六种楝科植物及广玉兰化学成分研究
罗晓东
学位类型博士
导师吴大刚
1999
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
关键词楝科 广玉兰 化学成分 植物化学
摘要楝科(Meliaceae)约有50个属,1400种,广布于热带,少数分布于亚热带,极少分布至温带。我国有15属约60种,大部分分布在华南和西南,少数属分布到长江以北,秦岭以北仅有香椿1种。云南有13属42种及10变种,主产南部和东南部。本科许多种类木材优良,有的种类入药,有些种类的花芳香,为熏茶香料。川楝(Melia toosendan)和苦楝(Melia azedarach)我国在民间广泛用于驱蛔、防蛀、杀虫。楝科富含三萜及四降三萜,其中四降三萜类化合物被府为是其中杀虫活性物质。一. 印楝(Azadirachta indica A. Juss)广泛分布或引种栽种于亚洲、非洲、美洲、澳大利亚及南矿平洋岛屿的热带及亚热带地区。在过去二十年中,随着印楝素结构的确定及其对昆虫生理的影响的认识,对印楝化学成分及生物活性的研究引起了人们广泛的兴趣。从印楝的各部位分离鉴定了100余个化合物,并且报道了印楝对昆虫的拒食、驱避、毒杀、生长发育调节、抑制生育等活性。此外,印楝作为医药用途的药理活性也有许多报道,其间召开了四次国际印楝学术大会,综述和专著也屡屡出版。八十年代中期,赵善欢先生等开始研究印楝对昆虫的影响,在广东,海南作过区域性引种载培。但国内缺乏对印楝化学成分的研究,为国内进一步开发利用印楝打下基础,本章对缅甸产的印楝种仁的化学成分进行研究,从甲醇提取物分离鉴定了十七个化合物(见Compounds from Azadirachta indica),包括十三个四降三萜,其中化合物2、3、13、16为新化合物。此外,还实现了从azadirachtin向azadirachtinin骨架的直接转化,并对重排机理作了初步探讨。二. 大蒜果树(Dysoxylum hainanense Merr.)为(左木右坚)木属植物,该属包括140种植物,分布于东南亚和澳大利亚,云南有10个种。文献报道该属含有三萜、三萜皂甙、四降三萜、二萜、甾体、生物碱等化合物。大蒜果树分布于广西、海南、云南西双版纳。其化学成分未见报道,本章报告从西双版纳采集的大蒜果树树皮的化学成分,从乙醇提取物分离鉴定了三十四个化合物(见Compounds from Dysoxylum hainanense),包括十个四降三萜,十二个三萜及四个二萜化合物,其中有二十一个鉴定为新化合物。三. 云南割舌树(Walsura yunnanensis C. Y. Wu.)为割舌树属植物,该属约30-40种,分布于我国、印度、中南半岛至印度尼西亚。我国有5种,产华南和西南。云南有四种。云南割舌树产于西双版纳海拔950-1000米左右的山谷或斜坡疏林内。其化学成分未见报道。本章对云南割舌树树皮的化学成分进行研究,从乙醇提取物分离鉴定了二十一个化合物(见Compounds from Walsura yunnanensis),包括九个四降三萜,五个甾醇。其中十一个化合物鉴定为新化合物。四. 香椿(Cedrela sinensis A. Juss.)为椿属植物。全国各地均有栽植,文献报道椿叶含胡萝卜素、维生素、黄酮及酚性化合物,幼叶可食用。椿叶民间用于消炎、解毒、杀虫、治肠炎、痢疾、皮肤搔痒。树皮含川楝素、甾醇及鞣质,民间用于除热、燥湿、止血、杀虫。香椿叶的甲醇提取物经德国Bayor公司测定具有NGF和NefHCK的生物活性。本章报告香椿叶中化学成分。从中分离鉴定了十四个化学成分(见Compunds from Cedrela sinensis),包括四个四降三萜,五个酚性化合物,及三个植物醇类化合物4、11、12、13为新化合物。五. 浆果楝(Cipadessa baccifera (Roth) Miq.)为浆果楝属植物,该属4-5种,2-3种分布于印度、马来半岛,2种产马达加斯加和科摩罗群岛。我国有2种,广西南部、云南都有。浆果楝生长于海拔500-1600米的常绿阔叶林、铁刀木林、灌丛中。分布于印度、斯里兰卡、泰国、越南到印尼及菲律宾,根或树皮民间用于治疟疾、感冒、腹泻、痢疾、皮肤搔痒、外伤出血。前人从该植物中分离得到黄酮、黄酮甙及二萜化合物,但没有四降三萜化合物的报道。本章介绍了从浆果楝的干浆果中分离鉴定的十三个化合物(见Compounds from Cipadessa baccifera),包括三个四降三萜,三个倍半萜,四个甾醇及二个脂肪醇衍生物。其中化合物3、8、12、13为新化合物。六. 云南崖摩[Amoora yunnanensis (H. L. Li) C. Y. Wu)]为崖摩属植物,该属约25-30种,分布于印度、马来半岛一带自印度至伊里安岛。我国产6-7种,见于西南和华南,云南有6种和一个变种。而Pennington和Styles认为崖摩不能成为一个有效的属。我们对该植物的树皮的化学成分进行研究,从乙醇提取物中分离鉴定了二十个化合物(见Compounds from Amoora yunnanensis),包括十五个三萜四个甾醇及一个倍半萜。其中化合物10、11、12、13、18、19鉴定为新化合物。本次实验未得到四降三萜类化合物。七. 广玉兰(Magnolia grandiflora L.)是木兰科(Magnoliaceae)木兰属植物,该植物作为民间用药有着悠久的历史。在美国印地安人用于治疗疟疾和作发汗药。在中国民间用治疗感冒、头痛及胃痛。文献报道该植物含有生物碱、糖甙和倍半萜为其主要活性成分,其中小白菊内酯(parthenolide)具有细胞毒、抗菌、抗真菌、脱粒细胞等生物等生物活性。本章介绍了从该植物叶子中分离鉴定的九个倍半萜及二个木质素(见Compounds from Magnolia grandiflora),其中化合物3、4、6、7、9为新化合物。八. 本章总结了从1990年到现在四降三萜化合物的研究概况,涉及四降三萜的生物合成途径,分离鉴定,杀虫及药用活性及类似物的合成。参考134篇文献,列出了其间发表的223个新化合物的结构式。
