A new saponin from Deeringia amaranthoides

A new triterpenoid saponin, 3-O-[alpha-L-rhamnopyranosyl (1----3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-xylopyranosyl (1----2)-beta-D-glucopyranosyl]-3 beta-hydroxyolean-12-en-28-oate [3] has been isolated together with two known saponins, 3-O-[alpha-L-rhamnopyranosyl (1----3)-beta-D-glucuronopyranosyl]-3 beta- hydroxyolean-12-en-28-oic acid [1] and 3-O-[alpha-L-rhamnopyranosyl (1----3)-beta-D-glucuronopyranosyl]-28-O-[beta-D-glucopyranosyl]-3 beta- hydroxyolean-12-en-oate [2], from the fruits of Deeringia amaranthoides.     

Antifungal activities and action mechanisms of compounds from Tribulus terrestris L

Antifungal activity of natural products is being studied widely. Saponins are known to be antifungal and antibacterial. We used bioassay-guided fractionation to have isolated eight steroid saponins from Tribulus terrestris L., which were identified as hecogenin-3-O-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-8), tigogenin-3-O-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-9), hecogenin-3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-10), hecogenin-3-O-beta-D-xylopyranosyl (1-->3)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-11), 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 (TTS-12), 3-O-[beta-D-xylopyranosyl (1-->2)-[beta-D-xylopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-[alpha-L-rhamnopyranosyl (1-->2)]-beta-D-galactopyranosyl]-26-O-beta-D-glucopyranosyl-22-methoxy-(3beta,5alpha,25R)-furostan-3,26-diol (TTS-13), hecogenin-3-O-beta-D-glucopyranosyl (1-->2)-[beta-D-xylopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-14), tigogenin-3-O-beta-D-glucopyranosyl (1-->2)-[beta-D-xylopyranosyl (1-->3)]-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside (TTS-15). The in vitro antifungal activities of the eight saponins against five yeasts, Candida albicans, Candida glabrata, Candida parapsilosis, Candida tropicalis and Cryptococcus neoformans were studied using microbroth dilution assay. In vivo activity of TTS-12 in a Candida albicans vaginal infection model was studied in particular. The results showed that TTS-12 and TTS-15 were very effective against several pathogenic candidal species and Cryptococcus neoformans in vitro. It is noteworthy that TTS-12 and TTS-15 were very active against Candida albicans (MIC(80) = 10 and 2.3 microg/mL) and Cryptococcus neoformans (MIC(80) = 1.7 and 6.7 microg/mL). Phase contrast microscopy showed that TTS-12 inhibited hyphal formation, an important virulence factor of Candida albicans, and transmission electron microscopy showed that TTS-12 destroyed the cell membrane of Candida albicans. In conclusion, TTS-12 has significant in vitro and in vivo antifungal activity, weakening the virulence of Candida albicans and killing fungi through destroying the cell membrane.     

Triterpenoid saponins from the roots of Pulsatilla koreana

Six new saponins, five lupanes (1-5) and one oleanane (6), along with 11 known saponins, were isolated from the roots of Pulsatilla koreana. The structures of the new saponins were found to be 23-hydroxy-3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (1), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (2), 3beta-[(O-alpha-L-rhamnopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)]-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (3), 3beta-[(O-beta-D-glucopyranosyl-(1-->3)-O-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (4), 23-hydroxy-3beta-[(O-beta-D-glucopyranosyl-(1-->4)-alpha-L-arabinopyranosyl)oxy]lup-20(29)-en-28-oic acid (5), and hederagenin 3-O-beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside (6). Their structures were determined on the basis of 1D and 2D NMR ((13)C NMR, (1)H NMR, (1)H-(1)H COSY, HMQC, and HMBC) methods, FABMS, and hydrolysis. All isolated compounds were evaluated for their cytotoxic activity against A-549 human lung carcinoma cells.     

Floratheasaponins A-C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis)

The methanolic extract and its n-butanol-soluble fraction from the flowers of the tea plant (Camellia sinensis) were found to suppress serum triglyceride elevation in olive oil-treated mice. From the n-butanol-soluble fraction, three new acylated oleanane-type triterpene oligoglycosides, floratheasaponins A-C (1-3), were isolated together with several flavonol glycosides and catechins. The structures of 1-3 were elucidated on the basis of chemical and physicochemical evidence as 21-O-angeloyl-22-O-acetyltheasapogenol B 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, 21,22-di-O-angeloyl-R1-barrigenol 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, and 21-O-angeloyl-22-O-2-methylbutyryl-R1-barrigenol 3-O-[beta-D-galactopyranosyl(1-->2)][beta-D-xylopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->3)]-beta-D-glucopyranosiduronic acid, respectively. Floratheasaponins (1-3) showed inhibitory effects on serum triglyceride elevation, with their activities being more potent than those of theasaponins E1 (4) and E2 (5) obtained previously from the seeds of C. sinensis.     

