传统中药徐长卿的化学成分、生理活性及指纹图谱的研究
其他题名Studies on the Chemical Constituents, Bioactivities and the Establishment of Aquality Analysis Method for Cynanchum Paniculatum
李顺林
学位类型博士
导师郝小江
2004
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
摘要本论文由四个章节组成:第一章为徐长卿(Cynanchun paniculatum)的化学成分研究。从徐长卿中分离得到了53个化合物,鉴定了48个(包括β-谷甾醇,胡萝卜苷),其中C21甾体类化合物35个,23为个新化合物;其它类型化合物11个,三个为新化合物。在35个C21甾体类化合物中,包含有13种C21甾体苷元,它们是:20-羟基-4,6-二烯-孕甾-3-酮;3β,14β-二羟基-孕甾-5-烯-20-酮;白前苷元C;白前苷元A;白前苷元D;新徐长卿苷元G;白前苷元B;新徐长卿苷元H;新徐长卿苷元B;新徐长卿苷元D;新徐长卿苷元E;新徐长卿苷元C;新徐长卿苷元F。其中新徐长卿苷元G;新徐长卿苷元H;新徐长卿苷元B;新徐长卿苷元D;新徐长卿苷元E;新徐长卿苷元C;新徐长卿苷元F等7个是在本次研究中首次发现的新苷元。在第一种苷元中,分离得到一个化合物,20-羟基-4,6-二烯-孕甾-3-酮(1)。在第二种苷元中,分离得到两个化合物,3β,14β-二羟基-孕甾-5-烯-20-酮(2)和Carumbelloside 11(3)。 第三种苷是以白前苷元C为苷元,连接不同的糖链(从1糖到5糖),共分离得到了10个化合物,分别是:白前苷元C(4),cynantratosideA(5),白前苷元C 3-O-β-D-磁嘛吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖苷(6),cynantratosideC(7),cynantratosideB(8),白前苷元C 3-O-β-D-葡萄吡喃糖基-(1→4)-α-L-2-脱氧毛地黄吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖苷(9),白前苷元C 3-O-β-D-葡萄吡喃糖基-(1→4)-α-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖苷-(1→4-β-D-夹竹桃吡喃糖苷(10),白前苷元C3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-O-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-夹竹桃吡喃搪苷(11),白前苷元c3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-O-L-2-脱氧毛地黄砒喃糖基-(1→4)-β-D-磁嘛吡喃糖基-(1→4)-β-D-竹桃吡喃糖苷(12),白前苷元C3-O-β-D-葡萄吡喃糖基-(1→4)-β-D-葡萄吡喃糖基-(1→4)-α-L-磁嘛吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖苷(13)。其中6、9、10、11、12、13是新化合物。第四种苷是以白前苷元A为苷元的化合物,这类化合物共分离得到两个,他们是:白前苷元A3-O-β-D-吡喃夹竹桃糖苷(14)和白前苷元A3-O-α-L-磁嘛吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-磁嘛吡喃糖苷(15)。其中15是新化合物。第五种苷是以白前苷元D为苷元的化合物,共分离得到4个,它们是:cynapanosideA(16),cynapanosideC(17),白前苷元D3-O-α-L-吡喃磁嘛糖基-(1→4)-β-D-吡喃洋地黄毒糖基-(1→4)-β-D-吡喃磁嘛糖苷(18),白前苷元D3-O-α-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-磁嘛吡喃糖苷(19)。其中18、19为新化合物。第六种苷是以17α-羟基-白前苷元C,命名为新徐长卿苷元G为苷元的化合物,共分离得到两个,一个是新徐长卿苷元G(20),这是一个新苷元,另一个为新徐长卿苷元G3-O-β-D-夹竹桃吡喃糖苷(21)。两个均为新化合物。第七种苷是以白前苷元B为苷元的化合物,共分离得到5个,它们是:glaucosideA(22),白前苷元B3-O-β-D-磁嘛糖苷(23),白前苷元B3-O-α-L-磁嘛吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-磁嘛吡喃糖苷(24),白前苷元B3-O-α-D-夹竹桃吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-磁嘛吡喃糖苷(25),白前苷元B3-O-α-L- 磁嘛吡喃糖基-(1→4)-β-D-磁嘛吡喃糖基-(1→4)-β-D-磁嘛吡喃糖苷(26)。其中24、25、26为新化合物。