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甘草中的二氢异香豆素

Dihydroisocoumarins from Radix Glycyrrhizae.

作者信息

Zhao Songsong, Yan Xinjia, Zhao Ying, Wen Jing, Zhao Zhenzhen, Liu Hongwei

机构信息

School of Pharmacy, Harbin University of Commerce, Harbin, 150076, China.

Department of Educational Administration, First Affiliated Hospital of Jinzhou Medical University, Jinzhou, 121000, China.

出版信息

Chem Cent J. 2018 May 11;12(1):58. doi: 10.1186/s13065-018-0427-0.

DOI:10.1186/s13065-018-0427-0
PMID:29748827
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5945569/
Abstract

BACKGROUND

Radix Glycyrrhizae is the rhizome of Glycyrrhiza inflata Bat., Glycyrrhiza uralensis Fisch. or Glycyrrhiza glabra L. The present paper describes the isolation and the structural elucidation of three new dihydroisocoumarins obtained from the 70% EtOH extract of Radix Glycyrrhizae. And the cytotoxic activities of these new compounds were also evaluated using four cell lines, subsequently.

RESULTS

A pair of new dihydroisocoumarin epimers ((3R,4S)-4,8-dihydroxy-3-methyl-1-oxoisochroman-5-yl)methyl acetate (1) and ((3R,4R)-4,8-dihydroxy-3-methyl-1-oxoisochroman-5-yl)methyl acetate (2) along with a new dihydroisocoumarin (3R,4R)-4,8-dihydroxy-3,5-dimethylisochroman-1-one (3) were isolated from Radix Glycyrrhizae. Their structures were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses, HR-ESI-MSand ECD calculation comparing with those of experimental CD spectra. Cytotoxic activities of the three compounds were evaluated using the HepG2, A549, LoVo and Hela cell lines, respectively. IC values indicated compounds 1-3 exhibited moderate or less cytotoxic activity in vitro.

CONCLUSIONS

Dihydroisocoumarin is not the common components in Radix Glycyrrhizae, a series of dihydroisocoumarin were obtained in this plant could be a supplement to the chemical study of this plant.

摘要

背景

甘草是胀果甘草、乌拉尔甘草或光果甘草的根茎。本文描述了从甘草70%乙醇提取物中获得的三种新的二氢异香豆素的分离和结构鉴定。随后还使用四种细胞系评估了这些新化合物的细胞毒性活性。

结果

从甘草中分离出一对新的二氢异香豆素差向异构体（(3R,4S)-4,8-二羟基-3-甲基-1-氧代异苯并二氢吡喃-5-基）甲基乙酸酯（1）和（(3R,4R)-4,8-二羟基-3-甲基-1-氧代异苯并二氢吡喃-5-基）甲基乙酸酯（2）以及一种新的二氢异香豆素（3R,4R）-4,8-二羟基-3,5-二甲基异苯并二氢吡喃-1-酮（3）。它们的结构通过化学和光谱分析得以阐明，包括一维、二维核磁共振分析、高分辨电喷雾电离质谱以及与实验圆二色光谱比较的电子圆二色计算。分别使用HepG2、A549、LoVo和Hela细胞系评估了这三种化合物的细胞毒性活性。IC值表明化合物1 - 3在体外表现出中等或较低的细胞毒性活性。

结论

二氢异香豆素不是甘草中的常见成分，该植物中获得的一系列二氢异香豆素可为该植物的化学研究提供补充。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/00d76dd5534e/13065_2018_427_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/2cef9d88676f/13065_2018_427_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/251b6ad4717a/13065_2018_427_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/8f1e3596d63f/13065_2018_427_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/c7ccd8056833/13065_2018_427_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/00d76dd5534e/13065_2018_427_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/2cef9d88676f/13065_2018_427_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/251b6ad4717a/13065_2018_427_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/8f1e3596d63f/13065_2018_427_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/c7ccd8056833/13065_2018_427_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6419/5945569/00d76dd5534e/13065_2018_427_Fig5_HTML.jpg

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