山莓中两个新二萜的分离与鉴定

为研究山莓(Rubus corchorifolius L.f)的化学成分，应用硅胶柱色谱进行分离纯化，根据化合物的理化性质和波谱数据鉴定结构。本文分离鉴定了2个贝壳杉烷二萜化合物，其结构分别为对映-贝壳杉烷-3α，16α，17，19-四醇(1)，对映-2-羰基-16α-羟基-贝壳杉烷-17-β-D-葡糖苷(2)。化合物1、2均为新化合物。     

彭泽贝母中二萜类成分

为了研究彭泽贝母的化学成分。利用多种柱色谱方法进行分离纯化，根据光谱数据和理化性质进行结构鉴定。共分离并鉴定了6个对映-贝壳杉类二萜化合物： ent-kauran-15-en-17-ol (I)， ent--kauran-15-en-3α,17-diol (II)， 鄂贝新醇(III)， ent--kauran-16α,17-diol (IV)， ent--kauran-3α，16α,17-triol (V)， ent--16,17-epoxy-kauran-3α-ol (VI)。6个化合物均为首次从彭泽贝母中分得，其中ent--16,17-epoxy-kauran-3α-ol (VI)为新化合物。     

溪黄草甲素的结构研究

从溪黄草Rabdosia serra(Maxim.)Hara干叶、茎中共分得八个化合物,其中化合物Ⅲ～Ⅷ经鉴定分别为excisanin A(Ⅲ),kamebakaurin(Ⅳ),2α-羟基乌苏酸(Ⅴ),β-谷甾醇(Ⅵ),乌苏酸(Ⅶ)和β-谷甾醇D-葡萄糖甙(Ⅷ)。Ⅰ为新化合物,经光谱分析和衍生物制备证明其结构为1,14-二羟基,7,20,19,20-二环氧-16-贝壳杉烯-15-酮,命名为溪黄草甲素。药理实验表明化合物Ⅰ,Ⅲ和Ⅳ对Hela细胞具有显著的抑制作用。     

5α-△9(11)-16β-甲基-3β,17α,21-三羟基-孕甾烯-3β,21-双醋酸酯-20酮和5α,17α-甲基-17β-羟基-雄甾-3酮的微生物转化

用诺卡氏菌与节杆菌混合菌种转化从蕃麻皂素制得的中间体5α-△⁹⁽¹¹⁾-16-16β-甲基-3β,17α,21三羟基孕甾烯-3β,21-双醋酸酯-20酮(Ⅰ)得50%的16β-甲基-△^1,4,9(11)-孕甾三烯-20酮(Ⅱ)和少量的16β-甲基-9,11α环氧-△¹,4孕甾二烯-20酮(Ⅲ)。另外,又用同样的混合菌种转化从剑麻皂素制得的中间体5α,17α甲基-17β羟基-雄甾-3酮(Ⅳ)得50%17α甲基-17β羟基-△^1,4-雄甾二烯-3酮(Ⅴ)。如改变培养基则得3,17β-羟基-17α-甲基-9酮基-9,10开环-1,3,5(10)雄甾三烯化合物。     

藤山柳根茎中的三萜成分

目的　研究我国特有的单种属药用植物藤山柳[Clematoclethrascandens (Franch .)Maxim .]根茎的甲醇提取物正丁醇萃取部分的化学成分。方法　将甲醇提取物分散于水中,经石油醚和乙酸乙酯萃取后,再用正丁醇进行萃取,对正丁醇萃取物进行柱色谱分离纯化,用波谱方法鉴定化合物结构。结果　分离鉴定了5个三萜化合物:2α,3β,24-三羟基乌苏-12 ,18-二烯-28-酸-28-O-β-D-吡喃葡糖酯(I) ,niga-ichigoside F₁ (II) ,asiaticacid (III) ,2α,3α,24-三羟基乌苏-12-烯-28-酸(IV) ,2α,3α,19α,24-四羟基乌苏-12-烯-28-酸(V)。结论　以上三萜化合物均为首次从该属植物中获得,其中I是一个新三萜皂苷     