第八种类型仅分离得到一个不连糖的化合物,结构为7,17α-二羟基-白前苷元C(27),命名为新徐长卿苷元H,为一新化合物。第九种苷是以新徐长卿苷元B为苷元的化合物,新徐长卿苷元B为本次研究中,分离得到的新苷元,共分离得到两个化合物,它们是:新徐长卿苷元B3-O-β-D-夹竹桃吡喃糖苷(28),新徐长卿苷元B3-O-β-D-磁嘛吡喃糖基-(1~4)-β-D-夹竹桃吡喃糖苷(29),两个均为新化合物。第十种苷是以新徐长卿苷元D为苷元的化合物,为一新苷元,仅分离得到新徐长卿苷元D3-O-β-D-夹竹桃吡喃糖一个化合物(30),为一新化合物。第十一种苷是以新徐长卿苷元E为苷元的化合物,新徐长卿苷元E也是从徐长卿中首次分离得到的新苷元,分离得到了新徐长卿苷元E3-O-d-L-磁嘛吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖苷(31),为一个新化合物。第十二个种苷元的化合物为以新徐长卿苷元C这苷元的化合物,共分离得到三个,它们是:新徐长卿苷元C3-O-β-D-夹竹桃吡喃糖苷( 32),新徐长卿苷元C3-O-β-D-葡萄吡喃糖基-(1→4)-α-L-2-脱氧毛地黄吡喃糖基-(1→4)-β-D-洋地黄毒吡喃糖基-(1→4)-β-D-夹竹桃吡喃糖苷(33),18-OMe-新徐长卿苷元C3-O-β-D-夹竹桃吡喃糖苷(34)。三个均为新化合物。第十三种苷元是以新徐长卿苷元F为苷元化合物,仅分离得到新徐长卿苷元F3-O-β-D-夹竹桃吡喃糖苷一个化合物。为一新化合物(35)。从徐长卿中还分离得到非浴体类型的11个化合物,包括一个生物碱,4个酚性化合物及其苷,2个呋喃类化合物,两个糖醚类化合物及两个单甘酯。它们依次是:二乙酰胺(36),丹皮酚(37),3-羟基-4-甲氧基-苯乙酮(38),2,3-二羟基,4-甲氧基-苯乙酮(39),丹皮酚-2-O-α-D-吡喃阿拉伯糖基-(1→6)-β-D-葡萄吡喃糖苷(40),2-丙酰基-3-羟基-呋喃(41),5-羟甲基-呋喃甲醛(42),α-D-2,6-二去羟基-阿拉伯吡喃搪纂-乙基醚(43),4-OMe-β-D-2-脱氧毛地黄吡喃糖基β-D-夹竹桃吡喃糖基甲基醚(44),1-十八碳酸单甘酯(45),1-亚油酸单甘酝(46)。其中40、41、43为新化合物。第二章为徐长卿中分离得到的部分化合物的活性研究。主要进行了以下四种体外活性实验:l、抗菌活性实验选择了从徐长卿中分离得到的具有不同结构类型的5个化合物,进行了对甲氧苯青霉素抵抗型金黄色葡萄球菌(MRSA,methicillin-resistantStaPhyloc)的抗菌活性研究,结果显示,化合物8有一定的活性,其余化合物均未表现出抗菌活性。2、抗疟活性实验 选择了20个从徐长卿中分离得到的化合物进行了对人血红细胞培养恶性疟原虫(D6)和(w2)的抗疟活性实验,结果显示,化合物8、9、17、18、21、23、25等7个化合物对WZ有弱活性,所有化合物对D6均没有活性。3、细胞毒活性实验选用了6个化合物进行了体外抗肿瘤细胞A549和MCF-7的活性实验,实验结果表明:所有6个化合物中,化合物28对MCF-7菌株表现了一定的抑制活性,其余化合物均未表现出细胞毒活性。4、抗HIV活性实验选用了6个化合物进行了抗HIV活性实验,结果显示:所有化合物均没有表现出抗HW的活性。第三章对徐长卿进行了指纹图谱及药材质量标准研究,分离制备含量99.35%的Xl标准对照品25omg:98%以上的XI标准对照品1 50omg;99.27%丹皮酚标准对照品Z000mg。建立了徐长卿指纹图谱的分析方法;制定了徐长卿药材的质量标准(草案)。第四章为文献综述,总结概括了萝蘑科植物中非C21浴体类化合物中四类化合物的研究进展。
其他摘要This thesis consists of four chapters. In chapter A, the chemical components from Cynanchum paniculatum, a Chinese traditional medicine, were studied. During the phytochemical investigation, 53 compounds were isolated from this plant by different means, such as column chromatography (CC), low and medium pressure liquid chromatography (LPLC, MPLC), with different solid-phase including silica gel, reversed-phase C18 and C8 silica gel, and sephadex LH-20 as well. All the compounds were identified based on IR, MS, ID and 2D NMR spectral data, and their structures was characterized to be 20-hydroxypregna -4,6-dien-3-one(1), 14-hydroxypregnenolone (2), corurnbelloside II(3). glaucogenic C (4), glaucogenic C 3-0-β-D-oleandropyranoside (5), glaucogenic C 3-0-β-D-cymaropyranosyl-(l→4)-β-D-oleandropyranoside (6), cynantratoside C (7), cynantratoside B (8), glaucogenic C 3-0-β-D- glucopyranosyl-(l→4)-α-L-diginopyranosyl-(1→4)-(3-D-digitoxopyranosyl-(l→4)-(3-D-oleandr opyranoside (9), glaucogenic C 3-O-β-D-glucopyranosyl-(l→4)-α-D- oleandropanyanosyl-(l→4)-β-D-digitoxopyranosyl-(l→4)-β-D-oleandropyrano -side (10), glaucogenic C 3-0-β-D-glucopyranosyl-(l→4),-β-D-glucopyranosyl- (l→4)-α-D-oleandropanyanosyl-(l→4)-P-D-digitoxopyranosyl-(l→4)-β-D- oleandropanyanoside (11), glaucogenic C 3-0-β-D-glucopyranosyl-( 1 →4)-β-D- glucopyranosyl-(l→4)- α-L-diginopyranosyl-(l→4).-β-D-cymaropyranosyl- (1→4)-β-D-oleandropyranoside (12), glaucogenic C 3-O-β-D- glucopyranosyl- (1→4).-β-D-glucopyranosyl-(l →4)-α-L-cymaropyranosyl-(l→4)-β-D-digitoxo- pyranosyl-(l→4)-β-D-oleandropanyanoside (13), glaucoside A (14),glaucogenic A 3-0-α-L-cymaropyranosyl-(l→4)-β-D- digitoxopyranosyl- (1→4)-β-D-cymaropyranoside (15), cynapanoside A (16), cynapanoside C (17), glaucogenic D 3-0-α-L-cymaropyranosyl-(l→4)-β-D-digitoxopyranosyl- (l→4) -β-D-cymaropyranoside (18), glaucogenic D 3-O-α-L-cymaropyranosyl- (1→4)-β-D-digitoxopyranosyl-(l→4)-β-D-cymaropyraiioside (19), neocyna- panogenin g (20), neocynapanogenin D 3-O-β-D-oleandropan-yanoside (21). glaucoside A (22), glaucogenic B 3-O-β-D-cymaropyranoside (23), glaucogenic B 3-O-β-L- cymaropyranosyl-(l→4)-β-D-digitoxopyranosyl-(l →4),-β-D- cymaropyranoside (24),glaucogenic B 3-O-α-D-oleandropanyanosyl .(1→4)-β-D-digitoxopyranosyl-(l→4)-β-D-cymaropyranoside (25), glaucogenic B 3-O-α-L- cymaropyranosyl-(l→4)-βdigitoxopyranosyl- (1→ 4)-β-D-cymaropyranoside (26), neocynapanogenin H (27), neocynapanogenin B 3-O-β-D- oleandropyranoside (28), neocynapanogenin B 3-0-β-L-cymaropyranosyl-(l→4)-β-D-digitoxopyranosyl-(l→4)-D-cymaropy- ranosyl-(l→4)-β-D-oleandro- pyranoside (29), neocynapanogenin D 3-O-β-D-oleandropyranoside (30), neocynapanogenin D3-O-β-L- cymaropyranosyl-(l→4)-β-D-digitoxo-pyranosyl-(l→4)-β-D-oleandropyrano- side (31), neocynapanogenin C 3-O-β- D-oleandropyranoside (32), neocynapanogenin C 3-O-β-D-glucopyranosyl- (l→4)-a-L-diginopyranosyl- (1→4)-β-D-digitoxopyranosyl-(l →4)-β-D-oleandropyranoside (33), 