杠柳根皮化学成分研究

目的：对杠柳根皮的化学成分进行研究。方法：采用色谱技术进行分离,通过NMR等谱学方法确定化合物的结构。结果：分离并鉴定了8个化合物,分别为异香草醛(1),香草醛(2),4-甲氧基水杨酸(3),(24R)-9,19-cycloart-25-ene-3β,24-diol(4),(24S)-9,19-cycloart-25-ene-3β,24-diol(5),cycloeucalenol(6),β-香树脂醇乙酸酯(7),α-香树脂醇(8)。结论：化合物1～6为首次从杠柳中分离得到,并首次从杠柳属植物中分离得到环阿尔廷型三萜化合物4～6。     

Cancer chemopreventive effects of cycloartane-type and related triterpenoids in in vitro and in vivo models

Forty-eight natural and semisynthetic cycloartane-type and related triterpenoids have been evaluated for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells as a primary screening test for anti-tumor promoters. In addition, these triterpenoids have been tested for their inhibitory effects on activation of (+/-)-(E)-methtyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitric oxide (NO) donor, as a primary screening test for anti-tumor initiators. All of the compounds tested exhibited inhibitory effects on both EBV-EA and NOR 1 activation. Six of these compounds having a C-24 hydroxylated side chain, viz., (24R)-cycloart-25-ene-3beta,24-diol (9), (24R)-cycloartane-3beta,24,25-triol (11), (24S)-cycloartane-3beta,24,25-triol (12), (24xi)-24-methylcycloartane-3beta,24,241-triol (14), (24xi)-241-methoxy-24-methylcycloartane-3beta,24-diol (15), and (24xi)-24,25-dihydroxycycloartan-3-one (27), showed higher inhibitory effects than the others tested on both EBV-EA (IC50 values of 6.1-7.4 nM) and NOR 1 activation. Furthermore, compounds 14 and 15 exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.     

Cycloartane-type triterpenoids from the resinous exudates of Commiphora opobalsamum

Eight new cycloartane-type triterpenoids, cycloartan-24-ene-1alpha,2alpha,3alpha-triol (1), 3beta-acetoxycycloartan-24-ene-1alpha,2alpha-diol (2), 1alpha-acetoxycycloartan-24-ene-2alpha,3beta-diol (3), 3beta-isovaleroyloxycycloartan-24-ene-1alpha,2alpha-diol (4), cycloartan-24-ene-1alpha,3beta-diol (5), cycloartan-23 E-ene-1alpha,2alpha,3beta,25-tetrol (6), and an epimeric mixture of 24 R,25-epoxycycloartane-1alpha,2alpha,3beta-triol (7) and 24 S,25-epoxycycloartane-1alpha,2alpha,3beta-triol (8), together with one known compound, cycloartan-24-ene-1alpha,2alpha,3beta-triol (9), were isolated from the resinous exudates of Commiphora opobalsamum. Their structures were established on the basis of mass spectrometry and multidimensional NMR spectroscopy. The cytotoxicity of compounds 1-9 was evaluated against the PC3 and DU145 human prostate tumor cell lines. All of the compounds except 1 and 5 exhibited moderate cytotoxicity against PC3 or DU145 cells with IC50 values ranging from 10.1 to 37.2 microM.     

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.     

Beesiosides G, H, and J-N, seven new cycloartane triterpene glycosides from Beesia calthifolia

