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PubMed2001

Saponin content and trypsin inhibitor activity in processed and cooked pigeon pea cultivars.

Four high-yielding varieties of pigeon pea namely UPAS-120, Manak, JCPL-151. ICPL-87 had considerable amounts of antinutrients i.e. saponins and trypsin inhibitors. Saponin content of these unprocessed cultivars ranged from 2164 to 3494 mg/100 g. There were significant varietal variations in trypsin inhibitor activity (1007-1082 TIU/g) of these pigeon pea cultivars. Some simple, inexpensive and easy-to-use domestic processing and cooking methods, namely, soaking (6, 12, 18 h), soaking (12 h)-dehulling, ordinary cooking, pressure cooking and germination (24, 36, 48 h) were found to be quite effective in lowering the level of saponins and trypsin inhibitors in all the pigeon pea cultivars. Pressure cooking of soaked and dehulled seeds lowered the content of saponins to a maximum extent (28 to 38%) followed by ordinary cooking of soaked and dehulled seeds (28 to 35%), soaked dehulled raw seeds (22 to 27%) and 48 h germinated seeds (15 to 19%). Loss of TIA was marginal due to soaking but ordinary as well as pressure cooking of unsoaked and soaked-dehulled pigeon pea seeds reduced the TIA drastically. Pressure cooking of pigeon pea seeds completely destroyed the TIA while it was reduced to the extent of 86-88% against the control in 48 h pigeon pea sprouts.

Analysis of Variance↗

PubMed2005

Antinociceptive and anti-inflammatory effects of the saponin and sapogenins obtained from the stem of Akebia quinata.

The stem of Akebia quinata Decasisne (Lardizabalaceae) has been used to treat urinary tract inflammatory disease. It has been reported that saponins in medicinal plants may act as bioactive components after biodegradation to sapogenins in the gastrointestinal tract. To find the active components, we obtained the methanol (MeOH) extract from A. quinata stems and fractionated this extract into CHCl(3), butanol (BuOH), and H(2)O fractions. A saponin-containing BuOH fraction was refluxed in an acidic solution to yield the hydrolyzed fraction. Silica gel column chromatography separated kalopanaxsaponin A (1) from the BuOH fraction, and oleanolic acid (2) and hederagenin (3) were obtained from the hydrolyzed fraction. The antinociceptive effect was tested by hot plate-writhing and tail-flicks methods using mice, and the anti-inflammatory effect was assayed using carrageenan-induced rat edema against the following samples: the MeOH extract of A. quinata stems, its fractions, the isolated saponin, kalopanaxsaponin A, and the sapogenins hederagenin and oleanolic acid. The MeOH extract exhibited antinociceptive/anti-inflammatory effects by oral administration of 100 and 250 mg/kg doses, indicating that the MeOH extract has an antinociceptive/anti-inflammatory activity. The BuOH fraction (crude saponin) also significantly exhibited those bioactivities. Treatments with 10 and 30 mg/kg perorally of these two sapogenins produced significant antinociceptive/ anti-inflammatory effects in the rat, suggesting that the sapogenins may act as resultant active compounds. Compounds 2 and 3 inhibited dye leakage into the peritoneal cavity induced by acetic acid, and the latter was more active than the former. The anti-inflammtory effects were further supported by the reduction of carrageenan-induced lipid peroxidation and hydroxy radical content in serum. These results suggest that the antinociceptive/anti-inflammatory properties of the stem of A. quinata can be attributed to the sapogenins oleanolic acid and hederagenin.

Administration, Oral↗

PubMed1977

Effect of alfalfa saponins on intestinal cholesterol absorption in rats.

Five to 20 mg of saponins obtained from alfalfa tops or roots were introduced intragastrically in rats also receiving oral and intravenous ring-labeled cholesterol. The saponins were tested before and after partial acid hydrolysis. Absorption of cholesterol was determined by estimation of fecal sterols and by a dual isotope technique involving assay of plasma radioactivity. Alfalfa top saponins (nonhydrolyzed) reduced absorption of cholesterol. Acid hydrolysis of alfalfa top or root saponins enhanced their ability to inhibit cholesterol absorption.

Animals↗

PubMed1980

Effects of dietary saponins on fecal bile acids and neutral sterols, plasma lipids and lipoprotein turnover in the pig.

