三种仙茅属药用植物和天麻的化学成分研究
其他题名Chemical Constituents of Curculigo Crassifolia, C.Capitulata, C. Orchioides and Gastrodia Elata
李宁
学位类型博士
导师周俊
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
摘要本论文为三年期间攻读博士学位的研究工作。报道仙茅科仙茅属三种药用植物,绒叶仙茅[Curculigo crassolia(Baker)Hook.f.],大叶仙茅[C,capituIata(Lour.) O.Ktze],仙茅(C.orchioides Gaertn)和兰科天麻属名贵中药天麻(Gastrodia elata Blume)化学成分的系统研究。通过使用多种分离手段和技术,从四种植物中共分离、鉴定了77个化合物,其中包括48个已知化合物、29个新的化合物。已鉴定的化合物类型涉及酚、酚苷、木脂素苷、降新木脂素及其苷、环阿尔廷醇型三萜皂苷、黄酮、(口山)酮、按烷型倍半萜、豁体及其苷、苯环取代物、苯丙素、黄嘿吟、吡啶生物碱和二糖等。并对绒叶仙茅中部分化合物的心血管活性进行了初步研究。第一章研究了绒叶仙茅(Ccrassolia)的化学成分。目前,还不曾见有关.该植物化学成分的报道。从该植物根茎的乙醇提取物中分离鉴定了16个已知化合物,16个新化合物。大部分化合物为降新木脂素及其苷(1-25,29),化合物26-28和31是酚和酚苷类化合物,30和32是2,6-二甲氧基苯甲酸及其苷类化合物。其中化合物1-6、8-11、13、17-21为新化合物。并对部分化合物的心血管活性经合作单位进行了初步测定,结果显示12和13混合物和TS具有增强去甲肾上腺素引起主动脉环收缩的作用;而化合物26、15、6、22和23混合物、20和21混合物则具有抑制去甲肾上腺素引起主动脉环收缩的趋势,ICS。分别为0.19nlnloL、0.50mmol/L、0.027mmol/L、0.70mmol/L、0.096mmol/L。第二章报道了大叶仙茅(C.capitulata)的化学成分。从该植物根茎的乙醇提取物中分离鉴定了14个已知化合物,6个新化合物。分别是酚苷(1,12,13)、酚(15,17)、降新木脂素及其苷(2-8)、按烷型倍半萜(9,10)、木脂素苷(11)、黄酮(14)、苯丙素(16)、甾体及其苷。其中1-4,9,11为新的化合物。第三章为传统中药仙茅(Corchioides)的化学成分研究。从仙茅根茎的乙醇提取物中分离鉴定了10个已知化合物,3个新化合物,分别是环阿尔廷醇型三萜皂苷(1,2)、黄酮(3)、(口山)酮(4)、酚苷(5-7,10)、木脂素苷(8)、苯环取代物(9)、黄嘌呤(11)、甾体及其苷。其中化合物1-3为新化合物,4、8、10、11是首次从该植物中分离得到。第四章研究天麻(G.elata)的化学成分。从其根茎的乙醇提取物中分离鉴定了8个已知化合物,4个新化合物,主要是酚及酚苷类化合物(1-4,6-9)、吡啶生物碱(11)、三柠檬酸酯(12)和二糖(5,10)。其中化合物5-7和11是新化合物。第五章综述了仙茅属植物的化学成分和生物活性的研究概况。第六章综述了天麻的化学成分及生理活性的研究进展。
其他摘要During the chemical investigations on four medicinal plants, Curculigo crassifolia, C. capitulata, C. orchioides and Gastrodia elata, 11 compounds including 29 new ones were isolated and identified. Those compounds coverd phenoloids and glycosides, norneolignans and glycosides, cycloartane-type triterpene glycosides, lignan glycosides, flavanones, xanthone, sesquiterpenoids, steroids and glycosides, aromatic derivatives, phenylpropanoids, xanthine, alkaloids and disaccharide. Curculigo crassifolia (Baker) Hook. f. (Hypoxidaceae) is distributed in the western and southern regions of China. The rhizomes of this plant are used as a folk medicine for treating child pneumonitis. However, so far, no extensive studies of this plant with respect to its chemical characteristics have been reported. In this work, 32 compounds were isolated from the ethanolic extract of the rhizomes of C. crassifolia, mainly including norneolignans and glycosides, phenoloids and glycosides. They were crassifogenin A (1), crassifogenin B (2), crassifoside A (3), crassifoside C (4), crassifoside B (5), crassifoside D (6), curcapital (7), crassifoside E (8), crassifoside F (9), a mixture of crassifogenin C and isocrassifogenin C (10, 11), 1 - O -methylnyasicoside (12) and 1 - O - methylisonyasicoside (13), nyasicoside (14), isonyasicoside (15), nyasicol (16), isonyasicol (17), crassifogenin D (18), isocrassifogenin D (19), a mixture of isocrassifoside G and crassifoside G (20, 21), a mixture of 1 - O - methylisocurculigine and 1-0- methylcurculigine (22, 23), a mixture of isocurculigenin and curculigenin (24, 25), 3, 4 - dihydroxy - benzoic acid (26), 4 -hydroxyphenol (27), 3, 4 - dihydroxy - benzoic alcohol (28), pilosidine (29), 2, 6 - dimethoxy - benzoic acid (30), Curculigoside I (31), glucosyringic acid (32). Among them, compounds 1 -6, 8-11, 13, 17-21 are new. Effects of compounds on calcium-related contractions of isolated rabbit tlioracic aortic smooth muscle showed 26、15、6、a mixture of 22 and 23、a mixture of 20 and 21 with IC50 value 0.19、0.50、0.027、0.70 and 0.096mmol/L, respectively. A