Cytotoxic hydroxylated triterpene alcohol ferulates from rice bran

Three hydroxylated triterpene alcohol ferulates, (24S)-cycloart-25-ene-3 beta,24-diol-3 beta-trans-ferulate (1), (24R)-cycloart-25-ene-3 beta,24-diol-3 beta-trans-ferulate (2), and cycloart-23Z-ene-3 beta,25-diol-3 beta-trans-ferulate (3), along with known compounds cycloartenol trans-ferulate (4) and 24-methylenecycloartanol trans-ferulate (5) were isolated from rice bran. Their structures were elucidated by means of chemical and spectroscopic analysis. Compounds 2-5 showed moderate cytotoxicity against MCF-7 cells.     

Two new glycosides from Astragalus caprinus

A new glycoside of flavonol (1) and a new glycoside of a cycloartane-type triterpene (2) were isolated from the leaves and the roots of Astragalus caprinus, respectively. Their structures were elucidated in turn by spectroscopic data interpretation as 3-O-[[beta-D-xylopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->6)][beta-D-apiofuranosyl(1-->2)]]-beta-D-galactopyranosyl kaempferol (1) and 3-O-(beta-D-xylopyranosyl)-24-O-(beta-D-glucopyranosyl)-20,25-epoxycycloartane-3beta,6alpha,16beta,24alpha-tetrol (2).     

Triterpene saponins, quaternary ammonium compounds, phosphatidyl cholines, and amino acids in the pronotal and elytral secretions of Platyphora opima and Desmogramma subtropica

Secretions of the pronotal and elytral glands of adults of the chrysomelid beetle Platyphora opima from Panama have been shown to contain two oleanane triterpene saponins: the known 3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl-oleano lic acid-28-O-beta-D-glucopyranoside and compound 1, whose structure was established as 3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucuronopyranosyl-29- hydrox yoleanolic acid-28-O-beta-D-glucopyranoside by a combination of 1D and 2D NMR methods (COSY, HMQC, HMBC, and TOCSY) and FABMS. The secretions also contained N,N,N-trimethylcadaverine and its 1, 2-dehydro derivative 3, as well as the nicotinamide derivative 4. Secretions of Desmogramma subtropica, also from Panama, contained as sole triterpene derivative 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-24- hydrox yoleanolic acid (2), together with glutamic acid, glutamine, pyroglutamic acid, and arginine. A mixture of phosphatidylcholines was also present in the secretions of both species.     

A New Triterpene Saponin from Gynostemma pentaphyllum

Objective To study the triterpene saponins from Gynostemma pentaphyllum with antitumor activities. Methods The 75% EtOH extract of G. pentaphyllum was used for isolation by silica gel column chromatography and preparative HPLC. The structures of pure compounds isolated were identified by the spectral analysis and chemical evidence. Results Two compounds were isolated and identified as 23(S)-3β,20ξ,21ξ-trihydroxy-19-oxo-21,23-epoxydammar-24-ene 3-O-α-L-rhamnopyranosyl (1→2)-[β-D-xylopyranosyl (1→3)]-β-D-arab...     

Sulfated alkenes from the echinus Temnopleurus hardwickii

Three new sulfated alkenes (1-3), trimethylammonium (5R)-5,9-dimethyl-(3E)-3,8-decadienyl-1-sulfate, dimethylammonium (5R)-5,9-dimethyl-(3E)-3,8-decadienyl-1-sulfate, and 2'-methyl-4'-oxobutan-2-ylammonium (5R)-5,9-dimethyl-(3E)-3,8-decadienyl-1-sulfate, were isolated from an echinoderm, Temnopleurus hardwickii. Their structures were elucidated by spectral analysis and chemical degradation 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).     

Triterpene Glycosides from Sea Cucumber Holothuria scabra with Cytotoxic Activity

Objective To study the new triterpene glycosides from sea cucumber Holothuria scabra with cytotoxic activity.Methods Triterpene glycosides from H.scabra were separated and purified by chromatography on...     

