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Phytochemiafry, Vol. 21, No. 5. pp. 959-978, 1982. 0031~9422/82/05095%20$10.

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Printed in Great Britain. @ 1982 Pergamon Press Ltd.

REVIEW

STEROID SAPONINS

S. B. MAHATO, A. N. GANGULY and N. P. SAHU


Indian Institute of Experimental Medicine, Calcutta 700 032, India

(Revised received 18 August 1981)

Key Word Index-Steroid saponins; sapogenins; isolation; structure elucidation; natural distribution.

Ah&a&-Steroid saponins isolated from various plants are reviewed. The newer techniques used in their
isolation and strucure elucidation are discussed. A compilation of the saponins isolated up to 1980 along with
their available physical data is included. The basic steroidal saponins isolated after 1972 are also compiled.

INTRODUCTION procedure involving Si gel CC and Sephadex LH-20


The saponins are plant glycosides which have the for the separation of furostanol oligosides of
property of forming a soapy lather when shaken with Asparagus cochinchinensis has been described by
water. The cardiac glycosides also possess this pro- Konishi and Shoji [19]. The technique of DCC [20,21]
perty but these are classified separately because of has been applied successfully for the separation of
their specific biological activity. The saponins are saponins. The technique is based on the difference of
classified as steroid or triterpenoid saponins depend- the partition coefficients of compounds in liquid-
ing upon the nature of the aglycone. The aglycone of liquid phases such as countercurrent distribution.
a steroid saponin is usually a spirostanol or its Those solvent systems which form two immiscible
modification. A third group of saponins which are layers are selected for the separation of the com-
called basic steroid saponins contain nitrogen analo- pounds by this method. In the case of Sephadex
gues of steroid sapogenins as aglycones. Some LH-20 chromatography, plant extracts are partially
natural products may produce froth with water but purified by the usual Si gel CC methods before sub-
only exhibit some of the properties of saponins. jecting them to DCC. This technique is useful for the
Excellent general reviews on saponins [l-7] have small scale and semi-micro qualitative and quan-
been published. Particular mention may be made of titative determination of saponins. Nevertheless, it
the comprehensive reviews on the triterpenoid requires a longer time, viz., a period of four days to a
saponins by Rastogi et al. [&lo]. Steroid saponins week even for effective semi-micro separation. The
have been reviewed briefly by Elks [11,12] and molluscidal saponins from Comus florida have been
Takeda [13]. The basic steroid saponins have been separated by Hostettman et al. [22]. The methanol
reviewed by Schreiber [14], Roddick [IS], Herbert extract of the plant was first fractionated by
[16] and Harrison [17]. This review deals with recent Sephadex LH-20 CC followed by the separation of
developments with regard to isolation and structure pure saponins by DCC. This method has also been
elucidation of steroid saponins including the applied for the separation of the dammarane-type
configuration of the carbohydrate moieties. saponins of Panax ginseng and P. japonicum by
Tanaka et al. [23,24]. The separation of the major
ISOLATION saponins of Bupleuri radix has been achieved using
The methods of isolation of steroid saponins are the DCC technique by Otsuka et al. [251.
essentially the same as those of triterpenoid saponins.
The classical methods of isolation of triterpenoid High performance liquid chromatography (HPLC)
saponins have been reviewed [8-101. The separation The very efficient newer technique of HPLC is
of a saponin mixture into individual components is a increasingly being used for the separation of various
formidable task. The development of recent chroma- compounds including saponins. The technique has
tographic techniques has provided valuable means been described in a recent book by Simpson [26].
for isolation of pure saponins and their derivatives. A Rapid, selective, and highly sensitive separation of
convenient method of separation of steroidal gly- saponins can be effected by HPLC using a variety of
cosides has been described by Nohara et al. [18]. stationary and mobile phases. Successful separation
of the major saponin components in liquorice has
Sephadex LH-20 chromatography and droplet been achieved using HPLC [27]. Tanaka et al. [28]
countercurrent chromatography @CC) have analysed the saponin constituents of Bupleuri
Sephadex LH-20 has successfully been used for the radix on a column of octadecylsilylated (ODS) Si gel
separation of steroidal saponins. A typical isolation LS-410 with a mixture of methanol, water, acetic acid