香茶菜抗癌成分的研究

从香茶菜属植物香茶菜Rabdosia amethystoides(Benth) Hara中分得七种成分,其中之一香茶菜甲素为一新的四环二萜,有抗实验肿瘤及抑制金黄色葡萄球菌作用。用光谱法配合衍生物制备,确定甲素为7α,14β=羟基-20α羟甲基-16-贝壳杉烯-11,15=酮乙素为乌苏酸,丙素为β-谷甾醇,己素为硬脂酸,其余成分尚在研究中。     

大花美人蕉根中1个新的对映-贝壳杉烷型二萜类化合物

采用硅胶柱色谱、高效液相色谱等方法对大花美人蕉根的乙醇提取物中的化学成分进行分离纯化,并运用现代波谱学手段鉴定化合物结构。从中分离得到2个对映-贝壳杉烷型二萜类化合物,鉴定为(5R,8S,9S,10R,13R)-2-酮-对映-贝壳杉-15-烯-17-酸(1)和(4R,5S,8S,9S,10S,13R)-19-羟基-对映-贝壳杉-15-烯-17-酸(2),化合物1为新化合物,化合物2为首次从大花美人蕉根中分离得到。     

安徽贝母中的新二萜成分

为了研究安徽贝母(Fritillaria anhuiensis S.C.Chen et S.E.Yin)的化学成分。将安徽贝母的干燥鳞茎用95%乙醇回流提取后，用硅胶柱色谱进行分离纯化，得到了3个化合物。根据化合物的理化性质和光谱数据进行结构鉴定，分别为12,15-epoxy-8(17),13-labdadien-19-ol (1)，ent-3β-acetoxy-kauran-16β,17-diol (2)，ent-kaurane-3β,16β,17-triol (3)。化合物1为新的labdane型二萜类化合物，化合物2和3为首次从该植物中得到。     

刺梨酸的分离与结构研究

从刺梨中分离出一种新的五环三萜酸,命名为刺梨酸。通过光谱分析和衍生物的制备,确定其化学结构为2β,3α,7β,19α-四羟基乌苏-12-烯-28-羧酸。     

苦葛蔓中的新三萜成分

目的： 对苦葛蔓(Pueraria peduncularis Grah.)酸水解产物中的化学成分进行分离和结构鉴定。方法： 用各种色谱技术进行分离,得到3个五环三萜化合物,用MS,¹HNMR,¹³CNMR(DEPT),HMQC,HMBC和NOESY谱鉴定化合物。结果： 经光谱鉴定化合物1为3β,15α,23-三羟基齐墩果-12-烯-16-酮,化合物2为3β,15α-二羟基齐墩果-12-烯-16-酮,化合物3为3β,22β,24-三羟基齐墩果-12-烯(soyasapogenol B)。结论： 化合物1和化合物2为新化合物。     

番荔枝化学成分研究

从番荔枝(Annona squamosa)中分离得到12个化合物,分别鉴定为liriodenine(AS—1),穆坪马兜铃酰胺(moupinamide,AS-2),-(-)-kauran-16α-01-19-oic acid(AS-3),16β,17-dihydroxy-(-)-kauran-19-oic acid(AS-4),anonaine(AS-5),16α,17-dihydroxy-(-)-kauran-19-oic acid(AS-6),(-)-isokaur-15(16)-en-17,19-dioic acid(AS-7),番荔枝酰胺squamosamide(AS-8),16α-methoxy-(-)kauran-19-oicacid(AS-9),sachanoic acid(AS-10),(-)-kauran-19-al-17-oic acid(AS-11),daucosterol(AS-12)。其中,番荔枝酰胺(AS-8)是新化合物,AS-9是第一次从植物中得到的天然产物。     

Cytotoxicity of prenylated xanthones and other constituents from the wood of Garcinia merguensis

One new prenylated xanthone 5-farnesyltoxyloxanthone B ( 4), three known xanthones alpha-mangostin ( 1), rubraxanthone ( 2) and isocowanol ( 3) as well as (2 E,6 E,10 E)-4beta-hydroxy-3-methyl-5beta-(3,7,11,15-tetramethylhexadeca-2,6,10-tetraenyl)-cyclohex-2-en-1-one ( 5) and 3,3',4- O-trimethylellagic acid were isolated from the wood of GARCINIA MERGUENSIS Wight. The cytotoxic activities of compounds 1 - 5 were evaluated against the MCF-7, MDA-MB-231, NCI-H-460 and SF-268 cell lines with rubraxanthone 2 and 5 exhibiting the highest activity at 9.0 and 12.1 microM, respectively, against MCF-7 cells.     

