骆驼蒿的化学成分

目的：对骆驼蒿（Peganum nigellastrumBge.）地上部分进行化学成分的研究。方法：运用萃取、结晶及各种层析方法进行分离纯化,并通过理化鉴别和波谱分析鉴定化合物结构。结果：从骆驼蒿中分离鉴定了6个化合物,分别为：O-amino-N-formylbenzyamine（1）,butyl 1H-imidazole-4-carboxylate（2）,liriodendrin（3）,trans-Ferulic acidβ-D-glucopy-ranoside（4）,（6S,7E,9R）-6,9-dihydroxymegastigma-4,7-dien-3-one-9-O-β-D-glucopy-ranoside（orroseoside）（5）,（3S,5R,6R,7E,9S）-megastigman-7-ene-3,5,6,9-tetrol-3-O-β-D-glucopyranoside（6）。结论：化合物1,2为首次从自然界分离得到,化合物3-6首次从骆驼蓬属中分得。     

维吾尔药大戟脂中2个新的三萜

目的 研究大戟脂(多脂大戟Euphorbia resinifera的树脂状分泌物)的化学成分.方法 采用反相C18、硅胶、凝胶柱色谱、制备型HPLC等方法进行分离纯化,通过红外、紫外、高分辨质谱、一维和二维的核磁数据和结合参考文献鉴定化合物的结构.结果 从大戟脂甲醇提取物中分离得到了2个化合物,分别鉴定为大戟烷-8-烯...     

Four new triterpenoids from Maytenus ilicifolia

Four new triterpenoids with various skeletons, maytefolins A-C (1-3) and uvaol-3-caffeate (4), were isolated from the leaves of a Brazilian medicinal plant, Maytenus ilicifolia, together with five known triterpenoids. Of these triterpenoids only erythrodiol exhibited significant cytotoxicity against KB/S, KB/VJ300, and KU 19-20 cells.     

反柄紫芝中2个新三萜类化合物

目的研究反柄紫芝Ganoderma cochlear子实体的化学成分。方法利用硅胶和凝胶柱色谱及半制备HPLC进行分离纯化,采用多种谱学技术(1D、2D NMR)并根据理化常数鉴定结构。结果分离并鉴定了5个化合物,分别为拱状灵芝素G(1)、拱状灵芝素H(2)、麦角甾醇(3)、5α,8α-环二氧-6,22-麦角甾二烯-3β-醇(4)和(22E,24R)-7,22-麦角甾二烯-3β-醇(5)。结论化合物1和2为新化合物,其余化合物均为首次从灵芝属真菌中分离得到。     

A new prenylated isoflavone and triterpenoids from Erythrina eriotriocha

In addition to known triterpenoids maniladiol [6] and serrat-14-ene-3 beta,21 alpha-diol [7], two new compounds, one oleanane derivative designated as 28-acetoxyerythrodiol [1] and one isoflavone designated as 5,4'-dimethoxy-3'-prenylbiochanin A [5], have been isolated and characterized from the CHCl3 extract of the stem bark of Erythrina eriotriocha. Their structures have been established on the basis of the spectrocopic techniques (ir, nmr, uv, ms) and chemical evidence.     

Two new triterpenoids from Azadirachta indica and their insecticidal activity

Two new triterpenoids, 22,23-dihydronimocinol (1) and desfurano-6alpha-hydroxyazadiradione (2), were isolated from a methanolic extract of the fresh leaves of Azadirachta indica (neem) along with a known meliacin, 7alpha-senecioyl-(7-deacetyl)-23-O-methylnimocinolide. The structures of 1 and 2 were elucidated through spectral and chemical studies. Compounds 1 and 2 showed mortality for fourth instar larvae of the mosquito (Anopheles stephensi), with LC(50) values of 60 and 43 ppm, respectively.     

Four new trisnorlanostene-type triterpenoids from the stem bark of Pinus luchuensis

Four new 25,26,27-trisnorlanostene-type triterpenoids were isolated from the stem bark of Pinus luchuensis, together with five known compounds. These new compounds were characterized as 25,26, 27-trisnor-3 alpha-hydroxy-lanost-9(11)-en-24-oic acid (1), 25,26, 27-trisnor-3 alpha-methoxy-lanost-9(11)-en-24-oic acid (2), 25,26, 27-trisnor-3 beta-methoxy-lanost-9(11)-en-24-oic acid (3), and 25,26, 27-trisnor-3-oxo-lanost-9(11)-en-24-oic acid (4) on the basis of MS and NMR evidence.     

