吴茱萸、粉花绣线菊的化学成分及抗真菌活性研究
其他题名STUDIES ON CHEMICAL CONSTITUENTS OF EVODIA RUTAECARPA, SPIRAEA JAPONICA VAR. OVALIFOLIA AND ANTIFUNGAL ACTIVITIES OF RELATED COMPOUNDS
左国营
学位类型博士
导师郝小江
2001
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
关键词吴茱萸 粉花绣线菊 化学成分 抗真菌活性
摘要该论文主要由三章组成.第一、二章分别论述了两种药用植物芸香料(Rutaceae)吴荣萸[EvodiaRutaecarpa(Juss.)Benth]和蔷薇科(Rosaceae)椭圆叶绣线菊(Spiraeajaponicavar.ovalifoliaFranch.)的吼跺生物碱、二萜生物碱、二萜和木脂素及其苷等的研究及新化合物的结构解析;第三章介绍了吲跺类化合物的化学合成,天然及合成吲哚跺类化合物、二萜生物碱和二萜的抗真菌活性研究.最后,本论文对β-咔啉(β-Carboline)系列生物碱的化学结构、来源和生物活性进行了综述.
其他摘要This thesis contains three charpters. Chapter 1 and 2 discussed the isolation and identification of indole alkaloids, diterpene and diterpenoid alkaloids, ligans and their glycosides, including the new compounds from two medicinal plants, Evodia rutaecarpa Benth and Spiraea japonica ovalifolia Franch, respectively. Chapter 3 deals with the synthesis of twenty four compounds belonging to indole-type, and the antifungal activity about ten of the synthetic and fifteen of the natural compounds from the two plants. And finally, serial bioactive p-carboline type alkaloids are reviewed. 1. Chemical Constituents found in Evodia rutaecarpa Benth and Spiraea japonica var. ovalifolia Franch. Sixty five compounds were isolated and characterized from the two medicinal plants employing different methods, such as column chromatography(CC), low and medium pressure liquid chromatography (LPLC, MPLC), vacuum liquid chromatography (VLC), normal pressure and vacuum dry column chromatograph (DCC, VDCC), silica gel, D101 type of large porous absorption resin, sephadex LH-20, and other as separation materials. UV, IR, MS, one and two dimensional NMR were used in the identification of the compounds. Alkaloids (indole, indoline, diterpenoid, quinolone, quinazoline, and phenylehylamine), flavonoid, limonoid, ligan, diterpenoid, triterpenoid, sterol and derivatives of minor molecule of phenolic propenyl acid were obtained. Fourteen of all compounds were new. 1.1 Chemical Constituents found in Evodia rutaecarpa Benth For the purpose of providing samples to determine antifungal activity, and developing traditional Chinese medicinal plant, E. rutaecarpa Benth., further study based on the investigated results was focus on the indole alkaloids. Thirty-seven compounds, of which a new indole alkaloid glucoside has a special structure, were isolated and characterized from the fruits and aerial parts of the plant. They are: eleven indoloquinazoline alkaloids, Rutaecarpine (1), Evodiamine (2), Hydroxy-evodiamine (3), 13a-Acetonyl-hydroxyevodiamine (4), Dehydroevodiamine hydrochloride (5), 14-Formyldihydrorutaecarpine (6), 7,8-Dehydrorutaecarpine (7), Dihydrorutaecarpine (8), 7-Hydroxyrutaecarpine (9), Goshuyuamide-I (10), Evodiamide (11), two indolinone-quinazolinone alkaloids, Wuchuyuamide-I (12), Wuchuyuamide-II (13); one indole alkaloid glucoside, Rutaecarpine-2-(9-p--D-glucopyranoside (14); five quinolone alkaloids, l-Methyl-2-[(Z)-5-undecenyl] -4(lH)-quinolone (15), l-Methyl-2-[(Z)-6-undecenyl]-4(lH)-quinolone (16), l-Methyl-2-[(Z)-7-tridecenyl]-4(lH)-quinolone (17), Evoearpine (18), l-Methyl-2-[ (6Z, 9Z) -6, 9-pentadecadienyl]-4(lH)-quinolone (19) ; one furoquinoline alkaloid, Skimmianine (20); one quinazoline alkaloid, Evoquinazoline (21); two p-Phenethylamines, Synephrine (22), Synephrine-4'-6>-propyl-ketal (23); three limonoids, Limonin (24), 12a-Hydroxy- limonin (25), Rutaevine (26); three flavonoids, Flavaprin (27), Phellamurin (28), 5,7,3'-Trihydroxy, 4'-methoxy-flavonone-3-0-p-D-glucoside (29); six phenolic propenyl acids and esters, 3-(4'-Hydroxyphenyl)-2-propenyl acetate (30), 3- (3', 4'-Dihydroxyhenyl)- 2-propenyl acid (31), 3-(3'-Hydroxy, 4'-methoxyhenyl)- 2-propenyl acid (32), 3-(3', 4'-Dihydroxyhenyl)-2-propenyl acetate(33), 3-(3', 4'-Dihydroxyhenyl)-2-propenyl butyrate (34), 3-(3'-Hydroxy, 4'-methoxy-phenyl)-2-Propenyl