Nortriterpenoids from Schisandra lancifolia

Six new nortriterpenoids, lancifodilactones I-N (1-6), as well as nine known ones, were isolated from the leaves and stems of Schisandra lancifolia. Their structures were elucidated on the basis of spectroscopic methods including 2D NMR analysis, and the structures of compounds 1 and 4 were further confirmed by single-crystal X-ray crystallography. In addition, all new compounds were tested for anti-HIV-1 activity.     

Triterpenoids from Schisandra rubriflora

Investigation of an organic extract of Schisandra rubriflora led to the isolation of three new highly oxygenated nortriterpenoids, named rubriflorins A-C (1-3), together with six related known compounds (4-9). Their structures were elucidated by spectroscopic evidence. Compounds 1-3 feature the opening of ring A compared with related known nortriterpenoids isolated from the genus Schisandra and showed anti-HIV-1 activities with EC50 values of 10.0, 16.2, and 81.3 microg/mL, respectively.     

Lancifodilactones B-E, new nortriterpenes from Schisandra lancifolia

Four new nortriterpenes, lancifodilactones B-E (1-4), were isolated from the leaves and stems of Schisandra lancifolia. Their structures were determined by analysis of 1D and 2D NMR spectroscopic data. These compounds are members of a new highly oxygenated cycloartane skeletal class with a biosynthetically modified eight-membered ring D.     

Lindenane disesquiterpenoids with anti-HIV-1 activity from Chloranthus japonicus

Five new lindenane disesquiterpenoids, chlorajaponilides A-E (1-5), together with 11 known analogues were isolated from whole plants of Chloranthus japonicus. The structure and absolute configuration of 1 was confirmed by X-ray crystallography. Compounds 1 and 2 represent the first examples of lindenane disesquiterpenoids with a C-5 hydroxy group and a C-4-C-15 double bond. Compounds 8, 9, 11, and 12 showed anti-HIV-1 replication activities in both wild-type HIV-1 and two NNRTIs-resistant strains. Shizukaol B (8) exhibited the best activity against HIV(wt), HIV(RT-K103N), and HIV(RT-K103N) with EC?? values of 0.22, 0.47, and 0.50 μM, respectively. Compounds 8, 9, 11, and 12 had significant cytotoxicities against C8166 cells with CC?? values of 0.020, 0.089, 0.047, and 0.022, respectively, and exhibited inhibitory activities against HIV-1 with EC?? values of 0.0014, 0.016, 0.0043, and 0.0033 μM, respectively.     

狭叶五味子中化合物扁枝杉香豆素和(-)-表儿茶酸体外抗乙型肝炎病毒活性研究

目的 研究从狭叶五味子Schisandra lancifolia中分离化合物扁枝杉香豆素(phyllocoumarin)和(-)-表儿茶酸[(-)-epicatechin]的体外抗乙型肝炎病毒(HBV)活性.方法 为了筛选和确认扁枝杉香豆素和(-)-表儿茶酸体外抗HBV活性,以HepG2.2.15细胞为体外研究HBV模型,分别用RPMI 1640完全培养基稀释不同质量浓度的药物作用于细胞,培养3 d后收集上清,采用MTT法检测药物对HepG2.2.15细胞的生长影响和ELISA法检测培养上清中HBsAg和HBeAg的水平,评价扁枝杉香豆素和(-)-表儿茶酸对HBsAg和HBeAg的影响.结果 扁枝杉香豆素和(-)-表儿茶酸具有一定的体外抗HBV活性,其细胞毒性非常小,CC_(50)均大于200μg/mL.扁枝杉香豆素具有较强的抑制HBsAg和HBeAg分泌作用.阳性对照药物阿德福韦酯也抑制HBVHBsAg和HBeAg分泌,但在相同质量浓度(1.6μg/mL)下其抑制作用较扁枝杉香豆素弱.结论 狭叶五味子中化合物扁枝杉香豆素和(-)-表儿茶酸具有一定体外抑制HBV HBsAg和HBeAg分泌的作用,从而起到抗HBV作用.     

