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.     

Cytotoxic cardenolide glycosides of Roupellina (Strophanthus) boivinii from the Madagascar rainforest

Bioassay-guided fractionation of an ethanol extract of Roupellina (Strophanthus) boivinii from the rainforest of Madagascar afforded the six new cardenolide glycosides boivinides 1-6, as well as the four known cardenolide glycosides digitoxigenin 3-O-[beta-D-glucopyrananosyl-(1-->4)-alpha-L-acofriopyranoside], corotoxigenin 3-O-beta-D-boivinoside, 17alpha-corotoxigenin 3-O-beta-D-sarmentoside, and uzarigenin 3-O-alpha-L-rhamnoside. The structures of these compounds were elucidated by various 1D and 2D NMR techniques. All new compounds showed significant antiproliferative activity against the A2780 human ovarian cancer cell line, with boivinide A being the most active at IC50 = 0.17 microM.     

Tetranorclerodanes and clerodane-type diterpene glycosides from Dicranopteris dichotoma

The acetone extract of Dicranopteris dichotoma afforded two new tetranorclerodanes, 18-hydroxyaylthonic acid (1) and 18-oxo-aylthonic acid (2), and four new clerodane-type diterpene glycosides, (6S,13S)-6-O-[6-O-acetyl-beta-d-glucopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl]cleroda-3,14-dien-13-ol (3), (6S,13S)-6-O-[4-O-acetyl-beta-d-glucopyranosyl-(1-->4)-alpha-l-rhamnopyranosyl]cleroda-3,14-dien-13-ol (4), 6-O-[6-O-acetyl-beta-d-glucopyranos-yl-(1-->4)-alpha-l-rhamnopyranosyl]-(13E)-cleroda-3,13-dien-15-ol (5), and 6-O-[beta-d-glucopyranosyl]-(1-->4)-alpha-l-rhamnopyranosyl-(13E)-cleroda-3,13-dien-15-ol (6), together with two known compounds, aylthonic acid (7) and (6S,13S)-cleroda-3,14-diene-6,13-diol (8). The structures of these new compounds were established by a combination of 1D and 2D NMR techniques, MS, and acid hydrolysis. Compound 8 showed modest anti-HIV-1 activity.     

Cytotoxic furostanol saponins and a megastigmane glucoside from tribulus parvispinus

Two new furostanol saponins, (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-2alpha,3beta,22alpha,26-tetraol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (1) and (25R)-26-O-beta-D-glucopyranosyl-5alpha-furostan-3beta,22alpha,26-triol 3-O-{beta-D-galactopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside} (2), and their O-methyl derivatives (3 and 4), and a new megastigmane glucoside, (6S,7E,9xi)-6,9,10-trihydroxy-4,7-megastigmadien-3-one 10-O-beta-D-glucopyranoside (6), along with one known spirostanol saponin, gitonin (5), and four known megastigmane glucosides were isolated from the aerial parts of Tribulus parvispinus. Their structures were established by detailed spectroscopic analysis. The cytotoxic activities of 1-6 against U937, MCF7, and HepG2 cells were evaluated. Compounds 2 (IC(50) 0.5 microM) and 5 (IC(50) 0.1 microM) showed the highest activity against U937 cells.     

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.     

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.     

Acetals of three new cycloartane-type saponins from Egyptian collections of Astragalus tomentosus

Three new cycloartane-type saponin ethyl acetals, deacetyltomentoside I (2), tomentoside III (3), and tomentoside IV (4), were isolated along with the known acetal tomentoside I (1) from the aerial parts of Astragalus tomentosus of Egyptian origin. The saponins from which the acetals are most probably derived are also new compounds. The structures of the acetals were established as 6alpha-hydroxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-beta-d-xyloside (2), 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-(4'-trans-2-butenoyl)]xyloside (3), and 6alpha-acetoxy-23alpha-ethoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-[beta-d-glucopyranosyl(1 --> 2)]-beta-d-xyloside (4), by detailed spectroscopic and chemical 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 。     

Phytochemical investigation of Turnera diffusa

A phytochemical investigation of Turnera diffusa afforded 35 compounds, comprised of flavonoids, terpenoids, saccharides, phenolics, and cyanogenic derivatives, including five new compounds (1-5) and a new natural product (6). These compounds were characterized as luteolin 8-C-E-propenoic acid (1), luteolin 8-C-beta-[6-deoxy-2-O-(alpha-l-rhamnopyranosyl)-xylo-hexopyranos-3-uloside] (2), apigenin 7-O-(6' '-O-p-Z-coumaroyl-beta-d-glucopyranoside) (3), apigenin 7-O-(4' '-O-p-Z-coumaroylglucoside) (4), syringetin 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside] (5), and laricitin 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside] (6). Their structures were determined by spectroscopic and chemical methods.     

