Spiranoid withanolides from Jaborosa odonelliana

Six new spiranoid withanolides, (20R,22R,23S)-5alpha-chloro-6beta,12beta,17beta,22-tetrahydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (2), (20R,22R,23S)-5beta,6beta-epoxy-12beta,17beta,22-trihydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (3), (20R,22R,23S)-5beta,6beta-epoxy-4beta,12beta,17beta,22-tetrahydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (4), (20R,22R,23S)-5alpha,6beta,12beta,17beta,22-pentahydroxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (5), (20R,22R,23S)-6beta,12beta,17beta,22-tetrahydroxy-5alpha-methoxy-1-oxo-12,23-cycloergosta-2,24-dien-26,23-olide (6), and (20R,22R,23S)-6beta,12beta,17beta,22-tetrahydroxy-2alpha,5alpha-epidioxy-1-oxo-12,23-cycloergosta-3,24-dien-26,23-olide (7), were isolated from the leaves of Jaborosa odonelliana. Compounds 2-7 were characterized by a combination of spectroscopic methods (1D and 2D NMR, MS) and molecular modeling.     

Microbial transformation of 20(S)-protopanaxatriol-type saponins by Absidia coerulea

Three 20(S)-protopanaxatriol-type saponins, ginsenoside-Rg1 (1), notoginsenoside-R1 (2), and ginsenoside-Re (3), were transformed by the fungus Absidia coerulea (AS 3.3389). Compound 1 was converted into five metabolites, ginsenoside-Rh4 (4), 3beta,2beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-glucopyranoside (5), 20(S)-ginsenoside-Rh1 (6), 20(R)-ginsenoside-Rh1 (7), and a mixture of 25-hydroxy-20(S)-ginsenoside-Rh1 and its C-20(R) epimer (8). Compound 2 was converted into 10 metabolites, 20(S)-notoginsenoside-R2 (9), 20(R)-notoginsenoside-R2 (10), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (11), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (12), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-beta-D-xylopyranosyl-(1-->2)-beta-D-glucopyranoside (13), and compounds 4-8. Compound 3 was metabolized to 20(S)-ginsenoside-Rg2 (14), 20(R)-ginsenoside-Rg2 (15), 3beta,12beta,25-trihydroxydammar-(E)-20(22)-ene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (16), 3beta,12beta-dihydroxydammar-(E)-20(22),24-diene-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (17), 3beta,12beta,20,25-tetrahydroxydammaran-6-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside (18), and compounds 4-8. The structures of five new metabolites, 10-13 and 16, were established by spectroscopic methods.     

Taraxastane-type triterpenes from the aerial roots of Ficus microcarpa

Seven new taraxastane-type triterpenes-20-taraxastene-3beta, 22alpha-diol (1), 3beta-acetoxy-20-taraxasten-22alpha-ol (2), 3beta-acetoxy-22alpha-methoxy-20-taraxastene (3), 3beta-acetoxy-20alpha,21alpha-epoxytaraxastan-22alp ha-ol (4), 3beta-acetoxy-19alpha-methoxy-20-taraxastene (5), 3beta-acetoxy-19alpha-hydroperoxy-20-taraxastene (6), 3beta-acetoxy-20alpha,21alpha-epoxytaraxastane (7)-were isolated from the aerial roots of Ficus microcarpa. Their structures were elucidated by spectroscopic and chemical methods.     

New steroidal glycosides from the fruits of Tribulus terrestris

Three new steroidal saponins (1-3) were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic methods (IR, HRESIMS, 1D- and 2D-NMR) as 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl- (1-->4)]-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1 -->4)]-beta-D-galactopyranoside (2), and 25(S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl-( 1-->2)-[b eta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (3). Compound 3 showed cytotoxicity against a human malignant melanoma cell line (SK-MEL).     