Inhibitory Constituents against Cyclooxygenases fromAralia cordata Thunb

Seven diterpenes, four polyacetylenes, a lipid glycerol, and two sterols were isolated from the methylene chloride fraction of the root of Aralia cordata. Their chemical structures were determined as (-)-pimara-8(14),15-dien-19-oic acid (2), pimaric acid (3), (-)-kaur-16-en-19-oic acid (4), 17-hydroxy-ent-kaur-15-en-19-oic acid (9), 7alpha-hydroxy-(-)-pimara-8(14),15-dien-19-oic acid (10), 16alpha,17-dihydroxy-(-)-kauran-19-oic acid (11), 16-hydroxy-17-isovaleroyloxy-ent-kauran-19-oic acid (12), falcarindiol (5), dehydrofalcarindiol (6), dehydrofalcarindiol-8-acetate (7), falcarindiol-8-acetate (8), alpha-mono palmitin (13), stigmasterol (1), and daucosterol (14) by the spectral evidences. These compounds were tested with COX-1 and COX-2 inhibition assays. This study found that compounds 2, 4, 5, 6, 7, 8, and 10 inhibited COX-1 dependent conversion of the exogenous arachidonic acid to PGE2 in a dose-dependent manner with IC50 values of 134.2 microM, 121.6 microM, 170 microM, 50.4 microM, 11.7 microM, 99.6 microM, and 69.6 microM, respectively. But, most of these compounds weakly inhibited COX-2 dependent PGE2 generation. Among them, only compound 4 showed relatively significant inhibitory activity (IC50: 127.6 microM).     

Bioactive triterpenoids from Symplocos chinensis

A new triterpenoid, 2beta,3beta,19alpha,24-tetrahydroxy-23-norurs-12-en-28-oic acid (4), together with three known triterpenoids 3-oxo-19alpha,23,24-trihydroxyurs-12-en-28-oic acid (1), 2alpha,3beta,19alpha,23-tetrahydroxyurs-12-en-28-oic acid (2), 2alpha,3alpha,19alpha,23-tetrahydroxyurs-12-en-28-oic acid (3), was isolated from the roots of Symplocos chinensis. The new triterpenoid shows significant cytotoxic activity against B16 and BGC-823 cells.     

Chemical constituents of Nouelia insignis Franch

Two new diterpenes and ent-15alpha-hydroxykaur-16-en-19-oic acid 11,12-acetonide (3), together with 23 known compounds were isolated from the dried aerial parts of Nouelia insignis Franch. The structures of new compounds were determined to be ent-14beta,15alpha-dihydroxykaur-16-en-19-oic acid (1), ent-14beta-hydroxy-15-oxokaur-16-en-19-oic acid (2) on the basis of spectral and chemical evidence. The structure of ent-11alpha,16alpha-epoxy-15alpha-hydroxy-16S-kaur-19-oic acid (4) was confirmed by X-ray crystallographic analysis.     

Cytotoxic activity of diterpenoids isolated from the aerial parts of Elaeoselinum asclepium subsp. meoides

The phytochemical investigation of the acetone extract of the aerial parts of Elaeoselinum asclepium (L.) Bertol. subsp. meoides (Desf.) Fiori afforded several known diterpenoids as well as meoidic acid ( 5), new in the literature. The cytotoxic activities of elasclepic acid ( 1), ENT-atis-16-en-19-oic acid ( 2), ent-beyer-15-en-19-oic acid ( 3), ent-kaur-16-en-19-oic acid ( 4) and meoidic acid ( 5) were investigated on rat glioma C6 cells by evaluation of cell growth inhibition.     

