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题名: 五种药用植物化学成分的研究
作者: 汪琼
学位类别: 博士
答辩日期: 2007-06-06
授予单位: 中国科学院昆明植物研究所
授予地点: 昆明植物研究所
导师: 罗士德
关键词: 小花锥花 ; 绣球防风 ; 香花藤 ; 锥序蜜心果 ; 桂火绳 ; 化学成分 ; 研究
学位专业: 植物学
中文摘要: 本论文对五种药用植物:小花锥花,绣球防风,香花藤,锥序蜜心果,桂火绳的化学成分进行了初步研究。通过层析硅胶、葡聚糖凝胶(LH-20)、反相硅胶(RP-18)、MCI CHP-20P、Merck硅胶等分离材料和多种分离技术,从五种植物中共分离、鉴定了92 个化合物,包括三萜、降三萜、二萜、甾体、黄酮、香豆素、木脂素、环烯醚萜、生物碱、酚性小分子化合物及其甙类化合物。其中7个新化合物,结构类型涉及降三萜、三萜、甾体甙和二萜。 第一章为小花椎花化学成分的研究。从其地上部分共分离鉴定了15个化合物,其中包括3个新化合物,Gomphoparvin A(1), Gomphoparvin B(2),Gomphoparvin C(3), 5个甾体Ergosta-7, 22-diene-3β,5α, 6β,9α-tetrol(4), E Ergosta-7,22-diene-3β, 5α, 6β-triol(5), Ergosta-7,22-dien-3-ol(6), β-Sitosterol(7), 胡萝卜甙(8), 3个黄酮类化合物apigenin 7-O-β-D- (6'"-O-p-coumaroyl)glucopyranoside(9), apigenin 7- O-β- D- [(6'"-O-p-coumaroyl) glucopyranosyl]-(2'''→1"")-α-D-glucopyranoside(10),kaemp ferol 7-O-β-D-glucopyranoside(11), 1个脂肪酸酯化合物Glycerol 1-octadecanoate( 12), 3个生物碱类化合物Auranamide(13), (2S,3S, 4R)-Phytosphingosine(14), Halice rebroside(15), 这些化合物都是首次从该属植物中分离得到。 第二章为绣球防风化学成分的研究,对其全草用70%的乙醇进行热提取,从乙酸乙脂部分分离到5个化合物,从正丁醇部分分离到8个化合物,包括2个新化合物13-epimer-(rel5S,6R,8S,9R,10S,13R,15R)-6-acetoxy-9,13,15,16-diepoxy-3β, 15-dihydroxyabdane-3-β-glucopyranoside(11), 13-epimer-(rel5S,6R,8S,9R,10S,13R, 15S)-6-acetoxy-9,13,15,16-diepoxy-3β,15-dihydroxyabdane-3-β-glucopyranoside(12)。6个黄酮5,7,4'-trihydroxy-3', 5'-dimethoxyflavone(1),5, 4' -dihydroxy-7,3', 5' –trimethoxyflavone(2),5,7-dimethoxychromanone (5), 5-hydroxy-3', 4',5'-trime thoxyflavone-7-O-β- glucopyranoside (6), 5-hydroxy-3', 4'-dimethoxyflavone-7- O-β- glucopyranoside (7), apigenin 7-O-β-D- (2",6"-di-O-p-coumaroyl) glucopyranoside (13), 2个甾体:胡萝卜甙(3), Stigmast-5-ene-7-ol-3-O-β- glucoside(4), 3个苯丙素类化合物:Acteoside (8), 3,4-dihydroxy-β-phenylethoxy-O-α-L-arabinopyranosyl-(1""→2")-α-L-rhamnopyranosyl-(1"'→3")-4"-O-caffeoyl-β-D-glucopyranoside (Angorosi de) (9), 3-hydroxy-4-methoxy-β-phenylethoxy-O-[α-L-arabinopyranosyl-(1""→6")-α -L-rhamnopyranosyl-(1'"→3")-4"-O-caffeoyl-β-D-glucopyranoside(10), 这些化合物首次从该属植物中分离得到。 