Seven new cycloartane glycosides (1-7), beesiosides G, H, and J-N, together with beesioside I (8) and beesioside A, were isolated from the rhizomes of Beesia calthifolia, and their structures were established by spectroscopic and chemical methods. Beesiosides G, H, and J-N were assigned as 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,16beta,18,25-tetraol-3-O-beta-D-glucopyranoside (1), 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,16beta,18,25-tetraol-3-O-[beta-D-glucopyranosyl-(1-->6)]-beta-D-glucopyranoside (2), (20S,24R)-15alpha,16beta-diacetoxy-20,24-epoxy-9,19-cyclolanostane-3beta,18,25-triol-3-O-beta-D-xylopyranoside (3), (20S,24S)-16beta-acetoxy-18,24;20,24-diepoxy-9,19-cyclanostane-3beta,15beta,25-triol-3-O-beta-D-xylopyranoside (4), (20S,24S)-16beta-acetoxy-18,24;20,24-diepoxy-9,19-cyclanostane-3beta,25-diol-3-O-beta-D-xylopyranoside (5), 20xi(1),24xi(2)-epoxy-15alpha-acetoxy-9,19-cyclolanostane-3beta,16beta,25-triol-3-O-beta-D-xylopyranoside (6), and 20xi(1),24xi(2)-epoxy-9,19-cyclolanostane-3beta,12alpha,15alpha,16beta,25-pentaol-3-O-beta-D-xylopyranoside (7), respectively.     

Steroidal saponins from the rhizomes of Polygonatum sibiricum

Four new steroidal saponins, named neosibiricosides A-D (1-4), were isolated from the rhizomes of Polygonatum sibiricum, along with two known spirostanol glycosides. The structures of the new glycosides were elucidated by spectroscopic methods and acid hydrolysis as (23S,24R,25R)-1-O-acetylspirost-5-ene-1beta,3beta,23,24-tetrol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-fucopyranoside (1), (25S)-1-O-acetylspirost-5-ene-1beta,3beta-diol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (2), (25S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-[beta-D-xylopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-2-O-acetyl-beta-D-galactopyranoside (3), and (25R,S)-spirost-5-en-3beta-ol 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside (4). The cytotoxic activity of the isolated compounds was evaluated with human MCF-7 breast cancer cells.     

Antitubercular activity of triterpenoids from Lippia turbinata

Assay-guided fractionation of the antitubercular MeOH-CH(2)Cl(2) extract obtained from Lippia turbinata led to the isolation of four novel triterpenoids-3beta,25-epoxy-3alpha,21alpha-dihydroxy-22beta-(3-methylbut-2-en-1-oyloxy)olean-12-ene-28-oic acid (1); 3beta,25-epoxy-3alpha,21alpha-dihydroxy-22beta-angeloyloxyolean-12-ene-28-oic acid (2); 3beta,25-epoxy-3alpha,21alpha-dihydroxy-22beta-tigloyloxyolean-12-ene-28-oic acid (3); and 3beta,25-epoxy-3alpha-hydroxy-22beta-(2-methylbutan-1-oyloxy)olean-12-ene-28-oic acid (4)-together with the known triterpenoids lantanilic acid (5), camaric acid (6), lantanolic acid (7), and rehmannic acid (8). The MIC values of 1-8 for growth inhibition of Mycobacterium tuberculosis were determined in the radiorespirometric BACTEC system.     

海南狗牙花化学成分的研究

目的：对夹竹桃科植物海南狗牙花Ervatamia hainanensis中化学成分进行系统研究。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：从海南狗牙花中分离到8个化合物：α-amyrin acetate(1),11-oxo-α-amyrin acetate(2),β-谷甾醇(β-sitosteol,3),cycloart-23-ene-3β,25-diol(4),cycloart-25-ene-3β,24-diol(5),5α,8α-epidioxyergosta-6,22-dien-3β-ol(6),ibogamin-3-one(7),β-胡萝卜苷(β-daucosterol,8)。结论：化合物1,2,4～7为首次从该植物中获得。     

Biotransformation of cycloartane-type triterpenes by the fungus Glomerella fusarioides

Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3beta,24-diol (4), and cycloartane-3beta,24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3beta,24-diol (8). Compound 3 was converted into two new metabolites, 4alpha,4beta,14alpha-trimethyl-9beta,19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.     

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).     

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).     

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.     

Gelliusterols A--D, new acetylenic sterols from a sponge, Gellius species.