959
PHYTO Vol. 21. No. 5-A
960 S.B.MAHATO, A.N. GANGLJLYand N. P. SAW

and triethylamine as the mobile phase. Anthracene saponin consisting of kammogenin and five molecules
was used as an appropriate int. standard for quan- of 2deoxyribose has been reported by Backer et al.
titative analysis. The saponin mixture obtained from [37]. The furostanol bisglycosides so far isolated
Tribulus terrestris (Mahato, S. B. et al., unpublished contain a glucose unit attached to the C-26 hydroxyl.
results) was separated on a column of p-Bondapak In the classical method, the structure of the sugar
Cl8 using methanol as the mobile phase. The very moieties of the saponins is determined by
complex mixtures of saponins which were not identification of the monosaccharides obtained on
amenable to separation previously can now be acid hydrolysis by PC and GLC, quantitative deter-
effectively separated by a combination of silica gel mination of monosaccharides by GLC, partial
CC, gel chromatography on Sephadex LH-20 and hydrolysis followed by isolation and characterization
HPLC on a reversed phase column. of prosapogenins and also, where possible, by charac-
terization of oligosaccharides. The points of attach-
STRUCTUREELUCIDATION ment of different sugar units are revealed by per-
The conventional method of structure elucidation of methylation of the saponins followed by hydrolysis or
steroidal saponins starts with acid hydrolysis which methanolysis and identification of the methylated
yields the aglycone and the sugar moieties which are sugars by PC or GLC. The mode of sugar linkage in
separately investigated. Extensive chemical studies saponins is determined by enzymic hydrolysis with a-
on the aglycones revealed that they are almost and @glycosidases or by the application of Klyne’s
exclusively spirostane derivatives. But furostanol rule [38] on molecular rotation difference. However,
glycosides, which according to Marker and Lopez [29] both of these methods are not always applicable,
are precursors of spirostane glycosides, have also particularly in the case of complex glycosides.
been isolated and characterized. A simple qualitative
test for furostanol glycoside has been developed by Mass spectrometry
Kawasaki et al. [30]. The furostanol glycosides with Until very recently MW determination of saponins
some exceptions [18], show a characteristic red was a difficult task. But newer developments in mass
colour on a TLC plate when sprayed with p- spectrometry have almost solved this problem. Elec-
dimethylaminobenzaldehyde and hydrochloric acid tron impact mass spectrometry (EIMS) has been
(Ehrlich reagent). Moreover, the furostane skeleton shown to be a very useful method [39-42] for
does not exhibit the characteristic IR absorptions of identification, determination of purity and structural
spirostane derivatives [6]. Confirmatory evidence for elucidation of saponins, although volatile derivatives
the furostane structure is obtained by examination of have to be produced. Moreover, saponins containing
the products of Marker’s degradation or Baeyer- more than four sugars do not give molecular ions,
Villiger oxidation followed by hydrolysis. The first even when derivatized.
isolation of a furostanol glucoside, jurubine (l), was Field ionization mass spectrometry (FIMS) has
announced by Schrieber and Ripperger [31] and later been applied to the structural analysis of permethyl-
Tschesche et al. [32, 331 isolated and characterized a ated oligosaccharides r43,441, underivatized
furostanol bisglycoside, sarsaparilloside (2), cor- nucleosides [451, naturally occurring glycosides, e.g.
responding to the spirostanol glycoside, parillin. somalin [46] and cardiac glycosides [47,48].
Moreover, some glycosides have been isolated whose However, mass spectrometry has had limited ap-
aglycones are not spirostanol but a modification. In plication in the field of underivatized oligosaccharides
general, the sugar moieties of steroidal saponins are because it requires volatilization and ionization of the
oligosaccharides which consist of 2-4 kinds of sugar sample. Ionization and volatilization are coupled in
units, e.g. D-glucose, u-galactose, u-xylose and L- one process in field desorption mass spectrometry
rhamnose. DXylose and L-rhamnose generally occur (FDMS) [49,50]. Very little of the energy goes into
at the terminal positions. Arabinose-containing internal excitation and the degree of fragmentation is
steroidal saponins are also known. In a very few relatively small. FDMS of underivatized steroid and
cases, quinovose occurs as the carbohydrate moiety. triterpenoid saponins have been reported 151-551. The
Trillenoside A, a novel ll-norspirostanol glycoside, spectra show the intense ions formed by attachment
contains xylose, rhamnose, arabinose and apiose as of alkali cations to the neutral molecule. The FDMS
the sugar constituents [34-361. Another unusual of the saponins not only gives the MW but also clear

I Jurubine 2 Sarsaparil loside


Steroid saponins 961

information with regard to the sequence of the sugar 27


units in the molecule and their individual chemical
structures by the fragment ions formed by the direct
bond cleavages in the oligosaccharide moiety of the
saponins. The formation of the fragment ions in
FDMS has been discussed in relation to the well 2
established mechanisms of glycosidic bond cleavage 3
by the acidic hydrolysis.
The new technique of plasma desorption mass
spectrometry (PDMS) [56,57] has also been success-
fully employed for MW determination of under-
ivatized steroidal saponins [22]. This technique util-
3 Pigwenin, 25R, Jp-OB
izes energetic fission fragments from the decay of
4 Gitogenin, 25R, 2q rp-OH
“*Cf to volatilize and ionize a solid sample. The rapid
sample heating (flash desorption) technique has been 5 Ka~tawwnin, 25R, 2a-OBe, 36, 5a, @-OH
used for the structural analysis of o-hederin, a triter- 6 Alliogenin. 25R. 2a, 38, 3a, 66-0~
penoid saponin [58]. 7 Heowen% 25R, 38-OH, 12-130
8 Wgenin, 25R, 2a, 3B, 6p-OH
‘H NMR spectroscopy 9 Digalogenin, 25R. 3@, 156-0~
peracetate or IO F.cckogenin, 25R, Ji3, 128-0~
permethylate sometimes helpful in determining the II a-OhlorogenIn, 25R, 3p, Q-m
mode of sugar When the spectrum shows an
12 Wsitogenin, 25R, 2a, 36, ls~-cxr
anomeric proton signal as a doublet with J - 7 Hz
I3 Nectigogenin, 255, 36-0~
which is assignable
I4 Keochlorcgcnin, 25s. 39, 6a-aE
I5 P~iculwenin, 25% 3P, 6cr, 23p-OII
formation (a- and ‘C, in L-arabinose) I6 Aeoegigenin, 25S, 2a, 313, q-m
I7 Neo~lNwnin, 25S, 2a, 3p, 50, @-m
residues. I6 Solagenin, 255, ~-CO, 6a-oxi
However, when several anomeric proton signals ap- I9 Siealegenin, 25.S, 3f~-OH. 12-co
pear and when J is small (1-3 Hz), suggesting

Moreover, it is
observed that the anomeric proton signal of (Y-D-
glucosides, a-D-mannosides,
generally at lower field (8
5.0-6.0) than those of the corresponding
4.5-5.0). This difference

structure.

“C NMR spectroscopy
developed and
20 Yonogenin, 25 R, 28, 3a-OH
very useful tool for the elucidation of the structures
Tokorogenin, 25 R, 18, 28, 3a-OH

aglycones and sugar 2’: Epimetagenin, 25 R, 28,3a, I la-OH


23 Metagenin, 25R, 28, 38, I la-OH
moieties are available.
available [59-64] and the 24 Protometagenin, 25 R,2/3, 38, I la-OH, 4-ene
carbon chemical shifts of a number of 25 Nagiragenin, 25R, 38, Ila-OH
sapogenins 26 Isorhodeasapogenin, 25 R, Ip, 3/3-OH
27 Sarsasapogenenin, 25 S, 38 -OH
26 Rhodeasapagenin, 25S, I/?, 3/3-OH
29 Conval lagenin A, 25 S, IB, 38, 5fl-OH
30 Convol lagenin 6, 25 s, 11%3&4&5fl- OH
31 Neotokorogenin , 25 S, 18, 2p, 3a-OH
@anomeric pairs of u-glucopy-
ranosides
the direct bonded C-H coupling constant of the
C-l signal (.L.w_J of hexapyranoses and pento-
steroid-, and triterpenoid- pyranoses are characteristic of the anomeric
oligoglycosides have been reported [63,72-751. configuration. Jc.r.w.l - 155 Hz when H-l is axial
The anomeric configuration different sugar whereas it is cu 165 Hz when H-l is equatorial [76].
moieties in a saponin can also be determined Thus it is evident that “C NMR spectroscopy is of
difference in immense help in the elucidation of the structure of
chemical shifts of a- and carbons, saponins.
S. B. MAHATO,A. N. GANGULYand N. P. Sanu