Oleanane-type triterpenes from the flowers and roots of Saussurea muliensis

Six new oleanane-type triterpenes (1- 6), along with five known compounds, were isolated from the flowers and roots of Saussurea muliensis. On the basis of spectroscopic methods, with special emphasis on 1D and 2D NMR techniques, the structures of the new compounds were characterized as 3beta,22alpha-dihydroxyolean-12-en-30-oic acid (1), 3alpha-(E)-caffeoyloxyolean-12-en-30-oic acid (2), 3alpha-(E)-coumaroyloxyolean-12-en-30-oic acid (3), 3alpha,22alpha-diacetoxy-20beta,21alpha,29-trihydroxy-30-norolean-12-ene (4), 3alpha,22alpha-diacetoxy-21alpha,29-dihydroxy-20beta-methoxy-30-norolean-12-ene (5), and 3alpha,22alpha-diacetoxy-20beta,21alpha-dihydroxy-29-palmityloxy-30-norolean-12-ene (6). The isolated compounds (1- 6) were not active against Staphylococcus aureus, Escherichia coli, Bacillus cereus, and Candida albicans.     

Novel epoxy steroids from the indian ocean soft coral Sarcophyton crassocaule

A detailed further examination of the Indian Ocean soft coral Sarcophyton crassocaule resulted in the isolation of altogether 17 compounds of which two (1 and 2) are novel 17beta,20beta-epoxy steroids and one is a new dihydroxygorgost-5-en (3). The other compounds include the four hippurin steroids (4-7) reported earlier, and some known derivatives such as methyl arachidonate, batyl alcohol, a mixture of monohydroxy sterols, 3beta-hydroxypregn-5-en-20-one, two prostaglandin derivatives (PGB(2) acid and its methyl ester), and 9-oxo-9, 11-secogorgost-5-ene-3beta,11-diol (8). The structure of new dihydroxygorgostene derivative was established as gorgost-5-ene-3beta,11alpha-diol (3), while the structures of the novel epoxy steroids were established as 17beta,20beta-epoxy-23, 24-dimethylcholest-5-ene-3beta,22-diol (2) and its 3beta, 22-diacetate (1), respectively.     

Tupichigenin A, a new steroidal sapogenin from Tupistra chinensis

From the underground parts of Tupistra chinensis, a novel polyhydroxylated spirostanol sapogenin, tupichigenin A [(20S, 22R)-spirost-25(27)-ene-1beta,2beta,3beta,5beta- tetraol] (1), was isolated and determined structurally on the basis of spectroscopic methods. Also isolated was the known steroidal sapogenin (20S, 22R)-spirost-25(27)-ene-1beta,2beta,3beta,4beta, 5beta, 7alpha-hexaol-6-one (2).     

Four new dammarane saponins from Zizyphus lotus

Five dammarane-type saponins were isolated by means of centrifugal partition chromatography from the leaves of Zizyphus lotus. Their structures were elucidated using a combination of 1D and 2D 1H and 13C NMR spectra and mass spectroscopy. One of these glycosides is the known jujuboside B (5). Three are new jujubogenin glycosides, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-(2,3,4-O-triacetyl)-alpha-L-rhamnopyranoside (1), 3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyljujubogenin-20-O-alpha-L-rhamnopyranoside (2), and 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-alpha-L-arabinopyranosyljujubogenin (3). The last is a new sulfated derivative of jujubasaponine IV, identified as 3-O-alpha-L-rhamnopyranosyl-(1-->2)-[(4-sulfo)-beta-D-glucopyranosyl-(1-->3)]-beta-D-galactopyranosyl-(20R,22R)-16beta,22:16alpha,30-diepoxydammar-24-ene-3beta,20-diol (4).     

担子菌黄卷缘齿菌的化学成分

目的研究担子菌黄卷缘齿菌Hydnum rep andum的化学成分。方法通过硅胶、Sephadex LH-20、反相硅胶柱色谱分离化合物,运用氢谱、碳谱、二维核磁共振(1H1-HCO SY,HM QC,HM BC,NOESY)、质谱、高分辨质谱、旋光鉴定结果。结果共分离鉴定了11个化合物,分别是:sarcodon in A(Ⅰ)、scabron ine B(Ⅱ)、3β-羟基-5,α8α-过氧麦角甾-6,22-二烯-3β-醇(Ⅲ)、(22E,24R)-麦角甾-7,22-二烯-3,β5,α6β-三醇(Ⅳ)、(22E,24R)-麦角甾-7,22-二烯-3β-醇(Ⅴ)、苯甲酸(Ⅵ)、对羟基苯甲醛(Ⅶ)、对羟基苯甲酸乙酯(Ⅷ)、乙基-β-D-吡喃葡萄糖苷(Ⅸ)、硫代乙酸酐(Ⅹ)、(2S,2′R,3S,4R)-2-(2-羟基-十八碳酰胺)二十二碳烷-1,3,4-三醇(Ⅺ)。结论所有化合物都是首次在黄卷缘齿菌中分到。     