Triterpenoids from the Flower of Campsis grandiflora K. Schum. as Human Acyl-CoA: Cholesterol Acyltransferase Inhibitors

The flower of Campsis grandiflora K. Schum. was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and H2O. From the EtOAc fraction, seven triterpenoids were isolated through the repeated silica gel, ODS column chromatographies and preparative HPLC. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as 3beta-hydroxyolean-12-en-28-oic acid (oleanolic acid, 1), 3beta-hydroxyurs-12-en-28-oic acid (ursolic acid, 2), 3beta-hydroxyurs-12-en-28-al (ursolic aldehyde, 3), 2alpha,3beta-dihydroxyolean-12-en-28-oic acid (maslinic acid, 4), 2alpha,3beta-dihydroxyurs-12-en-28-oic acid (corosolic acid, 5), 3beta,23-dihydroxyurs-12-en-28-oic acid (23-hydroxyursolic acid, 6) and 2alpha,3beta,23-trihydroxyolean-12-en-28-oic acid (arjunolic acid, 7). These teriterpenoids were isolated for the first time from this plant. Also, compounds 4, 5, 6, and 7 revealed relatively high hACAT-1 inhibitory activity with the value of 46.2+/-1.1, 46.7+/-0.9, 41.5+/-1.3 and 60.8+/-1.1% at the concentration of 100 microg/mL, respectively.     

Trypanosomicidal kaurane diterpenes from Wedelia paludosa

The diterpenes ent-kaur-16-en-19-oic acid, ent-kaur-9(11),16(17)-dien-19-oic acid and 3 alpha-angeloiloxy-ent-kaur-16-en-19-oic acid were identified as trypanosomicidal compounds of the ethanolic extract from the aerial parts of Wedelia paludosa D.C. (Asteraceae), showing activity up to the lowest dose of 0.68 mg/mL in the in vitro assay against trypomastigotes of T. cruzi, the causative agent of Chagas' disease (American trypanosomiasis). The other isolates, friedelan-3 beta-ol, ent-kaur-16 alpha-ol-19-oic acid, beta-amyrin acetate and (22-E)-stigmasta-5,22-dien-3 beta-ol, were inactive. This is the first report on the trypanosomicidal activity of ent-kaur-9(11),16(17)-dien-19-oic acid and 3 alpha-angeloiloxy-ent-kaur-16-en-19-oic acids; this effect was already known for ent-kaur-16-en-19-oic acid.     

Inhibitory effect of kaurane type diterpenoids from<Emphasis Type="Italic">Acanthopanax koreanum</Emphasis> on TNF-α secretion from trypsin-stimulated HMC-1 cells

Five known kaurane type diterpenoids, 16alphaH,17-isovaleryloxy-ent-kauran-19-oic acid (1), 16alpha-hydroxy-17-isovaleryloxy-ent-kauran-19-oic acid (2), paniculoside-IV (3), 16alpha-hydroxy-ent-kauran-19-oic acid (4), and ent-kaur-16-en-19-oic acid (5) were isolated from the root of Acanthopanax koreanum by repeated column chromatography and reversed phase preparative HPLC. The structures of these compounds were established from physicochemical and spectral data. Among the isolated compounds 16alphaH,17-isovaleryloxy-ent-kauran-19-oic acid (1) showed potent inhibitory activity (IC50 value, 16.2 uM) on TNF-alpha secretion from HMC-1, a trypsin-stimulated human leukemic mast cell line.     

Kaurane-type diterpene glycoside from the stem bark of Acanthopanax trifoliatus

A new diterpene glycoside, acantrifoside D ( 1), as well as three known diterpenes (2 - 4) were isolated from the stem bark of Acanthopanax trifoliatus from Vietnam. Based on 1D and 2D NMR spectroscopic data, their chemical structures were determined to be 16alpha,17-dihydroxy- ent-kauran-19-oic acid 16- O-beta- D-glucopyranoside 19- O-beta- D-glucopyranosyl ester (1), 16alpha H,17-isovalerate- ent-kauran-19-oic acid (2), ent-kaur-16-en-19-oic acid ( 3), and ent-pimara-8(14),15-dien-19-oic acid (4). Compounds 2 - 4 had strong inhibitory effects against COX-1 in an in vitro assay, with IC50 values of 0.21, 0.15 and 0.19 mM, respectively.