绿升麻中具有抗肿瘤活性的三萜类化合物

目的研究绿升麻中具有抗肿瘤活性的化学成分。方法以硅胶柱色谱、凝胶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,以各有机波谱鉴定化合物结构。结果分离得到7个环菠萝蜜烷型三萜类化合物,鉴定为25-脱水升麻醇-3-O-β-D-木糖苷(25-anhydrocimigenol-3-O-β-D-xylopyranoside,Ⅰ)、25-乙酰升麻醇-3-O-β-D-木糖苷(25-O-acetylcimicigenol-3-O-β-D-xylopyranoside,Ⅱ)、升麻醇-3-O-α-L-阿拉伯糖苷(cimigenol-3-O-α-L-arabinopyranoside,Ⅲ)、升麻醇-3-O-β-D-木糖苷(cimigenol-3-O-β-D-xylopyranoside,Ⅳ)、3′-乙酰升麻醇-3-O-β-D-木糖苷(3′-O-acetylcimigenol-3-O-β-D-xylopyranoside,Ⅴ)、24-乙酰升麻醇-3-O-β-D-木糖苷[24-O-acetyl-shengmanol-3-O-β-D-xylopyranoside(23R,24R),Ⅵ]、24-O-acetylisodahurinol-3-O-β-D-xylopyranoside(Ⅶ)。结论化合物Ⅰ~Ⅶ首次从绿升麻中分离得到,抗肿瘤药理实验显示化合物Ⅰ、Ⅱ在质量浓度30μg/mL时对宫颈癌细胞(HeLa)和小鼠成纤维细胞(L929)具有较强细胞毒作用。     

Triterpenoid saponins from Symplocos lancifolia

Three new bidesmosidic saponins (1-3) and a new ursane triterpenoid, 2α,3β,11α,23-tetrahydroxyurs-12-en-28-oic acid (4), along with seven known compounds, were isolated from a methanolic extract of the leaves of Symplocos lancifolia. The bidesmosidic saponins were found to possess the same sugar unit part, composed of two β-d-glucose moieties and one α-l-rhamnose moiety, linked to maslinic acid, arjunolic acid, and asiatic acid, respectively. Their structures were elucidated by interpretation of their 1D and 2D NMR spectra and completed by analysis of the HRESIMS data. The antibacterial activity of the isolated triterpenoids was evaluated against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa, and several showed activity against Gram-positive bacteria.     

蒲葵籽提取物体外抗HIV-1活性及机制的初步研究

目的研究蒲葵籽提取物的体外抗HIV-1活性,对有活性粗提物进行初步机制研究。方法采用细胞毒性、合胞体抑制、HIV-1感染细胞保护实验和HIV-1 p24抗原测定等实验对蒲葵籽提取物体外抗HIV-1活性进行筛选和确认;采用重组HIV-1逆转录酶和蛋白酶活性抑制实验,融合阻断实验初步探讨活性粗提物的作用机制。结果蒲葵籽的醋酸乙酯(P3)提取物具有较强的体外抗HIV-1活性,P3抑制HIV-1诱导C8166细胞形成合胞体的EC50为5.64μg/mL,对C8166细胞的毒性较小,CC50大于200μg/mL,治疗指数(TI)大于35.46;P3抑制HIV-1急性感染中p24抗原表达的EC50为23.04μg/mL,抑制正常C8166细胞与慢性感染细胞H9/HIV-1 B融合的EC50为8.00μg/mL;P3在质量浓度为200μg/mL时,对HIV-1逆转录酶的抑制率为28.86%;P3抑制重组HIV-1蛋白酶活性的EC50为1.77μg/mL。结论蒲葵籽的醋酸乙酯提取物(P3)具有较强的体外抗HIV-1活性,其作用机制可能主要为阻断病毒进入和抑制HIV-1蛋白酶活性。     

点柄乳牛肝菌子实体中抗HIV-1活性成分

目的研究点柄乳牛肝菌的化学成分,并对分离鉴定的化合物进行抗HIV-1的活性研究。方法将野外采集的点柄乳牛肝菌子实体用溶剂提取,采用硅胶柱色谱进行分离,通过波谱技术(NMR,MS,IR等)对结构进行鉴定。结果分离鉴定了9个化合物,分别为:酒渣碱(Ⅰ)、5α,8α-过氧麦角甾-6,22-二烯-3β-醇(Ⅱ)、麦角甾-5,7,22-三烯-3β-醇(Ⅲ)、麦角甾-5,7,22-三烯-3β-O-β-D-吡喃葡萄糖苷(Ⅳ)、尿嘧啶(Ⅴ))、硫代乙酸酐(Ⅵ)、硬脂酸(Ⅶ)、3-吡啶甲酸(Ⅷ)和D-阿洛糖醇(Ⅸ)。结论化合物Ⅰ为首次从高等真菌中分离。经生物活性测试,该化合物具有抗HIV-1活性,对C8166细胞的毒性较小,CC50为87.86μg/mL,对HIV-1诱导C8166细胞形成合胞体抑制的EC50为7.27μg/mL,治疗指数(TI值)为12.09。     

Biological activity of Anthraquinones and Triterpenoids from Prismatomeris fragrans

