. There is a long list of saponins present
in Sapindus mukorossi. It needs individual attention so that they can be
explored in different pharmacological studies. The literature reviewed
gives a limited picture of pharmacological effects of Sapindus mukorossi.
There is a need for much additional research regarding pharmacological
effects of Sapindus mukorossi at molecular level to explain their mode
of action.
CONCLUSION
Sapindus mukorossi is a tropical tree whose numerous economic
applications and whose facility of propagation are arousing international
interest. It needs to be widely cultivated in most of the areas where
climatic conditions favor its optimum growth. In this way, a maximum
yield of its different usable parts could be achieved to derive the
maximal amount of commodities of a multifarious nature for the
welfare of mankind. This plant has been used as traditional medicine
for various ailments. The earlier reports on chemical investigation and
pharmacological evaluation showed that Sapindus mukorossi contains a
number of bio-active novel compounds. As literature illustrates, many
biological and pharmacological activities are shown by fractions of crude
extracts and isolated substances. Furthermore, the detailed chemical
analysis is required to isolate bio-active constituents from Sapindus
mukorossi and to trace out their biological activities. Thus, it can be
concluded that Sapindus mukorossi can play an important role in modern
medical system in near future.
RESUMO
Efeitos farmacológicos do Sapindus mukorossi
Sapindus mukorossi é planta medicinal extremamente valiosa
distribuída nas regiões tropical e subtropical da Ásia. O propósito da
presente revisão é uma compilação curta da composição fitoquímica e
das propriedades farmacológicas desta árvore que apresenta múltiplos
propósitos. O principal fitoconstituinte isolado e identificado das diferentes
partes desta planta são as saponinas triterpenoidais do tipo da oleana,
damarana e tiruculana. A estrutura e o nome químico de todos os tipos
de saponinas triterpenoidais encontrados no Sapindus mukorossi estão
incluídos nesta revisão. Muitas pesquisas tem sido conduzidas para provar o
potencial desta planta como espermaticida, contraceptivo, hépato-protetor,
emético, anti-inflamatório e anti-protozoário. A presente revisão exalta
alguns principais usos farmacológicos do Sapindus mukorossi.
ACKNOWLEDGEMENT
One of the authors Aparna Upadhyay is thankful to Department of
Science and Technology, New Delhi for financial assistance (Inspire
Fellowship number- IF10296).
REFERENCES
1. Chakraborty A, Amudha P, Geetha M, Surjit Singh N. Evaluation of anxiolytic activity
of methanolic extract of Sapindus mukorossi Gaertn. in mice. Int J Pharm Bio Scie.
2010;1:1-8.
2. Chen CY, Kuo PL, Chen YH, Huang JC, Ho ML, Lin RJ, et al. Tyrosinase inhibition,
free radical scavenging, antimicroorganism and anticancer proliferation activities of
Sapindus mukorossi extracts. J Taiwan Inst Chem Engrs. 2010;41:129.
3. Chirva V, Kintya PK, Sosnovskii VA. Triterpene glycosides of Sapindus mukorossi.
V. The structure of sapindoside E. Chem Nat Compounds. 1970;6:440-2.
4. Chirva V, Kintya PK, Sosnovskii VA. Triterpene glycosides of Sapindus mukorossi.
III. The structure of sapindoside C. Chem Nat Compounds. 1970;6:380-1.
5. Chirva V, Kintya PK, Sosnovskii VA, Zolotarev BM. Triterpene glycosides of Sapindus
mukorossi. IV. The structure of sapindoside D. Chem Nat Compounds. 1970;6:316-8.
6. Chirva V, Kintya P, Sosnovskii VA, Krivenchuk PE, Zykova NY. Triterpene glycosides
of Sapindus mukorossi. II. The structure of Sapindoside A & B. Chem Nat Compounds.
1970;6:213-5.
7. Chopra R, Ghosh S. Poisonous plants of India. Delhi: The Manager of Publishers;
1946. p. 308.

UPADHYAY, A. & SINGH, D.K. - Pharmacological effects of Sapindus mukorossi. Rev. Inst. Med. Trop. Sao Paulo, 54(5): 273-80, 2012.