New triterpene glycosides from the stems of Anomospermum grandifolium

Two new dammarane saponins identified as jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[beta-d-glucopyranosyl(1-->6) beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (2) and jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[6-O-[3-hydroxy-3-methylglutaryl]-beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (3) and a new lupane saponin, 3beta-hydroxylup-20(29)-en-27,28-dioic acid 28-O-beta-d-glucopyranosyl(1-->2)-[beta-d-xylopyranosyl(1-->3)]-beta-d-xylopyranosyl(1-->2)-beta-d-glucopyranoside ester (5), along with the known jujubogenin 3-O-alpha-l-arabinofuranosyl(1-->2)-[beta-d-glucopyranosyl(1-->3)]-alpha-l-arabinopyranoside (1) and 3beta-hydroxylup-20(29)-ene-27,28-dioic acid (4), were isolated from the methanol extract of the stems of Anomospermum grandifolium. The structures of the new compounds were established by spectral analysis. Antimicrobial activity screening of compounds 1-3 revealed antifungal properties against C. albicans ATCC 3153 for compounds 2 and 3. The antibacterial and antifungal activities of the petroleum ether, chloroform, and methanol extracts of A. grandifolium stems were also evaluated.     

Phenolic compounds from the roots of Jordanian viper's grass, Scorzonera judaica

Nine new phenolic compounds, 3S-hydrangenol 40-O-R-L-rhamnopyranoysl-(1-->3)-β-D-glucopyranoside (1), thunberginol F 7-O-β-D-glucopyranoside (2), 2-hydroxy-6-[2-(4-hydroxyphenyl)-2-oxo-ethyl]benzoic acid (3), 2-hydroxy-6-[2-(3,4-dihydroxyphenyl)-2-oxo-ethyl]benzoic acid (4), 2-hydroxy-6-[2-(3,4-dihydroxyphenyl-5-methoxy)-2-oxoethyl]benzoic acid (5), hydrangeic acid 40-O-β-D-glucopyranoside (6), E-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)dihydrofuran-2-one (7), Z-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)-2(3H)-furanone (8), and 4-[β-D-glucopyranosyl)hydroxy]-pinoresinol (9), and nine known compounds were isolated from the roots of Scorzonera judaica. Structures of 1-9 were elucidated by mass spectrometry, extensive 1D and 2D NMR spectroscopy, and CD spectroscopy.All compounds were evaluated for cytotoxic activity.     

Nitrogen-containing phorbol esters from Croton ciliatoglandulifer and their effects on cyclooxygenases-1 and -2

Four new phorbol derivatives, 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (1), 12-O-[(2S)-N,N-dimethyl-3-methylbutanoyl]-4-deoxyphorbol 13-acetate (2), 12-O-[3-methyl-2-butenoyl]-4-deoxyphorbol 13-acetate (3), and 12-O-[(2R)-N,N-dimethyl-3-methylbutanoyl]phorbol 13-acetate (4), along with six known compounds, were isolated from the aerial parts of Croton ciliatoglandulifer. An anti-inflammatory activity of a hexane extract of this plant was demonstrated against ear edema in mice produced by 12-O-tetradecanoylphorbol 13-acetate, and compounds 1, 4, and 3beta-O-acetyloleanolic acid (5) were active when evaluated against cyclooxygenases-1 and -2.     

Chemical constituents of the aerial parts of Schnabelia tetradonta

A phytochemical study on the ethanol extract of the aerial parts of Schnabelia tetradonta led to the isolation of five new compounds, 1-5, together with seven known compounds. The structures of the new compounds were elucidated on the basis of spectral data interpretation as 2alpha,3alpha,23,29-tetrahydroxyolean-12-en-28-oic acid (1), 3-O-beta-d-glucuronopyranosyl-2beta,3beta,16beta-trihydroxy-28-norolean-12-en-15-on-23-oic acid (2), 21-O-beta-d-glucopyranosyl-3beta,21alpha,30-trihydroxyolean-13(18)-en-24-oic acid (3), 6-C-beta-l-arabinopyranosyl-8-C-alpha-l-arabinopyranosylapigenin (4), and 4-acetylaminoethylphenyl 1-O-[6-O-(Z)-p-methoxycinnamoyl-beta-d-glucopyranosyl(1-->2)]-[beta-d-glucopyranosyl(1-->3)]-alpha-l-rhamnopyranoside (5), respectively.     

Monoterpene glycosides and triterpene acids from Eriobotrya deflexa

A phytochemical study on a methanolic extract of leaves of Eriobotrya deflexa led to the isolation and characterization of nine terpenoid compounds. Four of these are new chemical entities, including two monoterpene glycosides, (3S)-O-alpha-L-rhamnopyranosyl-(1-->3)-[4-O-(E)-coumaroyl]-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-linalool (1) and (3S)-O-alpha-L-rhamnopyranosyl-(1-->3)-[4-O-(Z)-coumaroyl]-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-linalool (2), and two triterpene acids, 1beta,2alpha,19alpha-trihydroxy-3-oxo-12-ursen-28-oic acid (3) and 2alpha,3alpha,19alpha-trihydroxy-12-oleanen-28-oic acid (4). Their structures were elucidated on the basis of spectroscopic analysis. The activities of these isolates in an in vitro antiproliferation test were also determined.     

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.     

Phenylvaleric acid and flavonoid glycosides from Polygonum salicifolium.