江南山梗菜中1个新的三萜类化合物及其生物活性研究

目的 对江南山梗菜Lobelia davidii中的三萜类成分及其生物活性进行研究。方法 采用硅胶柱色谱、Sephadex LH-20及HPLC等色谱技术进行分离纯化,运用NMR、MS等波谱技术进行化合物的结构鉴定。采用四甲基偶氮唑盐[3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl tetrazolium bromide,MTT]法筛选分离得到化合物对人非小细胞肺癌A549细胞的细胞毒性;采用4-硝基苯基-α-D-吡喃葡萄糖苷(4-nitrophenyl-α-D-glucopyranoside,PNPG)法测定分离得到化合物对α-葡萄糖苷酶的抑制活性。结果 从江南山梗菜的醋酸乙酯部位中分离得到6个三萜类化合物,分别鉴定为3β-正十六酸酯-齐墩果烷-12-烯-11-酮(1)、熊果酸(2)、齐墩果酸(3)、sumaresinolic acid(4)、3β-羟基-齐墩果烷-12-烯-11-酮(5)、32,33,34-三甲基-细菌藿烷-16-烯-3-O-β-D-吡喃葡萄糖苷(6)。细胞毒活性筛选结果表明,化合物1和5对A549细胞增殖有显著的抑制活性,其半数...     

Tyromycic acids B-E, new lanostane triterpenoids from the mushroom Tyromyces fissilis

Four new triterpenoids, tyromycic acids B-E (1-4), were isolated from a methanol-soluble extract of the fruit bodies of the Japanese inedible mushroom Tyromyces fissilis. Tyromycic acids B-D possess a lanostane skeleton, while tyromycic acid E is based on a rare 14(13-->12)abeo-lanostane skeleton. Their structures were determined by spectral data analysis and by single-crystal X-ray crystallography.     

Bioactive triterpenoids from Salvia species

Salvia species are important medicinal and culinary plants, and they have been the subject of numerous chemical and biological studies. The bioactive triterpenoids of Salvia species, reported in the literature to date, are reviewed. About 200 triterpenoids, almost 80 of which are new, isolated, and characterized from about 100 Salvia species, are presented herein. In addition to the diverse biological activities of the pure triterpenoids, studies on biological activity of extracts of Salvia species are also described.     

Serratene-type triterpenoids from Huperzia serrata

Seven new and 15 known serratene-type triterpenoids were isolated from the whole plant of Huperzia serrata. The structures of these new triterpenoids were elucidated as 21alpha-hydroxyserrat-14-en-3beta-yl p-dihydrocoumarate (1), 21alpha-hydroxyserrat-14-en-3beta-yl dihydrocaffeate (2), 21alpha-hydroxyserrat-14-en-3beta-yl propanedioic acid monoester (3), 3alpha,21alpha-dihydroxyserrat-14-en-24-oic acid (4), 16-oxo-3alpha,21beta-dihydroxyserrat-14-en-24-al (5), 16-oxo-3alpha,21beta-dihydroxyserrat-14-en-24-oic acid (6), and 16-oxo-21beta-hydroxyserrat-14-en-3alpha-yl acetate (7), respectively, by means of spectroscopic analysis.     

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.     

Antiplasmodial triterpenoids from Ekebergia capensis

From the stem bark of Ekebergia capensis, 10 new triterpenoid compounds, ekeberins A (1), B (2), C1 (3), C2 (4), C3 (5), D1 (6), D2 (7), D3 (8), D4 (9), and D5 (10), were isolated together with 17 known compounds. The structures of these new compounds were elucidated on the basis of the results of spectroscopic analysis, and the absolute configuration of compounds 6-10 were determined by partial synthesis from known compounds and using the Mosher ester method. Several of these compounds were screened in vitro against both chloroquine (CQ)-sensitive and -resistant Plasmodium falciparum isolates and were found to exhibit moderate antiplasmodial activity, with compounds 20 (7-deacetoxy-7-oxogedunin) and 27 (2-hydroxymethyl-2,3,22,23-tetrahydroxy-2,6,10,15,19,23-hexamethyl-6,10,14,18-tetracosatetraene) showing IC50 values of 6 and 7 microM, respectively. Compound 27 at a dose of 500 mg/kg showed moderate parasitemia suppression of 52.9% against P. berghei NK 65 in a mouse model.     

