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题名: 三种芸香科药用植物的化学成分研究
作者: 汪云松
学位类别: 博士
答辩日期: 2004
授予单位: 中国科学院昆明植物研究所
授予地点: 中国科学院昆明植物研究所
导师: 郝小江
关键词: 芸香科 ; 九里香属 ; 黄皮属 ; 化学成分 ; 研究
学位专业: 植物学
中文摘要: 本文系统研究了三种芸香科药用植物,九里香属植物(aya)细叶九里香(M.koenigii),黄皮属植物(Clausena)细叶黄皮(C.anisum-olens)以及毛叶黄皮(C.vesitta)的化学成分及其生理活性。通过使用多种分离手段和技术,从三种植物中共分离、鉴定了105个化合物(从各种植物中重复分离到的未计入),其中有23个新化合物。化合物类型涉及到环肽、咔吧唑生物碱、吲哚生物碱,香豆素、苯丙素及其苷、倍半萜及其苷、二降倍半萜及其苷、黄酮、黄酮醇、黄酮苷、甾体、酚性化合物、长链烷烃及脂肪酸等。并对部分咔吧唑生物碱类化合物的生物活性进行了初步研究;通过固相催化偶联反应,由单体化合物(koenigine14)合成了新二聚咔吧唑生物碱(17);首次分离得到在稠合吡喃咔吧唑生物碱的8位上通过碳碳键与苯丙素形成二氢呋喃环的结构新颖的咔吧唑生物碱(21),以及9'位连有酰胺的结构新颖的香豆素(52);首次在黄皮属植物中发现环肽类化合物(97-105)并初步探讨了二维核磁共振技术在环肽研究中的运用。第一部分为细叶九里香(Murraya koenigii)的化学成分及其生物活性研究。从细叶九里香(M .koenigii)中分离鉴定了25个化合物(1-5)。分别是咔吧唑生物碱、吲哚生物碱、黄酮及其苷、香豆素等类型化合物。其中有2个新化合物,化合物17为新二聚咔吧唑生物碱,21为新颖结构的稠合吡喃咔吧唑生物碱。部分化合物的活性研究表明,新二聚咔吧唑生物碱17具有抗骨质疏松活性,IC5o为1.30μg/毫升。通过固相催化偶联反应,由单体化合物(k oenigine14)合成了新二聚咔唑生物碱(17),初步研究了新化合物(21)的固相催化偶联反应。第二部分研究了细叶黄皮(Clausena anisum-olens)的化学成分,分离和鉴定了57个化合物,其中涉及到化合物的类型有环肽,香豆素,咔唑生物碱,苯丙素及其苷,二降倍半萜及其苷,黄酮及其苷,长链烷烃等。其中化合物52-63,101-105为17个新化合物。7位氧取代单萜基香豆素以及咔吧只会类生物碱类化合物是该种植物的主要化学成分:其中9'位连有酰胺的7位氧取代单萜基香豆素,为首次发现香豆素与酰胺相连。从该种植物中获得的环肽类化合物,是首次从黄皮属植物中分离得到,这些化学成分的分离鉴定对该属植物的分类学研究有一定的学术意义。第三部分研究了毛叶黄皮(Clausena vesitta)的化学成分。分离鉴定了28个化合物,其中涉及到化合物的类型有环肽、苯丙素·甾体及其苷、黄酮及其苷、倍半萜、生物碱、长链烷烃和脂肪酸等。其中化合物97-100为4个新的环肽类化合物。毛叶黄皮(C.vesitta)是本属植物中的一个新种,其化学研究未见报到,该种植物产地特殊,其主要化学成与同属其它植物差异较大;从该种植物中分离得到的环肽类化合物,是首次从黄皮属植物中分离得到;这些化学成分的分离鉴定对该植物的分类学研究有重要的意义。我们的研究表明毛叶黄皮(C.vesitta夕的化学成分与该属其它植物的化学成分有显著的差异,应对该种从分类学,植物地理,植物衍化等多方面进一步深入研究,考虑是否归为黄皮属中一个独立类群。第四部分综述了芸香科九里香属植物的化学成分及其生物活性研究进展(1980-2003年)。
英文摘要: This thesis mainly reported the chemical constituents on three medicinal plants murraya koenigii, clausena anisum-olens and clausena vesitta. Systemic phytochemical investigation on above-mentioned three plants led to the isolation and identification of 105 natural compounds, 23 of which are new ones. The elucidated structures covered sesquiterpenoids and their glycoside., norsesquiterpenoids and glycoside, steroids and glycoside, flavones and glycoside , coumarins, phenylpropanoids and glycoside, lignans, indole alkaloids, carbazole alkaloids, cyclopeptides, long-chain alkanes and fatty acid, phenolic derivatives as well. Bioactivities of some carbazole alkaloids were carried out. The thesis first reported the synthesis of a new dimeric carbazole alkaloid 17, isolated from murraya koenigii, from its monomer koenigine through oxidative coupling reaction in a solid state. A noval carbazole alkaloid 21 with a rare phenylpropanyl substitution from murraya koenigii and a noval coumarin with amide at C-9' were isolated. Moreover, the new cyclopeptides were isolated for the first time from the plants of genus Clausena and a preliminary 2D NMR study on plant cyclopeptides was reported Charpter 1 Study on chemical constituents and bioactivities of Murraya koenigii. Plants of the genus Murraya (Rutaceae) are shrubs mainly distributed in southern Asia. The leaves and barks are used as folk medicines for analgesia and local anesthesia and for treatment of eczema, rheumatism, and dropsy. The ethanolic extract of murraya koenigii displayed cytotoxic activity against cultured KB cells. In investigation of the active principles of murraya koenigii, 25 compounds including 2 new carbazole alkaloids were isolated and identified. These compounds covered carbazole alkaloids, indole alkaloids, steroids, sesquiterpenoids, flavones and glycoside , coumarins . Compound 17 was a new symmetric dimmer of the carbazole alkaloid koenigine. Compound 21 was a noval carbazole alkaloid with a rare phenylpropanyl substitution. The synthesis of 17 from its monomer koenigine was carried out through oxidative coupling using a solid state reaction. This is the