圆锥绣球的化学成分及生物活性研究
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摘要
圆锥绣球(Hydrangea paniculata Sieb)为虎耳草科(Saxifragaceae)绣球属(Hydrangea)植物,广泛分布于我国安徽、江西、浙江、广西、云南等地。《中国中药资源志要》记载圆锥绣球全株清热抗疟,根截疟退热,消积和中。实验动物药效学结果表明,圆锥绣球茎提取物对顺铂所致的急性肾损伤有一定的保护作用,作用与阳性对照药相当。因此,为了寻找生物活性成分,本文采用硅胶柱层析、凝胶柱层析、中压柱色谱、高效液相柱色谱等方法对圆锥绣球茎提取物和叶提取物分别进行了系统的化学成分分离。
从圆锥绣球茎枝中分离得到了55个化合物,经理化及波谱数据分析,发现11个新化合物(1*-11*)。其中1*-8*为香豆素苷类化合物,分别命名为：伞形花内酯7-O-β-D-槐糖苷(1*),伞形花内酯7-O-β-D-葡萄糖基-(1→3)-β-D-葡萄糖苷(2*),伞形花内酯7-O-β-D-葡萄糖基-(1→3)-[β-D-芹糖基-(1→6)]-β-D-葡萄糖苷(3’),伞形花内酯7-O-β-D-葡萄糖基-(1→2)-β-D-芹糖基-(1→6)-β-D-葡萄糖苷(4*),伞形花内酯7-O-β-D-葡萄糖基-(1→5)β-D-芹糖基-(1→6)-β-D-葡萄糖苷(5*),(7"'R,8"'R)-umbelliferone-7-O-[6'-(4-guaiacylglycerol-β-ether)-feruloyl)]-β-D-glucopyranoside (6*)(7"S,8"'R)umbelliferone-7-O-[6'-(4-erythro-guaiacylglycerol-β-ether)-feruloyl)]-β-D-glucopyranoside (7*), hydrangeside A (8)。化合物9*-11*为环烯醚萜苷类化合物,分别命名为：7-0-/β-D-glucopyranosyl loganin (9*),7-O-E-isoferuloyl loganic acid (10*), hydrangeside B (11*)。通过对照文献鉴定化合物12-19为香豆素类,20-32为环烯醚萜类,33-42,54为木脂素类,43-51为酚酸类,52,53,55为其他类。
从圆锥绣球叶中分离得到了34个化合物,发现3个新的单萜类化合物(56*-58‘),分别命名为hydrangenine A, B, C。其余通过对照文献鉴定：化合物59-63为单萜类,64-66为二萜类,67-71为降碳异戊二烯类,72-75为黄酮类,76,77为香豆素苷类,78,82-85为酚酸类,80,81为木脂素类,79为生物碱类,86-89为其他类。
本文在多种药理模型上对这些单体化合物进行了活性筛选。在浓度为10μM时,香豆素类化合物1、3、5、10、12-14、17、19,环烯醚帖类化合物20、21、25、31、32,及化合物39、40、50对鱼藤酮或去血清诱导损伤的PC12细胞有保护作用。化合物3、10、14、21、23、24、28、29、31、32及45-48对DL-半乳糖胺诱导损伤的肝细胞有保护活性。化合物32对醛糖还原酶有一定的抑制活性。
圆锥绣球中含有大量的茵芋苷及其苷元伞形花内酯。动物药效评价实验结果表明,茵芋苷对糖尿病肾病有较好的治疗作用。药物所筛选中心研究发现另一个与茵芋苷结构相似的香豆素苷类化合物秦皮甲素具有较好的AGES抑制作用,能对抗实验性高脂血症,抑制动脉粥样硬化的形成,是一个潜在的抗糖尿病血管病变的药物。基于两者结构及活性的类似性,为了寻找抗糖尿病血管病变的化合物,本论文根据药物设计中的拼合原理,分别在茵芋苷、秦皮甲素及伞形花内酯上引入一些结构片段,合成了19个化合物(1-19)。包括3个苯丙烯酸茵芋苷酯(1-3),2个苯甲酸茵芋苷酯(4,5),4个苯丙烯酸秦皮甲素酯(6-8,11),2个苯甲酸秦皮甲素酯(9,10),3个苯丙烯酸香豆素酯(12-14),5个7-O-烷基化秦皮甲素(15-19),其中1-10,16,18,19为新化合物。并对化合物1-19进行了与糖尿病血管病变相关的生物活性的评价。体外活性评价显示,化合物5、8、11、12、14、17对ADP诱导的血小板聚集表现出显著的抑制作用,化合物3、8、13表现出明显的自由基清除作用。动物药效评价实验结果表明,化合物15能对抗实验性高脂血症,抑制动脉粥样硬化的形成。
Hydrangea paniculata Sieb.(Saxifragaceae) is widely distributed in Anhui, Jiangxi, Zhejiang, Guangxi, Yunnan Provinces and so on. The plant is used to bring down fever, relieve sore throat and treat malaria in folk medicine. Our previous studies have found that the effective fraction of H. paniculata is used to make pharmaceutical components for the prevention and/or treatment of renal insufficiency, hypertension and diabetic nephropathy. As a part of our ongoing screening program for bioactive compounds, we studied the chemical constituents of the stems and leaves of H. paniculata systematically by means of chromatography methods and spectral technologies.
