从银杏中分离两种罕见的 N-糖苷及其抗炎活性。

Isolation of two rare N-glycosides from Ginkgo biloba and their anti-inflammatory activities.

机构信息

Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, China.

Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guangxi Zhuang Autonomous Region and Chinese Academy of Sciences, Guilin, 541006, China.

出版信息

Sci Rep. 2020 Apr 7;10(1):5994. doi: 10.1038/s41598-020-62884-1.

DOI:10.1038/s41598-020-62884-1

PMID:32265463

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7138816/

Abstract

Two rare N-β-D-glucopyranosyl-1H-indole-3-acetic acid conjugates, N-[2-(1-β-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-glutamic acid (1) and N-[2-(1-β-D-glucopyranosyl)-1H-indol-3-yl)acetyl]-L-aspartic acid (2) were isolated from Ginkgo biloba. The structures were elucidated by analyses of HRMS and NMR spectroscopic data. In addition, a simplified and efficient synthetic route for compounds 1 and 2 is also disclosed to determine the absolute configurations of them. This concise syntheses of compounds 1 and 2 may facilitate studies of the biology of this type alkaloids. Compounds 1 and 2 were also tested for their cytotoxic and anti-inflammatory activities. The biological evaluation showed that compounds 1 and 2 led to the decrease of interleukin (IL)-6, nitric oxide synthase (iNOS) and cyclooxygenase (COX)-2 at mRNA level in lipopolysaccharide (LPS)-stimulated murine macrophage RAW264.7 cells.

摘要

从银杏中分离得到两种罕见的 N-β-D-吡喃葡萄糖基-1H-吲哚-3-乙酸缀合物，N-[2-(1-β-D-吡喃葡萄糖基)-1H-吲哚-3-基)乙酰基]-L-谷氨酸（1）和 N-[2-(1-β-D-吡喃葡萄糖基)-1H-吲哚-3-基)乙酰基]-L-天冬氨酸（2）。通过高分辨质谱和 NMR 光谱数据分析阐明了它们的结构。此外，还披露了一种简化和有效的合成 1 和 2 的方法，以确定它们的绝对构型。该简洁的合成方法可促进此类生物碱的生物学研究。还测试了化合物 1 和 2 的细胞毒性和抗炎活性。生物评价表明，化合物 1 和 2 可降低脂多糖（LPS）刺激的小鼠巨噬细胞 RAW264.7 细胞中白细胞介素（IL）-6、一氧化氮合酶（iNOS）和环加氧酶（COX）-2 的 mRNA 水平。