小驳骨的化学成分研究  

Study on chemical constituents of Gendarussa vulgaris

作　　者：张海新 夏召 许天启 陈宜敏 周光雄[1] ZHANG Hai-xin;XIA Zhao;XU Tian-qi;CHEN Yi-min;ZHOU Guang-xiong(Guangdong Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and Natural Medicines,Institute of Traditional Chinese Medicine and Natural Product,College of Pharmacy,Jinan University,Guangzhou 510632,China)

机构地区：[1]暨南大学药学院中药及天然药物研究所/广东省普通高校中药和天然药物药效物质基础重点实验室,广东广州510632

出　　处：《中草药》2020年第18期4620-4626,共7页Chinese Traditional and Herbal Drugs

基　　金：国家重点研究计划项目(2017YFC1703800);国家自然科学基金面上项目(81573578);广州市科技计划项目(201704030120)。

摘　　要：目的研究小驳骨Gendarussavulgaris地上部分的化学成分。方法采用反复硅胶柱色谱、ODS开放柱、凝胶柱色谱以及反相半制备型HPLC等各种现代色谱分离技术对其化学成分进行分离纯化,通过HR-ESI-MS、NMR等光谱数据及X-ray单晶衍射鉴定化合物结构。结果从小驳骨地上部分95%乙醇提取物的醋酸乙酯萃取物中分离得到了17个化合物,分别鉴定为24-降胆-5-烯-3β-醇(1)、dihydrobetulic acid(2)、桦木酸(3)、3-羟基-30-去甲基-20-酮基-28-羽扇豆酸(4)、6-羟基-7,8-二甲氧基香豆素(5)、6,7-二甲氧基香豆素(6)、5,6,7-三甲氧基香豆素(7)、6,7,8-三甲氧基香豆素(8)、左旋香树脂酚葡萄糖苷(9)、4-O-咖啡酰奎宁酸甲酯(10)、N-反式阿魏酸酪胺(11)、N-(2-羟基-3-苯丙基)乙酰胺(12)、3-O-咖啡酰奎宁酸甲酯(13)、3,5-O-二咖啡酰奎宁酸甲酯(14)、对-E-香豆素奎宁酸甲酯(15)、3,4,5-O-三咖啡酰基奎尼酸甲酯(16)、1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′-trimethylcyclohex-2-enyl)-6-methyloct-3E,5E,7E-trien-2-one(17)。结论化合物1、2为新天然产物,除化合物6以外,其他化合物均为首次从该植物中分离得到。对分离得到的17个化合物进行抗炎活性筛选,其中,化合物2、3、11、13、17具有抑制LPS诱导RAW 264.7巨噬细胞释放NO的作用,其半数抑制浓度(IC50)值分别为(30.91±0.50)、(4.66±0.56)、(17.67±0.57)、(28.45±0.67)、(20.79±0.24)μmol/L。Objective To study the chemical constituents of aerial part of Gendarussa vulgaris. Methods The compounds were separated and purified by silica gel column chromatography, ODS and Sephadex LH-20 chromatography and semi-preparative HPLC. Base on HR-ESI-MS, NMR, and other spectral data, their structures were identified. Results A total of 17 compounds were isolated from the EtOAc fraction of 95% ethanol extract and identified as 24-norchol-5-en-3β-ol(1), dihydrobetulic acid(2), betulinic acid(3), 3-hydroxy-30-nor-20-oxo-28-lupanoic acid(4), 6-hydroxy-7,8-dimethoxycoumarin(5), 6,7-dimethoxycoumarin(6), 5,6,7-trimethoxycoumarin(7), 6,7,8-trimethoxycoumarin(8), syringaresinol-4-O-β-D-glucopyranoside(9), 4-O-caffeoylquinic acid methyl ester(10), N-trans-feruloyl tyramine(11), N-(2-hydroxy-3-phenylpropyl) acetamide(12), 3-O-caffeoylquinic acid methyl ester(13), 3,5-O-dicaffeoylquinic acid methyl ester(14), p-E-coumarin quinic acid methyl ester(15), 3,4,5-O-tricaffeoyl quinic acid methyl ester(16) and 1′S*,4′R*-8-(4′-hydroxy-2′,6′,6′-trimethylcyclohex-2-enyl)-6-methyloct-3 E,5 E,7 E-trien-2-one(17). Conclusion Compounds 1 and 2 are new natural products. All Compounds are isolated from this plant for the first time except compound 6. Besides, all compounds are screened for anti-inflammatory activity and compounds 2, 3, 11, 13, and 17 have NO release inhibiting activities on LPS-induced RAW 264.7 macrophage cells with IC50 values of(30.91 ± 0.50),(44.66 ± 0.56),(17.67 ± 0.57),(28.45 ± 0.67) and(20.79 ± 0.24) μmol/L, respectively.

关 键 词：小驳骨 24-norchol-5-en-3β-ol dihydrobetulic acid 桦木酸 6 7-二甲氧基香豆素 3-O-咖啡酰奎宁酸甲酯 抗炎活性 

分 类 号：R284.1[医药卫生—中药学]