中药复方制剂炎宁颗粒的化学成分研究
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摘要
炎宁颗粒为我国中药保护品种,具有清热解毒,消炎止痢之功效,主要由玄参科鹿茸草属植物鹿茸草(Monochasma savatieri Franch)、茜草科耳草属植物白花蛇舌草(Hedyotis diffusa)和鸭跖草科鸭跖草属植物鸭跖草(Commelina communis)以2：1：1比例组成,临床用于上呼吸道感染,扁桃体炎,尿路感染,急性菌痢,肠炎等多种炎症型疾病。本论文采用活性跟踪分离等现代天然药物研究思路和方法,对炎宁颗粒的化学成分和药理活性进行了较系统研究,旨在为炎宁颗粒的二次开发和临床应用提供化学及药理学基础。
本研究采用滤纸片法对不同提取方案的炎宁颗粒进行体外抗菌的活性筛选,并采用巴豆油和二甲苯致小鼠耳廓肿胀急性炎症模型,研究不同提取方案的炎宁颗粒的抗炎作用,确定了炎宁颗粒AB-8大孔树脂30%乙醇洗脱部位为具有明显抗菌抗炎活性部位。
本文在综述了炎宁颗粒处方中三种药材的化学成分和药理活性研究的基础上,采用反复硅胶柱色谱法、大孔树脂、sephadex LH-20、反相ODS、半制备型HPLC等多种色谱手段从炎宁颗粒抗菌抗炎活性部位中,分离得到40个化合物。并通过理化性质、波谱数据分析(IR, NMR、MS等)和化学方法鉴定了它们的结构,分别为savatisideA、B、C、D、E、F、G、H(1-8)、异阿克替苷(isoacteoside,9)、肉苁蓉苷D (cistanoside D,10)、广防风苷A(epimeridinoside A,11)、Parvifloroside B (12)、Torenoside-B (13)、阿克替苷(acteoside,14)、osmanthuside B (15)、(7S,8R) dehydrodiconiferyl alcohol9'-β-glucopyranoside (16)、(+)-isolariciresinol (17)、5-methoxy-(+)-isolariciresinol (18)、(-)-secoisolariciresinol (19)、7,7'-dihydrosecoisolariciresinol (20)、7-hydroisolariciresinol (21)、8-O-乙酰基玉叶金花苷(8-O-Acetylmussaenoside,22)、8-O-乙酰基玉叶金花苷酸(8-O-Acetylmussaenosidic acid,23)、Nepetanudoside B(24)、7-O-乙酰基马钱子酸(7-O-acetylloganic acid,25)、Methyl9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoeate (26)、9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoic acid (27) Methyl9,12,13-trihydroxyoctadeca-10(E)-enoeate (28)、9,12,13-trihydroxyoctadeca-10(E)-enoic acid (29)、 Methyl8,11,12-trihydroxyoctadeca-9(E)-enoeate(30)、对羟基桂皮酸(p-hydroxy cinnamic acid,31)、异阿魏酸(isoferulic acid,32)、香草酸(Vanillic acid,33)、齐墩果酸(Oleanolic acid,34)、芹菜素(Apigenin,35)、木犀草素(Luteolin,36)、槲皮素(Quercetin,37)、芦丁(Rutin,38)、山奈酚(Kaempferol,39)、4-羟基-1-甲氧基蒽醌(4-hydroxy-1-methoxyanthraquinone,40)。
其中未见文献报道的新化合物8个,分别为化合物1-8,其中化合物7、8为新骨架类型化合物。
通过经典途径对分离得到的12个苯乙醇苷类单体化合物的抗补体活性进行了初步筛选,结果显示：与阳性对照化合物肝素钠盐比较,12个苯乙醇苷类均具有明显抗补体活性,其中苷元7位未羟基化的化合物体外抗补体活性要强于苷元7位羟基化的化合物。
Yanning granula consists of Monochasma savatieri Franch、Commelina communis L.and Hedyotis diffusa Willd.(2:1:1), which has been listed in the Catalogue of National Protected TCM Medicines, clinically used for the treatment of upper respiratory tract infection, tonsillitis, urinary tract infection, acute dysentery, enteritis and other inflammatory diseases.
In order to get some information for the further R&D clinical application, the chemical constituents and their antibacterial and anti-inflammatory activities were investigated systematically.