New 3,4-seco-lupane-type triterpene glycosides from Acanthopanax senticosus forma inermis

Four new 3,4-seco-lupane-type triterpene glycosides (1-4) were isolated from the leaves of Acanthopanax senticosus forma inermis. The structures of 1-4 were established as 11alpha-hydroxy-3, 4-seco-lup-4(23),20(30)-dien-3-oic acid methyl ester 28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-be ta-D-glucopyranoside, designated as inermoside (1); 1-deoxychiisanoside (2); 24-hydroxychiisanoside (3); and 11-deoxyisochiisanoside (4) by (1)H-(1)H COSY and (1)H-(13)C COSY(HMBC, HMQC) methods and FABMS.     

Total synthesis and biological evaluation of (5Z,9Z)-5,9-hexadecadienoic acid,an inhibitor of human topoisomerase I

The naturally occurring (5Z,9Z)-5,9-hexadecadienoic acid was synthesized stereochemically pure in six steps starting with commercially available 1,5-hexadiyne. The title compound was antimicrobial against the Gram-positive bacteria Staphylococcus aureus (MIC 80 microM) and Streptococcus faecalis (MIC 200 microM), but inactive against Gram-negative bacteria such as Pseudomonas aeruginosa. In addition, the (5Z,9Z)-5,9-hexadecadienoic acid completely inhibits human topoisomerase I at a concentration of 800 microM, while 5,9-hexadecadiynoic acid and hexadecanoic acid do not inhibit topoisomerase I (>1000 microM). This comparison reveals that the cis double bond geometry in the title compound is required for topoisomerase I inhibition. Moreover, these results suggest that the antimicrobial activity of (5Z,9Z)-5,9-hexadecadienoic acid against either S. aureus or S. faecalis could be a result, at least in part, of the inhibitory activity of the acid against topoisomerases.     

Actaeaepoxide 3-O-beta-D-xylopyranoside, a new cycloartane glycoside from the rhizomes of Actaea racemosa (Cimicifuga racemosa)

A new cycloartane glycoside (1) was obtained from a minor triterpene fraction of the rhizome extract of Actaea racemosa (synonym: Cimicifuga racemosa) along with a known compound, cimigenol 3-O-beta-D-xylopyranoside. The structure of 1 was elucidated as 20(S),22(R),23(R),24(S)-12beta-acetoxy-16beta:23,23alpha:24-diepoxy-3beta,22beta,25-trihydroxy-9,19-cyclolanost-7-ene 3-O-beta-D-xylopyranoside (actaeaepoxide 3-O-beta-D-xylopyranoside) on the basis of spectral and chemical evidence.     

A new dammarane-type triterpene glycoside from Polyscias fulva

A new dammarane-type triterpene glycoside, polysciasoside A (1), and three known compounds have been isolated from the leaves of Polyscias fulva. The structure of the new compound was established as 12-oxo-3beta,16beta,20(S)-trihydroxydammar-24-ene-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside.     

复方鱼腥草改善db/db小鼠肾损伤及对JAK/STAT通路部分基因的影响

目的:比较复方鱼腥草不同提取部位对db/db小鼠肾损伤和JAK/STAT通路中部分基因的影响,探讨其防治糖尿病肾病的机制。方法:8周龄的db/m和db/db小鼠分为7组:db/m小鼠为正常组,db/db小鼠分为模型组,JAK酶抑制剂治疗组(AG490,1 mg·kg-1),复方鱼腥草石油醚提取部位组(SYM组),复方鱼腥草乙酸乙酯提取部位组(YSYZ组),复方鱼腥草正丁醇提取部位组(ZDC组),复方鱼腥草水提组(ST组),ig给药8周(7.8 g·kg-1)。检测小鼠尿白蛋白(Alb),24 h尿蛋白定量,血糖,天冬氨酸转氨酶(AST),丙氨酸转氨酶(ALT);粘连蛋白(FN);RT-PCR检测肾组织中的JAK2mRNA,STAT1mRNA,STAT3mRNA,SOCS-1mRNA的变化。结果:与正常组比较,模型组尿Alb,24 h尿蛋白定量,血糖,FN显著升高(P0.05);与模型组比较,尿Alb,24 h尿蛋白定量,FN均有不同程度的改善,且各提取部位组与水提组比较,复方鱼腥草正丁醇提取部位好于其他组,其中尿Alb与FN降低明显(P0.05)。与模型组比较,AG490组,SYM组,YSYZ组,ZDC组肾组织中的STAT1mRNA表达均明显下降(P0.05);ST组,ZDC组的SOCS-1mRNA表达升高(P0.05);但各治疗组的JAK2mRNA,STAT3mRNA表达没有显著差异。结论:复方鱼腥草能降低尿Alb,24 h尿蛋白定量及FN的分泌,且其正丁醇提取部位好于其他提取物组,并能调节JAK-STAT-SOCS-1相关基因表达,改善糖尿病肾损伤。     