Four young mature male pigs, 110 to 120 kg of body weight, were maintained on a low (0.01%) cholesterol diet. A double changeover design was used so that at any time two pigs received additionally 20 g/day of saponins as a 0.33% solution in drinking water. Saponins raised concentrations of fecal bile acids and neutral sterols and increased the contribution of primary acids to excretion. Neither the concentration of total plasma cholesterol nor low-density and high-density lipoprotein cholesterol were affected by saponins. There was also no change in either absolute or fractional catabolic rate of low-density or high-density lipiproteins. The data are discussed in relation to the effects of cholestyramine on plasma cholesterol and bile acid excretion in the pig and to the possible role of saponin-containing foods in the control of plasma cholesterol in man.

Animals↗

PubMed2004

Induction of macroautophagy in human colon cancer cells by soybean B-group triterpenoid saponins.

The impact of triterpenoid saponins isolated from soybeans on suppression of colon cancer cell proliferation was evaluated. Experiments were conducted to determine the effects of a purified soybean B-group saponin extract on cell proliferation, cell-cycle distribution and programmed cell death in cultures of human HCT-15 colon adenocarcinoma cells. Treatment of cells with the soyasaponins at concentrations of 25-500 p.p.m. significantly reduced viable cell numbers after 24 and 48 h of exposure. Treatment of cells with 25 and 100 p.p.m. of saponins also resulted in a transient accumulation of cells in the S-phase of the cell cycle that was associated with a significant reduction of cyclin-dependant kinase-2 (CDK-2) activity. More striking was that, when examined by transmission electron microscopy, soyasaponin-treated cells exhibited an approximately 4.5-fold increase in cell morphologies characteristic of Type II non-apoptotic programmed cell death (PCD) including numerous autophagic vacuoles, changes that collectively suggest autophagic cell death. In addition, the protein levels of microtubule-associated protein light chain 3 (LC-3), a specific marker of macroautophagy, increased substantially following soyasaponin treatment. Taken together these results thus indicate that soybean saponins, at physiologically relevant doses, can suppress HCT-15 colon cancer cell proliferation through S-phase cell-cycle delay, and can induce macroautophagy, the hallmark of Type II PCD. These findings suggest that B-group soyasaponins may be another colon-cancer suppressive component of soy that warrants further examination as a potential chemopreventive phytochemical.

Adenocarcinoma↗

PubMed2001

Saponins in garlic as modifiers of the risk of cardiovascular disease.

Most chemical and biological studies about garlic have been conducted using organosulfur compounds. However, a variety of steroid saponins from garlic and related Allium species are being increasingly recognized for their importance in biological processes. This report demonstrates the isolation and structure determination of steroid saponins from garlic and aged garlic extract (AGE). In addition, the in vitro antifungal antitumor cytotoxicity and blood coagulability effects of steroid saponins from garlic and related Allium species are provided. Animal studies on the cholesterol-lowering effects of the saponin fractions from garlic are also summarized.

Animals↗

PubMed1975

Studies on the biochemical action of ginseng saponin. I. Purification from ginseng extract of the active component stimulating serum protein biosynthesis.

Systematic isolation and purification of the biologically active component of ginseng extract were followed by observing the incorporation of labeled leucine into serum protein at 6 hr after a single intraperitoneal injection in a mouse. Ginseng saponin mixture (fraction 5) exhibited high activity for such incorporation. Seven saponins were isolated from fraction 5 by means of preparative TLC, and assayed. Administration of all these saponins (ginsenoside-Rb2, Rc, Rc2, Rd, Re, and Rg1)except for ginsenoside-Rb1, caused an increase of leucine incorporation over that in control animals. The incorporation rate was directly proportional to the dose in the case of ginsenoside-Rd, which had the highest activity. The increase specific radio-activity of serum protein was not due to a decrease in the pool size of free amino acids in the liver. It was conclusively shown that the active component stimulating serum protein biosynthesis is saponin.

Animals↗

PubMed2006

The dynamics of major fibrolytic microbes and enzyme activity in the rumen in response to short- and long-term feeding of Sapindus rarak saponins.