32 Diosgenin, 25 R, 3f3-OH
33 Ruscogenin, 25 R, I/3, 3fi-OH
34 Yuccagen in, 25177, 2a, 3/3-OH
35 Kammogenin, 25R, 20, 3/3-OH, 12-w
36 Pennogenin, 2!iR, 38, 17a-OH
37 Prazerigenin A, 25 R, 38, 14a-OH
36 Epidiosgenin, 25R, 3a-OH
39 Epiruscogenin, 25 R, Ig, 3a-OH
40 Yamogenin, 25 S, 38-OH

OH

*--

HO- HO@

OH

41 Cryptogenin 43 Hispigenin
42 17 (201- Dehydrocryptogenin

HO
H

45 Convallaaarogenin
44 Trillenqenin 46 A5- Convallamarogeain

HO”

47 Episceptrumgenin 46 Nuatigenin 49 Solanidine

..

HO

50 Solasodine
Steroid saponins 963

Table 1. Steroidal saponins whose genins and sugars have been fully characterized

Wonins (mp, MD) Source structure Reference

Agave saponin C Agaoc americana Hecogenin 0, 77-79


xyl-2gic-4glc-‘gla_(3B_OH)
Agave saponin D Agaue americana Hecogenin (7), 77-79
rha
)&Ic-‘glc-‘gal_(3kWH)
xyl
Agave saponin E, Agave americana Hecogenin (7) 77.78. 80
304-3W, - 130” (MeOH) rha-‘rha
)$glc-‘glc-‘gal-(3g-oH)

xyl
Agave saponin H Agave americana Hecogenin (7). 77,80
rha-‘rha
)Lc-‘glc-‘ga1~3a-0H,:

XYl
dc-W-OW
Agavoside A Agave americana Hecogenin (7). 77,83
gal-Q&OH)
Agavoside B Agave americana Hecogenin (7). 77, 83
glc-‘gal-(3g-OH)
Agavoside C Agaue americana Hecogenin (7). 77,a4
275”, - 55’ (DMP) glc-‘glc-‘gal-(3&OH)
Agavoside G Agave americana Hecogenin (7). 78.81
rha
)&-‘glc-‘gal-(36 - OH);

xyl
glc-(26-OH)
Aginoside All&m gigantenin Agigenin (8). a2
XYl

)&lc-‘gal_(3g-OH)

glc
Allionin Allium karataviense Alliogenin (0, 85
gW3@-OH)
Alliumoside B Album narcissiflorum Diosgenin (32). a6
glc-‘glc-3glc-(3&OH);
glc-@-OH)
Alliumoside C Allium narcissiflorum Diosgenin (32). 86
rha-4rha-4rha-6gal-6Blc-(3B-OH);
glc-(26-OH)
Alliumoside D Allium narcissiflorum Diosgenin (32), 86
rha-‘rha-$&z
>&lc<3&OH);

gl~_(26Xr:)~
Alliumoside E Allium narcissifloncm Diosgenin (32). 86
glc-‘rha-‘rha-6glc
-
)&tlc_(3&OH);

glc
glc-(26-OH)
ASP-IV, 165-167’ Asparagus Sarsasapogenin (27)
- 23” (MeOH) cochinchinensis xyl-‘glc-Q/&OH); glc_(26-OH); (22-OMe) I9
ASP-V, 150-156” (dec), Asparagus Sarsasapogenin (27). 19
- 45.5” (MeOH) cochinchinensis rha-6glc-(3&OH); glc_(26_OH); (22-OMe)
964 S. B. MAHATO,A. N. GANGULYand N. P. SAHU

Table l-continued
Saponins (mp, [&) Source Structure Reference

ASP-VI, 165-168” (dec), Asparagus Srasasapogenin (27), 19


cochinchinensis

- 50” (MeOH) &-(3g-OH); glc-(26-OH); (22-OMe)


>
XYl
ASP-VII, 179-181’ (dec), Asparagus Sarsasapogenin (27). 19
- 27” (MeOH) cochinchbwnsis rha
xylf 44 glcO@OH); glc-f26-OH); (22-OMe)

dc
Asparagoside A Asparagus Sarsasapogenin (27). 87
0fEcinalis gw38-OH)
Asparagoside B Asparagus Sarsasapogenin (27). 87
oficinalis dc-wOH)
Asparagoside D Asparagus Sarsasapogenin (87). 88
oficinalis glc
>kdc-c3/3-oH)

glc
Asparagoside G Asparagus Sarsasapogenin (27). 88
oflicinalis dc
>!c_(38_OH); glc-W-OH)

dc
Asperin, 222-231”. Smilax opera Yamogenin (48). 89
rha-‘rha
- loo” (pyridine) 1.
,&_(38-OH)
rha
Asperoside Smilax aspem Yamogenin (48), 89
rha-%a

>‘kdc_(38_OH); gL(26-OH)
rha
Aspidistrin, Aspidistra elatior Diosgenin (32). 90
265-267”, - 65” ac
>&lo’gal-(3&OH)

XYl
Avenacoside A Avena sativa Nnatigenin (48). 91
rha
)Wc-(3&OH): glc-(26-OH)

glc
Avenacoside B Avena sativa Nuatigenin (48), 92
rha-‘$_(3&OH); glc-(26_OH)

dc-*glc
Balanitiscin A, Balanites Diosgenin (32). 93
274278”, - 39” roxburghii rha

):glc-(38-OH)

glc
Capsicoside, 295”. Capsicum annum Gitogenin (4). 94
glc
- 35’ (CHClr + MeOH) >&k-$aL3glc-(3~-OH); glc-(26OH)

glc
Capsicosin Capsicum annum Gitogenin (4). 94
glc
>&c-4gal-3glc-(3g-OH)

glc
Convallamaronin, Convallaria Convallamarogenin (4fl). 95
215-218’. - 30” (MeOH) majalis rha-(3g-OH); rha-‘qui-(l&OH)
Steroid sapottins 965

