草珊瑚的保肝活性成分研究
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摘要
草珊瑚Sarcandra glabra(Thunb.)Nakai[曾用名Chloranthus glabra(Thunb.)Makinol,又名接骨金粟兰(通称)、肿节风、九节风(江西)、九节茶(浙江)等,属于金粟兰科(Chloranthaceae)草珊瑚属(Sarcandra Gardn.)植物,产于安徽、浙江、江西、福建、台湾、广东、广西、湖南、四川、贵州和云南。全株供药用,有良好的生物学活性,如抗肿瘤、抗炎、抗病毒、提高机体免疫力等。药理筛选结果表明:草珊瑚70%乙醇提取物过大孔树脂柱,70%乙醇洗脱部分有良好的肝保护活性,将70%乙醇洗脱部分过聚酰胺柱,得到的水、30%乙醇、60%乙醇洗脱部分均具有显著的保肝活性。
为了从草珊瑚中找到保肝活性成分,本论文运用多种色谱方法和波谱技术,对聚酰胺30%乙醇和60%乙醇洗脱部分进行了系统的化学成分研究,从中分离到了16个化合物,分别为7个倍半萜(苷)类化合物(1-7),2个香豆素类化合物(8-9),1个黄酮类化合物(10),3个酚酸类化合物(11-13),3个木脂素苷类化合物(14-16)。经理化及波谱数据分析结构鉴定为:8β,9α-dihydroxyeudesman-4(15),7(11)-dien-8α,12-olide(1),8β,9α-dihydroxylindan-4(5),7(11)-dien-Sα,12-olide(2),8β,9α-dihydroxylindan-4(15),7(11)-dien-8α,12-olide(3),chloranoside B(4),金粟兰内酯E(5),(-)-istanbulin A(6),白术内酯Ⅲ(7),isofraxidin(8),hemidesmin-1(9),(2R,3R)-3,3′,5,5′,7-五羟基双氢黄酮(10),methyl rosmarinate(11),ethylrosmarinate(12),N-trans-feruloyltyramine(13),(7S,8R) -dihydrodehydrodiconiferylalcohol(14),(7S,8R) -dihydrodehydrodiconiferyl alcohol 9-O-p-D-glucopyranoside(15),glochidioboside(16)。其中化合物1-3为三个新的倍半萜类化合物,化合物9-10,12-14为首次从该属植物中得到。药理筛选结果表明,化合物3,7对D-GalN引起的肝细胞损伤有保护作用。
化合物glabraoside A和glabraoside B为本课题组从草珊瑚70%乙醇提取物过大孔树脂柱30%乙醇洗脱部分中分得的苯丙素取代的儿茶素苷类化合物,在体外保肝活性筛选中,它们显示了一定的保肝活性。通过HPLC分析,发现大孔树脂70%乙醇洗脱部分过聚酰胺60%乙醇洗脱部分也含有此类成分,此类成分含有多个酚羟基,很难通过现有的分离手段进行大量分离,为了进一步研究该类成分的体内保肝活性,本论文探索了化合物glabraoside A和glabraoside B的合成方法,同时也对它们的葡萄糖苷衍生物进行了合成探索。
Sarcandra glabra(Thunb.) Nakai[syn.Chloranthus glabra(Thunb.) Makino] belongs to the genus Sarcandra of Chloranthaceae,which is distributed in Anhui, Zhejiang,Jiangxi,Fujian,Taiwan,Guangdong,Guangxi,Hunan,Sichuan,Guizhou and Yunnan Provinces.The whole plant was used as a drug for anticancer,antibacterial, antivirus and increasing the level of immunity.We separated the 70%alcohol extract of Sarcandra glabra on macroporous resin D101 using water and 30%,70%,95% EtOH-H_2O to elute.The result of bioassay displayed that the 70%EtOH- H_2O elution showed potent hepatoprotective activity.So we separated the 70%EtOH- H_2O elution on a polyamide column eluted with water and 30%,60%EtOH-H_2O,acetone to give four fractions.The subsequent bioassay showed that the polyamide 30%,60%EtOH-H_2O fractions have remarkable potent hepatoprotective activity.
In order to find the compounds have hepatoprotective activity from Sarcandra glabra,we studied the polyamide 30%,60%EtOH-H_2O fractions systemically in chemistry by means of chromatography methods and spectral technologies.Sixteen compounds were obtained and identified as 7 sesquiterpenoids(1-7),2 coumarins(8-9), 1 flavonoids(10),3 phenolic acids(11-13),3 lignans(14-16).Their structures were determined as:8β,9α-dihydroxyeudesman-4(15),7(11)-dien-8α,12-olide(1), 8β,9α-dihydroxylindan-4(5),7(11)-dien-Sα,12-olide(2),8α,9α-dihydroxylindan-4(15), 7(11)-dien-8α,12-olide(3),chloranoside B(4),chloranthalactone E(5),(-)-istanbulin A (6),atractylenolideⅢ(7),isofraxidin(8),hemidesmin-1(9),(2R,3R) -3,3',5,5',7-pentahydroxyflavanonol(10),methyl rosmarinate(11),ethyl rosmarinate(12), N-trans-feruloyltyramine(13),(7S,8R)-dihydrodehydrodiconiferyl alcohol(14), (7S,8R)-dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside(15), glochidioboside(16).Among them,compounds 1-3 are new sesquiterpenoids, compounds 9-10,12-14 were isolated from this genus for the first time.Compounds 3 and 7 showed hepatoprotective activity against D-GaiN-induced toxicity in WB-F344 cells.