Cytotoxic withaphysalins from the leaves of Acnistus arborescens

Three withaphysalins, rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-2,24-dienolide(withaphysalin M) (1), rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-18-ethoxy-1-oxowitha-2,24-dienolide (withaphysalin F ethyl ether, withaphysalin O) (2), and rel-(17S,20R,22R)-5 beta,6 beta:18,20-diepoxy-4 beta-hydroxy-1,18-dioxowitha-24-enolide (withaphysalin N) (3), were isolated from the leaves of Acnistus arborescens. The structures were deduced from 1D ((1)H NMR, (13)C NMR, DEPT-(13)C NMR) and 2D (COSY, HMQC, HMBC) NMR analysis and the relative stereochemical assignments based on 1D NOESY correlations and analysis of coupling constants. Compounds 1 and 2 displayed potent cytotoxic activity against a panel of human cancer cell lines.     

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.     

包疮叶的化学成分研究

目的：研究包疮叶的化学成分。方法：采用硅胶柱层析法进行分离，根据光谱数据鉴定结构。结果：从中分得6个化合物，分别为：22-O-(2-methylbutyryl)-28-al-12-en-olean-3β，16α-diol(1)，22-O-hexanoyl-28-al-12-en-olean-3β，l6α-diol(2)，l，12-bis(3，3′-dihydroxy-4，4′-dimethyl-5，5′-dimethoxypheny(l)dodecane(3)]，3β，16α，22α，28β-tetrahydroxy-13β,28-epoxy-olean(4)，(24R)-stigmast-7，22(E)-dien-3α-ol(5)，(24R)-stigmast-7，22(E)-dien-3β-D-glucopyranoside(6)。结论：化合物1为一新的齐墩果烷型甙元，其它5个化合物均为首次从该植物中得到。     

Triterpene glycosides from Cimicifuga racemosa

Eight new triterpene glycosides named cimiracemosides A-H, respectively, and eight known triterpene glycosides were isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa). The new compounds were determined by spectral data to be 21-hydroxycimigenol-3-O-alpha-L-arabinopyranoside (1), 21-hydroxycimigenol-3-O-beta-D-xylopyranoside (2), cimigenol-3-O-alpha-L-arabinopyranoside (3), 12beta-acetoxycimigenol-3-O-alpha-L-arabinopyranoside (4), 24-acetylisodahurinol-3-O-beta-D-xylopyranoside (5), 20(S),22(R), 23(S),24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3be ta,23, 24-trihydroxy-9,19-cycloanost-7-ene-3-O-beta-D-xylopyranoside (6), 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-12beta -acetoxy-3beta, 23,24-trihydroxy-9,19-cycloanost-7-en-3-O-alpha-L-arabinopyrano side (7), and 20(S),22(R),23(S), 24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3beta,23, 24-trihydroxy-9,19-cycloanostane-3-O-beta-D-xylopyranoside (8).     