AIMS: To investigate the short- and long-term effects of an extract of Sapindus rarak saponins (SE) on the rumen fibrolytic enzyme activity and the major fibrolytic micro-organisms. METHODS AND RESULTS: Two feeding trials were conducted. In the short-term trial, four fistulated goats were fed a basal diet containing sugar cane tops and wheat pollard (65:35, w/w) and were supplemented for 7 days with SE at a level of 0.6 g kg(-1) body weight. Rumen liquor was taken before, during and after SE feeding. In the long-term trial, 28 sheep were fed the same basal diet as the goats and were supplemented for 105 days with 0.24, 0.48 and 0.72 g kg(-1) body mass of the extract. Rumen liquor was taken on days 98 and 100. Protozoal numbers were counted under the microscope. Cell wall degradation was determined by enzyme assays and the major fibrolytic micro-organisms were quantified by dot blot hybridization. Sapindus extract significantly depressed rumen xylanase activity in both trials and carboxymethylcellulase activity in the long-term trial (P < 0.01). Fibrobacter sp. were not affected by the SE in both trials, while ruminococci and the anaerobic fungi showed a short-term response to the application of saponins. Protozoal counts were decreased only in the long-term trial with sheep. CONCLUSION: These data suggest that there is an adaptation of Ruminococcus albus, Ruminococcus flavefaciens and Chytridiomycetes (fungi) to saponin when fed over a long period. The fact that no correlation between the cell wall degrading enzyme activities and the cell wall degrading micro-organisms was observed suggests that the organisms tracked in this experiment are not the only key players in ruminal cell wall degradation. SIGNIFICANCE AND IMPACT OF THE STUDY: Sapindus rarak saponins partially defaunate the rumen flora. Their negative effect on cell wall degradation, however, is not related to rumen organisms currently recognized as the major cell wall degrading species. The adaptation of microbes in the long-term feeding experiment suggests that the results from short-term trial on the ruminal microbial community have to be interpreted carefully.

Animal Feed↗

PubMed1979

Structure of a new saponin: chrysantellin A from Chrysanthellum procumbens Rich.

A new saponin has been isolated from a tropical plant Chrysantellum procumbens Rich. which is thought to be useful in the therapy of digestive troubles. The structure of this saponin was determined by chemical methods, nuclear magnetic resonance and mass spectrometry. The aglycone moiety is a triterpene, echinocystic acid; D-glucose, D-xylose and L-rhamnose are carbohydrate components. The structure of saponin was established as 3-O-beta-D-glucopyranosyl [L-rhamnopyranosyl-(alpha 1 leads to 3)-D-xylopyranosyl-)beta 1 leads to 4)-L-rhamnopyranosyl-(alpha 1 leads to 2)-D-xylopyranosyl]-(alpha 1 leads to 28)-echinocystyl. The name, chrysantellin A, is proposed for this new saponin.

Carbohydrates↗

PubMed1993

Saponin treatment for in situ hybridization maintains good morphological preservation.

The commonly used procedures for in situ hybridization require treatment of the tissue with non-ionic detergents and proteolytic enzymes, resulting in considerable loss of morphological detail. In this study proteinase pre-treatment of the tissue was replaced by saponin, a highly surface-active plant glycoside. This saponin treatment allowed good preservation of tissue morphology, as determined by differential interference and contrast enhanced video microscopy. Saponin pre-treatment resulted in an equal or even better hybridization sensitivity with probes recognizing viral (canine distemper virus) and cellular (myelin) nucleic acid sequences in tissue cultures as well as in paraffin sections. Probable mechanisms of how saponin allows probe penetration while maintaining the morphological details are discussed.

Animals↗

PubMed1997

Influence of OSW-1 [3 beta,16 beta,17 alpha-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-xylopyranosyl)-(1--> 3)-(2-O-acetyl-alpha-L-arabinopyranoside)], a steroidal saponin, on endothelium dependent relaxation caused by acetylcholine in rat aorta.

The tension of isolated ring preparation of the aorta from rats was measured isometrically to study the influence of OSW-1 [3 beta,16 beta,17 alpha-trihydroxycholest-5-en-22-one 16-O-(2-O-4-methoxybenzoyl-beta-D-xylopyranosyl)-(1 right arrow 3)-(2-O-acetyl-alpha-L-arabinopyranoside)], a steroidal saponin, on the endothelium dependent and independent relaxation caused by acetylcholin (ACh) and sodium nitroprusside (SNP), respectively. OSW-1 (10(-7) M), which has more than 100 times higher concentration for anti-tumor activity, had no influence on either the endothelium dependent or independent relaxation. OSW-1 (10(-6) M, 0.9 microgram/ml) slightly reduced the endothelium dependent relaxation caused by ACh but did not affect the SNP-induced relaxation. In contrast to OSW-1, 1 mg/ml of saponin significantly suppressed the ACh-induced relaxation and shifted the dose-relaxation curve for SNP to the right. OSW-1 (10(-7) and 10(-6) M) did not affect the norepinephrine-induced contraction but 1 mg/ml of saponin significantly attenuated it. The results suggest that though the higher concentration of OSW-1 shows weaker influence on the endothelium function compared with saponin, OSW-1 at an anti-tumor dose has no influence on either endothelium or smooth muscle function.