Using the filter paper method to study the antibacterial activity in vitro of Yanning granula extracted in different ways, and using croton oil and paraxylene induced mouse ear edema acute inflammation models to study their anti-inflammatory effects, the30%EtOH fraction eluted by Diaion AB-8column of Yanning granula was confirmed as the active site.
Guided by active tracking method, forty compounds were isolated by chromatography on silica gel, Sephadex LH-20gel columns, and reverse phase Semi-preparation HPLC repeatedly from the active fraction of Yanning granula, and their structures were identified by spectroscopic analysis (NMR and MS). These isolates were identified to be savatiside A、B、C、D、E、F、G、H (1-8), isoacteoside (9), cistanoside D (10), epimeridinoside A (11), Parvifloroside B (12), Torenoside-B (13), acteoside (14), osmanthuside B (15),(7S,8R)dehydrodiconiferyl alcohol9'-β-glucopyranoside (16),(+)-isolariciresinol (17),5-methoxy-(+)-isolariciresinol (18),(-)-secoisolariciresinol (19),7,7'-dihydrosecoisolariciresinol (20),7-hydroisolariciresinol (21),8-O-Acetylmussaenoside (22),8-O-Acetylmussaenosidic acid (23), Nepetanudoside B (24),7-O-acetylloganic acid (25), Methyl9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoeate (26),9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoic acid (27), Methyl9,12,13-trihydroxyoctadeca-10(E)-enoeate (28),9,12,13-trihydroxyoctadeca-10(E)-enoic acid (29), Methyl8,11,12-trihydroxyoctadeca-9(E)-enoeate (30),p-hydroxy cinnamic acid (31), isoferulic acid (32), Vanillic acid (33), Oleanolic acid (34), Apigenin (35), Luteolin (36), Quercetin (37), Rutin (38), Kaempferol (39),4-hydroxy-l-methoxyanthraquinone (40).
Among them, compounds1-8were new compounds, and compounds7and8have a rare skeleton of bis-iridoid glycoside with a carbohydrate chain located at C-3.
Moreover, all of the12phenylethanoid glycosides isolated were evaluated for anticomplement activities using an in vitro assay of the complement system of the classical pathway, and all the compounds were proved to be capable of inhibiting complement activity with IC50value of95-135μM. Preliminary analysis of the structure-activity relationship from these natural phenyethanoid glycosides revealed that compounds with a hydroxy group at C-a (1,2,3,4,5and11) had a slightly decreased anticomplement activity.
本研究采用滤纸片法对不同提取方案的炎宁颗粒进行体外抗菌的活性筛选,并采用巴豆油和二甲苯致小鼠耳廓肿胀急性炎症模型,研究不同提取方案的炎宁颗粒的抗炎作用,确定了炎宁颗粒AB-8大孔树脂30%乙醇洗脱部位为具有明显抗菌抗炎活性部位。
本文在综述了炎宁颗粒处方中三种药材的化学成分和药理活性研究的基础上,采用反复硅胶柱色谱法、大孔树脂、sephadex LH-20、反相ODS、半制备型HPLC等多种色谱手段从炎宁颗粒抗菌抗炎活性部位中,分离得到40个化合物。并通过理化性质、波谱数据分析(IR, NMR、MS等)和化学方法鉴定了它们的结构,分别为savatisideA、B、C、D、E、F、G、H(1-8)、异阿克替苷(isoacteoside,9)、肉苁蓉苷D (cistanoside D,10)、广防风苷A(epimeridinoside A,11)、Parvifloroside B (12)、Torenoside-B (13)、阿克替苷(acteoside,14)、osmanthuside B (15)、(7S,8R) dehydrodiconiferyl alcohol9'-β-glucopyranoside (16)、(+)-isolariciresinol (17)、5-methoxy-(+)-isolariciresinol (18)、(-)-secoisolariciresinol (19)、7,7'-dihydrosecoisolariciresinol (20)、7-hydroisolariciresinol (21)、8-O-乙酰基玉叶金花苷(8-O-Acetylmussaenoside,22)、8-O-乙酰基玉叶金花苷酸(8-O-Acetylmussaenosidic acid,23)、Nepetanudoside B(24)、7-O-乙酰基马钱子酸(7-O-acetylloganic acid,25)、Methyl9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoeate (26)、9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoic acid (27) Methyl9,12,13-trihydroxyoctadeca-10(E)-enoeate (28)、9,12,13-trihydroxyoctadeca-10(E)-enoic acid (29)、 Methyl8,11,12-trihydroxyoctadeca-9(E)-enoeate(30)、对羟基桂皮酸(p-hydroxy cinnamic acid,31)、异阿魏酸(isoferulic acid,32)、香草酸(Vanillic acid,33)、齐墩果酸(Oleanolic acid,34)、芹菜素(Apigenin,35)、木犀草素(Luteolin,36)、槲皮素(Quercetin,37)、芦丁(Rutin,38)、山奈酚(Kaempferol,39)、4-羟基-1-甲氧基蒽醌(4-hydroxy-1-methoxyanthraquinone,40)。