轮叶棘豆的化学成分研究

目的：研究轮叶棘豆的化学成分。方法：90%乙醇冷浸提取,所得浸膏经硅胶,聚酰胺,C-18,Sephadex LH-20等多种材料进行柱色谱分离,通过波谱学方法鉴定化合物的结构。结果：分离鉴定了8个化合物,分别鉴定为azukisapogenol(1),(22E,24R)-24-甲基-5α-胆甾-7,22-二烯-3β,5α,6β-三醇(2),芹菜素(3),3′,4′-二甲氧基-槲皮素-3-O-β-D-半乳糖吡喃苷 (4),7,4′- 二甲氧基-槲皮素-3-O-α-L-鼠李糖吡喃基(1→2)-β-D-葡萄糖吡喃苷(5),(2S,3S,4R)-N-［(R)-2′-羟基二十四烷醇基］-1,3,4-三羟基-2-氨基-十八-6-烯(6),β-谷甾醇(7),胡萝卜苷(8)。结论：所有化合物均为首次从该植物中分得。     

厚蜂窝菌的化学成分研究

目的研究厚蜂窝菌发酵液的化学成分。方法厚蜂窝菌发酵液的乙酸乙酯提取部位经过硅胶、RP-18、Seph-adex LH-20等多种材料进行分离纯化,通过理化方法和波谱分析进行结构鉴定。结果分离鉴定了11个化合物,经波谱数据分析分别鉴定为角鲨烯(1)、9(Z)-十八烷烯酸(2)、麦角甾-4,6,8(14),22-四烯-3-酮(3)、麦角甾-5,7,22-三烯-3β-醇(4)、过氧麦角甾醇(5)、麦角甾-6β-甲氧基-7,22-二烯-3β,5α-二醇(6)、麦角甾-7,22-二烯-3β,5α,6β-三醇(7)、8,14-环氧麦角甾-4,22-二烯-3,6-二酮(8)、麦角甾-3β,5α,9α-三羟基-7,22-二烯-6-酮(9)、2,2-二甲基-1-苯并吡喃-6-醇(10)、2-呋喃甲酸(11)。结论以上化合物均是首次从该种真菌中分离得到。     

紫芝的化学成分研究

目的:研究紫芝子实体的化学成分。方法:采用硅胶、凝胶色谱法进行分离纯化,波谱法进行结构鉴定。结果:从紫芝乙醇提取物的氯仿部分分离得到6个甾醇,1个脂肪酸和1个哌嗪二酮衍生物。结构鉴定为:麦角甾-7,22-二烯-3β-醇(1),麦角甾醇(2),6,9-环氧麦角甾-7,22-二烯-3β-醇(3),过氧麦角甾醇(4),麦角甾-7,22-二烯-3-酮(5),β-谷甾醇(6),α-羟基-二十四烷酸(7),cyc lo(D-Pro-D-Val)(8)。结论:化合物1~8均为首次从紫芝子实体中分离得到。     

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??OBJECTIVE To study the chemical constituents from the root bark of Celastrus monospermus Roxb. METHODS The compounds were isolate and purified by repeated column chromatography on silica gel, ODS and Sephadex LH-20, and the chemical structures of compounds were determined by spectral data analyses. RESULTS Twenty-three compounds were isolated from this plant, which were identified as ??-sitosterol palmitate (1), friedelan-3-one (2), 3??-hydroxyolean-12-en (3), 3??-hydroxylcholest-5,22-dien (4), ??-sitosterol (5), 3,22-dioxo-20-taraxastene (6), 3,12-dioxofriedelane (7), 3-oxo-28-hydroxyfriedelane (8), 3-oxo-11??-hydroxyfriedelane (9), 3-oxo-12??-hydroxyfriedelane (10), pristimerin(11), 3-oxo-30-hydroxyfriedelane (12), 3-oxo-29-friedelanoic acid (13), salaspermic acid (14), celastrol (15), 3??, 21??-dihydroxy-30-nor-friedelan-20(29)-en-27-oic acid (16), 3??, 22??-dihydroxy-olean-12-en-29-oic acid (17), wilforol A (18), orthosphenic acid (19), p-hydroxybenzoic acid (20), 3-oxo-2??-hydroxyfriedelan-29-oic acid (21), 21-oxo-2??,3??,22??-trihydroxy-29-nor-friedelan-24,2??-lactone (22)and daucosterol (23). CONCLUSION Compounds 1,6, 13-14,16-22 are obtained from this plant for the first time, and compounds 16, 20-22 are isolated from the genus Celastrus for the first time.     