Acetylcholine↗

PubMed2005

In vitro and in vivo antifungal activities of the eight steroid saponins from Tribulus terrestris L. with potent activity against fluconazole-resistant fungal pathogens.

Antifungal activity of natural products is being studied widely. Saponins are known to be antifungal and antibacterial. We have isolated eight steroid saponins from Tribulus terrestris L., namely TTS-8, TTS-9, TTS-10, TTS-11, TTS-12, TTS-13, TTS-14 and TTS-15. TTS-12 and TTS-15 were identified as tigogenin-3-O-beta-D-xylopyranosyl(1-->2)-[beta-D-xylopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D-galactopyranoside and tigogenin-3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-xylopyranosyl(1-->3)]-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside, respectively. The in vitro antifungal activities of the eight saponins against six fluconazole-resistant yeasts, Candida albicans, Candida glabrata, Candida parapsilosis, Candida tropicalis, Candida krusei, and Cryptococcus neoformans were studied using microbroth dilution assay. The results showed that TTS-12 and TTS-15 were very effective against several pathogenic candidal species and C. neoformans in vitro. It is noteworthy that TTS-12 and TTS-15 were very active against fluconazole-resistant C. albicans (MIC(80)=4.4, 9.4 microg/ml), C. neoformans (MIC(80)=10.7, 18.7 microg/ml) and inherently resistant C. krusei (MIC(80)=8.8, 18.4 microg/ml). So in vivo activity of TTS-12 in a vaginal infection model with fluconazole-resistant C. albicans was studied in particular. Our studies revealed TTS-12 also showed in vivo activities against fluconazole-resistant yeasts. In conclusion, steroid saponins TTS-12 and TTS-15 from Tribulus terrestris L. have significant in vitro antifungal activity against fluconazole-resistant fungi, especially TTS-12 also showed in vivo activity against fluconazole-resistant C. albicans.

Animals↗

PubMed1991

Studies on absorption, distribution, excretion and metabolism of ginseng saponins. VII. Comparison of the decomposition modes of ginsenoside-Rb1 and -Rb2 in the digestive tract of rats.

In order to clarify some similarities and differences of decomposition modes between 20(S)-protopanaxadiol (20(S)-ppd) saponins, represented by ginsenoside Rb1 (Rb1) and ginsenoside Rb2 (Rb2), the decompositions of Rb1 and Rb2 in the rat gastrointestinal tract, 0.1 N HCl and crude hesperidinase were investigated in detail. As in the case of Rb2 reported previously, Rb1 was hydrolyzed to 20(R,S)-ginsenoside Rg3 in 0.1 N HCl. On the other hand, hydroperoxidation of Rb1 occurred in rat stomach; the major hydroperoxide was separated and identified as the 25-hydroperoxy-23-ene derivative of Rb1 (VIII) by 1H- and 13C-nuclear magnetic resonance and fast atom bombardment mass spectrometry. The decomposition modes of 20(S)-ppd saponins (Rb1 and Rb2) differed from that of 20(S)-protopanaxatriol saponin (Rg1) in rat stomach. In rat large intestine, five decomposition products of Rb1 were observed by thin-layer chromatography, and these were identified as gypenoside XVII (G-XVII), ginsenoside Rd (Rd), ginsenoside F2 (F2), compound K (C-K) and VIII. The decomposition modes of Rb1 and Rb2, both 20(S)-ppd saponins, are considered to be different because of the hydrolysis rate in the terminal sugar moiety at the C-20 hydroxyl group in the rat large intestine. Using crude hesperidinase, Rb1 was decomposed to G-XVII, F2 and C-K, and Rb2 was decomposed to 3-O-beta-D-glucopyranosyl-20-O-[alpha-L-arabinopyranosyl(1----6)-b eta-D- glucopyranosyl]-20-(S)-ppd, F2 and C-K. Consequently, it appears that hydrolysis by beta-glucosidase, which is present in the rat large intestine, is distinct from that by crude hesperidinase.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗

PubMed1994

New steroidal saponins from the bulbs of Allium giganteum exhibiting potent inhibition of cAMP phosphodiesterase activity.

