北葶苈子化学成分的研究
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摘要
目的研究北葶苈子的化学成分。方法采用Dianion HP-20、Toyopearl HW-40柱、ODS、Sephadex LH-20、半制备液相等方法对北葶苈子水提物进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。结果从中分离得到19个化合物,分别鉴定为3,5-二羟基-4-甲氧基苯甲酸(1)、原儿茶酸甲酯(2)、对羟基苯甲酸(3)、1,2-benzenedicarboxylic acid-1,2-bis [2-(2-hydroxyethoxy) ethyl] ester (4)、苄基-β-D-葡萄糖苷(5)、2-苯乙基-1-O-β-D-吡喃葡萄糖苷(6)、对羟基苯乙腈(7)、邻羟基苯乙腈(8)、N-乙酰基色氨酸(9)、尿嘧啶核苷(10)、methyl dioxindole 3-acetate (11)、dioxindole-3-acetic acid (12)、环(L-脯氨酸-L-苯丙氨酸)(13)、4-amino-4-carboxychroman-2-one (14)、槲皮素-3-O-β-D-吡喃半乳糖苷(15)、异鼠李素-3-O-β-D-吡喃半乳糖苷(16)、山柰酚-3-O-β-D-半乳糖苷(17)、三叶苷(18)、根皮素-2',4'-二-O-β-D-吡喃葡萄糖苷(19)。结论化合物1～9、11～19为首次从该植物中分离得到。
AIM To study the chemical constituents from the seeds of Lepidium apetalum Willd.. METHODS The aqueous extract from the seeds of L. apetalum was isolated and purified by Dianion HP-20,Toyopearl HW-40 column,ODS,Sephadex LH-20 and semi-preparative column,then the structures of obtained compounds were identified by physicochemical properties and spectral data. RESULTS Nineteen compounds were isolated and identified as 3,5-dihydroxy-4-methoxy-benzoic acid( 1),protocatechuic acid methyl ester( 2),1,2-benzenedicarboxylic acid-1,2-bis [2-( 2-hydroxyethoxy) ethyl] ester( 3),benzyloxy-1-O-β-D-glucopyranoside( 4),2-phenylethy-1-O-β-D-glucopyranoside( 5),4-hydroxybenzyl cyanide( 6),2-hydroxy-benzeneacetonitrile( 7),Nacetyltryptophan( 8),uridine( 9),2-hydroxybenzamide( 10),methyl dioxindole 3-acetate( 11),dioxindole-3-acetic acid( 12),cyclo( L-Pro-L-Phe)( 13),4-amino-4-carboxychroman-2-one( 14),quercetin-3-O-β-D-galactopyranoside( 15), isorhamnetin-3-O-β-D-galactopyranoside( 16), kaempferol-3-O-β-D-galactopyranoside( 17),trilobatin( 18),phloretin-2',4'-di-O-β-D-glucopyranoside( 19). CONCLUSION Compounds 1-9,11-19 are isolated from this plant for the first time.
AIM To study the chemical constituents from the seeds of Lepidium apetalum Willd.. METHODS The aqueous extract from the seeds of L. apetalum was isolated and purified by Dianion HP-20,Toyopearl HW-40 column,ODS,Sephadex LH-20 and semi-preparative column,then the structures of obtained compounds were identified by physicochemical properties and spectral data. RESULTS Nineteen compounds were isolated and identified as 3,5-dihydroxy-4-methoxy-benzoic acid( 1),protocatechuic acid methyl ester( 2),1,2-benzenedicarboxylic acid-1,2-bis [2-( 2-hydroxyethoxy) ethyl] ester( 3),benzyloxy-1-O-β-D-glucopyranoside( 4),2-phenylethy-1-O-β-D-glucopyranoside( 5),4-hydroxybenzyl cyanide( 6),2-hydroxy-benzeneacetonitrile( 7),Nacetyltryptophan( 8),uridine( 9),2-hydroxybenzamide( 10),methyl dioxindole 3-acetate( 11),dioxindole-3-acetic acid( 12),cyclo( L-Pro-L-Phe)( 13),4-amino-4-carboxychroman-2-one( 14),quercetin-3-O-β-D-galactopyranoside( 15), isorhamnetin-3-O-β-D-galactopyranoside( 16), kaempferol-3-O-β-D-galactopyranoside( 17),trilobatin( 18),phloretin-2',4'-di-O-β-D-glucopyranoside( 19). CONCLUSION Compounds 1-9,11-19 are isolated from this plant for the first time.