Four new flavonol glycosides from the leaves of Astragalus caprinus

Four new flavonol 3-O-glycosides were isolated from the leaves of Astragalus caprinus. Their structures were elucidated by spectroscopic methods as rhamnocitrin-3-O-[3-hydroxy-3-methylglutaroyl(1-->6)][beta-D-apiofuranosyl(1-->2)]-beta-D-galactopyranoside (1), rhamnetin-3-O-[3-hydroxy-3-methylglutaroyl(1-->6)][beta-D-apiofuranosyl(1-->2)]-beta-D-galactopyranoside (2), kaempferol-3-O-[beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->6)]-beta-D-galactopyranoside (3), and quercetin-3-O-[beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->6)][beta-D-apiofuranosyl(1-->2)]-beta-D-galactopyranoside (4).     

A new triterpenoidal saponin from Acacia auriculiformis.

A new triterpenoidal saponin has been isolated from an aqueous EtOH extract of the legumes of Acacia auriculiformis and characterized as 3-O-([beta-D-xylopyranosyl(1----3)-beta-D-xylopyranosyl(1----4)-alpha-L- rhamnopyranosyl(1----2)]-[alpha-L-rhamnopyranosyl(1----4)]-beta-D- glucopyranosyl)-3,16,21-trihydroxyolean-12-en-28-oic acid [1] by chemical studies and spectral data.     

Kinmoonosides A-C, three new cytotoxic saponins from the fruits of Acacia concinna, a medicinal plant collected in myanmar

Three genuine saponins, named kinmoonosides A-C (1-3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A-C were elucidated on the basis of spectral analysis as 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-?(6R, 2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymet hyl-6'-methyl-2',7'-octadienoyl-beta-D-quinovopyranosyl]-2, 7-octadienoyl?acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (1); 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-?(6S, 2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymet hyl-6'-methyl-2',7'-octadienoyl-beta-D-quinobopyranosyl]-2, 7-octadienoyl?acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (2); and 3-O-?alpha-L-arabinopyranosyl(1-->6)-[beta-D-glucopyranosyl(1-->2) ]-b eta-D-glucopyranosyl?-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl- 2,7-octadienoyl]acacic acid 28-O-alpha-L-arabinofuranosyl(1-->4)-[beta-D-glucopyranosyl(1-->3)]-a lpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2, 7-octadienoyl]-D-quinovopyranose. Compounds 1-3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.     

Trypanocidal withanolides and withanolide glycosides from Dunalia brachyacantha.

Two new withanolide glycosides, (20R,22R)-O-(3)-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide (3) and (20R,22R)-O-(3)-beta-D-xylopyranosyl(1-->3)-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranosyl-1 alpha-acetoxy-12 beta,20-dihydroxywitha-5,24-dienolide (4), were isolated from the leaves and root of Dunalia brachyacantha. Their aglycones, (20R,22R)-1 alpha,12 beta-diacetoxy-3 beta,20-dihydroxywitha-5,24-dienolide (or 1 alpha,12 beta-diacetyldunawithagenine) and (20R,22R)-1 alpha-acetoxy-3 beta,12 beta,20-trihydroxywitha-5,24-dienolide (or 1 alpha-acetyl-12 beta-hydroxydunawithagenine), are novel. The known 18-acetoxywithanolide D (1) and 18-acetoxy-5,6-deoxy-5-withenolide D (2) were also isolated from the leaves. These last two compounds were shown to be responsible for the trypanocidal, leishmanicidal, and bactericidal activities manifested by the crude ethanolic extract. The structures were deduced from spectroscopic data and on the basis of chemical evidence.     

Yemuoside I, a new nortriterpenoid glycoside from Stauntonia chinensis.

A new nortriterpenoid glycoside, named yemuoside [I] was isolated from Stauntonia chinensis. On the basis of chemical and spectral evidence, it structure was determined as 3-O-[alpha-L-arabinopyranosyl-(1----3)-alpha-L-rhamnopyranosyl-(1- ---2)-alpha-L-arabinopyranosyl]-30-noroleana-12,20(29)-di en-28-oic acid 28-O-[beta-D-glucopyranosyl-(1----6)-beta-D-glucopyranosyl] ester.     

Triterpenoid saponins from Isertia pittieri.

