Steroids from Harrisonia abyssinica

In addition to the known sterols and ketosteroids beta-sitosterol (24 alpha-ethylcholest-5-en-3 beta-ol), stigmasterol (24 alpha-ethylcholesta-5,22-dien-3 beta-ol), campesterol (24 alpha-methylcholest-5-en-3 beta-ol), beta-sitostenone (stigmast-4-en-3-one, 24 alpha-ethylcholest-4-en-3-one), stigmastenone (stigmasta-4,22-dien-3-one, 24 alpha-ethylcholesta-4,22-dien-3-one), campestenone (24 alpha-methylcholest-4-en-3-one), and stigmasta-3,5-dien-7-one (24 alpha-ethylcholesta-3,5-dien-7-one), the new steroids stigmasta-3,5,22-trien-7-one (24 alpha-ethylcholesta-3,5,22-trien-7-one), and campesta-3,5-dien-7-one (24 alpha-methylcholesta-3,5-dien-7-one) were isolated from the stem bark of Harrisonia abyssinica and identified by NMR and mass spectrometry.     

6-hydroxy-4-en-3-one sterols from the marine sponge Iotrochoto birotulata

Five sterols with a nucleus skeleton of 6-hydroxy-4-en-3-one, namely cholesta-6beta-hydroxy-4-en-3-one (1), ergosta-6beta-hydroxy-4,24(28)-dien-3-one (2), ergosta-6alpha-hydroxy-4,24(28)-dien-3-one (3), ergosta-6alpha-hydroxy-4,22-E-dien-3-one (4), and ergosta-28-methyl-6beta-hydroxy-4,24(28)-dien-3-one (5) have been isolated from the marine sponge Iotrochoto birotulata, collected from the southern China sea. Sterols 2-4 are new compounds, and 1 has been isolated from marine organisms for the first time. The structures have been elucidated on the basis of extensive spectroscopic and chemical properties.     

Biological Activities of the Chemical Constituents of<Emphasis Type="Italic">Erythrina stricta</Emphasis> and<Emphasis Type="Italic">Erythrina subumbrans</Emphasis>

Phytochemical investigation of the hexane and CH2Cl2 extracts of Erythrina stricta roots and E. subumbrans stems led to the isolation of six pterocarpans, one flavanone, one isoflavone, two alkaloids, five triterpenes, six steroids and alkyl trans-ferulates. The structures of all known compounds were determined on the basis of spectroscopic evidence. Sophoradiol (15), a mixture of stigmast-4-en-3-one (19) and stigmasta-4,22-dien-3-one (20), lupeol (21), cycloeucalenol (22), a mixture of 3beta-hydroxystigmast-5-en-7-one (23) and 3beta-hydroxystigmast-5,22-dien-7-one (24) and melilotigenin C (25) were first isolated from the genus Erythrina. The isolated compounds were evaluated for antiplasmodial activity, antimycobacterial activity and cytotoxicity. Among the tested compounds, 5-hydroxysophoranone (8) exhibited the highest antiplasmodial activity against Plasmodium falciparum (IC50 2.5 microg/mL). Compound 8, erystagallin A (5), erycristagallin (7) and erysubin F (10) showed the same level of antimycobacterial activity against Mycobacterium tuberculosis (MIC 12.5 microg/mL). For cytotoxicity, erybraedin A (2) showed the highest activity against the NCI-H187 and BC cells (IC50 2.1 and 2.9 microg/mL, respectively), whereas 10 exhibited the highest activity against the KB cells (IC50 4.5 microg/mL).     

