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PubMed1991

Inhibition of 12-O-tetradecanoylphorbol-13-acetate-promoted mouse skin papilloma by saponins.

Papillomas in mouse skin were initiated with 390 nmol of 7,12-dimethylbenz(a)anthracene and 1 week later, were promoted 2 times a week with 4.1 nmol of 12-O-tetradecanoylphorbol-13-acetate (TPA). Five saponin-related compounds used as potential anti-inflammatory agents were applied in the same position with 82 nmol. Saponin-related compounds effectively inhibited tumor formation in the sensitive mouse stock even when these compounds were given 1 h prior to TPA treatment. These results suggested that there was a general correlation between the anti-inflammatory and antitumor-promoting activities of saponins.

Animals↗
PubMed1989

Plant saponins can affect DNA recombination in cultured mammalian cells.

Some plant extracts and products are known to affect mammalian cells, tissues and organisms as they contain a toxic substance or a metabolic stimulant. Our biochemical investigations revealed that some plant saponins can increase the cellular DNA repair activity and the general recombinase activity measured by in vitro assay (1). In the experiments described here, HeLa cells were cultured for several days with plant saponins or flavonoids and analyzed to measure i) recombination activity of the cell extract by induction of Tcr colonies from two mutant DNAs (mutants 1 and 2, which are both tetracycline sensitive) after transformation into E. coli recA-, and ii) repair synthesis of nuclear DNA followed by incorporation of 3H-thymidine. Saikosaponins a, b1, d, ginsenosides Rb1, Re, Rh and flavonoid baicalin caused a significant stimulation of intermolecular recombination. It is worth noting that none of the plant saponins and flavonoids had any inhibitory or toxic effect at concentrations less than 25 micrograms/ml in the culture media.

Animals↗
PubMed2003

Effect of the absorption enhancer saponin on the intrarenal distribution of 5-fluorouracil following its kidney surface application in rats.

The present study was undertaken to examine the effects of the absorption enhancer saponin on the intrarenal distribution of 5-fluorouracil (5-FU) following the kidney surface application of 5-FU in rats. We selected an experimental system utilizing a cylindrical diffusion cell attached to the kidney surface. The intrarenal concentration of 5-FU 120 min after right kidney surface application of 5-FU with saponin at concentrations of 0.25 and 1 mg/ml was modified. Among four sites in the right kidney, the concentration of 5-FU under the diffusion cell was selectively increased by saponin. These results suggest it may be possible to control the intrarenal distribution of the drug following its application with an absorption enhancer on the kidney surface.

Absorption↗
PubMed2004

The mitotic-arresting and apoptosis-inducing effects of diosgenyl saponins on human leukemia cell lines.

Diosgenyl saponins are the most abundant steroid saponins, and exert a large variety of biological functions. In a previous report, we showed that dioscin was able to induce cytotoxicity and apoptosis in human myeloblast leukemia HL-60 cells. This study further investigated the action mechanisms underlying this effect. The activation of caspase-9 and -3, but not caspase-8, together with the down-regulation of anti-apoptotic Bcl-2 protein, demonstrated that the apoptotic signaling triggered by dioscin was mediated through the intrinsic mitochondria-dependent pathway. We also investigated its anti-proliferative effect on human chronic myelogenous leukemia K562 cells. Flow cytometry analysis showed that dioscin treatment induced the accumulation of cells in the G(2)/M phase. Cytomorphology with DAPI and Wright-Giemsa staining demonstrated the enlargement of cell volume and multinucleation in the treated cells. Subsequent apoptosis was delineated with phosphatidylserine externalization and DNA hypodiploidy. Trillin was one of the hydrolysates of dioscin. We demonstrated that it could induce multinucleation in HL-60, K562 and human promyelocytic leukemia NB(4) cells, suggesting its extensive mitotic-arresting effects. As the diosgenyl sapogenin, diosgenin was also shown to be able to induce multinucleation and apoptosis in K562 cells in a similar manner to dioscin. These findings suggest that diosgenyl saponins have the properties to induce mitotic arrest and apoptosis, suggesting that they may be a new kind of antimitotic agent.

Antineoplastic Agents, Phytogenic↗
PubMed1989

Saponins from leaves of Kalopanax pictum var. maximowiczii, a Korean medicinal plant.

From leaves of Kalopanax pictum var. maximowiczii, a Korean medicinal plant, six known saponins of hederagenin were isolated. One of the monodesmosides was identified as sapindoside A, previously isolated from Sapindus spp. Another monodesmoside and four bisdesmosides were proved to be identical with saponins-K3, -K10 and -K12 and Kizuta saponins-K8 and -K11, respectively, all of which have been isolated from Hedera rhombea. It was observed that the water solubilities of these monodesmosides were increased in the presence of the co-occurring bisdesmosides. The relationship between structure and solubilizing effect is reported.

Animals↗
PubMed1993

Saponin and sapogenol. XLIX. On the constituents of the roots of Glycyrrhiza inflata Batalin from Xinjiang, China. Characterization of two sweet oleanane-type triterpene oligoglycosides, apioglycyrrhizin and araboglycyrrhizin.