acetate (35); one lignan, [2-(3'-Methoxy, 4'-hydroxy)-3-(3', 4'-dimethoxy)]-diphenyl-y-butyl lactone (36) and one butyl glycoside, w-Butyl -p-D-fructopyranoside (37). Compounds 4, 6, 10-13, 20-23 and 29-37 were isolated from the fruits of Evodia rutaecarpa Benth and 7-9, 14, 27, 28 were from its aerial parts. The rest were from both parts of the plant. Fourteen compounds 7, 9, 20 and 27-37 were obtained from this plant first time, and six compounds 4,12-14,21,23 are new. 1.2 Chemical constituents found in Spiraea japonica van ovalifolia Francta The chemical constituents of Spiraea japonica var. ovalifolia Franch which is a shrub belonging to the group of seven varieties of S. japonica has not been investegated. To supply sample for bioactive study and get the distribution of the chemical constituents in this plant and then to compare the distribution difference of compounds with those of the other variety, the isolation and identification about it has been done. Twenty-eight compounds were obtained and characterized, including thirteen diterpenoid alkaloids, Spiramiries A (1), B (2), C (3) , D (4), F (8), G (9), H (10), I (11), Spiramines Z-2 (5), Z-3 (6), 15-Deacetyl spiramine F (7), 15-Deacetylspiramine S (12), 19-0-deethylspiramine N (13); three diterpenes, Spiraminol (14), 15-Acetylspiraminol (15), Spiramilactone B (16); two diterpenoid glucosides, Spiraminol-19-0-(3-D-glucopyranoside(l 7), SpirarnilactoneC-15-<9-P-D-gluco pyranoside (18); two sterols, p-Sitosterol (19) and Daucosterol (20); one triterpenoid, 18-Hydroxy-ursolic acid (23); two lignans, Syringaresinol (24), Cyclo- olivil(25), three lignan glucosides, (+)-Isolariciresinol -9-P-D.- xylopyrano- side(26), 5-Methoxy-isolariciresinol-9-p-D- xylopyranoside (27), Isolariciresinol-9-P-D-glucopyranoside (28); one alcohol, (S)-lO-Nonacosanol (21); one unsaturated acid, Sanleng acid (22). 5-7,12,13,15,17,18 are eight new compound . Nine compounds (21-28) were obtained from the group for the first time. The discovery of new diterpenes and diterpenoid glucosides provided additional evidences to show the biosynthesis route which diterpenoid alkaloid erives from diterpene. 2. Antifungal activities of Some Indole and Diterpenoid Compounds Starting from a phytoalexin as the leading compound, an possible candidate of new type highly effective and safe bactericide may be found through idealizing of its structure and synthesizing of its derivatives. Rice indole alkaloid phytoalexin PI, together with its nine of the twenty four chemically synthesized derivatives and nine naturally occurring similarities, were screened through measuring inhibitory activities against the spore germination and germ tube growth of Maganaporthe grisea races PI31 and SI528 by germination test. Most of them showed their activities are greater than those of PI. The best one's activity is 100 times bigger than the lead compound's. Some of the compounds also showed inhibitory activity against Fusarium oxysporum f.sp.niveum and effect on the infection of Fusarium oxysporum f.sp. vasinfectum. The results offered new basis for revealing of the structure-activity relationship (SAR). The inhibition of the six indole alkaloids and diterpenoids each, agains human Candida albicans BERK ATCC10231, CCCCM(C1A) and CCCCM(C6E), were also tested in the study, respectively. The results of indole alkaloids showing higher activity were obtained. 3. Review At the end of the thesis was a review of sixty three bioactive P-Carboline alkaloids. The plant resources, chemical structures and types of activities were presented in the review.
页数135
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/582
专题昆明植物所硕博研究生毕业学位论文
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左国营. 吴茱萸、粉花绣线菊的化学成分及抗真菌活性研究[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,2001.
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