Two new 27-nor-triterpenoid saponins, pyrocincholic acid 3 beta-O-beta-D-quinovopyranosyl-28-[beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl] ester (1) and pyrocincholic acid 3 beta-O-beta-D-quinovopyranosyl(1-->6)-beta-D-glucopyranosyl-28-[beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl] ester (2) were isolated from the stem bark of Isertia pittieri, together with two known bidesmosidic quinovic acid glycosides. The structures of 1 and 2 were determined on the basis of spectroscopic studies.     

Five new triterpene saponins from Pulsatilla patens var. multifida

Five new oleanane-type glycosides (1-5), along with two known triterpene saponins, were isolated from the roots of Pulsatilla patens var. multifida (Ranunculaceae). The structures of the new triterpene saponins were elucidated as 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranosyl hederagenin 28-O-beta-D-glucopyranosyl ester (1), hederagenin 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->6)]-beta -D-galactopyranoside (2), 3-O-beta-D-glucopyranosyl bayogenin 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-galactopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (4), and 3-O-[beta-D-glucopyranosyl(1-->2)][beta-D-glucopyranosyl(1-->6)]-beta -D-galactopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester (5). Structure elucidation was accomplished by 1D and 2D NMR (HMQC, HMBC, and ROESY) methods, FABMS, and hydrolysis.     

Two new glycosides from Astragalus caprinus

A new glycoside of flavonol (1) and a new glycoside of a cycloartane-type triterpene (2) were isolated from the leaves and the roots of Astragalus caprinus, respectively. Their structures were elucidated in turn by spectroscopic data interpretation as 3-O-[[beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->6)][beta-D-apiofuranosyl(1-->2)]]-beta-D-galactopyranosyl kaempferol (1) and 3-O-(beta-D-xylopyranosyl)-24-O-(beta-D-glucopyranosyl)-20,25-epoxycycloartane-3beta,6alpha,16beta,24alpha-tetrol (2).     

Two major saponins from seeds of Barringtonia asiatica: putative antifeedants toward Epilachna sp. larvae

Two major saponins have been isolated from a methanol extract of the seeds of Barringtonia asiatica, and their structures elucidated (mainly by two-dimensional NMR spectroscopy) as 3-O-[[beta-D-galactopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)]-beta-D-glucuronopyranosyloxy]-22-O-(2-methylbutyroyloxy)-15,16,28-trihydroxy-(3beta,15alpha,16alpha,22alpha)-olean-12-ene (3) and 3-O-[[beta-D-galactopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->2)]-beta-D-glucuronopyranosyloxy]-22-O-[2(E)-methyl-2-butenyloyloxy]-15,16,28-trihydroxy-(3beta,15alpha,16alpha,22alpha)-olean-12-ene (4). The antifeedant properties of 3 and 4 toward Epilachna larvae are discussed.     

Triterpenoid saponins from Bongardia chrysogonum

Two new triterpenoid saponins, 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-alph a-L-arabinopyranosyl]-hederagenin (1) and 3-O-[beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->4)-alph a-L-arabinopyranosyl]-hederagenin 28-O-[beta-L-glucopyranosyl-(1-->6)-beta-L-glucopyranosyl] ester (2), together with five known saponins, were isolated from an ethanolic extract of the tubers of Bongardia chrysogonum. The structures of 1 and 2 were determined on the basis of spectroscopic studies.     

合欢皂甙J6的结构鉴定

目的 :从合欢皮中分离皂甙。方法 :用色谱法分离 ,波谱法鉴定其结构。结果和结论 :从合欢皮的 95%乙醇提取物中分得 1个三糖链八糖皂甙 ,结构为 3-O [β-D 吡喃木糖基 ( 1→ 2 )-α-L 吡喃阿拉伯糖基 ( 1→ 6)-β-D 2 去氧 2 乙酰胺基 吡喃葡萄糖基 ] 21O {6S2 反式2羟甲基6甲基6-o[4-O ( 6S-2 反式-2 羟甲基 6-甲基 6-羟基 2 ,7 辛二烯酰基 ) β D 吡喃鸡纳糖基 ] 2 ,7 辛二烯酰基 } 金合欢酸-28-O-β-D 吡喃葡萄糖基 (1→ 3)[α- L 呋喃阿拉伯糖基 (1→ 4) ] α L 吡喃鼠李糖基 (1→ 2)-β-D 吡喃葡萄糖酯 ,为新化合物 ,命名为合欢皂甙J6 。     

Oleanane saponins in "kancolla", a sweet variety of Chenopodium quinoa

Seven triterpenoid saponins were isolated from the seeds of "kancolla", a sweet variety of Chenopodium quinoa. Their structures were phytolaccagenic acid 3-O-[alpha-L-arabinopyranosyl-(1' '-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, hederagenin 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, phytolaccagenic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, oleanolic acid 3-O-[alpha-L-arabinopyranosyl-(1'-->3')-beta-D-glucuronopyranosyl]-28-O-beta-D-glucopyranoside, and the new compound serjanic acid 3-O-[beta-D-glucopyranosyl-(1'-->3')-alpha-L-arabinopyranosyl]-28-O-beta-D-glucopyranoside (1). The structure of 1 was characterized on the basis of spectroscopic and chemical evidence.     