其中未见文献报道的新化合物8个,分别为化合物1-8,其中化合物7、8为新骨架类型化合物。
通过经典途径对分离得到的12个苯乙醇苷类单体化合物的抗补体活性进行了初步筛选,结果显示：与阳性对照化合物肝素钠盐比较,12个苯乙醇苷类均具有明显抗补体活性,其中苷元7位未羟基化的化合物体外抗补体活性要强于苷元7位羟基化的化合物。
Yanning granula consists of Monochasma savatieri Franch、Commelina communis L.and Hedyotis diffusa Willd.(2:1:1), which has been listed in the Catalogue of National Protected TCM Medicines, clinically used for the treatment of upper respiratory tract infection, tonsillitis, urinary tract infection, acute dysentery, enteritis and other inflammatory diseases.
In order to get some information for the further R&D clinical application, the chemical constituents and their antibacterial and anti-inflammatory activities were investigated systematically.
Using the filter paper method to study the antibacterial activity in vitro of Yanning granula extracted in different ways, and using croton oil and paraxylene induced mouse ear edema acute inflammation models to study their anti-inflammatory effects, the30%EtOH fraction eluted by Diaion AB-8column of Yanning granula was confirmed as the active site.
Guided by active tracking method, forty compounds were isolated by chromatography on silica gel, Sephadex LH-20gel columns, and reverse phase Semi-preparation HPLC repeatedly from the active fraction of Yanning granula, and their structures were identified by spectroscopic analysis (NMR and MS). These isolates were identified to be savatiside A、B、C、D、E、F、G、H (1-8), isoacteoside (9), cistanoside D (10), epimeridinoside A (11), Parvifloroside B (12), Torenoside-B (13), acteoside (14), osmanthuside B (15),(7S,8R)dehydrodiconiferyl alcohol9'-β-glucopyranoside (16),(+)-isolariciresinol (17),5-methoxy-(+)-isolariciresinol (18),(-)-secoisolariciresinol (19),7,7'-dihydrosecoisolariciresinol (20),7-hydroisolariciresinol (21),8-O-Acetylmussaenoside (22),8-O-Acetylmussaenosidic acid (23), Nepetanudoside B (24),7-O-acetylloganic acid (25), Methyl9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoeate (26),9,12,13-trihydroxyoctadeca-10(E),15(E)-dienoic acid (27), Methyl9,12,13-trihydroxyoctadeca-10(E)-enoeate (28),9,12,13-trihydroxyoctadeca-10(E)-enoic acid (29), Methyl8,11,12-trihydroxyoctadeca-9(E)-enoeate (30),p-hydroxy cinnamic acid (31), isoferulic acid (32), Vanillic acid (33), Oleanolic acid (34), Apigenin (35), Luteolin (36), Quercetin (37), Rutin (38), Kaempferol (39),4-hydroxy-l-methoxyanthraquinone (40).
Among them, compounds1-8were new compounds, and compounds7and8have a rare skeleton of bis-iridoid glycoside with a carbohydrate chain located at C-3.
Moreover, all of the12phenylethanoid glycosides isolated were evaluated for anticomplement activities using an in vitro assay of the complement system of the classical pathway, and all the compounds were proved to be capable of inhibiting complement activity with IC50value of95-135μM. Preliminary analysis of the structure-activity relationship from these natural phenyethanoid glycosides revealed that compounds with a hydroxy group at C-a (1,2,3,4,5and11) had a slightly decreased anticomplement activity.
引文
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