Two sweet oleanane-type triterpene oligoglycosides named apioglycyrrhizin and araboglycyrrhizin were isolated from the air-dried roots of Glycyrrhiza inflata Batalin, collected in Xinjiang province (Shinkyo-Kanzo in Japanese), together with glycyrrhizin (3), licorice-saponins A3 (8), G2 (10), and H2 (11) and known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of apioglycyrrhizin and araboglycyrrhizin have been determined to be expressed as 3-O-[beta-D-apiofuranosyl(1-->2)-beta-D- glucuronopyranosyl]glycyrrhetic acid (1) and 3-O-[alpha-L- arabinopyranosyl(1-->2)-beta-D-glucuronopyranosyl]glycyrrhet ic acid (2), respectively. During the course of these studies, it has been found that the hydroxyl groups in the oligosaccharide moiety of the glucuronide saponins may be partially methylated by prolonged treatment with diazomethane in methanol. The sweetness of the saponins hitherto isolated from various Glycyrrhizae Radix has been examined and a structure-sweetness relationship, as compared with glycyrrhizin, has been found.

China↗
PubMed1994

Studies on the constituents of Calliandra anomala (Kunth) Macbr. II. Structure elucidation of four acylated triterpenoidal saponins.

Four new triterpenoidal saponins, called calliandra saponins B (8), C (9), D (10), and F (12), were isolated from the branches of Calliandra anomala (Kunth) Macbr. The structures of these compounds were established on the basis of NMR spectra, FAB-MS, and the chemical evidence. These saponins, interestingly, have a N-acetyl glucosamine at the 3 position of the genin, and one or two monoterpene glycosides at the position of the sugar chain.

Acetylglucosamine↗
PubMed1994

New steroidal saponins from the rhizomes of Anemarrhena asphodeloides Bunge (Liliaceae).

From the rhizome of Anemarrhena asphodeloides Bunge (Liliaceae), four new steroidal saponins named anemarrhenasaponins I-IV (1-4) were isolated, together with known saponins, timosaponin A-III (5), marcogenin diglycoside (6) and timosaponin B-II (7) and a xanthone C-glycoside, mangiferin. These saponins are coprostane type steroidal glycosides. Their structures were established on the basis of spectroscopic and chemical evidence.

Magnetic Resonance Spectroscopy↗
PubMed1996

Studies on the constituents of Calliandra anomala (Kunth) Macbr. III. Structure elucidation of six acylated triterpenoidal saponins.

Six new triterpenoidal saponins, called calliandra saponins G(1), H(2), I(3), J(4), K(5) and L(6), were isolated from the branches of Calliandra anomala (Kunth) Macbr. The structures of these compounds were established on the basis of NMR spectra, FAB-MS, and chemical evidence. These saponins, interestingly, have an N-acetyl glucosamine at the 3 position of the genin, and one or two monoterpene glycosides at the position of the sugar chain.

Hydrolysis↗
PubMed2000

Bioactive saponins and glycosides. XVI. Nortriterpene oligoglycosides with gastroprotective activity from the fresh leaves of Euptelea polyandra Sieb. et Zucc. (1): structures of Eupteleasaponins I, II, III, IV, V, and V acetate.

The saponin fraction from the fresh leaves of Euiptelea polyandra Sieb. et Zucc. was found to exhibit potent gastroprotective activity. Fourteen new nortriterpene saponins called eupteleasaponins were isolated from the saponin fraction with gastroprotective activity. The structures of eupteleasaponins I, I1, III, IV, V, and V acetate were determined on the basis of chemical and physicochemical evidence as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1 -->4)-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D- D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-rhamnopyranosyl(1 -->4)-beta-D-glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosyl(1 -->2)-[alpha-L-arabinopyranosyl(1-->4)-alpha-L-rhamnopyranosyl(1-- >4)]-beta-D- glucopyranosyl(1-->3)-beta-D-xylopyranosylakebonoic acid 28-O-beta-D-glucopyranosyl ester, 3-O-alpha-L-rhamnopyranosvl(1-->2)-[alpha-L-arabinopyranosyl (1 -->4)-beta-L-rhamnopyranosyl(1 -->4)]-beta-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosylakebonoic acid, 3-O-alpha-L-rhamnopyranosyl(1 -->2)-beta-D-glucopyranosvl(1-->3)-beta-D-xylopyranosyleupteleo genin, and 3-O-alpha-L-rhamnopyranosyl(1-->2)-6"-O-acetyl-gamma-D-glucopyranosyl(1 -->3)-beta-D-xylopyranosyleupteleogenin.

Animals↗
PubMed2002

Activity-guided isolation of saponins from Kalopanax pictus with anti-inflammatory activity.

By bioassay-guided separation, a known saponin, kalopanaxsaponin A (1) and a new saponin, pictoside A (2) were isolated from the stem bark of Kalopanax pictus as anti-inflammatory components when evaluated by vascular permeability test. Another novel saponin, pictoside B (3) was also isolated but was inactive in the test system used. The structures of pictosides A and B were elucidated as caulophyllogenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside (2) and pictogenin (3beta,6beta,16alpha,23-tetrahydroxyolean-12-ene-28-oic acid) 3-O-alpha-L-arabinopyranoside (3), respectively, by spectral analysis and by chemical degradation. Kalopanaxsaponin A and pictoside A showed significant anti-inflammatory activity at the oral doses of 50 mg/kg.