Cytotoxic constituents of the twigs and leaves of Aglaia rubiginosa

Activity-guided fractionation of a CHCl(3)-soluble extract of the twigs of Aglaia rubiginosa, using human oral epidermoid carcinoma (KB) cells as a monitor, led to the isolation of a new naturally occurring cyclopenta[b]benzofuran, 1-O-acetylrocaglaol (1), along with seven known compounds, methyl rocaglate (2), rocagloic acid (3), 1-O-acetylmethyl rocaglate (4), desyclamide, eryodictiol, 5-hydroxy-3,7,4'-trimethoxyflavone, and naringenin. A CHCl(3) extract of the leaves of A. rubiginosa yielded the new compound (3S,4R,22R)-cholest-7,24-diene-3,4,22-triol (5), as well as 11 known compounds, including 2 and 4 and cabraleone, dammarelonic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid methyl ester, (3beta,4beta,22R)-ergosta-5,24(24')-diene-3,4,22-triol, ocotillone, shoreic acid, beta-sitosterol, and beta-sitosterol glycoside. The structures of 1 and 5 were elucidated by spectral and chemical methods. Isolates were evaluated with a human cancer cell panel, and compounds 1-4 were found to exhibit potent cytotoxic activity.     

炮弹果果肉的化学成分研究

目的 研究炮弹果果肉的化学成分.方法 将炮弹果果肉用95％乙醇提取,通过硅胶、RP-18、Sephadex LH-20等色谱方法分离化合物,波谱方法鉴定化合物的结构.结果 从炮弹果果肉中分离得到18个化合物,ningpogenin (1)、6 -O-p-hydroxybenzoylaucubin (2)、3,3′-bisdemethylpinoresinol(3)、(22E,24R)-ergosta-7,22-dien-3β-ol (4)、麦角甾_4,6,8 (14),22-四烯-3-酮(5)、麦角甾-7,22-二烯-3β,5α,6β-三醇(6)、5α,8α-epidiory-(22E,24R)-ergosta-6,22-dien-3β-ol (7)、β-谷甾醇(8)、胡萝卜苷(9)、3β,5α,9α-三羟基-麦角甾-7,22-二烯-6-酮(10)、麦角甾-7,22-二烯-3-酮(11)、sesquiterpene (12)、对羟基苯甲酸(13)、苯甲酸(14)、对羟基苯乙醇(15)、对羟基苯甲醇(16)、D-阿洛醇(17)、5-hydroxymethyl-2-furancarboxaldehyde (18).结论 所有化合物都是首次从炮弹果果肉中分离得到.     

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??OBJECTIVE To study the chemical constituents of ethyl acetate fraction from Dioscorea bulbifera. METHODS This compounds were isolated and purified with silica gel and Sephadex LH-20 and preparative liquid chromatography. Their structures were determined on the basis of physicochemical properties and spectroscopic analysis. RESULTS Twenty-four compounds were isolated and identified as ephemeranyhoquinone(1), N-methyl-2-pyrolidinone(2), aurantiamide acetate(3), 3,4-dihydroxybenzoic acid ethyl ester(4), 2, 7-dihydroxy-3, 4-dimethoxyphenanthrene(5), 4, 5-dihydroblumenol A(6), C-veratroylglycol(7), teasperol(8), vomifoliol(9), Z-6, 7-ligustilide(10), 2, 3, 7-trihydroxy-4-methoxyphenanthrene(11), p-hydroxyphenylacetic acid methyl ester(12), 3, 5, 7, 4??-tetrahydroxyflavone(13), 3, 5, 3??-trimethoxyquercetin(14), 3, 4-dihydroxybenzoic acid(15), 3, 5, 7, 3??, 4??-pentahydroxyflavone(16), daucosterol(17), 5, 3 ??, 4??-trihydroxy-3, 7-dimethoxyflavone(18), epicatechin(19), 3, 7-dihydroxy-2, 4-dimethoxy-9, 10-dihydrophenanthrene(20), methyl eucomate(21), catechins(22), 5, 7-dihydroxy-3, 4??-dimethoxyflavone(23), and 3, 4-dihydroxybenzoic acid methyl ester(24). CONCLUSION Except compounds 11, 14, 15, 18-20, 22 other compounds are isolated from the plant for the first time.