Table l-continued

SaPonins(mp, MD) !3OUrCC Structure Reference


Convallamaroside Convallaria Convallamarogenin (4ft), 95
majalis gic-‘rha_(3/3_OH);rha-*qui-(l&OH):
glc_(26-OH)
Convallasaponin A. Convallaria Convallagenin A (29). %
238-M. - 400 (CHCis) keisukei ara-(3&OH)
Convallasaponin B, Convallaris Convallagenin B (30). %
273-274”, - 56” (CHC&+ MeOH) keisukei ara-(5@OH)
Convallasaponin C, Convallaria Isorhodeasapogenin (20, 91
218-221”. - 89.7” (CHCIa+ MeOH) keisukei rha-‘rha-*ara_(3&OH)
Convallasaponin D, Convallaria Rhodeasapogemn (28). 98.99
264-265”. - 66’ (MeOH) keisukei glc-(l@OH); rha-2xyl-3rha-(3g-OH)
Convallasaponin E, Convallaria Diosgenin (32). 100
213-217”. - 149” kcisukei ara-*am-*ara-(3&OH)
Cryptogenin glycoside, Paris tetraphylla Cryptogenin (41). 18
238-241” (dec), - 129”(EtOH) gW3WH)
Degalactotigonin, Digitalis pwpuna Tigogenin (3), 6, 101
284-286”. - 64’ (pyridiie) XYl

13
,2glc-‘gal_(3&OH)
BlC
Deglucoderhamnoruscin Ruscus aculteatus A5-Convallamarogenin (40, 103
ara-(l&OH)
Deglucodigitonin LXgitalis purpurea Digitogenin (12), 184
xyt
>&lc&al~3g-OH,
gal
Deglucoruscin Ruscus aculeatus A’-Convallamarogenin (46). 103
rha-zara-(l&OH)
Deglucoruscoside Ruscus aculeatus As-Convallamarogenin (40, 105
rha-*ara-(l&OH); glc-(26-OH)
Dehydrocryptogenindi- Trillium kamtschaticum 17(20)-Dehydrocryptogenin (42), 18
glycoside, 265-268” (dec), rha-*glc_(3S-OH); glc-@-OH)
- 80” (pyridine)
Dehydrocryptogenin- Paris tetraphyl~a 17(20)-dehydrocryptogenin (42). 18, 106
tetraglycoside rha-‘rha
)&_(3g_OH); glc_(26-OH)
rha
Deltonin Dtoscorca deltoidea Diosgenin (32). 107
dc
>&lc43&OH)
rha
Dioscorea ddtoidea Diosgenin (32). 108
dc
14
,&-(3g-OH); glc-(26-OH)
rha
Desghtcodesrhamnoparillin. Smilax aristolo- Sarsasapogenin (27) 109
250-265”. - 65.5” (CHCI, + MeOH) chiaefolia glc-“glc-(3S-OH)
Desghrco-lanatigonin, Digtialis lanata Tigogenin (3), 110
246-251”, -47.6” (CHCl3+ MeOH) gal
)$glc-‘gal~3S_OH)
xyl
Desglucoparillin, Smiiax aristolo- Sarsasapogenin (27). 109
250-265”. - 67.5” (EtOH) chiaefolia Blc
):glc_(3S-OH)
rha
Digalonin, 25tX295” LXgitalis purpurea Digalogenin (9) 6, 104
Blc-‘gal
S. B. MAHATO, A. N. GANGULY and N. P. SAHU

Table l-continued

Saponins (mp, [aln) Source Structure Reference

Digitalis purpurea Digitogenin (12). 104


24j-285’; - 40” (pyridine) gk-‘pl

Digitalis lanata

Dioscin, 2X-27?*, Costus speciosus, Diosgenin (32). 111-119


- 115” (EtOH) Dioscorea septemloba, rha
Paris polyphylla,
)&<3&OH)
Solanum introsum,
Tribulus term&s, rha
Trigonella foenum-
graecum, Trillium
tschonoskii
Diosgenin-3-O- Smilax excelsa Diosgenin (32). 120
rhamnoside rha-Q&OH)
Diosgenin tri- Dioscorea Diosgenin (32), 121
ghrcoside, 290’ deltoidea gtc
(dec), - 77” (pyridine)
)$lc-O&OH)

Blc

Epidiosgeninghrcoside, Gynura japonica Epidiosgenin (38). 122


2%221”, - 122” glc-(3n-OH)
Epimetageninglycoside, Metanarthecium Epimetagenin (22). 123
amorphous, - 154’ (CHCI,) luteo- uiride (tri-OAc)ara-(lla-OH), 2g-OAc
Epiruscogeninghrcoside ‘Senshokushichiken’ Epiruscogenin (39), 124
(Chinese name) glc-(3a-OH)
Episceptrumgeninghrcoside, Gynura japonica Episceptrumgenin (47). 122
236-238”, - 109” glc-(3a-OH)
Eruboside B Allium erubescens g-Chlorogenin (11), 125
.&
>~1c-‘ga1-(3@0H)

glc
Filiferine A, 292”. Yucca jihfera Sarsasapogenin (27). 126
- 50.5” (DMSO) xyl-‘gal-(3p-OH)
Filiferine B, Yucca filifera Sarsasapogenin (27), 126
319-321”, - 35” (DMSO) glc-*gaL(3/3-OH)
Floribundasaponin B, Dioscorea Pennogenin (36). 127
251-253” (dec), - 86:5” (pyridine) floribunda rha-‘glc-(3@-OH)
Floribundasaponin C, Dioscorea Diosgenin (32), 128
255-258”. - 93.6” (pyridine) fion’bunda rha-‘rha-‘glc-(3@OH)
Floribundasaponin D, Dioscorea Diosgenin (32). 128
232234”, - 85” (pyridine) floribunda rha-3rha-3rha-3rha-‘glc-(3g-OH)
Floribundasaponin E, Dioscorea Diosgenin (32). 128
226-229” (dec), - 66” (pyridine) floribunda rha-3rha-3rha-3rha-‘glc-(3&OH);
glc_(26-OH); (22a-OMe)
Floribundasaponin F, Dioscorea Diosgenin (32). 128
243-247” (dec), - 74.6’ (pyridine) jloribunda rha-%ha-3rha-3rha-4glc-(3/3-OH);
glc-(ZCOH)
Funkioside B, Funkia ovata Diosgenin (32), 129
258-266”. - 135’ (MeOH) glc-(3g-OH); glc-(26-OH)
Funkioside C Funkia ovata Diosgenin (32), 129-131
glc-‘gal-(38-OH)
Funkioside D Funkia ovata Diosgenin (32). 129-131
glc-*glc-‘gal-(38-OH)
Funkioside E Funkia ovata Diosgenin (32), 129, 130, 132
rha-‘glc-‘glc-‘gal-(3@-OH)
Funkioside F Funkia ovata Diosgenin (32), 129, 130
g)c
)fglc-‘gal-(3g-OH)