A new spirostanol saponin and two new furostanol saponins were isolated from the fresh bulbs of Allium giganteum together with several known saponins. The structures of the new compounds were determined on the basis of spectroscopic data, the products formed on hydrolysis and by comparing their properties with those of known compounds. The isolated saponins and their derivatives were evaluated for inhibitory activity by examining their action on cAMP phosphodiesterase as a primary screening test to identify new medicinal agents.

3',5'-Cyclic-AMP Phosphodiesterases↗

PubMed1997

New polyhydroxylated steroidal saponins from the tubers of Brodiaea californica.

New polyhydroxylated steroidal saponins (1, 2) were isolated from the tubers of Brodiaea californica. The structures were determined by spectroscopic analysis and acid-catalyzed hydrolysis. The bisdesmosidic saponin (2) is unique in structure, and is the first representative of a steroidal saponin bearing 6-deoxy-D-gulopyranose among both the steroidal and triterpene saponins reported up to the present.

Chromatography, High Pressure Liquid↗

PubMed2003

Triterpenes and triterpene saponins from the stems of Akebia trifoliata.

To characterize the stems of Akebia trifoliata chemically, a detailed phytochemical examination was carried out on A. trifoliata stems, with particular attention to the triterpene and triterpene saponin constituents, and resulted in the isolation of three new triterpenes (1-3) and three new triterpene saponins (11-13), together with seven known triterpenes (4-10) and 12 known triterpene saponins (14-25). The structures of the new compounds were determined on the basis of spectroscopic analysis, including two-dimensional NMR spectroscopic data, and the results of hydrolysis. Four saponins (22-25), which were obtained in good yields and were not isolated from Akebia quinata stems, are concluded to be applicable as marker compounds in chemically distinguishing between A. trifoliata and A. quinata by conventional TLC examination. To the best our knowledge, the current work is the first chemical investigation of A. trifoliata.

Plant Stems↗

PubMed2005

Antitumor activity of Pulsatilla koreana saponins and their structure-activity relationship.

Seventeen saponins isolated from the root of Pulsatilla koreana were examined for their in vitro cytotoxic activity against the human solid cancer cell lines, A-549, SK-OV-3, SK-MEL-2, and HCT15, using the SRB assay method, and their in vivo antitumor activity using BDF1 mice bearing Lewis lung carcinoma (LLC). The saponins 5-17, with a free acidic functional group at C-28 of aglycon, exhibited moderate to considerable cytotoxic activity, however, the saponins 1-4, esterified with a trisaccharide at C-28 of aglycon, did not exhibit cytotoxic activity (ED50; >300 microM). Among them, oleanolic acid 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranoside (10) exhibited the most potent cytotoxic activity (ED50; 2.56, 2.31, 1.57, 8.36 microM, respectively). In vivo test, hederagenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranoside (6, Inhibition Ratio, IR; 66.9%) exhibited more potent antitumor activity than taxol (IR; 35.8%) and doxorubicin (IR; 62.1%). Also, hedragenin 3-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (17, IR; 50.3%) exhibited potent antitumor activity. These two saponins were identically comprised of a hederagenin aglycon moiety and a sugar sequence O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside at C-3 of the hederagenin, suggesting that the two elements are essential factors for the antitumor activity.

Animals↗

PubMed2005

Saponins and other constituents from the leaves of Aralia elata.

A new triterpenoid saponin, together with five known saponins, were isolated from the nonpolar n-hexane fraction of the leaves of Aralia elata. The structure of the new saponin, durupcoside C, was elucidated as hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside on the basis of spectroscopic analysis. The known saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl ester, hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, oleanolic acid 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, hederagenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside (alpha-hederin), and hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside (collinsonidin). In addition, two known lipids, Arisaema glyceride 3 and ceramide mixtures were also isolated and characterized. Collinsonidin and two known lipids were isolated for the first time from this plant.

Aralia↗