A new 1,3-dihydroxy-2-methyl-5,6-dimethoxyanthraquinone (1); six known anthraquinones, nordamnacanthal (2), damnacanthal (3), rubiadin (4), rubiadin-1-methyl ether (5), lucidin-ω-methyl ether (6), and 1-hydroxy-2-hydroxymethyl-3-methoxyanthraquinone (7); a β-sitosterol (8); together with two known triterpenoids, β-acetylolean-12-en-28-olic acid (9), and 3β-O-acetyl-11,12-epoxyolean-28,13-olide (10) were isolated from the roots and stems of Prismatomeris fragrans. Their structures were established on the basis of spectral data. This is the first isolation of compounds 2, 6, 7, 9 and 10 from Prismatomeris genus. The isolated compounds were evaluated in antiplasmodial, antituberculosis, antifungal and anticancer cell lines tests. The bioactivity assays showed that only 9 exhibited moderate antimalarial activity, 2 and 3 exhibited antifungal activity while 2, 3, 4, 7 and 9 showed antituberculosis activity. In addition, compounds 2, 3 and 7 exhibited cytotoxicity to BC cell line while 1, 1a (the methyl ether derivative of 1), 2, 3, 4, 5, and 9 exhibited cytotoxicity to NCI-H187 cell line.     

Dihydrochalcones and flavonolignans from Iryanthera lancifolia

An extract from the pericarps of I. lancifolia afforded two dihydrochalcones (1 and 2) and two flavonolignans (3 and 4), with compounds 2-4 being of novel structure. The antioxidant activities of compounds 1-4 were evaluated through the measurement of malondialdehyde production, and Q(1/2) (concentration necessary for 50% inhibition of autoxidation) data were calculated. The Q(1/2) values obtained for 1-4 and the standard compounds alpha-tocopherol and quercetin were 6.9, 4.7, 5.5, 4.8, 12.1, and 7.6 microg/mL, respectively.     

Triterpenoids with rare carbon skeletons from Salvia hydrangea: antiprotozoal activity and absolute configurations

Salvadione C (1) and perovskone B (2), two new triterpenoids with rare carbon skeletons, were isolated from an antiplasmodial n-hexane extract of Salvia hydrangea. The absolute configuration was determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. In vitro activity against Plasmodium falciparum K1 strain, Trypanosoma brucei rhodesiense STIB 900 strain, and cytotoxicity in rat myoblast (L6) cells were determined. Compounds 1 and 2 showed in vitro antiplasmodial activity, with IC50 values of 1.43 and 0.18 μM and selectivity indices (SI) of 86.2 and 69.6, respectively. IC50 values against T. brucei rhodesiense were found to be 4.33 and 15.92 μM, respectively.     

Triterpenoids from Brazilian Ilex species and their in vitro antitrypanosomal activity

From the leaves of Ilex affinis and Ilex buxifolia, two adulterant species of "erva mate" (Ilex paraguariensis), three new triterpenoid glycosides were isolated. Affinoside 1 (3beta-O-[beta-D-glucopyranosyl-(1-->3)-[2-O-acetyl-(1-->2]]-alpha-L-arabinopyranosyl pomolic acid 28-O-beta-D-glucopyranosyl ester, 1) was isolated from I. affinis, while buxifolioside I (28-O-beta-D-glucopyranosyl ester of (20S)-3alpha,19alpha-dihydroxyurs-12-ene-23,28-dioic acid, 7) and buxifolioside II (28-O-beta-D-glucopyranosyl ester of (20S)-3beta,19alpha-dihydroxyurs-12-en-24,28-dioic acid, 8) were isolated from I. buxifolia. Along with these new compounds, ilexoside II (2), ursolic acid (3), 28-nor-ursolic acid (4), 3beta-O-acetylursolic acid (5), and uvaol (6) were also isolated. The observed results confirm the structural specificity of the I. paraguariensis triterpenoids and reinforce a previous proposal to detect mate adulteration by triterpenoid analysis. In addition, the in vitro antitrypanosomal activity of some Ilex triterpenoids is also reported.     

Triterpenoids from Rubia yunnanensis

Five new triterpenoids, rubiarbonones D (1), E (5), and F (2), and rubiarbosides F (3) and G (4), together with nine known compounds, were isolated from the roots of Rubia yunnanensis. The structures of 1-12 were elucidated by spectroscopic methods. The antiplatelet aggregation activities of rubiarbonone A (6) and rubiarbonol A (8) and B (9) were investigated with a standard protocol.     