XYl
Steroid saponins %7

Table l-continued

Saponins (mp, [alo) Source Structure Reference

Funkioside G Funkia ovata Diosgenin (32). 129, 130, 132


rha-‘glc

Funkioside I Funkia ovata Diosgenin (32), 129, 130


rha-‘rha
xy,)~lc-zglc-4gal_(3~-OH);

gic-(26OH)
Furostanol bisglycoside, Tribulus terrestris, Diosgenin (32). 133-13s
189-193” Trigonella coerulea rha
>&lc-c3@OH); gIc_(26-OH)
rha
Furostanol glycoside, Trigonella Neotigogenin (13).
242-246” joenum-graecum rha
)~c_c3s- OH); glc-(26-oH): (22-OMe)

tdc
Furostanol saponin, Lycopersicon Neotigogenin (13).
217-220” (dec), - 24” esculentum glc-*gl~-~gal-(3~-OH);
(CHCls + MeOH)
Furostanol saponin-1 Asparagus oficinalis

Furostanol saponin-2 Asparagus oficinalis

F-Citonin, 251-255” Digitalis purpurea


(dec), -66O (pyridine)

Gitonin, 276.5-282.5” Digitalis lanata

Glucoconvalla-saponin A, Convallaria
213&O (MeOH) keisukei
Glucoconvalla-saponin B, Convallaria
221-222’. - 35” (MeOH) keisukei
Glycoside A (identical Dioscorea prazeri
to Kallstroemin E)
Glycoside B Dioscorea prazeri

Glycoside B Trigonella
foenum-graecum

Glycoside B Allium
narcissif7orum
Glycoside C, Discorea prazeri
272-274”, - 87”
Glycoside D, Dioscorea prazeri
278-280”. - 85”
Glycoside I, 300-303” Methanarthecium
luteo-viride
Glycoside II, Methanarthecium
297-3W, - 84” (pyridine) luteo-viride
968 S. B. MAHATO, A. N. GANGIJLY and N. P. SAHU

Table l-continued

Saponins (mp. [alo) Source Structure Reference

Glycoside III Methanarthecium Nogiragenin (25), 143


lureo-viride gal-(lla-OH)
Gracillin, Costus speciosus, Diosgenin (32), 111-113
29@293”, - 88” (pyridine) rha
Dioscorea seplemloba, )!&_(3B_OH) 118. 134, 144
LXoscorea caucasica, plc

Tribulus rewestris
Hispigenin glycoside Solanum hispidum Hispigenin (4% 145
rha-‘rha_(3&OH)
Hispinin A, Solanum hispidum Solagenin (a), 146
220-224”. - 44” (pyridine) rha_(6a-OH)
Hispinin B, Solanum hispidum Solagenin (18). 146
258-260”. - 68” (pyridine) rha-%ha_(6a-OH)
Hispinin C, Solanum hispidum Neochlorogenin (II), 146
2%288”, - SSP (pyridine) rha-‘rha_(6a-OH)
Kallstroemin A, Kallstmemia Diosgenin (32), 147
235-238”, - 82” (pyridine) pubescens rha-%ha-%a-“glc-(3&OH); gl~-(26-OH)
Kallstroemin B, Kallstmemia Diosgenin (32), 147
232235”, - 79.5” (pyridine) pubescens rha-2rha-%ha-6glc-(3&OH); glc-(26_OH);
(22a-OMe)
Kallstroemin D, Kallsfmemia Diosgenin (32), 147
275-276”. - 94.5” (pyridine) pubescens rha-%ha-%ha-6glc_(3&OH)
Kallstroemin E, Kallstmemia Diosgenin (32). 147
218-219’, - 101” (pyridine) pubescens rha-6glc-(3&OH)
Karatavegenin B, Allium Karatavegenin (5). 148
glucoside. 294-298” karataviense gIc-(36-OH); gIc_(26-OH)
Karatavioside A Allium spp. Yuccagenin (34), 149
XYl
)&&al-(3/3-OH)

glc
Karatavioside C ANium spp. Yuccagenin (34). 150
XYl
>&lc-‘gal_(SB-OH): glc-(26-OH)

glc
Kikuba saponin, Dioscorea septemloba, Diosgenin (32), 113. 134
249-251”. - 77O (MeOH) Tn’bulus rerresMs glc-*glc
>jcsa-OH)
rha
Lanadigalonin Bgitalis lanata Digalogenin (9), 151
glc-‘gal
)&@gal-(3~-OH)

XYl
Lanagitoside Digitalis lanara Gitogenin (4), 110
glc-‘gal
)fgl&al_(3~-OH): glc_(26-OH)
XYl
Lanatigonin I, Digitalis lanato Tigogenin (3), 151
275-285” (de@, + 42’ (pyridine) glc-‘gal
>&Io’BalO@-OH)

XYl
Lanatigoside Digitalis lanata Tigonenin (3). 110
glc-‘gal
>:glc-‘gal-(3fl-OH): glc_(26-OH)

XYl
Metanartheticum Metanatihecium Z&acetyl metagenin (23), 152
prosapogenin luleo- viride 2,3,4-tri-O-acetyl ara_(lla-OH)
Steroid saponins %9