其他摘要Chapter 1. Study on Chemical Constituents of Azadirachta indica Four new compounds, 1α,7α-diacetoxyl-21,24-epoxy-apotirucall-14-ene-3α,23α,24β,25-tetraol (azadirachol A) (2), 1α,7α-diacetoxyl-apotirucall-14-ene-3α,21,22,24,25-pentaol (azadirachol B) (3), the first 29-oxymethylene azadirachtin analogue, 29-oxymethylene-11-demethoxycarbonyl-11α-hydroxyazadirachtin (azadirachtin M) (16) and 22,23-dihydro-23α-hydroxy-3-tigloyl-11-deoxyazadirachtinin (azadirachtin N) (13), together with thirteen known compounds, odoratone (1), nimbin (4), deacetylnimbin (5), salannolide (6), azadirachtin (7), vepaol (8), isovepaol (9), 3-tigloyl-azadirachtol (10), 1-tigloyl-3-acetyl-azadirachtinin (11), 3-tigloyl-azadirachtinin (12), 1-tigloyl-3-acetyl-11-hydroxymeliacarpinin (14), 11-epi-azadirachtin H(15), and 2β,3β,4β-trihydroxypregnan-16-one (17) were isolated from a methanolic extract of the seed kernels of Azadirachta indica. The structures of compounds were elucidated on the basis of spectral methods. In addition, the conversion from azadirachtin to azadirachtinin skeletons was also discussed. Chapter 2. Study on chemical constituents of Dysoxylum hainanense Twenty-one new compounds, including ten tetranortriterpenoids (1-10), six triterpenoids (11-14, 17, 18), four diterpenoids (23-26), and one isoflavanone were isolated from bark of Dysoxylum hainanense Merr. Their structures were established as dysoxylumic acids A (1), B (2), C (8), dysoxylumins A (3), B (4), C (5), D (6), E (7), F (9), G (10), 23,26-dihydroxy-tirucall-7,24-diene-3-one (11), 2,23-epoxy-tirucall-7-ene-3β,24-25-triol (12), 3β,22-dihydroxy-tirucall-7,24-diene-23-one (13), 3β,20-dihydroxy-tirucall-7,22-diene (14), 7α-acetoxyl-21,24-epoxy-apotirucall-14-ene-3α,23α,24β,25-tetraol (17), 7α-acetoxyl-21,24-epoxy-apotirucall-14-ene-3-one-23α,24β,25-triol (18), 18-acetoxyl-15,16-dihydroxy-8(14)-pimaren (23), 18-acetoxy-16-hydroxy-8(14)-pimaren-15-one (24), 16,18-dihydroxy-8(14)-pimaren-15-one (25), 19-nor-4,16,18-trihydroxy-8(14)-pimaren-15-one (26), and 1,9-seco-2,7,4'-trihydroxy-6,3'-dimethoxy isoflavanone (32), based on 1D and 2D NMR techniques. Chapter 3. Study on Chemical Constituents of Walsura yunnanensis Eleven new compounds and ten known compounds were isolated from the bark of Walsura yunnanensis C. Y. W.. The new compounds were elucidated as walsurins A (3), B (4), and C (5) isowalsuranolide (6), walsuranolide (7), 11β-acetoxylwalsuranolide (8), 20,22-dihydro-22,23 epoxy-walsuranolide (9), walsurol (17), α-D(L)-Ara [1,2,3,4-tetrahydron-6,7-dihydroxy-4-(3,4-dimethoxyphenyl)-2-hydroxymethyl-3-naphthalenyl] methyl, named walsuroside A (18), α-D(L)-Ara [1,2,3,4-tetrahydron-6,7-dihydroxy-4-(3,4,5-trimethoxyphenyl)-2-hydroxymethyl-3-naphthalenyl] methyl, named walsuroside B (19), 1,2,3-trimethoxyphenyl-5-[2-O-α-L-Fucopyranosyl]-O-β-D-glucopyranoside, named walsuroside C (20), on the basis of spectral evidences. Chapter 4. Study on Chemical Constituents of Cedreal sinensis Four new compounds together with ten known compounds were isolated from leaves of Cedreal sinensis (A. Juss). Their structures were determined on the basis of spectral methods. Four new compounds were elucidated as cedrenolide (4), decahydro-2,2,8-trimethyl-4-methene-7,8-epoxy-1H-cyclopentacyclooctene (11), 2,6,10-phytatriene-1,14,15-triol (12), 2,6,10,15-phytatetraen-14-ol (13). Chapter 5. Study on Chemical Constituents of Cipadessa baccifera Four new compounds together with nine known compounds were isolated from dry berry of Cipadessa baccifera (Roth) Miq. Their structures were elucidated on the basis of spectral evidences. Four new compounds were determined to be methyl 3β-pivalyloxy-1-oxomeliac-8(30)-enate, named cipadessin (3), 17,20-dihydroxypregnan-3,16-dione (8), 1,4-epoxy-16-hydroxy-1,3,12,14,18-penta-heneicosene (12), and 1,4-epoxy-16-hydroxy-1,3,12,4-tetra-heneicosene (13). Chapter 6. Study on Chemical Constituents of Amoora yunnanensis Six new compounds, 20,24-epoxy-24,25-dihydroxy-dammar-3-one (10), 20S,24R-expoxy-3α-acetoxyl-dammar-23-chlorine-24,25-diol (11), 20S,24S-expoxy-3α-acetoxyl-dammar-23-chlorine-24,25-diol (12), 20S,24-epoxy-24,25-dihydroxy-3,4-Secodammar-4(28)-en-3-oic acid (13), 3β,7α,16-trihydroxy-stigmast-5,22-diene (18), 3β,7α,16-trihydroxy-stigmast-5-ene (19), were isolated from the bark of Amoora yunnanensis. Their structures were elucidated using the combination of 1D and 2D NMR techniques. Chapter 7. Study on Chemical Constituents of Magnolia grandiflora Five new sesquiterpenoids were obtained from leaves of Magnolia grandiflora L. They were determined as 4,5-epoxy-13-acetoxyl-1(10)-germacradien-12,6-olide (3), 13-methoxydihydroparthenolide (4), 4,6α,10-trihydroxy-13-acetoxy-guaia-12-ene (6), 12,13-diacetoxy-guala-4,6α,10,11-tetraol (7) and 6α,11-dihydroxy-12,13-diacetoxy-elemeol (9) on the basis of spectral evidence.
页数149
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/502
专题昆明植物所硕博研究生毕业学位论文
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罗晓东. 六种楝科植物及广玉兰化学成分研究[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,1999.
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