Animals↗
PubMed2003

Two triterpenoid saponins from Neonauclea sessilifolia.

From the dried roots of Neonauclea sessilifolia (Rubiaceae), two new triterpenoid saponins, 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-quinovopyranosyl quinovic acid (1) and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-quinovopyranosyl pyrocincholic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (2), were isolated, together with five known saponins. The structures of the new saponins were determined by spectroscopic and chemical means.

Hydrolysis↗
PubMed2006

Two new triterpenoid saponins isolated from Polygala japonica.

Bioassay guided investigation of whole parts of Polygala japonica afforded two new triterpenoid saponins, characterized as 3-O-beta-D-glucopyranosyl medicagenic acid 28-O-{beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl} ester (1), 3-O-beta-D-glucopyranosyl 2-oxo-olean-12-en-23, 28-dioic acid 28-O-{beta-D-xylopyranosyl(1-->4)-[beta-D-apiofuranosyl(1-->3)]-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl} ester (2), together with four known triterpenoid saponins (3-6). Their structures were elucidated by spectroscopic and chemical methods. Saponins 3, 4 and 5 showed significant anti-inflammation effects on carrageenan-induced acute paw edema in mouse.

Molecular Structure↗
PubMed2006

Ginsenoside Rg8, a new dammarane-type triterpenoid saponin from roots of Panax quinquefolium.

A new dammarane-type triterpenoid saponin, ginsenoside Rg(8) (1), was isolated from the roots of Panax quinquefolium, along with five known saponins, (20E)-ginsenoside F(4) (2), ginsenosides Rh(1) (3), Rg(2) (4), F(1) (5), and (20R)-ginsenoside Rh(1) (6). The structure of ginsenoside Rg(8) (1) was determined to be (3beta,6alpha,12beta,20E)-24,25-epoxy-3,12,23-trihydroxydammar-20(22)-en-6-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranoside by various spectroscopic analyses. Among the known saponins, (20E)-ginsenoside F(4) (2) and ginsenoside F(1) (5) were first reported from the title plant.

Ginsenosides↗
PubMed2006

Furostanol saponins from the fresh rhizomes of Polygonatum kingianum.

Ten furostanol saponins were isolated as five pairs of 25R and 25S epimers from the fresh rhizomes of Polygonatum kingianum. Seven of them were identified as new compounds, (25S)-kingianoside D (2), (25S)-kingiano-side C (4), (25R,22)-hydroxylwattinoside C (5), kingianoside E (7), (25S)-kingianoside E (8), kingianoside F (9) and (25S)-kingianoside F (10), together with three known saponins, kingianoside C (1), kingianoside D (3), and 22-hydroxylwattinoside C (6). The structures of the new saponins were determinded by detailed analysis of their 1D and 2D NMR spectra, and by comparison of the spectral data with those reported.

Carbohydrate Sequence↗
PubMed2006

Structure-activity relationships of triterpenoid saponins on fruiting body induction in Pleurotus ostreatus.

To elucidate the structure-activity relationships of saponin on fruiting body induction in Pleurotus ostreatus, monodesmosidic saponins comprising a triterpenoid and glucose residues were synthesized. Betulin, a triterpenoid present in Birch bark, was used as the aglycon. The fruiting body induction activity increased with the number of glucose residues, from one to four. The most active betulinic saponin was betulin-3-yl beta-D-(4-O-beta-D-maltotriosyl)-glucoside.

Fruiting Bodies, Fungal↗
PubMedDate not supplied

Preventive effects of various ginseng saponins on the development of copulatory disorder induced by prolonged individual housing in male mice.

Recently, we found that virtually all male mice failed to display copulatory behavior following prolonged individual housing. The present study was conducted to investigate whether or not ginseng saponin components prevent the development of this copulatory disorder. ICR male mice were housed individually for 5 weeks after weaning, followed by a 10-min encounter with an estrous female mouse. The following constituents of red ginseng powder were administered intraperitoneally once per day throughout the individual housing period: crude ginseng saponins and pure ginsenoside Rb1, Rb2, Rg1, and Ro. Three elements of copulatory behavior (mounting, intromission and penis licking) were determined. Following prolonged individual housing only one mouse in the vehicle-treated group displayed mounting. Chronic treatment with crude ginseng saponins (25, 50 and 100 mg/kg) significantly lessened the severity of copulatory disorder in a dose-dependent manner. Ginsenoside Rg1 (2.5, 5 and 10 mg/kg) also resulted in a significantly higher incidence of copulatory behavior as compared to the individually housed vehicle-treated group, whereas ginsenoside Rb1, Rb2 and Ro were ineffective. This evidence indicates that ginsenoside Rg1 is one of the ingredients of red ginseng root that acts on male copulatory behavior.

Animals↗