滇桂艾纳香化学成分的分离与鉴定（Ⅱ）

目的分离鉴定中药滇桂艾纳香的化学成分。方法利用硅胶柱色谱、Sephadex LH-20柱色谱等方法进行分离纯化,根据理化性质和波谱数据进行结构鉴定。结果分离得到10个化合物,分别鉴定为：环（亮-脯）二肽（1）（、24S）豆甾-4-烯-3-酮（2）（、24S）豆甾-4-22-二烯-3-酮（3）、二氢槲皮素-4′-甲醚（4）、丁香酸（5）、没食子酸（6）、香草酸（7）、呋喃甲酸（8）、水杨酸（9）、咖啡酸（10）。结论化合物1~10均为首次从该植物中分离得到。     

中国南海短指软珊瑚化学成分研究

目的研究短指软珊瑚Sinulariasp.的化学成分。方法利用硅胶色谱、Sephadex LH-20凝胶色谱、HPLC等手段对化学成分进行分离纯化;通过理化性质、波谱分析方法结合文献对照,鉴定化合物的结构。结果从短指软珊瑚甲醇提取物中,共分离鉴定了11个单体化合物:胆甾醇(1)、(22E)-麦角甾-5,22-二烯-3β-醇(2)、胆甾-5,20-二烯-3β-醇(3)、麦角甾-5,24(28)-二烯-3β-醇(4)、柳珊瑚甾醇(5)、3β-羟基胆甾-5-烯-7-酮(6)、3β-羟基麦角甾-5,24(28)-二烯-7-酮(7)、(22E)-3β-羟基麦角甾-5,22-二烯-7-酮(8)、3β-羟基麦角甾-5-烯-7-酮(9)、(22E)-3β-羟基胆甾-5,22-二烯-7-酮(10)、鲨肝醇(11)。结论化合物6～10为首次从该属软珊瑚中分离得到。化合物7在10μg.mL-1浓度水平,对K562肿瘤细胞株的抑制率为22.74%,对HeLa肿瘤细胞株的抑制率为9.98%。     

天女木兰叶中甾类化合物的分离与鉴定

目的对天女木兰叶的化学成分进行分离和结构鉴定。方法采用硅胶、凝胶柱色谱和重结晶等分离方法对天女木兰叶的体积分数为90%的乙醇溶液提取物进行成分分离;通过谱学分析方法结合化合物理化性质对分离得到的化合物进行结构鉴定。结果分离得到8个化合物,分别鉴定为豆甾-4-烯-3,6-二酮(stigmast-4-en-3,6-dione,1),豆甾-4-烯-3β,6β-二醇(stigmast-4-en-3β,6β-diol,2),5α,8α-过氧-(22E,24R)-麦角甾-6,22-二烯-3β-醇[5α,8α-epidioxy-(22E,24R)-ergosta-6,22-dien-3β-ol,3],豆甾-4-烯-6β-羟基-3-酮(stigmast-4-en-6β-ol-3-one,4),β-谷甾醇(β-sitosterol,5),(22E,24R)-麦角甾-7,22-二烯-3β,5α,6β-三醇[(22E,24R)-ergosta-7,22-dien-3β,5α,6β-triol,6],豆甾-5-烯-3β,7α-二醇(stigmast-5-en-3β,7α-diol,7),胡萝卜苷(daucosterol,8)。结论化合物2-4、6、7为首次从木兰属植物中分离得到,化合物1为首次从该植物中分离得到。     

Isolation, synthesis, and biological activity of five metabolites of danazol.

Metabolites of danazol (17 alpha-pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol), an orally effective pituitary gonadotropin inhibitory agent devoid of estrogenic and progestational activites, were isolated from urine of a female subject who had taken danzol orally at a dose of 800 mg/day for 7 days, The metabolites isolated were 17-hydroxy-17alpha-pregn-4-en-20-yn-3-one (11), 17-hydroxy-2alpha-(hydroxymethyl)-17alpha-pregn-4-3n-20-yn-3-one (5), 17-hydroxy-2-(hydroxymethyl)-17alpha-pregna-1,4-dien-20-yn-3-one(7), 6beta,17-dihydroxy-2alpha-(hydroxymethyl)-17alphapregn-4-en-20-yn-3-one(8), and 6beta, 17-dihydroxy-2(hydroxymethyl)-17alphapregna-1,4-dien-20yn-3-one(10). None of these metabolites exhibited pituitary inhibiting activity comparable to danazol.     