Our investigation of the water extracts of stems of this plant led to the isolation of fifty-five compounds including eleven new compounds (1*-11*). Their structures were elucidated on the basis of spectroscopic and chemical methods. Compounds1*-8*were new coumarin glycosides, determined as:umbelliferone7-O-sophoroside(1*), umbelli-ferone7-O-β-D-glucopyranosyl(1→3)-β-D-glucopyranoside(2*), umbelliferone7-O-β-D-glucopyranosyl(1→3)-[β-D-apiofuranosyl(1→6)]-β-D-glucopyranoside (3*), umbe-lliferone7-O-β-D-glucopyranosyl(1→2)-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside (4*), umbelliferone7-O-β-D-glucopyranosyl(1→5)-β-D-apiofuranosyl(1→6)-β-D-glucop-yranoside (5*),(7"'R,8'"R) umbelliferone-7-O-[6'-(4-threo-guaiacylglycerol-β-ether)-feruloyl)]-β-D-glucopyranoside (6*),(7"'S,8"'R)-umbelliferone-7-O-[6'-(4-guaiacylgly-cerol-β-ether)-feruloyl)]-β-D-glucopyranoside (7*), hydrangeside A (8*). Compounds9*-11*were new iridoid glucosides, determined as:7-O-β-D-glucopyranosyl loganin (9*),7-O-E-isoferuloyl loganic acid (10*), hydrangeside B (11*). The other compounds were determined as known compounds including coumarin glucosides (12-19), iridoid glucosides (20-32), lignanoids (33-42,54), phenolic acids (43-51) and other type of compounds (52,53,55) on the basis of literatures.
Thirty four compounds were isolated from95%ethanol extracts of leaves of this plant. Their structures were elucidated on the basis of spectroscopic and chemical methods. Compounds56*-58*were new monoterpenes, named hydrangenine A, hydrangenine B, hydrangenine C. The other compounds were determined as known compounds including monoterpenoids (59-63), diterpenoids (64-66), C13nor-isoprenoids (67-71), flavones (72-75), coumarins (76,77), phenolic acids (78,82-85), lignans (80,81), alkaloid (79), other type of compounds (86-89) on the basis of literatures.
At10μM, compounds1,3,5,10,12-14,17,19,20,21,25,31,32,39,40and50showed neuroprotective effects against serum deprivation or rotenone induced PC12cell damage. Compounds3,10,14,21,23,24,28,29,31,32and45-48exhibited protective activity against a damage of hepatocyte, with significance compared to the blank control group. Compound32inhibited aldose reductase with a rate74.7%.
Hydrangea paniculata had lots of skimmin and umbelliferone. Skimmin was the basis constituent of the effective fraction of H. paniculata which was used to make pharmaceutical compounds for the prevention and/or treatment of renal insufficiency, hypertension and diabetic nephropathy. Furthermore, the previous studies have found that esculin whose strcture is similarly to skimmin could inhibit the product of AGEs and the progress of diabetic vascular complication. In order to find the compounds to cure diabetic vascular complication, we synthesized nineteen compounds based on skimmin, esculin and umbelliferone, including phenylacrylic acid-skimmin ester (1-3), benzoic acid-skimmin ester (4,5), phenylacrylic acid-esculin ester (6-8,11), benzoic acid--esculin ester (9,10), phenylacrylic acid-umbelliferone ester (12-14) and alkyl-esculin(15-19).1-10,16,18,19were new compounds. In the in vitro assay, compounds5,8,11,12,14and17showed inhibition of ADP induced platelet aggregation. Compounds3,8and13showed activity of scavenging free radicals. In vivo assay, compound15showed active in inhibitting hyperlipemia and the progress of diabetic vascular complication.
