广西产美味猕猴桃根正丁醇部位化学成分研究

目的：研究广西产美味猕猴桃根正丁醇部位的化学成分。方法：应用色谱技术分离纯化，根据理化性质和波谱数据鉴定化合物结构。结果：从美味猕猴桃根正丁醇部位中分离并鉴定了6个化合物，分别为毛花猕猴桃酸B(1)，2α，3β，24 -三羟基-12-烯-28-乌苏酸(2)，2α，3α，24 -三羟基-12-烯-28-乌苏酸(3)，2α，3α，23-三羟基-12，20(30)-二烯-28-乌苏酸(4)，2α，3α，24-三羟基-12，20(30)-二烯-28-乌苏酸(5)，正丁基-O-β-D-吡喃果糖苷(6)。结论：化合物1～4，6均为首次从该植物中分离得到，其中化合物6为首次从猕猴桃属植物中分得。     

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.     

Triterpenoids from the resin of Styrax tonkinensis and their antiproliferative and differentiation effects in human leukemia HL-60 cells

Four new triterpenoids, 6beta-hydroxy-3-oxo-11alpha,12alpha-epoxyolean-28,13beta-olide (1), 3beta,6beta-dihydroxy-11alpha,12alpha-epoxyolean-28,13beta-olide (2), 3beta,6beta-dihydroxy-11-oxo-olean-12-en-28-oic acid (3), and 3beta-hydroxy-12-oxo-13Halpha-olean-28,19beta-olide (4), and five known triterpenes, 19alpha-hydroxy-3-oxo-olean-12-en-28-oic acid (5), 6beta-hydroxy-3-oxo-olean-12-en-28-oic acid (6), sumaresinolic acid (7), siaresinolic acid (8), and oleanolic acid (9), were isolated from the resin of Styrax tonkinensis. The structures of these triterpenoids were determined by physicochemical and spectroscopic methods. The configuration of compound 4 was confirmed by X-ray crystallographic analysis. All these triterpenoids inhibited HL-60 cell growth with IG(50) values ranging from 8.9 to 99.4 microM. Oleanolic acid (9) was the most effective antiproliferative agent, with an IG(50) value of 8.9 microM. While 3beta,6beta-dihydroxy-11-oxo-olean-12-en-28-oic acid (3) exhibited the least effective growth inhibition among these triterpenoids, it induced HL-60 cells to undergo differentiation as measured by an NBT reduction assay.     

Chemical investigation and anti-inflammatory activity of Vitex negundo seeds.

The CHCl3 extract of the defatted seeds of Vitex negundo exhibited anti-inflammatory activity and yielded four triterpenoids: 3 beta-acetoxyolean-12-en-27-oic acid [1], 2 alpha, 3 alpha-dihydroxyoleana-5,12-dien-28-oic acid [2], 2 beta,3 alpha-diacetoxyoleana-5,12-dien-28-oic acid [3], and 2 alpha,3 beta-diacetoxy-18-hydroxyoleana-5,12-dien-28-oic acid [5]. This is the first report of the isolation of compounds 2, 3, and 5 from a natural source.     

Bioactive steroids from the whole herb of Euphorbia chamaesyce

Three new ergostane-type steroids, 3beta-hydroxy-4alpha, 14alpha-dimethyl-5alpha-ergosta-8,24(28)-dien-11 -one (1); 3beta, 11alpha-dihydroxy-4alpha,14alpha-dimethyl-5alpha -ergosta-8, 24(28)-dien-7-one (2); and 3beta,7alpha-dihydroxy-4alpha, 14alpha-dimethyl-5alpha-ergosta-8,24(28)-dien-11 -one (3), were isolated, together with two known triterpenoids, wrightial and lup-20(30)-ene-3beta,29-diol from the whole herb of Euphorbia chamaesyce. Compound 3 showed a potent inhibitory effect on Epstein-Barr virus early antigen activation induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate (TPA).     