Camelliols A-C, three novel incompletely cyclized triterpene alcohols from sasanqua oil (Camellia sasanqua)

Three novel triterpene alcohols, camelliols A (1), B (3), and C (5), possessing a mono-, bi-, and tricyclic ring system, respectively, have been isolated, along with achilleol A, a known monocyclic triterpene alcohol, from the nonsaponifiable lipids of sasanqua oil (Camellia sasanqua). The structures of these new alcohols were determined on the basis of spectroscopic methods.     

Triterpene saponins from the leaves of Ilex kudingcha

Nine new triterpene saponins, ilekudinosides K-S (1-9), and eight known triterpene saponins were isolated from the 70% ethanol extract of the leaves of Ilex kudingcha. The new saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (1), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-beta-kudinlactone (2), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-gamma-kudinlactone (3), 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl-alpha-kudinlactone (4), 3-O-beta-D-glucopyranosyl(1-->2)-alpha-L-arabinopyranosyl-alpha-kudinlactone (5), 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranosyl-alpha-kudinlactone (6), 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-beta-kudinlactone (7), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-beta-kudinlactone (8), and 3-O-alpha-L-rhamnopyranosyl(1-->2)-beta-D-glucopyranosyl-gamma-kudinlactone (9), respectively. The structures and stereochemistry of compounds 1-9 were elucidated by spectroscopic data interpretation and chemical degradation.     

白花蛇舌草中总三萜酸的提取纯化工艺优选

目的:优选白花蛇舌草中总三萜酸的提取纯化工艺。方法:以总三萜酸提取率为指标,选取乙醇用量、乙醇体积分数及回流时间为考察因素,采用正交试验优选白花蛇舌草中总三萜酸的提取工艺;通过静态吸附和解吸试验筛选树脂型号,采用单因素试验考察总三萜酸的大孔树脂纯化工艺。结果:最佳提取工艺为加10倍量70%乙醇回流提取1.5 h。采用AB-8型大孔树脂,其纯化工艺为上样流速2 BV.h-1,上样液pH 5,上样液质量浓度0.25 g.L-1,洗脱剂pH 7,洗脱乙醇体积分数80%,洗脱速度2 BV.h-1。结论:优选的工艺操作简单、稳定可行、重复性好,可推广于工业化生产应用。     

粉背南蛇藤中新三萜化合物对RKO细胞体外抗癌作用的研究

目的：探讨粉背南蛇藤中新的三萜齐墩果-12-烯-3β，6α-二醇对人结肠癌细胞系RKO细胞的体外增殖抑制作用和诱导凋亡作用。方法：采用MTT法检测齐墩果-12-烯-3β，6α-二醇对体外培养人结肠癌细胞系RKO细胞的增殖抑制作用，通过AO/EB双染色荧光显微镜、HE染色光学显微镜、DNA琼脂糖凝胶电泳、流式细胞仪分析齐墩果-12-烯-3β，6α-二醇对RKO细胞的诱导凋亡作用及对细胞周期的影响。结果：齐墩果-12-烯-3β，6α-二醇对RKO细胞生长抑制作用具有剂量依赖性和时间依赖性，作用48 h时IC₅₀为（12.20±0.79）μg·mL^-1；AO/EB双染色、HE染色可见典型的肿瘤细胞凋亡改变；10 μg·mL^-1的三萜处理RKO细胞48 h即可出现明显的DNA梯带、流式细胞仪可检测到亚二倍体峰，在10~20 μg·mL^-1内具有明显的量-效作用关系;　并可见RKO细胞G₀-G₁期、G₂-M期的细胞明显减少，而S期细胞无变化。结论：粉背南蛇藤中新的三萜齐墩果-12-烯/-3β，6α-二醇能抑制人结肠癌细胞系RKO细胞增殖和诱导凋亡。     