Table l-continued
Sawnins(mp, [eld source Structure Reference
Molluscicidal Comusjkwida Sarsasauogenin (27). 22
saponin-1,24&245’ (dec), - 68.5” gaM3&OH)
Mulluscicidal Comus florid0 Sarsasapogenin (27), 22
saponin-2,286-288O xyl-*gal-(3~-oH)
Molluscicidal Comus firida Sarsasapogenin (27). 22
saponin-3, 320-322” gic-*gaL(3/3-OH)
Neochlorogenin Solanum hispidum Neochlorogenin (18, 145
glycoside rha-‘rha-(3@OH)
Neohecogenin glucoside Tribulus rcnwtris Sisalagenin (19), 153
280-282“(dec), - 41” (pyridine) gW3bOH)
Neotokoronin, Dioscorea tenuipes Neotokorogenin (31). 154
270-274”(dec), - 11”(pfidine) ara-(l&OH)
Ophiopogonin A, Ophiopogon japonicus Ruscogenin (33). 155
183”. - 98” (pyridine) (3-0-acetyl) rha-%co~lfi-OH)
Ophiopogonin B, Ophiopogon japonicus Ruscogenin (X3), 155, 156
269-271”. - 105’ (pyridine) rh&uco-(lfi-OH)
Ophiopogonin D, Ophiopogon japonicus Ruscogenin (33). 155, 157
263-265”, - 108’ (pyridine) rha
>$fuco-(l&OH)
xyl
Ophiopogonin B’, Ophiopogon japonicus Diosgenin (32). 158
245-248”(dec), - 86” (pyridine) (4-0-acetyl) rha
>bW3a-oH)
XYl
Ophiopogonin C’, Ophiopogon japonicus Diosgenin (32). 158
238-W (dec), rha-*glc-(3p-OH)
- 99” (pyridine)
Ophiopogonin D’, Ophiopogon japonicus Diosgenin (32). 158
255-25T, - 41” Wridine) xyl
)&c-(3@-OH)
rha
Paniculonin A, Solanum paniculatum Paniculogenin (15). 159
262-264”. - 61’ (pyridine) xyC’qui_(6u-OH)
Paniculonin B, 237-238”. Solanum panicularum PanicLogenin (is, 160
- 79” (pyridine) rha-‘qui-(6a-OH)
Paniculogenin glycoside, Solanum paniculatum Paniculogenin (15). 160
262-264’. - 61” (pyridine) xyl-‘rha-(6a-OH)
Paniculogenin Solomon hispidum Paniculogenin (U), 145
glycoside rha-‘rha-(3&OH)
glc 109
Parillin, 22&223”, Smilax aristoloch- rhh>:$dc-(3B-OH)
- 64” (EtOH) iaefolia

Paryphyllin, Paris polyphylla Diosgenin (32), 161


294-298”. - 104”(pyridine) rha-‘ara-‘glc-(3p-OH)
Paryphyllin A, Paris polyphylla Diosgenin (32). 162
glc-‘rha
212-214’. -85” (pyridine) >&c-c3WH)
rha
Paryphyllin B, Paris polyphylla Diosgenin (32). 162
168-17Oe,-97.5” (pyridine) glc-‘rha
>:glc-(3fl-OH)
ara (fur)
Paryphyllin C, Paris polyphylla Diosgenin (32). 163
262266”, - 97” (pyridine) rha-‘glc-(3p-OH)
Pennogenin chacotrioside, Ttillium kamr- Pennogenin (jr), 18
297-299”(dec), - 127’ (pyridine) scharicum rha
):&_(3&OH)
rha
970 S. B. MAHATO,A. N. GANOULY and N. P. SAHU

Table I-continued
Saponins (mp, [alo) Source Structure Reference

Pennogenin diglycoside, TMium kamt- Pennogenin (jr), 18 -


273-276’ (dec), - 118’ (pyridine) schoticum rha-*glc(3&OH)
Pennogenin tetraglycoside, Heloniposis Pennogenin (jr), 18, 106, 117
224-228” (dec), - 136” (pyridine) orientalis rha-‘rha

>&-(3fl-OH)
rha
Polygonatoside E Polygonatum Diosgenin (32), 164
latijolium glc-3glc-4gal-3glc43~-OH)
Prazerigenin Dioscorea prazeri Prazerigenin A (37). 121
glucoside, 260”. glc-(3&OH)
- 79” (pyridine)
Protodioscin, 1904%” LXoscorea gracillima Diosgenin (32), 165
(dec), - 57.8 (pyridine) rha
> &lc-(3/3-OH); gb(26-OH)

rha
Protogracillin, Doscorea Diosgenin (32), 165
235-238” (dec), septemloba glc
- 57.8” (pyridine)
)&(3p_OH); glc-(ZCOH)
rha
Protometeogenin Metanatihecium Protometagenin (24), 166
glycoside, 265-270” luteo-viride ara-(1 la-OH)
Protopolygonatoside E’ Polygonatum Diosgenin (32), 164
latifolium glc-3glc-4gal-3glc-(3fl-OH); glc-(26-OH)
Prototokorin, Dioscorea tokoro Tokorogenin (21). 167
W-178”, - 3.8” (MeOH) glc-(l~3-OH); glc-(26-OH)
Protoyuccoside C, Yucca filamentosa Sarsasapogenin (27), 168
182WV’, - 30” (MeOH) gal-2glc-4glc-(3~-OH); glc-(26-OH)
Protoyuccoside E Yucca filamentosa Sarsasapogenin (27), 169
gal
>&lc-‘&-(Jg-OH); glc_(26-OH)

gal
Rockoside A Agave americana Rockogenin (lo), 170
gal-(3&OH)
Rockoside B Agave ameticana Rockogenin (lo), 170
glc-‘gal-(3&OH)
Rockoside C Agave americana Rockogenin (lo), 170
xyl-*glc-‘glc-‘gal_(3@OH)
Ruscin Ruscus aculeatus A’-Convallamarogenin (40, 103
glo3rha-*ara-(l@OH)
Ruscoside Ruscus aculeatus A’-Convallamarogenin (46), 105
glc-‘rha-*ara-(l/3-OH); glc (26-OH)
Saponin P-a, Paris polyphylla Diosgenin (32), 116, 161
276-278” - 133” rha
>&Jc-(3p-OH)
(fur)ara
Saponin P-d, Paris polyphylla Diosgenin (32), 116
203-206”, 153 rha-‘rha