18-0- methyl-neocynapanogenin C (34), neocynapanogenin F 3-O-β-D- oleandropyranoside (35), diacetamide (36), paeonol (37), 3,4-dihydroxyacetophenone (38), 3',6',-dihydroxy-2'-methoxyacetophenone (39), paeonol 2-0-β-D-glucopyranosyl-a-L-(l→6)-arabinopyranoside (40), 3-hydroxy-2-furyl propionate (41), 5-hydroxymethy- furfuraldehyde (42), a-D-2,6-dideoxy-arabinopyranosyl ethyl ether (43), 4-methoxy-P-D- diginopyranosyl-(l→6)-P-D-oleandropanyanosyl methyl ether (44), glycerin a-monosterate (45) glyceryl 9,12-cis-dien-octadecanate, respectively. Among them, 35 in eluding 23 new compounds belong to C2i-steroidal type, which possessed 13 different aglycones; (23 new compounds were 6,9,10,11,12,13,15,18,19,20,21,24,25,26,27, 28,29,30,31,32,33,34,35), 11 were non-C2i-steroidal chemical constituents (including 3 new ones, which were 40,41,43 ). The 35 C21-steroidal constituents belong to 13 different aglycones ( 7 were new ones, which were neocynapanogenin G, neocynapanogenin H, neocynapanogenin B, neocynapanogenin D, neocynapanogenin E, neocynapanogenin C, neocynapanogenin F). Chapter B The bioassays including four different models for compounds from cynanchum paniculatum comprise this chapter. 1. Antibacterial activity: Five compounds were subjected to anti-MRSA evaluation, and z-5 showed weak activity against MRSA in Vitro. 2.Antimalarial activity: Twenty compounds were selected to inhibit human malaria pathogen Plasmodhim falciparum (D6 and W2) in vitro, and seven of them showed weak activity against W2. 3. Cytotoxicity evaluation: Two tumor cell lines, lung carcinoma (A-549) and Breast cancer (MCF-7), were used in vitro to probe cytotoxicity of six compounds which showed slight active against MCF-7. 4. Anti-HIV activity: All the candidate compounds presented negative activity in an anti-HIV experiment. Chapter C, A quality analysis method for traditional Chinese medicine Cynanchum paniculatum was presented. Chapter D A review on non-C2i-steroidal from Ascepiadaceae.
页数160
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/710
专题昆明植物所硕博研究生毕业学位论文
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李顺林. 传统中药徐长卿的化学成分、生理活性及指纹图谱的研究[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,2004.
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