脚骨脆的化学成分研究

目的研究脚骨脆小枝和叶的化学成分。方法采用乙醇提取,提取物经萃取后以硅胶、凝胶和MCI等柱色谱法及高效液相色谱法进行分离纯化,采用波谱法进行结构鉴定。结果从该植物共分离得到8个化合物,其结构鉴定为:(6R,7E,9R)-9-hydroxymegastigm-4,7-dien-3-one,(6S,7E)-6-hydroxy-4,7-megastig-madiene-3,9-dione,(3S,5R,6S,7E)-5,6-epoxy-3-hydroxymegastigm-7-en-9-one,(6E,9S)-9-hydroxymegastigm-4,6-dien-3-one,caseamembrin A,casearlucin B,β-谷甾醇和胡萝卜苷。结论前6种化合物为首次从该植物中分离得到。     

New monoterpenes from Mentha microphylla

Four new monoterpenes, (1 R*,2 S*)-1,2-dihydroxy- p-menth-4(8)-en-3-one ( 1), (4 S*)-4-hydroxy- p-mentha-1,8-dien-3-one ( 2), (4 S*)-4-methoxy- p-mentha-1,8-dien-3-one ( 3), and (3 R*,4 R*,6 S*)-3-acetoxy-6-hydroxy- p-mentha-1,8-diene ( 4) together with four known compounds have been isolated from the aerial parts of Mentha microphylla. The structures were determined using spectroscopic methods particularly high resolution (1)H-, (13)C-NMR as well as 2D (1)H- (1)H COSY, HMQC and HMBC analysis.     

Steroids and polyketides from Uvaria hamiltonii stem bark

Two known steroids, stigmasterol and 6b-hydroxystigmasta-4,22-dien-3-one (1) and two unusual polyketides, cis-4-hydroxymellein (2) and trans-4-hydroxymellein (3) were isolated from the stem bark of Uvaria hamiltonii. The structures of the compounds were elucidated independently by high-resolution 2D-NMR techniques and confirmed by comparison with previously reported values.     

Alkyl phloroglucinol derivatives from Syzygium levinei and their differentiation-inducing activity

Eleven compounds have been identified from the whole plants of Syzygium levinei (Myrtaceae) on the basis of spectroscopic analysis and chemical methods. Among these compounds, (Z)-1-(2,6-dihydroxy-4-methoxyphenyl)-oct-5-en-1-one (1), (3 E,7 Z)-1-(2,6-dihydroxy-4-methoxyphenyl)-deca-3,7-dien-1-one (2), and 1-(2-O-beta-D-glucopyranosyl-5,6-dihydroxy-4-methoxyphenyl)-octan-1-one (3) were characterized as new alkyl phloroglucinol derivatives, and 1-(2,6-dihydroxy-4-methoxyphenyl)-hexan-1-one (4) was identified as a new natural product. Compounds 1, 2, and 4 were found to inhibit the proliferation of leukemia K562 and HL-60 cells and also to induce the differentiation of K562 cells as determined by the appearance of matured morphology and the increase in the intracellular hemoglobin level.     

New eremophilane-type sesquiterpenes from Ligularia hodgsonii

Four new eremophilanlides (1- 4) together with a known sesquiterpene were isolated from the roots and rhizomes of Ligularia hodgsonii. The structures of these new compounds were established as 6beta-(2'-methylbutanoyloxy)-10beta-acetoxy-3 beta, 8beta-dihydroxyeremophil-7(11)-en-8,12-olide (1), 6beta,10 beta-dihydroxyeremophil-7(11)-en-8alpha,12-olide (2), 3beta-acetoxy-6,9-dien-8-oxoeremophil-12-nor-11-ketone (3), and 3beta-acetoxy-6alpha, 8alpha-dihydroxyeremophil-7(11), 9-dien-8,12-olide (4) by means of mass, IR and NMR spectroscopy.     