mixture of 12 and 13 and T5 increased contractions induced by norepinephrine. Curculigo capitulata Lour. O. Ktze (Hypoxidaceae) is widely distributed in Southern and Southwestern China, Taiwan (China), Malaysia, India and Australia and used as a tonic and a medicine for treating ysmenorrhea and rheumatism. Twenty compounds were isolated from the ethanolic extract of the rhizomes of C. capitulata, mainly including phenoloids and glycosides, norneolignans and glycosides, sesquiterpenoids, et al. They were capitulatin A (1), capituloside (2), a mixture of curculigenin and isocurculigenin (3, 4), a mixture of 1 - O -methylcurculigine and 1 - O - methylisocurculigine (5, 6), a mixture of curculigine and isocurculigine (7, 8), 4α, 6α - epoxy - 1β - hydroxy - 4β - methyleudesmane (9), 6α, 15α - epoxy - 1β, 4β - dihydroxy eudesmane (10), 4, 4' - dimethoxy - 3' - hydroxy - 7, 9': 7', 9 - diepoxylignan -3-O-β-D- glucopyranoside (11), curculigoside I (12), orcinol glucoside (13), 4', 5, 7 - trihydroxyflavone (14), 3, 5 - dihydroxytoluene (15), 3 - (4 - Hydroxy - 3 - methoxy - phenyl) - propenal (16), 4 - Ethoxy - 3 - hydroxymethylphenol (17), 5, 22E - dien - 24 - isopropenyl - 25 - methyl - 3β - cholestanol (18), besides β-sitosterol and daucosterol. Among them, compounds 1-4, 9, 11 are new. Curculigo orchioides Gaertn(xian Mao) (Hypoxidaceae) are used in Chinese traditional medicine as a tonic agent for treatment of debility. Its rhizomes are used to cure for piles, asthma, jaundice, diarrhoea, colic and gonorrhoea. Thirteen compounds were isolated from the ethanolic extract of the rhizomes of C. orchioides, mainly including cyclpartane-type triterpene glycosides, phenoloids and glycosides, lignan glycosides, et al. They were 3β, llα, 16β - trihydroxycycloartane - 24 - one -3 -O- [β - D - glucopyranosyl (l→3) - β - D - glucopyranosyl (1→2) - β - D -glucopyranosyl] - 16-O-α-L- arabinopyranoside (1), (24S) - 3β, llα, 16β, 24 -tetrahydroxy cycloartane -3-O- [β-D- glucopyranosyl (l→3) - β - D -glucopyranosyl (1→2) -β-D - glucopyranosyl] -24-O-β-D- glucopyranoside (2), 3', 4', 5' - trimethoxy - 6, 7 - methylenedioxyflavone (3), 2, 3, 4, 7 -tetramethoxyxanthone (4), curculigoside I (5), curculigoside B (6), orcinol glucoside (7), 3, 3', 5, 5' - tetramethoxy - 7,9': 7', 9 - diepoxylignan - 4,4' - di - O -β-D - glucopyranoside (8), 2, 6 - dimethoxy - benzoic acid (9), 3 - hydroxy - 5 - methylphenol -1 - 0 - [β - D - glucopyranosyl - (l→6) -β-D - glucopyranoside] (10), 1,3,7- trimethylxanthine (11). Among them, compounds 1 -3 are new. Gastrodia elata Blume (Orchidaceae) are very important Chinese herbal medicines used for the medical treatment of headaches, migraine, dizziness, epilepsy, rheumatism, neuralgia, paralysis and other neuralgic and nervous disorders. Twelve compounds were isolated from the ethanolic extract of the rhizomes of G. elata, mainly including phenoloids and glycosides. They were 4 - hydroxybenzyl alcohol (1), gastrodin (2), p - hydroxybenzyl methyl ether (3), 4, 4' - dihydroxyphenyl methane (4), gastrabiose (5), elatoside (6), gastrol A (7), gastrol (8), 2, 4 - bis (4 -hydroxybenzyl) phenol (9), sucrose (10), gastrol B (11), parishin (12). Among them, compounds 5, 6, 7 and 11 are new.
页数153
语种中文
文献类型学位论文
条目标识符http://ir.kib.ac.cn/handle/151853/702
专题昆明植物所硕博研究生毕业学位论文
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李宁. 三种仙茅属药用植物和天麻的化学成分研究[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,2004.
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