New acetylenic sterols, gelliusterol A (1, 26,27-bisnorcholest-5-en-23-yn-3 beta,7 alpha-diol), its corresponding 7-ketone, gelliusterol B (2, 26,27-bisnorcholest-5-en-23-yn-3 beta-ol-7-one), and gelliusterols C (4, cholest-5-en-23-yn-3 beta,7-one) and D (5, cholest-5-en-23-yn-3 beta,25-diol-7-one), were isolated from an unidentified species of sponge, Gellius sp. The structures of the steroids were established from spectroscopic data.     

Cucurbitane-type triterpenoids from Momordica charantia

Five new cucurbitane-type triterpenes, (23E)-25-methoxycucurbit-23-ene-3beta,7beta-diol (1), (23E)-cucurbita-5,23,25-triene-3beta,7beta-diol (2), (23E)-25-hydroxycucurbita-5,23-diene-3,7-dione (3), (23E)-cucurbita-5,23,25-triene-3,7-dione (4), and (23E)-5beta,19-epoxycucurbita-6,23-diene-3beta,25-diol (5), together with one known triterpene, (23E)-5beta,19-epoxy-25-methoxycucurbita-6,23-dien-3beta-ol (6), have been isolated from the methanol extract of the stems of Momordica charantia. The structures of the new compounds were elucidated by spectroscopic methods.     

狼毒大戟的化学成分(英文)

目的:研究狼毒大戟根的化学成分。方法:用多种层析方法对化合物进行分离纯化,根据光谱数据和理化性质鉴定结构。结果:分离并鉴定了11个化合物,即(+)-nyasol(1),23(Z)-环阿尔廷-23-烯-3β,25-二醇(2),环阿尔廷-22-烯-3β,25-二醇(3),月腺大戟素A(4),2,4-二羟基-6-甲氧基-3-醛基苯乙酮(5),α-亚麻酸(6),24-亚甲基环木菠萝烷醇(7),环阿尔廷醇(8),β-谷甾醇(9),3,3’-二乙酰基-4,4’-二甲氧基-2,2’,6,6’-四羟基二苯甲烷(10),狼毒乙素(11)。结论:化合物1为该属首次分离,化合物2-6为该种植物首次分离。     

猫耳刺中三萜类化合物的结构研究

目的：研究猫耳刺Ilex pernyi叶的化学成分。方法：应用硅胶及Sephadex LH-20凝胶柱色谱法对其化学成分进行分离,并利用NMR和MS等方法鉴定分离得到的化合物。结果：从猫耳刺的干燥叶中分离得到8个三萜化合物,分别鉴定为熊果酸(1),羽扇豆醇(2),α-香树脂醇(3),熊果醇(4),3β-羟基-乌索-11-烯-28,13β-内酯(5),坡模酸(6),羽扇-20(29)-烯-3β,24-二醇(7),3β,23-二羟基乌索-12-烯-28-酸(8),结论：该8个化合物均为首次从猫耳刺中分离得到。     

红树林植物海漆中的三萜和甾体化合物

目的:对红树林植物海漆Excoecaria agallocha的化学成分进行研究。方法:采用多种色谱分析手段进行分离纯化,根据化合物的理化性质及波谱数据鉴定其结构。结果:从海漆甲醇提取物的石油醚相中分离、鉴定了6个三萜和3个甾体化合物,分别为蒲公英赛酮(1)、β-香树脂醇乙酸酯(2)、3-β[(2E,4E)-6-oxo-decad ienoy-loxy]-olean-12-ene(3)、蒲公英赛醇(4)、乙酰油酮酸(5)、cycloart-22-ene-3β,25-diol(6),β-sitostenone(7),(24R)-24-ethylcholesta-4,22-dien-3-one(8)和β-谷甾醇(9)。结论:化合物5~8为首次从海漆中分到。     

Oxygenated analogues of gorgosterol and ergosterol from the soft coral Capnella lacertiliensis