引文
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[18]吴慧星,李晓帆,李荣,等.番石榴叶中抗氧化活性成分的研究[J].中草药,2010,41(10):1593-1597.
[19]吴斌,林文辉.昙花化学成分的研究[J].中国药学杂志,2010,45(7):496-499.
[20]冯宁,卢成淑,南国,等.栀子花的化学成分研究[J].中草药,2016,47(2):200-203.
[21]卢静,杨丰庆,夏之宁.尖嘴林檎叶的化学成分[J].中成药,2014,36(8):1692-1696.
[22] Bognar R,Tokes A L,Frenzel H,et al. Flavonoids. XVI.Mono-and diglucosides of phloracetophenone and their conversion into chalcone,flavanone,and phlorizin glucosides[J]. Acta Chim,1969,61:79-91.
[2]冯卫生,张志广,李孟,等.北葶苈子化学成分研究[J].中国药学杂志,2018,53(1):16-19.
[3]李孟,郑晓珂,张志广,等.从北葶苈子中分离到的一个新苯乙酰胺类化合物[J].药学学报,2016,51(12):1881-1884.
[4]孔丽娟,梁侨丽,吴启南,等.黑三棱的化学成分研究[J].中草药,2011,42(3):440-442
[5]张翠,刘占云,於洪建,等.黑豆种皮的酚酸类成分研究[J].中草药,2013,44(24):3440-3443.
[6]李艳茸,李春,王智民,等.藏药甘青乌头化学成分研究(Ⅲ)[J].中国中药杂志,2014,39(7):1163-1167.
[7]张伟.化学表观遗传修饰法研究海葵来源月状旋孢腔菌代谢产物多样性初探[D].青岛:中国海洋大学,2014.
[8]贺兰云,黄海疆.红茴香甲醇部位化学成分研究[J].中国中药杂志,2014,39(5):857-859.
[9]夏芳,孙建,姜勇,等.白木香叶的化学成分研究(二)[J].中国中药杂志,2013,38(19):3299-3303.
[10]张普照,苏明声,王雅琪,等.白苞裸蒴化学成分研究[J].中草药,2016,47(19):3366-3369.
[11]张贞霞.中药天葵子化学成分的研究[D].天津:天津大学,2004.
[12]王宏鹏,楼坚,陈丽春,等.芽孢杆菌HZ16发酵产物中的环二肽类化学成分[J].天然产物研究与开发,2017,29(5):783-786.
[13]李雯,王国才,张晓琦,等.中药壁虎化学成分研究[J].中国中药杂志,2010,35(18):2412-2415.
[14] Ohmoto T,Yamaguchi K,Ikeda K. Constituents of Hibiscus mpscheutos L.Ⅰ[J]. Chem Pharm Bull,1988,36(2):578-581.
[15] Donoso R,Leiva-Novoa P,Zú1iga A,et al. Biochemical and genetic bases of indole-3-acetic acid(auxin phytohormone)degradation by the plant-growth-promoting rhizobacterium paraburkholderia phytofirmans PsJN[J]. Appl Environ Microbiol,2017,83(1):1-20.
[16]李旸,王芳,张普照,等.美洲大蠊化学成分研究[J].中药材,2015,38(10):2038-2041.
[17]蒲首丞,郭远强,高文远.鹅不食草化学成分的研究[J].中国中药杂志,2009,34(12):1520-1522.
[18]吴慧星,李晓帆,李荣,等.番石榴叶中抗氧化活性成分的研究[J].中草药,2010,41(10):1593-1597.
[19]吴斌,林文辉.昙花化学成分的研究[J].中国药学杂志,2010,45(7):496-499.
[20]冯宁,卢成淑,南国,等.栀子花的化学成分研究[J].中草药,2016,47(2):200-203.
[21]卢静,杨丰庆,夏之宁.尖嘴林檎叶的化学成分[J].中成药,2014,36(8):1692-1696.
[22] Bognar R,Tokes A L,Frenzel H,et al. Flavonoids. XVI.Mono-and diglucosides of phloracetophenone and their conversion into chalcone,flavanone,and phlorizin glucosides[J]. Acta Chim,1969,61:79-91.