Sarsaparilloside, Smilax aristo- Sarsasapogenin (27). 32,33


amorphous, - 44” (HzO) lochiaefolia
glc
rha>&lc-(3&OH); gk-(26-OH)
glc
Taccaoside Taccacheancer Diosgenin (32), 171
rha
‘, lc43&OH)
/*
rha
Steroid saponins 971

Table l-continued

Saponins (mp. [aln) Source structure Reference

‘TF’T, 217-220”, Lycoperscicum Neotigogenin (U), 172


- 24’ (MeOH + CHCl,) esculmtum dc-*gic-‘gaM3WH); Blc-WOH)
Tiionin Digitalis lanata Tiigenin (3), 6. 104
lwm’
Digitalis purpureo >W-‘gaW3g-OH)
xyl
Timosaponin A-I, Anemarrhenoe Sarsasapogenin (27). 173
240-245” (dec), asphodeloides gal-(3j?-OH)
- 68” (dioxan)
Timosaponin A-III, Anemarrhenae Sarsasapogenin 07). 173
320-322“ asphodeloides glc-$gal_(3g-OH)
Tokorogenin glucoside, Dioscorea tokoro Tokorogenin (21). 174
275-284”, - 43” (CHCI,) gh=US-OH)
Tokoronin, Dioscorea tokoro Tokorogenin (21). 175
27%277”, - 13” (pyridine) ara-(lg-OH)
Tribulosin, Tribulus terrestris Neotigogenin (13). 153
xyl
> 300”. - 61” (pyridine) >fglc-‘+36-OH)

xyl /ha
Trigonelloside C Trigonella Yamogenin 40). 176
joenum-graecum rha
)jglc_(3&OH); gM26-OH)
rha
Trillenoside A, Trillium kamtsch- Trillenogenin (44). 34-36
269-220” (dec), - 142” aticum, Trillium small, apio(fu+‘rha
Trillium eschonoskii
)$ua-(lg-OH)

xyl
Trillin, 260”, Dioscorea saliva, Diosgenin (32). 177, 178
- 89’ (dioxan) Polygonotum lotijolium glc_(3g-OH)
Trillioside A Trillium kamtschot- Diosgenin (32), 179
scense glc-‘rha-*glc-(3~-OH)
Trillioside B Trillium komtschat- Diosgenin (32). 180
scense glc
>&lcd3&OH,

glc
Turoside A Allium turcomanicum Neoagigenin (16). 181
xyl
)&zlc-‘gal_(3g-OH)

glc
Turoside A-6-0- Allium turcomonicum Neoagigenin (16). 182
bcnzoate xyl
13
,,&-‘gal-(3g-OH); 6-0-benxoate

glc
Turoside C Allium turcomanicum Neoagigenin (16). 183
glc-*glc
):glc&l_(3g-OH): glc-(26_OH)
xyl
Yononin, Dioscorea tokoro Yonogenin (28). 184, 185
238-240”. - 14” ara-(Zg-OH)
Yuccagenin glycoside Yucca schottii Yuccagenin (jr), 37
gal_(38-OH)
Yuccoside B Yucca jilamentoso Tigogenin (3) 186
gal-‘glc-(3g-OH)
Yuccoside C, Yucca filamentosa Sarsasapogenin (27). 168. 187-189
282-284”. - 41” gal-*glc-‘glc-(3&OH)
Yuccoside E Yucca jilamentosa Sarsasapogenin (87). 188,190
gal\
,$glc-‘&_0,9_OH)
gal
Abbreviations used: glc, g - D - glucopyranosyl; rha, a - L - rhamnopyranosyl; ara, (I - L - arabinopyranosyl; gal, g - n -
galactopyranosyl; xyl, g - D - xylopyranosyl; ara -fur, n - L - arabinofuranosyl; qui, B - D - quinovopyranosyl; api -fur, g - o -
apiofuranosyl.
972 S. B. MAHATO,A. N. GANGULY and N. P. SAHU

Table 2. Steroidal saponins whose genins and sugars have been identified

Saponins (mp, [alo) Source Genins and sugars Reference

Amolonin Chlorogalum Tigogenin (3), 11


pomeridianum glc (3) + gal (1) + rha (2)
Asparagoside C, Asparagus oficinalis Sarsasapogenin (27), 191
287-2W, - 130” (MeOH) Blc
Balanitscin B Balanites roxburghii Diosgenin (32), 192
gic + rha
Balanitscin C Balanites roxburghii Diosgenin (32), 192
glc + rha (1: 3)
Balanitscin D Balanites roxburghii Diosgenin (32), 192
glc + rha
Balanitscin E Balanites roxburghii Diosgenin (32), 192
gk+ara+xyl+rha
Caucasosaponin, Dioscorea caucasica Diosgenin (32), 144
218-220” (dec) - 62.5” rha (1) + glc (3)
(pyridine)
Dioscinin, 202-203”, Dioscorea polystachya Diosgenin (32), 193
- 70” (MeOH) glc (2) + rha (2)
Diosgenin glycoside Tribulus terrestris Diosgenin (32), 134
glc+glc
Diosgenin glycoside Polygonatum multifiorum Diosgenin (32), 194
glc+gat+xyl
Diosgenin rhamno- Tribulus terrestris Diosgenin (32), 195
ghlcosyl glc + rha
Fenugrin B Trigonella foenum Diosgenin (32), 1%
graecum glc + ara + rha
Graecunin B, Trigonella foenum- Diosgenin (32), 197
15b156”, - 47” (MeOH) graecum glc + xyl + rha
Graecunin C Trigonella foenum- Diosgenin (32), 198
graecum glc + rha
Ophiopogonin C, Ophiopogon japonicus Ruscogenin (33), 158
238-240”, - 93” (pyridine) fuc + xyl+ rha
Polygonatoside C Polygonatum latifolium Diosgenin (32), 178
glc + gal
Polygonatoside E Polygonatum latifolium Diosgenin (32). 178
glc + gal + xyl
Polygonatoside G Polygonatum latifolium Diosgenin (32). 178
glc + gal + xyl + ara
Ruscoside A RUSCUS
hyrcanus Ruscogenin (33), 199
gal + glc + rha (2)
Ruscoside B Ruscus hyrcanus Ruscogenin (33), 199
gal + glc + ara + rha (2)
Saponin C, 187” Tribulus terrestris Ruscogenin (33), 200
rha + glc + ara
Saponin D,, 272” Tribulus terrestris Diosgenin (32), 200
rha + glc
Saponin of kammogenin Yucca schotti Kammogenin (35). 37
5 units of deoxyribose
Sarsasapogenin glycoside, Narthecium essifragum Sarsasapogenin (27), 201
285”, - 35” (EtOH) ara+glc+gal+xyl
Sarsasaponin, 245” Smilax aristolochiae- Sarsasapogenin (37), 11
folia, Yucca schottii glc (2) + rha (1)
Tigogenin glycoside, Cestrum diumum Tigogenin (3), 202
260’ (dec) xyl + glc + gal
Tigogenin glycoside Yucca glorisa Tigogenin (3), 203
glc+gai+xyl+rha
Terrestroside F, Tribulus terrestris Tigogenin (3), 204
238-240’ gk + rha
Triharin, Trillium erectum Diosgenin (32), 11
21 l”, - 116’ (EtOH) glc (2)
T. T. Saponin Tribulus terrestris Diosgenin (32), 205
glc + ara + rha
Steroid saponins 973