From the dichloromethane solubles of Capnella lacertiliensis five new sterols were isolated that are highly functionalized with oxygen-containing substituents: 12beta-acetoxy-7alpha-hydroxygorgosterol (1), 12beta-acetoxy-7alpha,19-dihydroxygorgosterol (2), 12beta-acetoxyergost-5-ene-3beta,23-diol (4), 12beta-acetoxyergost-5-ene-3beta,11beta,16-triol (5), and 11beta-acetoxyergost-5-ene-3beta,12beta,16-triol (6). The structures of all compounds were deduced from interpretation of their spectroscopic data, mainly 1D and 2D NMR spectra and HREIMS. Biological activities of the isolates were assessed, and all were found to be weakly antifungal. Compounds 5 and 6 were also found to have weak tyrosine kinase p56(lck)() (TK) inhibitory activity at the 200 microgram/mL level.     

Five novel neuroprotective triterpene esters of Ulmus davidiana var. japonica

Investigation of the constituents of the stem and root barks of Ulmus davidiana var. japonica resulted in the isolation of five new triterpene esters named ulmicin A-E (1-5). Using several spectroscopic techniques, their structures were determined to be 3beta,11alpha,15alpha-trihydroxylup-20(29)-ene-11-(3'-methoxy-4'-hydroxybenzoyl ester) (1), 3beta,11alpha,15alpha-trihydroxylup-20(29)-ene-11-(4'-hydroxybenzoyl ester) (2), 3beta,11alpha,15alpha-trihydroxylup-20(29)-ene-11-(3'-methoxy-4'-hydroxybenzoyl)-15-(4'-hydroxybenzoyl ester) (3), 3beta,11alpha,15alpha-trihydroxylup-20(29)-ene-11,15-di(3'-methoxy-4'-hydroxybenzoyl ester) (4), and 3beta,11alpha,15alpha-trihydroxylup-20(29)-ene-11-(3'-methoxy-4'-hydroxybenzoyl)-15-(benzoyl ester) (5). All five compounds showed significant neuroprotective activities against glutamate-induced neurotoxicity in primary cultures of rat cortical cells.     

Three new triterpenes from Nerium oleander and biological activity of the isolated compounds

New ursane-type triterpene 1, oleanane-type triterpene 2, and dammarane-type triterpene 15 were isolated from the leaves of Nerium oleander together with 12 known triterpenes, 3beta-hydroxy-12-ursen-28-oic acid (ursolic acid, 3), 3beta,27-dihydroxy-12-ursen-28-oic acid (4), 3beta,13beta-dihydroxyurs-11-en-28-oic acid (5), 3beta-hydroxyurs-12-en-28-aldehyde (6), 28-norurs-12-en-3beta-ol (7), urs-12-en-3beta-ol (8), urs-12-ene-3beta,28-diol (9), 3beta-hydroxy-12-oleanen-28-oic acid (oleanolic acid, 10), 3beta,27-dihydroxy-12-oleanen-28-oic acid (11), 3beta-hydroxy-20(29)-lupen-28-oic acid (betulinic acid, 12), 20(29)-lupene-3beta,28-diol (betulin, 13), and (20S,24R)-epoxydammarane-3beta,25-diol (14). On the basis of their spectroscopic data, the structures of the new compounds 1, 2, and 15 were established as 3beta,20alpha-dihydroxyurs-21-en-28-oic acid, 3beta,12alpha-dihydroxyoleanan-28,13beta-olide, and (20S,24S)-epoxydammarane-3beta,25-diol, respectively. The anti-inflammatory activity of the seven isolated compounds and methyl esters of ursolic acid and oleanoic acid in vitro was examined on the basis of inhibitory activity against the induction of the intercellular adhesion molecule-1 (ICAM-1). The anticancer activity of the 14 isolated compounds, including 1, 2, 15, and methyl esters of ursolic acid and oleanolic acid in vitro was examined on the basis of the cell growth inhibitory activities toward three kinds of human cell lines.