第三章为香花藤化学成分的研究,其地上部分进行化学成分的分离,从石油醚、乙酸乙脂和正丁醇中分离到化合物23个,1个新化合物pregn-5-ene-3β,20β– diglucosides(1), 其中包括5个甾体,3-O-β-D-glucopyranosyl-3β,15α-dihydroxy pregn-5-en-20-one(2), 3β, 20α-dihydroxy-5-en-pregane(3), 28-methylstigmast-5-en -3-ol(4), 29-norcycloart-23-ene-3,25-diol(5), 29-norcycloartan-3-ol(6), 五个苯甲酸类化合物丁香酸- 4β-D-吡喃葡萄糖甙syringic acid 4-O-β-D-glucopyranoside(10),水杨酸salicylic acid(11), 壬二酸(13), bis(2-ethylhexyl) phthalate(15), 二个脂肪酸类化合物二十六碳酸-1-甘油酯(20), 5,8,12-trihydroxy-9-octadecenoic acid(21), 4个黄酮类化合物山萘酚3-O-α-L-吡喃鼠李糖-(1→4) -α-D-吡喃葡萄糖(16), 山萘酚3-O-α- D-吡喃葡萄糖(1→2)-β- D-吡喃葡萄糖甙(17), 山萘酚3-O-α-L-吡喃鼠李糖-(1→4) –[α-L-吡喃鼠李糖-(1→4)]-β-D-吡喃葡萄糖甙(kaempferol 3-O-α-L-rhamno pyranosyl (1→4)- [α-L-rhamnopyranosyl-(1→4)]-β-D-glucopyranoside)(18), 山萘酚3-O-α-L-吡喃鼠李糖-(1→4) –[ β-D-吡喃葡萄糖(1→4)]-β-D-吡喃葡萄糖甙[21](kaem pferol 3-O-α-L-rhamnopyranosyl-(1→4)- [ β-D-glucopyranosyl-(1→4)]-β-D-glucopyra noside)(19), 一个环烯醚萜化合物Geniposidic acid(7), 二个木脂素Syringaresinol (8), 丁香脂素-4,4'-O-双-β-D-葡萄糖苷(syringaresinol-4,4'-O-bis-β-D-glucopyrano side)(9), 二个生物碱(2S,3S,4R) –phytosphingosine(22), nebularine(23), 一个香豆素东莨菪内酯(12), 这些化合物首次从该属植物中分离得到。 第四章为锥序蜜心果化学成分的研究,从其茎叶中分离得到19个化合物,包括10个三萜,黄酮,苯甲酸类化合物,其中化合物 1个新化合物,2α,3α-二羟基-12-烯-23-醛基-28-乌索酸[3](7), 9个已知三萜化合物分别为:齐墩果酸(1)[4]、乌索酸[5](2), 2α,3β-二羟基乌索-12-烯-23-酸[ 6](4), 2α-羟基乌索酸(2α-hydroxyurso lic acid)[7](3), 2α, 19α-二羟基乌索-12-烯-28-酸[8 ](5), 2α,3α, 24-三羟基-12-齐墩果烯-28-酸[9](6), 3 -trans-p-coumaroyl-ursolic acid [10](8), 2α, 19α-二羟基乌索-12-烯-28-酸-28-O-β-D-吡喃葡萄糖甙[ 11](9), 2α, 19α, 23-三羟基乌索-12-烯-28-酸-28- O-β-D-吡喃葡萄糖甙[12 ](10)。3个黄酮类化合物quercetin 3-O-β-D-glucopyranoside (13)[ 13]、kaempferol 3-O-α-L-rhamnopynoside(14)[14], quercetin 3-O-α-L-rhamnopyno side(15)[15],2个苯甲酸类化合物(E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid carboxymethyl ester(11)、3, 4-dihydroxybenzoic acid [17] (12)、一个脂肪酸,十九脂肪酸(16),一个甘油酯,二十七碳酸-1-甘油酯(17),两个木脂素分别是Aschantin (18)[18 ]、grandisin(19)[ 19],这些化合物首次从该属植物中分离得到。 第五章为桂火绳化学成分的研究,从其茎叶中分离得到22个化合物,包括 个黄酮,3个三萜:羽扇豆醇(lupenol)[9](1)、白桦酸(3-hydroxy-20(29)-lupen-28-oic acid)[10](2)、齐墩果酸[11](3),2个木脂素syringaresinol [12](4)、(+)-异落叶松树脂醇[13](5),酚性化合物13个,1个香豆素东莨菪内酯[14](6),1个苯甲酸 (E)-对羟基桂皮酸naringeninic acid[15](7),11个黄酮类化合物,其中包括:儿茶素[19](11),表儿茶素[20](12), 表儿茶素-3-O-β-阿拉伯呋喃糖黄酮甙[18](13),山萘酚-3-O-α-吡喃葡萄糖甙(kaempferol 3-O-α-D-glucopyranoside) [22] (14),5,7, 4'-三羟基异黄酮[23](15),顺式-二氢槲皮素-3-O-α-阿拉伯呋喃糖甙[25](17),反式-二氢槲皮素-3-O-β-阿拉伯呋喃糖甙[26](18),反式二氢槲皮素-3-O-α-吡喃葡萄糖甙 [27](19),4'-甲氧基-3, 5, 7 ,3', 5'-五羟基黄酮烷(4'-methoxy-3, 5,7, 3', 5'-penthydroxyflavan[28](20)。山奈酚3-O-β-L-吡喃鼠李糖(1→6)-β-D-吡喃葡萄糖甙[29](21),槲皮素3- O-β-D-吡喃葡萄糖(1→6)-β-D-吡喃葡萄糖甙(22)[30],1个黄酮类木脂素4'-O-methylgallocatechin [24](16),2个甘油脂二十七碳酸-1-甘油酯[16](8),十八碳烯酸-1-甘油酯[17](9),1个甾体sitoindosideⅡ[18](10),这些化合物都是首次从该属植物中分离得到,迄今为止对其化学成分的研究未见报道。 最后综述了梧桐科化学成分的研究概况。总结了从1977年到2007年有关梧桐科植物的化学活性成分和列举了在此期间发表的78个化合物的化学结构。 关键词:小花锥花;绣球防风;香花藤;锥序蜜心果;桂火绳;梧桐科;化学成分;研究