Table 3. Basic steroid saponins (characterized and uncharacterized) isolated after 1972

Saponin (mp, b]D) Source Genins and sugars Reference

Dehydrocommersonine Solanum chacoense Solanidine (49), 206

fk’
Khasianine, Solanum khasianum Solasodine (SO), 63
226-228”, - 95” (MeOH) rha-‘glc-(3p-OH)
Solapersine, Solanum persicum Solasodine (50). 207
282-2&W, - 46” (MeOH) gal+glc+xy1
Solaplumbin, Nicotiana Solasodine (SO), 208
lNL181”, -90” plumbaginijolie glc-‘rha’-(3B-OH)

Solaplumbinin, Nicotiana Solasodine (SO), 208


184-185”, - 39.5” plumbaginijolie rha’-(3B-OH)
Solasodine Unidentified solanum Solasodine (50), 209
glycoside species (Spanish name: glc+gal+rha
noranjilla de Jibaro)
Solasodine Solanum Solasodine (50), 210
glycoalkaloid schimperianum glc + rha
Solatifoline, Solanum Solasodine (SO), 211
292293”, - 119” platanijolium glc+rha+gal

The steroidal saponins isolated and characterized and increase cholinesterase activity in the cytoplasm
up to 1980 are listed in Table 1 along with the mps [216]. The Na+ or K’ activated ATPase in rabbit red
and specific rotations and Table 2 shows the steroidal blood cell membranes is inhibited by low concen-
saponins which have not been fully characterized. As trations of saponin but activated by high concen-
comprehensive reviews [M-171 of basic steroidal trations while ouabain, a cardiac glycoside, inhibits
saponins are available, the characterized and un- the activating effect [217]. The effect of digitonin on
characterized basic steroidal saponins isolated after glucose uptake by isolated fat cells in the presence or
1972 are compiled in Table 3. absence of insulin was studied by Akhtar and Perry
[218] who observed that low concentrations of
BIOLOGICAL ACTIVITY saponin inhibited the stimulation of glucose uptake by
An extensive study of the physical, chemical and insulin without causing severe cell damage suggesting
physiological properties of saponins has been con- digitonin-cholesterol complex formation in the fat
ducted owing to their wide occurrence in nature. cell plasma membrane.
There are several excellent reviews on the properties
of saponins [6-l 1, 141 and on tomatine [15]. Saponins, Action on the cardio-vascular system
in general, are very powerful emulsifiers, toxic, The cardiotonic actions of g-strophanthin (0.15-
haemolytic and able to form complexes with choles- 3.25 mg/kg), a-solanine (2.5-5 mg/kg) and T.T.
terol. Here information on the biological activities of saponin were studied on a comparative basis. g-
various saponins, particularly the steroidal saponins, Strophanthin and T.T. saponin decreased the
reported durjng the period 1972 to 1979 is given. frequency of cardiac contraction whereas a-solanine
had no effect 12191. Cardiotonic activity of some
Action on metabolism glycoalkaloids, when compared with K-strophan-
Saponins (1%) in the diet of rats decreased the thoside by the use of isolated frog heart, is found to
plasma cholesterol level and increased bile acid be directly related to the nature of the aglycone and
production [212]. The depression of growth in vitro the number of sugar units [220]. Saponin isolated
caused by complex formation of saponin with fat- from the seeds of Achyranthes aspera is found to
soluble vitamins has been studied [213]. A change in increase the force of contraction of isolated frog
the thyroid gland in experimental haemolytic anaemia heart, guinea-pig heart and rabbit heart [221]. Two
has been observed [214] when subcutaneous injection new steroidal saponins ruscoside A (ruscogenin + 1
of saponin at doses of 1, 4 and 8 mg/kg once every glc + 1 gal + 2 rha) and ruscoside B (ruscogenin + 1
third day is given to rabbits. The development of gal+ 1 glc +2 rha+ 1 ara) isolated from Ruscus hyr-
proteins, carbohydrate and lipid dystrophy in the liver canus [ 1991 exhibit various biological activities. They
of rabbits is prevented by the oral administration of decrease the cholesterol content of the blood, lipid
Tribulus terrestris saponin at 10-15 mglkglday for 90 deposition in the aorta and liver arterial tension. They
days with the simultaneous administration of choles- also slow down the cardiac rhythm and respiration of
terol (200 mg/kg/day) [2151. Certain steroidal humans and rabbits suffering from arteriosclerosis.
saponins isolated from egg-plant, which contain Ruscoponin and ruscogiponin from R. penticus and
mainly tigogenin and neotigogenin as aglycones, par- R. hypophyllum exhibit fibrinolytic activity in oitro at
tially normalize lipase activity in the mitochondria 0.1 and 0.25% concentration, respectively. Ruscoponin
974 S. B. MAHATO,A. N. GAN~ULY
and N. P. SAHU

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varied and interesting biological activities. They have 16. Herbert, R. B. (1975) in Alkaloids. Specialist periodical
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effect to that produced by stilbesterol [230,231]. cal reports (Grundon, M. F. ed.) Vol. 6, p. 285. The
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[232]. An abortifacient effect has been shown by Chem. Pharm. Bull. 23,872.
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