(3R)-O-beta-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-beta-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[beta-D-glucopyranosyl-(1-->6)-glucopyranosyl]oxy-2'-hydroxy-3', 6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-beta-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-beta-D-galactopyranoside (5), quercetin-3-O-beta-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-beta-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2'-O-galloyl)-beta-D-glucopyranoside (8), and quercetin-3-O-beta-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays.     

Sesquiterpenes and flavonol glycosides from Zingiber aromaticum and their CYP3A4 and CYP2D6 inhibitory activities

Three new sesquiterpenes, (2R,3S,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one (1), (2R,3R,5R)-2,3-epoxy-6,9-humuladien-5-ol-8-one (2), and (5R)-2,6,9-humulatrien-5-ol-8-one (3), and two new flavonol glycosides, kaempferol-3-O-(2,3-di-O-acetyl-alpha-l-rhamnopyranoside) (4) and kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-l-rhamnopyranoside) (5), were isolated from the EtOAc-soluble fraction of the water extract of Zingiber aromaticum, along with 13 known compounds (6-18). The structures of the isolated compounds were elucidated on the basis of spectroscopic and chemical analyses. The isolated compounds were tested for their inhibitory activity on the metabolism mediated by CYP3A4 or CYP2D6 using [N-methyl-(14)C]erythromycin or [O-methyl-(14)C]dextromethorphan as a substrate, respectively. Kaempferol-3-O-(2,3,4-tri-O-acetyl-alpha-l-rhamnopyranoside) (5) showed the most potent inhibitory activity (IC(50), 14.4 microM) on the metabolism mediated by CYP3A4, and kaempferol-3-O-methyl ether (14) inhibited CYP2D6 most potently (IC(50), 4.63 microM).     

槐花炭化学成分的研究

目的:研究中药槐花炭的化学成分。方法:用硅胶柱色谱法和光谱分析法分离和鉴定化学成分。结果:分得6个化合物,经光谱分析鉴定其结构分别为麦芽酚(1),3-羟基吡啶(2),麦芽酚-3-氧-[6′-氧-(4″-羟基-反式-桂皮酰基)]-β-D-吡喃葡萄糖苷(3),3-氧-[β-D-半乳吡喃糖基-(1→2)-p-β-葡萄吡喃醛酸糖基]槐二醇乙酯(4),3-氧-[β-D-半乳吡喃糖基.(1→2)-β-D-葡萄吡喃醛酸糖基]槐二醇甲酯(5),芦丁(6)。结论:化合物4为新化合物,化合物1,2,3,5为首次从槐花炭中获得。     

Chemical constituents from the aerial parts of Aster koraiensis with protein glycation and aldose reductase inhibitory activities

Two new eudesmane-type sesquiterpene glucosides, 9β-O-(E-p-hydroxycinnamoyl)-1β,6β-dihydroxy-trans-eudesm-3-en-6-O-β-D-glucopyranoside (1) and 9α-O-(E-p-hydroxycinnamoyl)-1α,6α-11-trihydroxy-trans-eudesm-3-en-6-O-β-D-glucopyranoside (2), were isolated by the activity-guidedfractionation of an EtOAc-soluble fraction from the aerial parts of Aster koraiensis. A new dihydrobenzofuran glucoside, (2R,3S)-6-acetyl-2-[1-O-(β-D-glucopyranosyl)-2-propenyl]-5-hydroxy-3-methoxy-2,3-dihydrobenzofuran (3), was also isolated, in addition to 15 known compounds. The structures of 1-3 were determined by spectroscopic data interpretation. All of the isolates were evaluated for in vitro inhibitory activity against the formation of advanced glycation end-products and rat lens aldose reductase.     

New compounds from an extract of Vernonia colorata leaves with anti-inflammatory activity

Bioassay-directed fractionation of an anti-inflammatory CHCl(3)-MeOH (9:1) extract of leaves of Vernonia colorata, using a carrageenan-induced rat paw model, led to the isolation of six new compounds (1-6).These were assigned as two new androst-8-en glycosides, 3-O-[beta-d-galactopyranosyl-(1-2)-[beta-d-glucopyranosyl-(1-->6)]-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (1) and 3-O-[beta-d-glucopyranosyl-(1-->6)-beta-d-glucopyranoside]-5alpha,14alpha-androst-8-ene (2), two new stigmastane-type glycosides, 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-glucopyranoside (3) and 3beta,21,24-trihydroxy-21,23;22,28;26,28-triepoxy-5alpha-stigmasta-8(9),14(15)-dien-3-O-beta-d-galactopyranosyl-(1-->2)-beta-d-(6-acetyl)glucopyranoside (4), and two new stigmastane-type steroids, 3beta,25,29-trihydroxy-5alpha-stigmasta-8(9),14(15),24Z(28)-triene (5) and 3beta,23,25-trihydroxy-24,28-epoxy-5alpha-stigmasta-8(9),14(15)-diene (6). The structures of 1-6 were elucidated by spectral and chemical studies. Compounds 1-6 were tested for the anti-inflammatory activity, but all were inactive or weakly inactive as anti-inflammatory agents.