New lanostane-type triterpenoids from Ganoderma applanatum

Four new lanostane-type triterpenes were isolated from the MeOH extract of the fruiting bodies of Ganoderma applanatum. Their structures were established as 3beta,7beta,20,23xi-tetrahydroxy-11,15-dioxolanosta-8-en-26-oic acid (1), 7beta,20,23xi-trihydroxy-3,11,15-trioxolanosta-8-en-26-oic acid (2), 7beta,23xi-dihydroxy-3,11,15-trioxolanosta-8,20E(22)-dien-26-oic acid (3), and 7beta-hydroxy-3,11,15,23-tetraoxolanosta-8,20E(22)-dien-26-oic acid methyl ester (4), respectively, by extensive spectroscopic analyses.     

New cytotoxic oleanane-type triterpenoids from the cones of Liquidamber styraciflua

Two new oleanane-type triterpenoids (1 and 2), together with two known compounds, 6beta-hydroxy-3-oxo-lup-20(29)-en-28-oic acid (3) and 3,11-dioxoolean-12-en-28-oic acid (4), were isolated from the stem bark of Liquidamber styraciflua. The structures of 1 and 2 were determined to be 25-acetoxy-3alpha-hydroxyolean-12-en-28-oic acid (1) and 3alpha,25-dihydroxyolean-12-en-28-oic acid (2) on the basis of spectroscopic methods and chemical conversion. Compound 1 showed strong cytotoxicity against a disease-oriented panel of 39 human cancer cell lines, although compounds 2, 3, and 4 showed weaker activity compared to 1.     

New lanostanoids, elfvingic acids A-H, from the fruit body of Elfvingia applanata

Eight new lanostanoids, 12alpha,15beta-dihydroxy-3,7,11,23-tetraoxolanost-8,(20Z)(22)-dien-26-oic acid (1), 7beta,8beta-epoxy-15beta,20S-dihydroxy-3,12,23-trioxolanost-9(11),16-dien-26-oic acid (2), 7beta,8beta-epoxy-3beta,15beta,20S-trihydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (3), 7beta,8beta-epoxy-2alpha,3beta,15beta,20S-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (4), 7beta,8beta-epoxy-3beta,15beta,20S,28-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (5), 7beta,8beta-epoxy-3beta,15beta,19,20S-tetrahydroxy-12,23-dioxolanost-9(11),16-dien-26-oic acid (6), 8beta,15beta,20S-trihydroxy-3,7,12,23-tetraoxolanost-9(11),16-dien-26-oic acid (7), 7alpha,8alpha-epoxy-15beta,23xi-dihydroxy-12-oxo-3,4-secolanost-4(28),9(11),(20Z)(22)-trien-3,26-dioic acid (8), and the methyl ester of 8 (8a) were isolated from the fruit bodies of Elfvingia applanata. Their structures were established primarily by NMR experiments, and their biological activity against Kato III and Ehlrich cells was investigated.     

Natural products inhibiting Candida albicans secreted aspartic proteases from Lycopodium cernuum

Activity-guided fractionation of an ethanol extract of Lycopodium cernuum for Candida albicans secreted aspartic proteases (SAP) inhibition resulted in the identification of six new (1-6) and four known (7-10) serratene triterpenes, along with the known apigenin-4'-O-(2' ',6' '-di-O-p-coumaroyl)-beta-D-glucopyranoside (11). On the basis of spectroscopic analysis, the structures of 1-10 were established as 3beta,14alpha,15alpha,21beta,29-pentahydroxyserratane-24-oic acid (lycernuic acid C, 1), 3beta,14alpha,15alpha,21beta-tetrahydroxyserratane-24-oic acid (lycernuic acid D, 2), 3beta,14beta,21beta-trihydroxyserratane-24-oic acid (lycernuic acid E, 3), 3beta,21beta,29-trihydroxy-16-oxoserrat-14-en-24-methyl ester (lycernuic ketone A, 4), 3alpha,21beta,29-trihydroxy-16-oxoserrat-14-en-24-methyl ester (lycernuic ketone B, 5), 3alpha,21beta,24-trihydroxyserrat-14-en-16-one (lycernuic ketone C, 6), 3beta,21beta-dihydroxyserrat-14-en-24-oic acid (lycernuic acid A, 7), 3beta,21beta,29-trihydroxyserrat-14-en-24-oic acid (lycernuic acid B, 8), serrat-14-en-3beta,21beta-diol (9), and serrat-14-en-3beta,21alpha-diol (10). The 13C NMR data for the known compounds 7 and 8 are reported for the first time. Compounds 1 and 11 showed inhibitory effects against C. albicans secreted aspartic proteases (SAP) with IC50 of 20 and 8.5 microg/mL, respectively, while the other compounds were inactive.     