Eupha-7,9(11),24-trien-3beta-ol ("antiquol C") and other triterpenes from Euphorbia antiquorum latex and their inhibitory effects on Epstein-Barr virus activation

The structures of three triterpene alcohols isolated from the latex of Euphorbia antiquorum were established to be eupha-7,9(11),24-trien-3beta-ol (2; antiquol C), 19(10-->9)abeo-8alpha,9beta,10alpha-eupha-5,24-dien-3beta-ol (3; antiquol B), and 24-methyltirucalla-8,24(24(1))-dien-3beta-ol (4; euphorbol) on the basis of spectroscopic methods. Compounds 3 and 4 have previously been assigned the erroneous structures of 10alpha-cucurbita-5,24-dien-3alpha-ol and 24-methyleupha-8,24(24(1))-dien-3beta-ol, respectively. Compounds 2-4 and four other known compounds isolated from the latex, euphol (1), lemmaphylla-7,21-dien-3beta-ol (5), isohelianol (6), and camelliol C (7), showed potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).     

Inhibitory Effect of Poria cocos on 12-O-Tetradecanoylphorbol-13-Acetate-Induced Ear Oedema and Tumour Promotion in Mouse Skin

The methanol extract from the sclerotium of Poria cocos was found to inhibit 12- O -tetradecanoylphorbol-13-acetate (TPA)-induced tumour promotion in two-stage carcinogenesis in mouse skin. From the active fraction of the extract, eight lanostane-type triterpene acids and four 3,4-secolanostane-type triterpene acids were isolated. The isolated compounds showed inhibitory activity against TPA-induced ear inflammatory oedema. The 50% inhibitory dose of pachymic acid, 3- O -acetyl-16α-hydroxytrametenolic acid, dehydropachymic acid, dehydroeburiconic acid, 3β-hydroxylanosta-7,9(11),24-trien-21-oic acid, poricoic acid A and poricoic acid B for TPA-induced inflammation was 17–44 μg/ear, at a grade corresponding to that of hydrocortisone.     

Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea

Bioassay-guided fractionation of the active n-BuOH extract of the sea cucumber Holothuria fuscocinerea resulted in the isolation of three new triterpene glycosides, fuscocinerosides A (1), B (2), and C (3), along with two known glycosides, pervicoside C (4) and holothurin A (5), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Compounds 1-5 possess the same tetrasaccharide moiety, 3-O-methyl-beta-D-glucopyranosyl-(1-->3)-beta-D- glucopyranosyl-(1-->4)-beta-D-quinovopyranosyl-(1-->2)-4-O-sodiumsulfato-beta-D-xylopyranosyl, linked to C-3 of holostane triterpene aglycones that differ in their side chains and 17-substituents. Their structures were elucidated by extensive spectral studies as well as chemical evidence. All the glycosides showed in vitro cytotoxicity against two human tumor cell lines.     

Anti-inflammatory lanostane-type triterpene acids from Piptoporus betulinus

Six lanostane-type triterpene acids were isolated from the fruiting bodies of Piptoporus betulinus. They were identified as polyporenic acids A (1) and C (2), three derivatives of polyporenic acid A (3-5), and a novel compound, (+)-12 alpha,28-dihydroxy-3 alpha-(3'-hydroxy-3'-methylglutaryloxy)-24-methyllanosta-8,24(31)-dien-26-oic acid (6). All these compounds suppressed the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced edema on mouse ears by 49-86% with a 400 nmol/ear application.