first times to synthesize a new dimeric carbazole alkaloid from its monomer through oxidative coupling reaction in a solid state and the possible reactive mechanism was discussed. Meantime, we proposed its biosynthetic pathway. Carbazole alkaloids 17 and koeginine were tested using antibacterial (enolpyruvyl transferase, EPT), antifungal (Candida albicans, C. glabrata, Aspefgillus fumigatus, YNG), anticancer (cell division cycle 25, CDC25), antithrombus (plasminogen activator inhibitor, PAI), and antiosteoprosis (cathepsin B, CAT-B, caronic anhydrase II, CA-II) bioassays. Compound 17 showed antiosteoporotic activity in the CAT-B model with a IC50 of 1.3 fig/ml. Charpter 2 Study on chemical constituents from Clausena anisum-oleas The plants of the genus Clausena have been used as folk medicines for the treatment of dysenter, enteritis, urethra infection, dermatopathy. Previous chemical researchers on the genus Clausena revealed that clausenamide and its derivatives were active in lowering elevated blood SGPT levels, and that carbazole alkaloids had activities in 9KB, KBMRI, and A-549 test and showed inhibitions against Gram-positive and Gram-negative bacteria and fungi, and that O-terpenoidal courmarins possessed inhibitions against 12-O-tetradecanoylphorbol-13-acetate-Induced Epistein-Barr virus early antigen activation in Raji cells. So, as a continued principle investigation of the genus Clausena, the chemical constituents on the plants Clausena anisum-olens and Clausena vesitta were carried out. In the phytochemical investigation of the 90% EtOH extract of leaves and barks of Clausena anisum-olens, 57 compounds including 17 new ones were isolated and identified from EtOAc fraction. The studies revealed the 7-O-terpenoidal coumarins and carbazole alkaloids were main chemical constituents in this plant .On the other hand, steroids and glycosides, phenylpropanoids and glycosides , norsesquiterpenoids and glycosides, flavones and glycosides, lignans also existed in this plant. 7-O-terpenoidal coumarin with amide at C-9' was first isolated. Moreover the five new cyclopeptides were isolated for the first time from the plants of genus Clausena. Charpter 3 Study on the chemical constituents on Clausena vesitta The plant Clausena vesitta was a new species, first identified by Prof. Tao De-Ding. It is reported that the plants of the genus Clausena mostly were distributed in the southern Yunnan province, but the plant Clausena vesitta grows in Lijiang district, Jinsha Valley of the west northern Yunnan Province. No work was carried out before. The chemical investigation on this plant led to the isolation and identification of 28 compounds including four new cyclopeptides, from the EtOAc extract. The known compounds mainly were phenylpropanoids and glycosides, steroids and glycosides, sesquiterpenoids and glycosides, flavones and glycosides, alkaloids, long-chain alkanes and fatty acid .The chemical studies on this plant revealed the difference from those of the plant of genus Clausena. This is consistent with the special growing environment of this plant as a new species. This phenomenon suggested the results of the chemical constitutions were very useful to the study on chemotaxonomy. Charpter 4. The progress of studies on chemical constituents and bioactivities of the plants of genus Murraya (1980-2003) The end part reviews the progress of studies on chemical constituents and bioactivities of the plants of genus Murraya (1980-2003).
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/698
Appears in Collections:昆明植物所硕博研究生毕业学位论文_学位论文

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三种芸香科药用植物的化学成分研究.汪云松[d].中国科学院昆明植物研究所,2004.20-25
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