Antimicrobial constituents from fruits ofAilanthus altissima SWINGLE

A new naturally occurring sterol, compound 5, and six known stigmasterols were isolated from fruits of Ailanthus altissima Swingle by repeated column chromatography and RP-HPLC. Their structures were identified as, 5alpha-stigmastane-3,6-dione (1), 3beta-hydroxystigmast-5-en-7-one (2), stigmast-5-ene-3beta, 7alpha-diol (3), 6alpha-hydroxystigmast-4-en-3-one (4), 5alpha-stigmastane-3beta, 6beta-diol (5), stigmast-4-ene-3beta, 6alpha-diol (6), stigmast-5-ene-3beta, 7alpha, 20xi-triol (7) by spectral analysis and comparison with the published data. These compounds have not been reported from genus Ailanthus, whereas compound 7 was identified by NMR for the first time. In addition, the 95% ethanol extract and compounds from the fruits of Ailanthus altissima SWINGLE were assayed for in vitro antimicrobial activity. The extract was potent active against the assayed bacteria while compounds 3 and 7 exhibited moderate activity.     

A new bisabolane sesquiterpenoid from Euphorbia chrysocoma

The new sesquiterpenoid (6R)-2-chloro-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (1), together with ten known compounds, (6R)-6-[(1S)-1,5-dimethylhex-4-en-1-yl]-3-methylcyclohex-2-en-1-one (2), bauerenol acetate (3), lupenone (4), alpha-amyrenone (5), beta-sitosterol (6), stigmasterol (7), beta-amyrin (8), ursolic acid (9), betulinic acid (10), scopolin (11), have been isolated from the roots of Euphorbia chrysocoma Lévl. et Vant. Their structures have been elucidated by spectroscopic data.     

Non-taxane compounds from the bark of Taxus yunnanensis

From the bark of Taxus yunnanensis, 15 non-taxane compounds were isolated. Through spectroscopic methods such as ID and 2D NMR and MS experiments, one of them was determined as a new abietane-type diterpenoid named taxayunnin (1). The other 14 known compounds were identified as taxamairin C (2), taxamairin A (3), 3beta-hydroxy-sandaracopimaric acid (4), (+)-3-hydroxy-isodrimenin (5), rubrosterone (6), ponasterone A (7), ecdysterone (8), 20-hydroxy-echysone-20,22-monoacetonide (9), 7-oxositosterol (10), stigmast-4-en-6beta-ol-3-one (11), 5alpha,6beta-dihydroxy-daucosterol (12), beta-sitosterol (13), daucosterol (14), 1-O-beta-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-N-(2'-hydroxypalmitoy])-octadeca-sphinga-4,8-dienine (15), respectively. Compounds 4-6, 9-12 and 15 were isolated from Taxus plants for the first time.     

New compounds from Commiphora myrrha (Nees) Engl

Phytochemical investigation of Commiphora myrrha (Nees) Engl. has afforded six new compounds identified as cadina-3-en-15-ol (myrracadinol A) (1), 7, 8-seco-2, 5-dihydroxy-12-acetoxycalam-8-ene (myrracalamene A) (2), 7, 8-seco-2, 3, 5-hydroxy-12-acetoxycalame-8-ene (myrracalamene B) (3), 7, 8-seco-cadin-3, 8-dien-2beta, 12-diol (myrracadinol B) (4), 7, 8-seco-12-hydroxycalam-8-ene (myrracalamene C) (6), 7, 8-seco-cadin-3,7(12)-dien-5alpha,10alpha-diol (myrracadinol C) (7) along with a known compound tria-cont-1-ene (5). Their structures were elucidated on the basis of spectral and chemical analyses.     