Novel cytotoxic oxygenated C29 sterols from the Colombian marine sponge Polymastia tenax

Three new sterols, 5alpha,6alpha-epoxy-24R-ethylcholest-8(14)-en-3beta,7alpha-diol (1), 5alpha,6alpha-epoxy-24R-ethylcholest-8-en-3beta,7alpha-diol (2), and 3beta-hydroxy-24R-ethylcholesta-5,8-dien-7-one (3), have been isolated from the marine sponge Polymastia tenax, collected in the Colombian Caribbean, and their structures established on the basis of extensive NMR and MS studies. Compounds 1 and 2 showed antiproliferative activity toward A-549, HT-29, H-116, MS-1, and PC-3 tumor cells in the range 0.5-10 microg/mL.     

Triterpenes from natural and transformed roots of Plocama pendula

Plocama pendula root cultures transformed by Agrobacterium rhizogenes were established. From these cultures two new pentacyclic triterpenes, 3-epi-pomolic acid 3alpha-acetate (3alpha-acetoxy-19alpha-hydroxyursa-12-en-28-oic acid) (1) and baloic acid (3alpha-acetoxy-19alpha-hydroxyursa-12,20(30)-dien-28-oic acid) (9), were isolated. The former was also obtained from P. pendula natural roots, together with another two new pentacyclic triterpenes, 3-epi-pomolic acid (3alpha,19alpha-dihydroxyursa-12-en-28-oic acid) (3) and 19alpha-hydroxyoleanonic acid (19alpha-hydroxy-3-oxo-olean-12-en-28-oic acid) (12).     

Ursane- and oleanane-type triterpenes from Ternstroemia gymnanthera callus tissues

An investigation on the constituents of the callus tissues of Ternstroemia gymnanthera has led to the isolation of five phytosterols, 15 known triterpenoids, and four new triterpenoids (1-4). The new compounds were characterized by spectroscopic study as 3-epi-corosolic acid lactone (2 alpha,3 alpha-dihydroxyurs-11-en-13 beta,28-olide) (1), 3-epi-ternstroemic acid (2 alpha,3 alpha-dihydroxyurs-12-en-11-on-28-oic acid) (2), ternstroemic acid (2 alpha,3 beta-dihydroxyurs-12-en-11-on-28-oic acid) (3), and gymnantheraic acid (2 alpha,3 alpha-dihydroxy-11 alpha-methoxyurs-12-en-28-oic acid) (4). The isolated triterpenes were compared with those from actinidiaceous plant callus tissues from a chemotaxonomic point of view.     

Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products

Microbial transformation of betulin (1), a lupane-type triterpene obtained from the bark extract of white birch (Betula platyphylla Sukatshev var. japonica), and its chemical oxidation product, betulonic acid (2), by the fungus Chaetomium longirostre yielded 4,28-dihydroxy-3,4-seco-lup-20(29)-en-3-oic acid (3) and 4-hydroxy-3,4-seco-lup-20(29)-ene-3,28-dioic acid (4) from 1, and 4,7beta,17-trihydroxy-3,4-seco-28-norlup-20(29)-en-3-oic acid (5) and 7 beta,15 alpha-dihydoxy-3-oxolup-20(29)-en-28-oic acid (6) from 2. The four metabolites, 3-6, along with 1 and 2, were 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 inhibitors of tumor promotion. All of the triterpenes tested showed potent inhibitory effects, with the four metabolites 3-6 exhibiting the more potent effects.     

New lanostanoid glycosides from the fruit body of laetiporus versisporus

Four new lanostanoid glycosides, 3beta, 7alpha-dihydroxy-24-methylene-lanost-8-en-21-oic acid 7-O-beta-D-glucopyranoside (1), 3beta,7alpha-dihydroxy-lanost-8, 24-dien-21-oic acid 7-O-beta-D-glucopyranoside (2), 7alpha-hydroxy-3-keto-lanost-8,24-dien-21-oic acid 7-O-beta-D-glucopyranoside (3), and 7alpha-hydroxy-3-keto-24-methylene-lanost-8-en-21-oic acid 7-O-beta-D-glucopyranoside (4) were isolated from the fruit bodies of Laetiporus versisporus. Compounds 1-4 were named laetiposides A-D, respectively. Their structures were established by extensive NMR experiments and chemical methods.     

