首页|肾茶地上部分丹参素衍生物的分离与绝对构型的确定

肾茶地上部分丹参素衍生物的分离与绝对构型的确定

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目的 对肾茶(Clerodendranthus spicatus(Thunb.)C.Y.Wu ex H.W.Li)地上部分的化学成分进行研究,进一步丰富其物质基础.方法 采用加热回流提取法对肾茶的干燥地上部分进行提取,联合应用硅胶、ODS及高效液相色谱等多种色谱法对肾茶地上部分提取物的化学成分进行分离纯化,结合圆二色光谱、核磁、质谱等波谱技术以及化学反应的方法,鉴定化合物的结构,确定其绝对构型.结果 从肾茶地上部分分离鉴定了7 个丹参素衍生物,分别为(R)-迷迭香酸(1)、(R)-迷迭香酸甲酯(2)、(R)-迷迭香酸乙酯(3)、2R-羟基-3-(4-羟基苯基)丙酸甲酯(4)、2R-羟基-3-(3,4-二羟基苯基)丙酸(5)、2R-羟基-3-(3,4-二羟基苯基)丙酸甲酯(6)和 2R-羟基-3-(3,4-二羟基苯基)丙酸乙酯(7).结论 化合物4 为首次从肾茶属植物中分离得到.此外,发现对于α-羟基羧酸类化合物,即使是只有一个手性中心,也不能仅仅通过旋光值的比对确定其绝对构型.本文所提供的方法为该类成分构型的研究提供了借鉴.
Isolation and Absolute configuration determination of Danshensu derivatives from the areial part of Clerodendranthus spicatus
Objective To further enrich the composition of Clerodendranthus spicatus(Thunb.)C.Y.Wu ex H.W.Li,the constituents in its dried aerial parts were investigated.Methods The dried aerial parts of C.spicatus were refluxed by 70% EtOH.The obtained extract was isolated by using various column chromatographies,such as silica gel,ODS column,and HPLC chromatography.And then,the structures and absolute configurations of the isolated compounds were elucidated by using circular dichroism,nuclear magnetic resonance,and mass spectra,as well as chemical reaction methods.Results Seven Danshensu derivatives were obtained from the 70% EtOH extract of C.spicatus aerial parts.They were(R)-rosmarinic acid(1),(R)-rosmarinic acid methyl ester(2),(R)-rosmarinic acid ethyl ester(3),2R-hydroxy-3-(4-hydroxyphenyl)propionic acid methyl ester(4),2R-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid(5),2R-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid methyl ester(6),and 2R-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid ethyl ester(7),respectively.Conclusion Compound 4 is isolated from Clerodendranthus genus for the first time.In addition,it has been found that the absolute configuration of α-hydroxy carboxylic acids could not be determined by the comparison of optical rotation alone,though it is with only one chiral center.The method provided in this paper will supply a reference for the configuration study of these compounds.

Clerodendranthus spicatusDanshensu derivativesstructural identificationabsolute configuration

张雅琦、阮静雅、杨丁山、张倩倩、王涛、张祎

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天津中医药大学 天津市现代中药重点实验室,天津 301617

天津中医药大学 组分中药国家重点实验室,天津 301617

肾茶 丹参素衍生物 结构鉴定 绝对构型

国家自然科学基金面上项目

82074118

2024

沈阳药科大学学报
沈阳药科大学

沈阳药科大学学报

CSTPCD
影响因子:0.604
ISSN:1006-2858
年,卷(期):2024.41(7)
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