三种芸香料植物化学成分研究
其他题名Chemical Constituents of Three Rueaceae Plants
汪俊松
学位类型博士
导师郝小江
2005
学位授予单位中国科学院昆明植物研究所
学位授予地点中国科学院昆明植物研究所
学位专业植物学
关键词化学成分 华南吴茱萸 海南山小桔 五叶山小桔
摘要本论文对三种芸香科植物,吴茱英属华南吴茱英(Evodio austrosinensis),山小桔海南LlJ小桔(Glycosmis montana)和五叶山小桔(Glycosmis pentaphylla)的化学成分进行了系统研究,对部分成分进行了活性研究。应用多种分离材料和分离技术,结合现代波谱技术,从以上三种植物中共分离鉴定了106个化合物,其中新化合物26个。化合物类型涉及菇类、苯丙素、木脂素、黄酮、香豆素、含硫酰胺、咔唑、呋喃喹诺啉、喹诺酮等各种生物碱。第一章为华南吴茱英(Evodia austrosinensis)的化学成分及部分化合物的抗耐药菌及脑保护活性。从其枝叶提取物的正丁醇萃取部位分离鉴定了19个化合物,其中有2个降倍半菇普(1,2)是新化合物。化合物1对青霉素耐药金黄葡萄球菌有抑菌作用;化合物l,5,17和18显示出能提高HZOZ损伤的PC12 细胞的相对存活率。第二章为海南山小桔(Giycosnismonlana)的化学成分及部分生物碱的抗HIV和细胞毒活性。从其枝叶提取物的氯仿、乙酸乙酷萃取部位共分离鉴定了60个化合物,其中有10个是新化合物:化合物1为新的双异戊烯基叫噪生物碱;化合物12为新的quinololle类生物碱,化合物n可能是这类生物碱在植物体内的储备物质;化合物14为protoberberine类生物碱的季胺盐,是一新天然产物:化合物16,17为新奇的黄烷醇含硫酰胺分别命名为glymontaninesA和B,是自然界中唯一的天然黄酮类含硫酞胺化合物,GlymontanineA被“Natural ProduCtsSport[2005,22(l),l2]列为热点化合物;化合物18,19为新的通过亚甲基聚合的黄烷醇二聚体,分别命名为montahomobisflavansA和B,这种聚合方式较罕见;化合物29为新的吠喃香豆素:化合物49为新的简单酚普。化合物1-5对人白血病CC盯-CEM细胞株有一定的细胞毒作用,三个异戊烯基取代的生物碱(1-3)有抗HIV活性,其中新吲哚生物碱1具有最好的活性,这也是第一次这种类型生物碱的抗爱滋病活性报导。第三章为五叶山小桔(Glycosmis pentaPhylla)的化学成分研究,从其茎干醇提物的乙酸乙酷萃取部位中共分离鉴定了27个化合物,其中14个为新化合物,化合物4-10为新的异黄酮双糖营,化合物15和17为新的木脂素,化合物19-21为新的芹糖酚昔,化合物22为吡咯甲酸的醋昔,化合物23为新的倍半砧双糖营。化合物4-10,19-21及23均含芹糖,这是首次从山小桔属(Glycosmis)植物中大量发现含芹糖的化合物。第四章综述了芸香科山小桔属(Glycosmsis)植物化学成分研究概况。总结了从1977-2004年有关该属的研究成果。参考文献67篇,列出了在此期间发表的192个化合物。
其他摘要This thesis elaborated the studies on the chemical constituents of three Rutaceous plants (Evodia austrosinensis, Glycosmis montana and Glycosmis pentaphylla) and bioassay on some compounds isolated. By variety of cliromatographies over various materials, one hundred and six compounds, including twenty-six new ones were isolated, which covered terpenoids, phenylpropanoids, lignans, flavonoids, coumarins, sulfur-containing amides, various alkaloids (carbazole, furoquinoline, quinolone etc.). Their structures were elucidated major on the basis of spectroscopic studies. Chapter 1 Study on Chemical Constituents of Evodia austrosinensis Nineteen compounds including two new norsesquiterpenoid glucosides were isolated and elucidated from the n-butanol part of the twigs and leaves of Evodia austrosinensis. Compound 1 showed inhibitory activity against the penicillin resistant strain Staphylococcus aureus (CMEC 26003). Compounds 1, 5, 17 and 18 can enhance the survival rate of PC 12 cells damaged by H2O2. Chapter 2 Phytochemical Study on Glycosmis montana The chemical constituents of the twigs and leaves of Glycosmis montana are described for the first time. This investigation has resulted in the isolation of sixty compounds including ten new ones. Compund 1 is a new diprenylated indole alkaloid. Compound 12 is a new quinolone alkaloid and 11 maybe storage of this type of alkaloids in plant tissue. Glymontanines A (16) and B (17) are the first examples of flavonoids with sulfur-containing amide moiety in nature. Glymontanine A was selected as compound "Hot off the Press" by the journal "Natural Products Report" [2005, 22(1), 12]. Montahomobisflavans A (18) and B (19) are two new dimeric flavanols in which two units are linked through a methylene bridge at the 8,8'- and 8,6'-positions. This linkage is rarely encountered in dimeric flavanols. Other new compounds include a new protoberberine alkaloid (14), a furocoumarin (29) and a phenolic glucoside (49). Alkaloids 1-5 exhibited cytotoxic activity against the human leukaemia cell line CCRF-CEM. Three prenylated alkaloids 1-3 demonstrated anti-HIV activity. Among them, the new diprenylated indole alkaloid 1 exhibited the most potent anti-HIV activity with an IC50 value of 1.17 ug/ml and SI (Selective Index) value of 11.68. This is the first report of anti-HIV activity of this type of indole alkaloid. Chapter 3 Investigation on Chemical Constituents of Glycosmis pentaphylla In this work, fourteen new compounds including seven new isoflavone glycosides (4-10), two new lignans (15 and 17), three new phenolic glycosides (19-21), one glucopyranosyl pyrrole carboxylate (22), one new sesquiterpenoid ester (23) were isolated from the stem of Glycosmis pentaphylla. The most interesting part of this investigation is the discovery of isoflavone glycosides and other glycosides containing apiose in the species. This is the first report of such compounds in the genus Glycosmis. Chapter 4 Review Compounds isolated from the genus Glycosmis from 1977 to 2004 are reviewed.
页数129
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/774
专题昆明植物所硕博研究生毕业学位论文
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汪俊松. 三种芸香料植物化学成分研究[D]. 中国科学院昆明植物研究所. 中国科学院昆明植物研究所,2005.
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