青钱柳中的四氢萘酮类和奎宁酸类成分

Extraction of tetralones and quinic acids from Cyclocarya paliurus

摘要

对青钱柳 [Cyclocarya paliurus (Batalin) Iljinskaja]叶的乙醇提取物正丁醇萃取部位进行化学成分研究。综合应用硅胶、MCI、ODS、Sephadex LH-20 柱色谱及半制备高效液相色谱等多种色谱技术进行分离纯化，从中分离得到 10 个化合物。根据理化性质及波谱数据分别鉴定为 (4S)-4,8-二羟基-α-四氢萘酮-5-[6′-(3′′,5′′-二甲氧基-(E)-对香豆酰基)]-β-D-吡喃葡萄糖苷(1)、(4S)-4,8-二羟基-α-四氢萘酮-5-[6′-(E)-阿魏酰基]-β-D-吡喃葡萄糖苷(2)、(1S,3R,4S,5R)-4,5-O-双咖啡酰奎宁酸甲酯(3)、(1R,3R,4S,5R)-3,4-O-双咖啡酰奎宁酸甲酯 (4)、(3R,5R)-3,4,5-O-三咖啡酰基奎宁酸甲酯 (5)、(1R,3R,4S,5R)-3-O-咖啡酰基-5-O-对香豆酰基奎宁酸甲酯 (6)、(1R,3R,4S,5R)-3-O-对香豆酰基-4-O-咖啡酰基奎宁酸甲酯 (7)、(1R,3R,4S,5R)-3-O-咖啡酰基-4-O-对香豆酰基奎宁酸甲酯 (8)、(3R,5R)-3,5-O-双咖啡酰奎宁酸甲酯 (9)、(1S,3R,4R,5R)-4-O-咖啡酰基-5-O-阿魏酰奎宁酸甲酯 (10)。其中化合物 1 为新化合物，化合物 3~10 为首次从青钱柳属中分离得到。

Abstract

Chemical constituents of n-butanol fraction of ethanol extract from the leaves of Cyclocarya paliurus (Batalin) Iljinskaja were studied. Ten compounds were purified by silica gel, MCI, ODS, Sephadex LH-20 column chromatography and semi-preparative high-performance liquid chromatography. Based on the physicochemical properties and spectroscopic data, these compounds were identified as (4S)-4,8-dihydroxy-α-tetralone-5-[6′-(3′′,5′′-dimethoxy-(E)-p-coumaroyl)]-β-D-glucopyranoside (1), (4S)-4,8-dihydroxy-α-tetralone-5-[6′-(E)-feruloyl]-β-D-glucopyranoside (2), (1S,3R,4S,5R)-4,5-di-O-caffeoyl quinic acid methyl ester (3), (1R,3R,4S,5R)-3,4-di-O-caffeoyl quinic acid methyl ester (4), (3R,5R)-3,4,5-tri-O-caffeoylquinic acid methyl ester (5), (1R,3R,4S,5R)-3-O-caffeoyl-5-O-p-coumaroyl quinic acid methyl ester (6), (1R,3R,4S,5R)-3-O-p-coumaroy-4-O-caffeoyl quinic acid methyl ester (7), (1R,3R,4S,5R)-3-O-caffeoyl-4-O-p-coumaroy quinic acid methyl ester (8), (3R,5R)-3,5-di-O-caffeoyl quinic acid methyl ester (9) and (1S,3R,4R,5R)-4-O-caffeoyl-5-O-feruloyl quinic acid methyl ester (10). Among them, compound 1 was a new compound, and compounds 3–10 were isolated from the genus Cyclocarya for the first time.

关键词

青钱柳 / 四氢萘酮类化合物 / 奎宁酸类化合物

Key words

Cyclocarya paliurus / tetralones / quinic acid

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基金资助

国家自然科学基金项目(82574280)

江苏省自然科学基金项目(BK20252070)

江苏省中医药科技发展计划项目(ZD202418)