Compounds glabraoside A and glabraoside B are phenylpropanoid-substituted catechin glycosides isolated from the D101 30%EtOH-H_2O elution,which showed potent hepatoprotective activity in our pharmacological experiment in vitro.We found that the D101 70%EtOH-H_2O elution also had this kind of constituents by HPLC analysis.It is hard to get a large quantity of them by means of chromatography methods because their structures contain many phenolic hydroxyl groups.So it is necessary to synthesize or semisynthesize them to supply enough quantity for pharmacological research in vivo.This paper discussed the synthetic method of compounds glabraoside A, glabraoside B and their glucoside derivants.
为了从草珊瑚中找到保肝活性成分,本论文运用多种色谱方法和波谱技术,对聚酰胺30%乙醇和60%乙醇洗脱部分进行了系统的化学成分研究,从中分离到了16个化合物,分别为7个倍半萜(苷)类化合物(1-7),2个香豆素类化合物(8-9),1个黄酮类化合物(10),3个酚酸类化合物(11-13),3个木脂素苷类化合物(14-16)。经理化及波谱数据分析结构鉴定为:8β,9α-dihydroxyeudesman-4(15),7(11)-dien-8α,12-olide(1),8β,9α-dihydroxylindan-4(5),7(11)-dien-Sα,12-olide(2),8β,9α-dihydroxylindan-4(15),7(11)-dien-8α,12-olide(3),chloranoside B(4),金粟兰内酯E(5),(-)-istanbulin A(6),白术内酯Ⅲ(7),isofraxidin(8),hemidesmin-1(9),(2R,3R)-3,3′,5,5′,7-五羟基双氢黄酮(10),methyl rosmarinate(11),ethylrosmarinate(12),N-trans-feruloyltyramine(13),(7S,8R) -dihydrodehydrodiconiferylalcohol(14),(7S,8R) -dihydrodehydrodiconiferyl alcohol 9-O-p-D-glucopyranoside(15),glochidioboside(16)。其中化合物1-3为三个新的倍半萜类化合物,化合物9-10,12-14为首次从该属植物中得到。药理筛选结果表明,化合物3,7对D-GalN引起的肝细胞损伤有保护作用。
化合物glabraoside A和glabraoside B为本课题组从草珊瑚70%乙醇提取物过大孔树脂柱30%乙醇洗脱部分中分得的苯丙素取代的儿茶素苷类化合物,在体外保肝活性筛选中,它们显示了一定的保肝活性。通过HPLC分析,发现大孔树脂70%乙醇洗脱部分过聚酰胺60%乙醇洗脱部分也含有此类成分,此类成分含有多个酚羟基,很难通过现有的分离手段进行大量分离,为了进一步研究该类成分的体内保肝活性,本论文探索了化合物glabraoside A和glabraoside B的合成方法,同时也对它们的葡萄糖苷衍生物进行了合成探索。
Sarcandra glabra(Thunb.) Nakai[syn.Chloranthus glabra(Thunb.) Makino] belongs to the genus Sarcandra of Chloranthaceae,which is distributed in Anhui, Zhejiang,Jiangxi,Fujian,Taiwan,Guangdong,Guangxi,Hunan,Sichuan,Guizhou and Yunnan Provinces.The whole plant was used as a drug for anticancer,antibacterial, antivirus and increasing the level of immunity.We separated the 70%alcohol extract of Sarcandra glabra on macroporous resin D101 using water and 30%,70%,95% EtOH-H_2O to elute.The result of bioassay displayed that the 70%EtOH- H_2O elution showed potent hepatoprotective activity.So we separated the 70%EtOH- H_2O elution on a polyamide column eluted with water and 30%,60%EtOH-H_2O,acetone to give four fractions.The subsequent bioassay showed that the polyamide 30%,60%EtOH-H_2O fractions have remarkable potent hepatoprotective activity.
In order to find the compounds have hepatoprotective activity from Sarcandra glabra,we studied the polyamide 30%,60%EtOH-H_2O fractions systemically in chemistry by means of chromatography methods and spectral technologies.Sixteen compounds were obtained and identified as 7 sesquiterpenoids(1-7),2 coumarins(8-9), 1 flavonoids(10),3 phenolic acids(11-13),3 lignans(14-16).Their structures were determined as:8β,9α-dihydroxyeudesman-4(15),7(11)-dien-8α,12-olide(1), 8β,9α-dihydroxylindan-4(5),7(11)-dien-Sα,12-olide(2),8α,9α-dihydroxylindan-4(15), 7(11)-dien-8α,12-olide(3),chloranoside B(4),chloranthalactone E(5),(-)-istanbulin A (6),atractylenolideⅢ(7),isofraxidin(8),hemidesmin-1(9),(2R,3R) -3,3',5,5',7-pentahydroxyflavanonol(10),methyl rosmarinate(11),ethyl rosmarinate(12), N-trans-feruloyltyramine(13),(7S,8R)-dihydrodehydrodiconiferyl alcohol(14), (7S,8R)-dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside(15), glochidioboside(16).Among them,compounds 1-3 are new sesquiterpenoids, compounds 9-10,12-14 were isolated from this genus for the first time.Compounds 3 and 7 showed hepatoprotective activity against D-GaiN-induced toxicity in WB-F344 cells.
Compounds glabraoside A and glabraoside B are phenylpropanoid-substituted catechin glycosides isolated from the D101 30%EtOH-H_2O elution,which showed potent hepatoprotective activity in our pharmacological experiment in vitro.We found that the D101 70%EtOH-H_2O elution also had this kind of constituents by HPLC analysis.It is hard to get a large quantity of them by means of chromatography methods because their structures contain many phenolic hydroxyl groups.So it is necessary to synthesize or semisynthesize them to supply enough quantity for pharmacological research in vivo.This paper discussed the synthetic method of compounds glabraoside A, glabraoside B and their glucoside derivants.
引文
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