Cucurbitane triterpenoids from Leucopaxillus gentianeus

In addition to the known bioactive triterpene cucurbitacin B (1), two new cucurbitane triterpenoids, namely, leucopaxillones A (3) and B (4), exhibiting a new oxygenation pattern among cucurbitacins, have been isolated from the mushroom Leucopaxillus gentianeus (syn. L. amarus). Cucurbitacin B (1) imparts a bitter taste to the flesh of the fungus; however, it occurs in the fruiting bodies mainly esterified as tasteless fatty acid esters 2a-c. In vitro growth inhibitory effects of compounds 1-4 on proliferation of four different human tumor cell lines (A549, CAKI-1, HepG2, MCF-7) were evaluated by using a 1-day MTT assay. Only cucurbitacin B was highly active on all lines. Free cucurbitacin B is presumed to be formed in vivo by an enzyme-mediated scission of esters 2a-c, thus constituting a chemical weapon that protects the mushrooms against parasites and predators. Compounds 1-4 are structurally different from the other few cucurbitacins isolated from Basidiomycetes, being, instead, more similar to those occurring in plants. In particular, cucurbitacin B (1) seems to represent an interesting example of secondary metabolite convergence between distant taxa such as fungi and vascular plants, where they likely exert a similar role of protection. The structures of the compounds were established by means of spectroscopic methods and X-ray diffraction on a single crystal. The absolute configuration of leucopaxillone A has been assigned on the basis of CD chirality rules.     

Cytotoxic triterpenoids from Maytenus retusa

Seven new triterpenoids (1-7) and 36 known compounds were isolated from the root bark of Maytenus retusa. Their structures were determined by 1D and 2D spectroscopic studies. Several compounds were evaluated for their cytotoxicity against the human tumor cell lines HL-60 and MCF-7. Some of them were cytotoxic, with IC(50) values ranging between 0.2 and 4.7 μM.     

Tirucallane-type triterpenoids from Dysoxylum lenticellatum

Ten new tirucallane-type triterpenoids, represented by a rearranged skeleton dysolenticin A (1), dysolenticin B (2), a rare trinortriterpenoid dysolenticin C (3), three tirucallane triterpenoid derivatives with a hemiketal moiety dysolenticins D-F (4-6), dysolenticins G-I (7, 9, 10), and the new alkaloid dysolenticin J (12), together with seven known analogues were isolated from the twigs and leaves of Dysoxylum lenticellatum. Their structures were elucidated by extensive spectroscopic methods, and those of compounds 1, 3, 4, 6, and 10 were confirmed by single-crystal X-ray diffraction experiments. Dysolenticin J (12) showed significant vasodilative effects on intact rat aortic rings with a diastolic degree of 87.4% at 10 μg/mL.     

Cycloartane triterpenoids from Astragalus bicuspis

Three new cycloartane glycosides have been isolated from Astragalus bicuspis. They were identified as 6alpha-hydroxy-3-O-beta-xylopyranosyloxy-24,25,26,27-tetranor-9,19-cyclolanosta-16,23-lactone (1), 6alpha-hydroxy-23-methoxy-16beta,23(R)-epoxy-24,25,26,27-tetranor-9,19-cyclolanosta-3-O-beta-xyloside (2), and 23(R),24(S),25(R),26(S)-16beta/23,23/26,24/25-triepoxy-6alpha,26-dihydroxy-9,19-cyclolanosta-3-O-beta-xyloside (3), on the basis of their spectroscopic data. Two known cycloartane derivatives, 4 and 5, were also obtained from this plant. Compounds 2-5 were tested for leishmanicidal activity against Leishmania major promastigotes and for cytotoxicity against 3T3 cancer cells.     

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.     

Antimicrobial triterpenoids from Vladimiria muliensis

A new triterpenoid with a rearranged ursane skeleton, 3beta-acetoxyl-11alpha-methoxybauer-8-en-7alpha-ol ( 1), two new ursane triterpenoids, 1alpha,5alpha-dioxy-11alpha-hydroxyurs-12-en-3-one ( 2) and urs-3beta,13alpha,18beta-triol ( 3), together with three known ursane triterpenoids ( 4- 6) were isolated from the rhizome of Vladimiria muliensis. Their structures were elucidated on the basis of spectroscopic methods (IR, EIMS, HRESIMS, 1D and 2D NMR, and X-ray crystallography diffraction). Compounds 2 and 4 exhibited modest antimicrobial activity against Escherichia coli, Candida albicans, Pseudomonas aeruginosa, Enterococcus faecalis, Bacillus cereus, and Staphylococcus aureus.     

Lupane triterpenoids from Maytenus species

Five new lupane triterpenes (1-5), in addition to 24 known ones, were isolated from Maytenus cuzcoina and M. chiapensis. Their structures were elucidated on the basis of spectroscopic analysis, including homonuclear and heteronuclear correlation NMR (COSY, ROESY, HSQC, and HMBC) experiments. The compounds were assayed for antimicrobial and cytotoxic activities, with 3-epi-betulinic acid and 28,30-dihydroxy-3-oxolup-20(29)-ene showing moderate cytotoxicity.