从圆锥绣球茎枝中分离得到了55个化合物,经理化及波谱数据分析,发现11个新化合物(1*-11*)。其中1*-8*为香豆素苷类化合物,分别命名为：伞形花内酯7-O-β-D-槐糖苷(1*),伞形花内酯7-O-β-D-葡萄糖基-(1→3)-β-D-葡萄糖苷(2*),伞形花内酯7-O-β-D-葡萄糖基-(1→3)-[β-D-芹糖基-(1→6)]-β-D-葡萄糖苷(3’),伞形花内酯7-O-β-D-葡萄糖基-(1→2)-β-D-芹糖基-(1→6)-β-D-葡萄糖苷(4*),伞形花内酯7-O-β-D-葡萄糖基-(1→5)β-D-芹糖基-(1→6)-β-D-葡萄糖苷(5*),(7"'R,8"'R)-umbelliferone-7-O-[6'-(4-guaiacylglycerol-β-ether)-feruloyl)]-β-D-glucopyranoside (6*)(7"S,8"'R)umbelliferone-7-O-[6'-(4-erythro-guaiacylglycerol-β-ether)-feruloyl)]-β-D-glucopyranoside (7*), hydrangeside A (8)。化合物9*-11*为环烯醚萜苷类化合物,分别命名为：7-0-/β-D-glucopyranosyl loganin (9*),7-O-E-isoferuloyl loganic acid (10*), hydrangeside B (11*)。通过对照文献鉴定化合物12-19为香豆素类,20-32为环烯醚萜类,33-42,54为木脂素类,43-51为酚酸类,52,53,55为其他类。
从圆锥绣球叶中分离得到了34个化合物,发现3个新的单萜类化合物(56*-58‘),分别命名为hydrangenine A, B, C。其余通过对照文献鉴定：化合物59-63为单萜类,64-66为二萜类,67-71为降碳异戊二烯类,72-75为黄酮类,76,77为香豆素苷类,78,82-85为酚酸类,80,81为木脂素类,79为生物碱类,86-89为其他类。
本文在多种药理模型上对这些单体化合物进行了活性筛选。在浓度为10μM时,香豆素类化合物1、3、5、10、12-14、17、19,环烯醚帖类化合物20、21、25、31、32,及化合物39、40、50对鱼藤酮或去血清诱导损伤的PC12细胞有保护作用。化合物3、10、14、21、23、24、28、29、31、32及45-48对DL-半乳糖胺诱导损伤的肝细胞有保护活性。化合物32对醛糖还原酶有一定的抑制活性。
圆锥绣球中含有大量的茵芋苷及其苷元伞形花内酯。动物药效评价实验结果表明,茵芋苷对糖尿病肾病有较好的治疗作用。药物所筛选中心研究发现另一个与茵芋苷结构相似的香豆素苷类化合物秦皮甲素具有较好的AGES抑制作用,能对抗实验性高脂血症,抑制动脉粥样硬化的形成,是一个潜在的抗糖尿病血管病变的药物。基于两者结构及活性的类似性,为了寻找抗糖尿病血管病变的化合物,本论文根据药物设计中的拼合原理,分别在茵芋苷、秦皮甲素及伞形花内酯上引入一些结构片段,合成了19个化合物(1-19)。包括3个苯丙烯酸茵芋苷酯(1-3),2个苯甲酸茵芋苷酯(4,5),4个苯丙烯酸秦皮甲素酯(6-8,11),2个苯甲酸秦皮甲素酯(9,10),3个苯丙烯酸香豆素酯(12-14),5个7-O-烷基化秦皮甲素(15-19),其中1-10,16,18,19为新化合物。并对化合物1-19进行了与糖尿病血管病变相关的生物活性的评价。体外活性评价显示,化合物5、8、11、12、14、17对ADP诱导的血小板聚集表现出显著的抑制作用,化合物3、8、13表现出明显的自由基清除作用。动物药效评价实验结果表明,化合物15能对抗实验性高脂血症,抑制动脉粥样硬化的形成。
Hydrangea paniculata Sieb.(Saxifragaceae) is widely distributed in Anhui, Jiangxi, Zhejiang, Guangxi, Yunnan Provinces and so on. The plant is used to bring down fever, relieve sore throat and treat malaria in folk medicine. Our previous studies have found that the effective fraction of H. paniculata is used to make pharmaceutical components for the prevention and/or treatment of renal insufficiency, hypertension and diabetic nephropathy. As a part of our ongoing screening program for bioactive compounds, we studied the chemical constituents of the stems and leaves of H. paniculata systematically by means of chromatography methods and spectral technologies.