Flavonoid glycosides from Rhazya orientalis

Six new flavonoid glycosides, quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (1), quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (2), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (3), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (4), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-cis-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (5), and isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-feruloyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (6), were isolated from the dried aerial parts of Rhazya orientalis. The structures of 1-6 were determined by spectroscopic and chemical means.     

Four new triterpenoidal saponins acylated with one monoterpenic acid from Gleditsia sinensis.

Four new oleanane-type triterpenoidal glycosides, named gleditsiosides A-D (1-4), were isolated from the anomalous fruits of Gleditsia sinensis. Using modern NMR techniques, including DQF-COSY, HETCOR, HOHAHA, HMBC, and ROESY experiments and MS analysis as well as chemical methods, their structures were determined as 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(6S,2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (1); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl oleanolic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha- L-rhamnopyranosyl-(1-->2)-[(2E)-2-hydroxylmethyl-6-hydroxy-6-methy l-2 ,7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (2); 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(2E)-2-h ydroxylmethyl-6-hydroxy-6-methyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (3); and 3-O-beta-D-xylopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-(1-->6)- bet a-D-glucopyranosyl echinocystic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-[beta- D-galactopyranosyl-(1-->2)]-alpha-L-rhamnopyranosyl-(1-->2)-[(6S, 2E)-6-hydroxy-2,6-dimethyl-2, 7-octadienoyl-(1-->6)]-beta-D-glucopyranosyl ester (4).     

Saponarioside C, the first alpha-D-galactose containing triterpenoid saponin, and five related compounds from Saponaria officinalis

Six novel triterpenoid saponins, named saponariosides C-H, were isolated from the whole plants of Saponaria officinalis. Their structures were established as saponarioside C (1), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-alpha-D-galactopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-- >6)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside D (2), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside E (3), 3-O-beta-D-glucopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside F (4), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->6) -[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranoside; saponarioside G (5), 3-O-beta-D-xylopyranosyl-16alpha-hydroxygypsogenic acid-28-O-beta-D-glucopyranosyl-(1-->6)-[beta-D-glucopyranosyl-(1-->3 )]-beta-D-glucopyranoside; and saponarioside H (6), 3-O-beta-D-xylopyranosyl-gypsogenic acid-28-O-beta-D-glucopyranoside, by a combination of extensive NMR (DEPT, COSY, HOHAHA, HETCOR, HMBC, and NOESY) studies and chemical degradation.     

滇重楼的抗肿瘤活性成分研究

目的：研究滇重楼Paris polyphylla Smith var. yunnanensis根茎中具有抗肿瘤作用的活性成分。方法：利用硅胶柱色谱,Sephadex LH-20,反相制备HPLC等手段进行分离纯化,并通过波谱技术进行结构鉴定。采用MTT法对分离到的化合物进行抗肿瘤活性筛选。结果：从醋酸乙酯和正丁醇层中分离得到了6个化合物,鉴定为薯蓣皂苷元-3-O-α-L-呋喃阿拉伯糖基(1→4)-β-D-葡萄糖苷(1)、偏诺皂苷元-3-O-α-L-呋喃阿拉伯糖基(1→4)-β-D-葡萄糖苷(2)、异鼠李素-3-O-β-D-葡萄糖苷(3)、乙基-α-D-呋喃果糖苷(4)、偏诺皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-［α-L-吡喃鼠李糖基(1→2)］-β-D-葡萄糖苷(5)、偏诺皂苷元-3-O-α-L-吡喃鼠李糖基(1→4)-α-L-吡喃鼠李糖基(1→4)-［α-L-吡喃鼠李糖基(1→2)］-β-D-葡萄糖苷(6)。结论：化合物1～4为首次从滇重楼中分离得到,化合物3和4为首次从重楼属植物中分离得到,化合物5为首次从滇重楼的根茎中分离得到。药理实验表明,化合物1～3,5和6对小鼠肺腺癌细胞LA795都显示出一定的抑制作用,其中化合物5和6最显著。