桦叶荚蒾三萜成分的研究

目的研究桦叶荚蒾Viburnum betulifolium Batal.的三萜成分。方法采用硅胶、ODS、Sephadex LH-20柱,对桦叶荚蒾70%丙酮提取物的乙酸乙酯萃取部位进行分离纯化,通过波谱数据鉴定所得化合物的结构。结果从中分离得到15个化合物,分别鉴定为3β-hydroxy-11α,12α-epoxy-friedoolean-14-enyl palmitate(1)、1β-hydroxy-ursa-9(11),12(13)-dien-3β-yl palmitate(2)、11α,12α-环氧蒲公英赛醇(3)、β-乙酰香树脂醇乙酸酯(4)、齐墩果酸(5)、2α,3α-二羟基-12-烯-齐墩果酸(6)、2α-羟基齐墩果酸(7)、24-羟基-β-香树脂醇(8)、28-羟基-β-香树脂醇(9)、3β,23-dihydroxy-urs-12-ene(10)、坡模酸(11)、羽扇豆醇(12)、29-nor-20-oxolupeol(13)、白桦脂酸(14)、24-亚甲基环木菠萝烯酮(15)。结论化合物1~4、6~7为首次从荚蒾属植物中分离得到,化合物5为首次从该植物中分离得到。     

Triterpenoids from Tillandsia fasciculata

The leaves of Tillandsia fasciculata afforded four tetracyclic triterpenoids of the cycloartane type, two new compounds identified as cyclolaudenyl formate (2) and the (24S)-24-isopropenyl cycloartanone, which we named tillandsinone (1), and the known cyclolaudenone (3) and cyclolaudenol (4).     

络石藤中的三萜类化合物

目的对络石藤中的三萜类化合物进行分离鉴定。方法采用硅胶、反相硅胶、Sephadex LH-20等柱色谱方法进行分离,NM R等波谱学方法进行结构鉴定。结果从络石藤中分离鉴定8个三萜类化合物:络石苷F(tra-che losperos ide F,Ⅰ)、络石苷B-1(trache losperos ide B-1,Ⅱ)、络石苷D-1(trache losperos ide D-1,Ⅲ)、络石苷E-1(trache losperos ide E-1,Ⅳ)、3-βO-D-g lucopyranos ide qu inov ic ac id(Ⅴ)、3β-O--βD-g lucopyrano isde qu inov ic ac id27-O--βD-g lucopyranosy l ester(Ⅵ)、3β-O--βD-g lucopyranos ide c incho lic ac id 27-O--βD-g lucopyranosy l ester(Ⅶ)、络石苷元B(trache losperogen in B,Ⅷ)。结论Ⅰ为新化合物,其余均为首次从该植物中分离得到。     

合蕊五味子中两个新的三萜内酯及其在生物合成途径中的意义

目的：研究合蕊五味子（Schisdndrapropinqua var.propinqua）地上部分化学成分。方法：利用正反相硅胶、高效液相色谱等现代分离技术进行分离,利用IR,UV,MS和NMR等现代波谱技术手段鉴定了它们的结构。结果：分离得到两个分别具有3,4-seco—cycloartane和3,4：9,10-seco—cycloartane型骨架的新三萜内酯：propiniclactnnesA（1）和B（2）;同时分离得到了一个典型的cycloartane骨架三萜类化合物。结论：这两个新化合物在生源合成途径上具有重要意义,它们可能是连接cycloartane骨架三萜和schisandra降三萜骨架的重要中间体。     

土庄绣线菊五环三萜类化学成分

目的:研究土庄绣线菊乙醇提取物石油醚和氯仿分离部位的化学成分。方法:采用硅胶柱色谱和制备液相色谱等手段进行化学成分分离,运用理化性质和波谱数据(MS,1H-NMR,13C-NMR和HMBC等)鉴定化合物结构。结果:从土庄绣线菊乙醇提取物石油醚和氯仿分离部位分离得到6个五环三萜类化合物,分别鉴定为羽扇豆酮(1),木栓酮(2),羽扇豆醇(3),β-香树脂醇(4),白桦脂醇(5)和熊果醇(6)。结论:化合物1～5为首次从该属植物中分离得到,化合物6为首次从该植物中分离得到。     

扁枝石松中石杉型三萜成分研究

目的 对扁枝石松全草80 %乙醇提取物中的石杉型三萜类化学成分进行研究.方法 利用正相和反相硅胶柱色谱方法进行分离纯化,通过MS, 1H-NMR, 13C-NMR波谱数据鉴定化合物结构.结果 从扁枝石松共分离得到7个石杉型三萜类化合物,分别鉴定为serrat-14-en-3β, 21α-diol ①;serrat-14-en-3β, 21β-diol ②;3β-hydroxy-21α-acetoxy-14-serraten③;3β, 21β-dihydroxy-14-serraten-24-oic acid (lycernuic acid A, ④;14-serraten-3α, 21β, 24-triol (lycoclavanol, ⑤, 3α, 20β, 21β-trihydroxy-14-serraten- 24-oic acid ⑥;21-episerratenediol-3-α-L-arabinopyranoside (inundoside E, ⑦.结论 化合物7为首次从该属植物中分离得到,化合物3为首次从该植物中分到.