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茵陈蒿和桑叶的成分以及固相色谱法对茵陈蒿汤效应物质的研究
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摘要
通过各种现代色谱技术(大孔树脂柱色谱、硅胶柱色谱、Sephadex LH-20凝胶柱色谱、反相ODS中低压柱色谱和HPLC)从茵陈蒿的水提物中,分离得到33个单体化合物,通过理化性质和光谱分析,鉴定了其中30个化合物的结构,其中新化合物2个,3个聚炔类为该属植物中首次分离得到,分别为:6'-O-caffeoyl-p-hydroxy-acetophenone-4-O-β-D-glucopyranoside(1);9-[1-(3,4-dihydroxyphenyl)ethyl]benzene-adenin e(2);3(R)-癸-4,6,8-三炔-1,3-二醇(3);3(R)-癸烯-4,6-二炔-1,3,8-三醇(4);3(R)-9-癸-4,6,8-三炔-1,3-二醇一1-O-β-D-吡喃葡萄糖苷(5);7-羟基-香豆素(6);6,7-二甲氧基-香豆素(7);6-甲氧基-7-羟基-香豆素(8);7-甲氧基-香豆素(9);对羟基苯乙酮(10);4-羟基-3-甲氧基苯乙酮(11);烟酸(12);苯甲醇-O-β-D-吡喃葡萄糖苷(13);苯甲酸(14);乙二酸(15);丁二酸(16);槲皮素(17):金丝桃苷(18);胸腺嘧啶(19);胸腺嘧啶脱氧核苷(20);尿嘧啶(21);香草醛(22);香草酸(23);对羟基苯乙酮-4-O-β-D-吡喃葡萄糖苷(24);邻羟基苯甲酸(25);3-甲氧基咖啡酸-4-O-β-D-吡喃葡萄糖苷(26);槲皮素-7-α-D-吡喃鼠李糖苷(27);正丁基-β-D-吡喃果糖苷(28);loliolide(29);邻苯二甲酸二(2-乙基-己基)酯(30)。
     同时从桑叶的水提物中,分离得到31个单体化合物,通过理化性质和光谱分析,鉴定了其中25个化合物的结构,其中分别为acetyl-loliolide(1);对羟基苯甲酸(2);dehydrololiolide(3);loliolide(4);邻苯二酚(5);莨菪亭(6);苯甲醇-O-β-D-吡喃葡萄糖苷(7):3β-hydroxy-5α,6α-epoxy-7-megastimen-9-one(8);6,7-二羟基香豆素(9);环(亮氨酸-异亮氨酸)(10);槲皮素(11);3,4-二羟基苯甲酸(12);异落叶松脂素(13);刺五加酮(14);7,8-二羟基香豆素(15);环(丙氨酸-亮氨酸)(16):香草酸-4-O-β-D-葡萄糖苷(17);胸腺嘧啶(18);胸腺嘧啶脱氧核苷(19);环(苯丙氨酸-酪氨酸)(20);丁二酸(21);天冬氨酸(22);苯丙氨酸(23);缬氨酸(24);酪氨酸(25)。其中化合物1、3、4、7为从该植物中首次分离得到。
     生物亲和色谱是利用自然界中存在的特异性相互作用生物物质对,通常具有很高的选择性,代表性物质有酶-底物、酶-抑制剂、激素互补接受体、抗体-抗原、药物-受体等。是利用生物活性物质的特异性相互作用进行生物样品分离分析和生物活性参数测定的新兴技术。本文建立了肝细胞固相色谱法并应用其对茵陈蒿汤的组方中茵陈蒿,栀子,大黄的效应成分进行分析。结果在茵陈蒿中得到四个效应物质的特征峰,通过各种分离手段及应用各种波谱数据鉴定了其中三个成分,分别为7-羟基-香豆素、7-甲氧基-香豆素、Capillartemisin A。在栀子中得到两个效应物质的特征峰,其中一个经与对照品共液相鉴定为栀子苷。
The water extracts from Artemisia capillaries Thurb and Morus alba L leaves were individually separated by modem chromatographic methods,such as silica gel col umn chromatography,Sephadex LH-20,TLC and semi-preparative reversed phase HPL C,and so on.The structures of compounds were elucidated on the basis of spectrosco pic methods(UV,IR,NMR,MS and CD) and their physical-chemical properties.
     30 compounds were isolated from A.capillaries Thurb and were identified as 6'-O -caffeoyl-p-hydroxy-acetophenone-4-O-β-D-glucopyranoside(1);9-[1-(3,4- dihydroxyphe nyl)ethyl]benzene-adenine(2);3(R)-deca-4,6,8-triyne-l,3-diol(3);3(R)-decene-4,6-diyne-1, 3,8-triol(4);3(R)-9-deca-4,6,8-triyne-1,3-diol-1-O-β-D-glucopyranoside(5);7-hydroxycou marin(6);6,7-dimethoxycoumarin(7);6-methoxy-7-hydroxycoumarin(8);7-methoxycouma rin(9);4-hydroxyacetophenone(10);4-hydroxy-3-methoxyacetophenone(11);nicotinic aci d(12);benzenecarbinol-O-β-D- glucopyranoside(13);benzoic acid(14);oxalic acid(15); amber acid(16):quercetin(17);hyperoside(18);thymine(19);thymine ribonucleosi de(20);uracil(21);vanillin(22);vanillic acid(23);4-hydroxyacetophenone -4-O-β-D-glucopyranoside(24);2-hydro- benzoic acid(25);3-methoxy-caffeic acid a-4 -O-β-D-glucopyranoside(26);quercetin-7-β-D-glucopyranoside(27);isorhamnetin-3-O -β-D-glueopyranoside(28);loliolide(29);phthalic acid bis-(2-ethylhexyl) ester(30)。
     25 compounds were isolated from M.alba leaves and were identified as acetyl-lol iolide(1);4-hydroxy- benzoic acid(2);dehydrololiolide(3);loliolide(4);o-dihydrox ybenzene(5):scopoletine(6);benzenecarbinol-O-β-D-glucopyranoside(7);3β-hydroxy-5α,6α-epoxy-7-megastimen-9-one(8);6,7-dihydroxycoumarin(9);cyclo-(Leu-Ile) (10);cyclo(Phe-Tyr)(11);3,4-dihydroxy-benzoic acid(12);isolarieiresinol(13);ci wujiatone(14);7,8-dihydroxycoumarin(15);cyclo(ala-leu)(16);vanillic acid-4-O-β-D-glucopyranoside(17);thymine(18);thymine ribonucleoside(19);quercetin(20); amber acid(21);aspartate(22);thenylalanine(23);valine(24);tyrosine(25)。
     Bio affinity chromagraphy was a method which use some selective and specific pairs of substance existed in biological environment,such as enzyme-substrate,enzyme -inhibitor,hormone-receptor,antibody-antigen,medicine-receptor to analyze bio active s ubstance.Certain selective analysis and separation were archived by using these pairs. We established liver cell membrane solid phase chromatography in our reseach and pu t it into use in the analysis of active substance in Inchenhaotang.In result,we get 4 selected peaks in Artemisia capillaries Thurh and three of them were identified as 7-h ydroxycoumarin,7-methoxycoumarin and Capillartemisin A.2 peaks were obtained fro m Gardenia jasminoides Ellis and one of the them was identified as geniposide.
引文
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