中国南海海绵Spheciospongia sp.中的甾体化合物

目的研究中国南海海绵Spheciospongia sp.的化学成分。方法采用多种色谱方法分离纯化,依据理化性质、波谱数据和文献对照的方法鉴定结构。结果从中国南海海绵Spheciospongia sp.石油醚提取物中分离鉴定了6个甾体类化合物:胆甾醇(cholesterol,1),胆甾-4-稀-3-酮(cho-lest-4-en-3-one,2),胆甾-3,6-二酮(cholest-3,6-dione,3),3β-羟基-胆甾-5-稀-7-酮(3β-hydroxy-cholest-5-en-7-one,4),6β-羟基-胆甾-4-稀-3-酮(6β-hydroxy-cholest-4-en-3-one,5),胆甾-3β,5α,6β-三醇(cholest-3β,5α,6β-triol,6)。结论化合物2-6为首次从该属海绵中分离得到。     

New lignans and cytotoxic constituents from Wikstroemia lanceolata

Two new lignans, (-)-aptosimon ( 1) and (-)-diasesamin-di-gamma-lactone ( 2), together with twenty-two known compounds, have been isolated from the stems and roots of Wikstroemia lanceolata. The structures of the new compounds were determined through spectral analyses. The proton and carbon assignments of the known sesquiterpenoid, 1alpha,7alpha,10alpha H-guaia-4,11-dien-3-one ( 24) were revised by 2D NMR techniques. Among the isolates, three compounds, (+)-hinokinin ( 6), 2,6-dimethoxy- p-benzoquinone ( 17), and 1alpha,7alpha,10alpha H-guaia-4,11-dien-3-one ( 24) exhibited effective cytotoxicities (ED50 values < 4.0 microg mL-1) against P-388 and HT-29 tumor cell lines.     

一株软珊瑚共附生真菌Aspergillus versicolor(ZJ-2008015)的次级代谢产物及其生物活性研究

目的对一株软珊瑚共附生真菌进行次级代谢产物及生物活性研究。方法采用活性追踪分离的方法,利用硅胶柱层析、Sephadex LH-20凝胶柱层析和半制备HPLC等方法,对采自广西涠洲岛的肉芝软珊瑚Sarcophytonsp.中分离获得的杂色曲霉Aspergillus versicolor(ZJ-2008015)的发酵产物进行分离和纯化,利用NMR、MS等波谱方法,并与文献对照,确定化合物的结构;利用卤虫致死活性模型和抗菌活性模型评价化合物的生物活性。结果从该菌发酵液的乙酸乙酯提取物中分离鉴定了6个单体化合物,分别为:(+)-sydonic acid(1),expansol G(2),(+)-sydowic acid(3),cyclo(L-Trp-L-Phe)(4),homodimeric WIN 64821(5)和ergosta-6α-hydroxy-4,22-dien-3-one(6)。结论抗菌活性测试结果表明,没药烷型倍半萜类化合物1～3对白色葡萄球菌Staphylococcus albus和金黄色葡萄球菌Staphylococcus aureus显示较强的抗菌活性。     

A new cytotoxic amide from the stem wood of Hibiscus tiliaceus

A new coumarin, hibiscusin, and a new amide, hibiscusamide, together with eleven known compounds including vanillic acid, P-hydroxybenzoic acid, syringic acid, P-hydroxybenzaldehyde, scopoletin, N- trans-feruloyltyramine, N-cis-feruloyltyramine, a mixture of beta-sitosterol and stigmasterol, a mixture of beta-sitostenone and stigmasta-4,22-dien-3-one were isolated from the stem wood of Hibiscus tiliaceus. The structures of these new compounds were determined through spectral analyses. Among the isolates, three compounds exhibited cytotoxicity (IC (50) values < 4 microg/mL) against P-388 and/or HT-29 cell lines in vitro.