280
8. Dhar JP, Bajpai VK, Setty BS, Kamboj VP. Morphological changes in human
spermatozoa as examined under scanning electron microscope after in vitro exposure
to saponins isolated from Sapindus mukorossi. Contraception. 1989;39:563-8.
9. Dwivedi AK, Chaudhry M, Sarin JPS. Standardization of a new spermicidal
agent Sapindus saponin and its estimation in its formulation. Indian J Pharm Sci.
1990;52:165-7.
10. Francis G, Kerem Z, Makkar H, Becker K. The biological action of saponins in animal
systems: a review. Br J Nutr. 2002;88:587-605.
11. Garg S, Taluja V, Upadhyay M, Talwar GP. Studies on contraceptive efficacy of
Praneem polyherbal cream. Contraception. 1993;48:591-6.
12. Geyter ED, Geelen D, Smagghe G. First results on the insecticidal action of saponins.
Commun Agric Appl Biol Sci. 2007;72:645-8.
13. Geyter ED, Lambert E, Geelen D, Smagghe G. Novel advances with plant saponins
as natural insecticides to control pest insects. Pest Tech. 2007;1:96-105.
14. Huang HC, Tsai WJ, Liaw CC, Wu SH, Wu YC, Kuo YH. Anti-platelet aggregation
triterpene saponins from the galls of Sapindus mukorossi. Chem Pharm Bull (Tokyo).
2007;55:1412-5.
15. Huang HC, Wu MD, Tsai WJ, Liao SC, Liaw CC, Hsu LC, et al. Triterpenoid saponins
from the fruits and galls of Sapindus mukorossi. Phytochemistry. 2008;69:1609-16.
16. Huang HC, Liao SC, Chang FR, Kuo YH, Wu YC. Molluscicidal saponins from
Sapindus mukorossi, inhibitory agents of Golden Apple snails Pomacea canaliculata.
J Agric Food Chem. 2003;51:4916-9.
17. Huang HC, Tsai WJ, Morris-Natschke SL, Tokuda H, Lee KH, Wu YC, et al.
Sapinmusaponins F-J, bioactive tirucallane-type saponins from the galls of Sapindus
mukorossi. J Nat Prod. 2006;69:763-7.
18. Ibrahim M, Khaja MN, Aara A, Khan AA, Habeeb MA, Devi, YP, et al.
Hepatoprotective activity of Sapindus mukorossi and Rheum modi extracts: in vitro
and in vivo studies. World J Gastroenterol. 2008;14:2566-71.
19. Ibrahim M, Khan AA, Tiwari SK, Habeeb MA, Khaja MN, Habibullah CM.
Anti-microbial activity of Sapindus mukorossi and Rheum modi extracts against
Helicobacter pylori: in vitro and in vivo studies. World J Gastroenterol. 2006;12:7136-
42.
20. Kasai R, Fujino H, Kuzuki T, Wong WH, Goto C, Yata N, et al. Acyclic sesquiterpene
oligoglycosides from pericarps of Sapindus mukorossi. Phytochemistry. 1986;25:871-
6.
21. Kirtikar KR, Basu BD. Indian medicinal plants. Allahabad: B.L.M. Publication; 1991.
22. Man S, Gao W, Zhang Y, Huang L, Liu C. Chemical study and medical application
of saponins as anti-cancer agents. Fitoterapia. 2010;81:703-14.
23. Nakayama K, Fujino H, Kasai R, Mitoma Y, Yata N, Tanaka O. Solubilizing
properties of saponins from Sapindus mukorossi Gaertn. Chem Pharm Bull (Tokyo).
1986;34:3279-83.
24. Ni W, Hua Y, Liu HY, Teng RW, Kong YC, Hu XY, et al. Tirucallane-type triterpenoid
saponins from the roots of Sapindus mukorossi. Chem Pharm Bull (Tokyo).
2006;54:1443-6.
25. Ni W, Hua Y, Teng RW, Kong YC, Chen CX. New tirucallane-type triterpenoid
saponins from Sapindus mukorossi. J Asian Nat Prod Res. 2004;6:205-9.