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.     

Acinospesigenin-A, -B,and -C: three new triterpenoids from Phytolacca acinosa

Three new triterpenoids, designated as acinospesigenin-A (1), -B (2), and -C (3), isolated from the berries of Phytolacca acinosa, have been characterized as 3 beta-acetoxy-11 alpha,23-dihydroxytaraxer-14-en-28-oic acid, olean-12-en-23-al-2 beta,3 beta-dihydroxy-30-methoxycarbonyl-28-oic acid and olean-12-en-23-al-2 beta,3 beta,11 alpha-trihydroxy-30-methoxycarbonyl-28-oic acid, respectively. The compounds have shown antiedemic activity (LD(50) 10-15 mg/kg mass) in albino rats.     

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.     

委陵菜三萜成分研究

目的：研究委陵菜的化学成分及其抗癌活性。方法：用硅胶柱色谱、凝胶柱色谱等多种柱色谱分离,制备高效液相色谱纯化,得到单体化合物,用各种有机波谱鉴定化合物结构；并对化合物的抗癌活性进行研究。结果：分离得到15个三萜类化合物,鉴定为α-香树素(α-amyrin,1),β-香树素(β-amyrin,2),乌苏酸(ursolic acid,3),2α-羟基乌苏酸(corosolic acid,4),蔷薇酸(euscaphic acid,5),坡模酸(pomolic acid,6),委陵菜酸(tormentic acid,7),2α,3α-二羟基-12-烯-28-乌苏酸(2α,3α-dihydroxyurs-12-en-28-oic acid,8),2β,3β,19α-三羟基-12-烯-28-乌苏酸(2β,3β,19α-trihydroxyurs-12-en-28-oic acid,9),积雪草酸(asiatic acid,10),24-羟基委陵菜酸(24-hydroxy tormentic acid,11),2α,3α,19α,23-四羟基-12-烯-28-乌苏酸(myrianthic acid,12),齐墩果酸(oleanolic acid,13),2α-羟基齐墩果酸(maslinic acid,14),2α,3α-二羟基-12-烯-28-齐墩果酸(2α,3α-dihydroxyolean-12-en-28-oic acid,15)。结论：化合物1,2,4～15为首次从委陵菜中分离得到；化合物4,8～10,12,14和15对人宫颈癌细胞(Hela)和小鼠成纤维细胞(L929)具有一定的细胞毒作用,其中化合物4和9抗癌活性较强。     

Triterpenoid saponins of Acanthopanax nipponicus leaves

Five new triterpenoid saponins, nipponosides A-E (1, 3-6), were isolated from Acanthopanax nipponicus leaves, along with a known saponin, kalopanaxsaponin G (2). Nipponosides A-E were characterized as the 28-O-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta -D-glucopyranosyl ester of 3-oxohederagenin, oleanolic acid 3-O-beta-D-glucopyranoside, gypsogenin 3-O-beta-D-glucopyranoside, 3beta,23,29-trihydroxyolean-12-en-28-oic acid, and 3beta,20alpha, 23-trihydroxy-30-nor-olean-12-en-28-oic acid, respectively. The structures of these new compounds were based on chemical and spectral methods.     

Oculatol, oculatolide, and A-nor sterols from the sponge Haliclona oculata

Chemical investigation of the marine sponge Haliclona oculata resulted in the isolation of eight new compounds including oculatol (1) and oculatolide (2) and six unusual A-nor steroids, 2-ethoxycarbonyl-2beta-hydroxy-A-nor-ergosta-5,24(28)-dien-4-one (3), 2-ethoxycarbonyl-24-ethyl-2beta-hydroxy-A-nor-cholesta-5-en-4-one (4), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-ergosta-5,24(28)-dien-4-one (5), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-cholesta-5-en-4-one (6), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-24-methyl-A-nor-cholesta-5,22(E)-dien-4-one (7), and 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-cholesta-5,22(E)-dien-4-one (8), along with 16 known steroids and indole derivatives. Their structures were unambiguously determined on the basis of extensive spectroscopic analyses.