英文摘要: This thesis elaborated the studies on the chemical constituents of five medicinal plants, Totally 92 compounds were isolated and identified by various chromatographies over silica gel column, Sephadex LH-20, MCI CHP-20P, RP-18 si gel. Those compounds covered triterpenoids, diterpenoids,nortriterpenoids, steroids, flavanones, flavones, coumarins, lignans, alkaloids and aromatic compounds. Among them, 7 were new ones, including three nortriterpenoids, two diterpenoids, one triterpenoids and one steroid. Gomphostemma parviflorum is a plant belong to the family Labiatae and used as a traditional folk herb to treat pneumonia、tracheitis, cystitis, urethra infection , calculi and so on. In order to find out its active constituents, G. parviflorum collected at xishuangbanna in Yunnan province was investigated phytochemically. From the whole plant, 15 compounds were isolated and identified to be Gomphoparvin A(1),Gomphoparvin B(2), Gomphoparvin C(3), Ergosta-7, 22-diene-3β,5α, 6β,9α-tetrol(4), Ergosta-7,22-diene-3β, 5α, 6β-triol(5), Ergosta-7,22-dien-3-ol(6), β-Sitosterol(7),daucosterol(8), apigenin 7-O-β-D- (6'"-O-p-coumaroyl)glucopyranoside(9), apigenin 7- O-β-D- [(6'"-O-p-coumaroyl) glucopyranosyl]-(2'''→1"")-α-D-glucopyranoside(10), kaempferol 7-O-β-D-glucopyranoside(11), Glycerol 1-octadecanoate(12), Auranamide(13), (2S,3S, 4R)-Phytosphingosine(14), Halicerebroside(15), Which the compounds 1,2, 3 were the new ones and all the compounds were obtained from this plant for the first time.Leucas ciliata Benth is collected in gold temple mountain of Kunming, and widely used to treat arthrosis ache, diarrhea, tetter, rectocele, from the whole plant, 13 compounds were isolated and identified to be 13-epimer-(rel5S,6R,8S,9R,10S,13R,15R)-6-acetoxy-9,13,15,16-diepoxy-3β,15-dihydroxyabdane-3-β-glucopyranoside(11), 13-epimer-(rel5S,6R,8S,9R,10S,13R, 15S)-6-acetoxy-9,13,15,16-diepoxy-3β,15-dihydroxyabdane-3-β-glucopyranoside(12), 5,7, 4'-trihydroxy-3', 5'-dimethoxyflavone(1), 5, 4'-dihydroxy-7,3', 5' –trimethoxyflavone(2), daucosterol(3), Stigmast-5-ene-7-ol-3-O-β-glucoside(4), 5,7-dimethoxy chromanone (5), 5-hydroxy-3', 4',5'-trimethoxyflavone-7-O-β- glucopyranoside (6), 5-hydroxy-3', 4'-dimethoxyflavone-7-O-β-glucopyrano side (7), Acteoside (8), 3,4-dihydroxy-β-phenylethoxy-O-α-L-arabinopyranosyl-(1""→2")-α-L-rhamnopyranosyl-(1"'→3")-4"-O-caffeoyl-β-D-glucopyranoside (Angoroside) (9), 3-hydroxy-4-methoxy-β-phenylethoxy-O-[α-L-arabinopyranosyl- (1""→6")-α-L-rhamnopyranosyl-(1'"→3")-4"-O-caffeoyl-β-D-glucopyranoside(10), apigenin 7-O-β- D- (2",6"-di-O- p-coumaroyl) glucopyranoside(13), Among them, compound 11 and 12 were new diterpenoids, and compound 1-10, 13 were obtained from this plant for the first time. Aganosma marginata was one species of the Apocynaceae. Chemical studies on this plant haven’t been reported. 23 compounds were isolated from the 70% alcohol extract of the stems. Based on the spectroscopic and physic-chemical data, their struc tures were identified to be pregn-5-ene-3β,20β–diglucopyranosides(1),3-O-β-D-glucopyranosyl-3β,15α-dihydroxypregn-5-en-20-one(2), 3β, 20α-dihydroxy-5-en-pregane(3), 28-methylstigmast-5-en-3-ol(4), 29-norcycloart-23-ene-3,25-diol(5), 29-norcycloartan-3-ol(6), syringic acid -4-O-β-D-glucopyranoside(10), salicylic acid(11), nonanedioic acid(13), bis(2-ethylhexyl) phthalate(15), hexacosanoic acid-2,3-dihydroxy-propanenyl(20), 5,8,12-trihydroxy-9-octadecenoic acid(21), kaempferol 3-O-α-L-rhamnop yranosyl-(1→4)-α-D-glucopyranoside(16), kaempferol 3-O-α –glucopyranosyl(1→2)-β-D-glucopyranoside(17), kaempferol 3-O-α-L-rhamnopyranosyl-(1→4)- [α-L-rhamn opyranosyl-(1→4)]-β-D-glucopyranoside(18),kaempferol 3-O-α-L-rhamnopyranosyl-(1→4)-[ β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside(19), Geniposidic acid(7), Syringaresinol(8), syringaresinol-4,4'-O-bis-β-D-glucopyranoside(9), (2S,3S,4R) –phytosphingosine(22), nebularine(23), scopoletin(12), Among them, compound 1 was a new steroid, and compound 2-23 were obtained from this plant for the first time. Saurauia napaulensis, an endemic species belonging to the family of Saurauiaceae, is distributed in Xishuangbanna of Yunnan province. Some species of Saurauia were used in Chinese folk medicine for the treatment of fracture, injuries for falls, cold, cough, etc. since no work has been previously done on the chemical constituent of Saurauia napaulensis, we have, therefor, examined the stem and leaves of this plant and isolated 19 compounds and elucidated to be 2α,3α,24-trihydroxy-12-ursen-23-al -28-oic acid[3](7), oleanolic acid(1)[4],ursolic acid[5 ](2),2α,3β-dihydroxy-12-ursen-23-oic acid[ 6](4),2α-hydroxyursolic acid [7 ](3), 2α, 19α-dihydroxy-12-ursen-28-oic acid [8](5), 2α,3α, 24-trihydroxy-12-oleanen-28-oic acid[9](6),2α-hydroxy-3 -trans-p-c oumaroyl-ursolic acid [10](8), rosamultin [11](9), niga-ichigoside F1 [12 ](10), quercetin 3-O-β-D-glucopyranoside(13)[ 13],kaempferol 3-O-α-L-rhamnopynoside(14)[14], quercetin 3-O-α-L-rhamnopynoside(15)[15], (E)-3-(3-hydroxy-4-methoxyphenyl)acrylic acid carboxymethylester(11), 3, 4-dihydroxybenzoic acid[17](12), 19-fatty acid(16), 2S-heptacosanoic acid-2, 3-dihydroxy-propanenyl ester(17), Aschantin [18](18), grandisin (19) [ 19]. Erilaena kwangsiensis Hand., which is widely distributed in China was used as Lacciferlacca host, since no work has been previously done on the chemical constituents of Erilaenakwangsiensis, 22 compound were isolated from the 70% alcohol extract of the stems, based on the spectroscopic and physical-chemical data, their structures were identified to be lupenol[9](1),3-hydroxy-20(29)-lupen-28-oic acid [10](2), oleanolic acid[11](3), syringaresinol [12](4), (+)-pinoresinol[13](5),scopoletin [14](6),naringeninic acid[15](7),catechin [19](11),epicatechin[20](12), epicatechin-3-O-β-arabinofuranoside[18] (13),kaempferol 3-O-α-D-glucopyranoside [22](14), genistein [23]( 15), cis-dihydroquercetin-3-O-α-arabinofuranoside[25](17),trans-dihydroquercetin-3-O-β-arabinofuranoside[26](18), trans-dihydroquercetin-3-O-α-glucopyranoside [27](19), 4'-methoxy-3, 5, 7,3',5' –penthydroxyflavan[28](20), kaempferol 3-O-β-L-rha mnopyranosyl- (1→6)-β-D-glucopyranoside [29](21), quercetin 3-O-β-glucopyranosyl-(1→6)-β-D-glucopyranoside(22)[30], 4'-O-methylgallocatechin [24](16),2S-heptacosanoicacid-2, 3-dihydroxy-propanenyl ester [16](8),Glycerol 1-(9E-octadecenoate) [17](9),sitoindosideⅡ[18](10), all compounds were firesly isolated from this plant. The last chapter introduce the chemical constituents and active compounds from Sterculiaceae. Key words: Gomphostemma parviflorum; Leucas ciliata Benth; Aganosma marginata; Saurauia napaulensis; Erilaena kwangsiensis Hand; Sterculiaceae; chemical constituents; study
语种: 中文
内容类型: 学位论文
URI标识: http://ir.kib.ac.cn/handle/151853/198
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五种药用植物化学成分的研究.汪琼[d].中国科学院昆明植物研究所,2007.20-25
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