26. Rahman SS, Rahman M, Begum SA, Khan MMR, Bhuiyan MH. Investigation of
Sapindus mukorossi extracts for repellency, insecticidal activity and plant growth
regulatory effect. J Appl Sci Res. 2007;3:95-101.
27. Rastogi RP, Mehrotra BN. Compendium of Indian medicinal plants. New Delhi:
CDRI Publication; 1999. p. 609-10.
28. Saxena D, Pal R, Dwivedi AK, Singh S. Characterization of sapindosides in Sapindus
mukorossi saponin (Reetha saponin) and quantitative determination of sapindoside
B. J Sci Ind Res. 2004;63:181-6.
29. Sengupta A, Basu SP, Saha S. Triglyceride composition of Sapindus mukorossi seed
oil. Lipids. 1975;10:33-40.
30. Sharma A, Sati SC, Sati OP, Sati D, Maneesha Kothiyal SK. Chemical constituents
and bioactivities of genus Sapindus. Int J Res Ayurveda Pharm. 2011;2:403-9.
31. Singh A, Singh VK. Molluscicidal activity of Saraca asoca and Thuja orientalis
against the fresh water snail Lymnaea acuminata. Vet Parasitol. 2009;164:206-10.
32. Singh DK, Agarwal RA. In vivo and in vitro studies on synergism with
anticholinesterase pesticides in the snail Lymnaea acuminata. Arch Environ Contain
Toxicol. 1983;12:483-7.
33. Singh N, Kaur A, Yadav K. A reliable in vitro protocol for rapid mass propagation
of Sapindus mukorossi Gaertn. Nat Sci. 2010;8:41-7.
34. Singh S, Singh VK, Singh DK. Molluscicidal activity of some common spice plants.
Biol. Agric. Hortic. 1997;14:237-49.
35. Takagi K, Park EH, Kato H. Anti-inflammatory activities of hederagenin and crude
saponin isolated from Sapindus mukorossi Gaertn. Chem Pharm Bull(Tokyo).
1980;28:1183-8.
36. Takechi M, Tanaka Y. Structure-activity relationships of the saponin α-hederin.
Phytochemistry. 1990;29:451-2.
37. Tanaka O, Tamura Y, Masuda H, Mizutani K. Application of saponins in food and
cosmetics: saponins of Mohova Yucca and Sapindus mukorossi Gaertn, saponins used
in food and agriculture. New York: Plenum Press; Waller GR and Yamasaki K; 1996.
p.1-11.
38. Teng RW, Ni W, Hau Y, Chen CX. Two new tirucallane-type triterpenoid saponins
from Sapindus mukorossi. Acta Botanica Sinica. 2003;45:369-72. [Article in Chinese].
39. Tiwari P, Singh D, Singh MM. Anti-Trichomonas activity of Sapindus saponins, a
candidate for development as microbicidal contraceptive. J Antimicrob Chemother.
2008;62:526-34.
40. Tripathi SM, Singh DK. Molluscicidal activity of Punica granatum bark, Canna
indica root. Braz J Med Biol Res. 2000;33:1351-5.
41. Tsuzuki JK, Svidzinski TIE, Shinobu CS, Silva LFA, Rodrigues-Filho E, Cortex DAG,
et al. Antifungal activity of the extracts and saponins from Sapindus saponaria L..
An Acad Bras Cienc. 2007;79:577-83.
42. Upadhyay A, Singh DK. Molluscicidal activity of Sapindus mukorossi and Terminalia
chebula against the freshwater snail Lymnaea acuminata. Chemosphere. 2011;83:468-
74.
43. Vincken JP, Heng L, de Groot A, Gruppen H. Saponins, classification and occurrence
in the plant kingdom. Phytochemistry. 2007;68:275-97.
44. Virdi, GS. The piscicidal properties of Acorus calamus, Sapindus mukorossi and
Xeromphis spinosa on 7 species of fishes of North India. Indian J Phys Nat Sci.
1982;2:28-35.
45. Yao HK, Hui CH, Li-Ming YK, Ya-Wen H, Kuo-Hsiung L, Fang-Rong C, et al. New
dammarane-type saponins from the galls of Sapindus mukorossi. J Agric Food Chem.
2005;53:4722 -7.
Received: 17 December 2011
Accepted: 21 March 2012