Our investigation of the water extracts of stems of this plant led to the isolation of fifty-five compounds including eleven new compounds (1*-11*). Their structures were elucidated on the basis of spectroscopic and chemical methods. Compounds1*-8*were new coumarin glycosides, determined as:umbelliferone7-O-sophoroside(1*), umbelli-ferone7-O-β-D-glucopyranosyl(1→3)-β-D-glucopyranoside(2*), umbelliferone7-O-β-D-glucopyranosyl(1→3)-[β-D-apiofuranosyl(1→6)]-β-D-glucopyranoside (3*), umbe-lliferone7-O-β-D-glucopyranosyl(1→2)-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside (4*), umbelliferone7-O-β-D-glucopyranosyl(1→5)-β-D-apiofuranosyl(1→6)-β-D-glucop-yranoside (5*),(7"'R,8'"R) umbelliferone-7-O-[6'-(4-threo-guaiacylglycerol-β-ether)-feruloyl)]-β-D-glucopyranoside (6*),(7"'S,8"'R)-umbelliferone-7-O-[6'-(4-guaiacylgly-cerol-β-ether)-feruloyl)]-β-D-glucopyranoside (7*), hydrangeside A (8*). Compounds9*-11*were new iridoid glucosides, determined as:7-O-β-D-glucopyranosyl loganin (9*),7-O-E-isoferuloyl loganic acid (10*), hydrangeside B (11*). The other compounds were determined as known compounds including coumarin glucosides (12-19), iridoid glucosides (20-32), lignanoids (33-42,54), phenolic acids (43-51) and other type of compounds (52,53,55) on the basis of literatures.
Thirty four compounds were isolated from95%ethanol extracts of leaves of this plant. Their structures were elucidated on the basis of spectroscopic and chemical methods. Compounds56*-58*were new monoterpenes, named hydrangenine A, hydrangenine B, hydrangenine C. The other compounds were determined as known compounds including monoterpenoids (59-63), diterpenoids (64-66), C13nor-isoprenoids (67-71), flavones (72-75), coumarins (76,77), phenolic acids (78,82-85), lignans (80,81), alkaloid (79), other type of compounds (86-89) on the basis of literatures.
At10μM, compounds1,3,5,10,12-14,17,19,20,21,25,31,32,39,40and50showed neuroprotective effects against serum deprivation or rotenone induced PC12cell damage. Compounds3,10,14,21,23,24,28,29,31,32and45-48exhibited protective activity against a damage of hepatocyte, with significance compared to the blank control group. Compound32inhibited aldose reductase with a rate74.7%.
Hydrangea paniculata had lots of skimmin and umbelliferone. Skimmin was the basis constituent of the effective fraction of H. paniculata which was used to make pharmaceutical compounds for the prevention and/or treatment of renal insufficiency, hypertension and diabetic nephropathy. Furthermore, the previous studies have found that esculin whose strcture is similarly to skimmin could inhibit the product of AGEs and the progress of diabetic vascular complication. In order to find the compounds to cure diabetic vascular complication, we synthesized nineteen compounds based on skimmin, esculin and umbelliferone, including phenylacrylic acid-skimmin ester (1-3), benzoic acid-skimmin ester (4,5), phenylacrylic acid-esculin ester (6-8,11), benzoic acid--esculin ester (9,10), phenylacrylic acid-umbelliferone ester (12-14) and alkyl-esculin(15-19).1-10,16,18,19were new compounds. In the in vitro assay, compounds5,8,11,12,14and17showed inhibition of ADP induced platelet aggregation. Compounds3,8and13showed activity of scavenging free radicals. In vivo assay, compound15showed active in inhibitting hyperlipemia and the progress of diabetic vascular complication.
引文
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