Chiral resolution of furofuran lignans and their derivatives from the stems of Dendrobium 'Sonia'

IF 4 2区医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE

Chinese Journal of Natural Medicines Pub Date : 2024-10-01 DOI:10.1016/S1875-5364(24)60725-9

Kaimei QIU , Hao QIU , Yanqiao XIE , Siyu ZHANG , Qian ZHANG , Zhengtao WANG , Zhuzhen HAN , Li YANG

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引用次数: 0

Abstract

Five new furofuran lignans and their derivatives, (−)-glaberide I 4-O-β-D-glucopyranoside (1a), (+)-glaberide I 4-O-β-D-glucopyranoside (1b), (+)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside (2a), (−)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside (2b), and (−)-isoeucommin A (3b), along with fifteen known analogs were isolated from the stems of Dendrobium 'Sonia'. These compounds were classified into ten pairs of enantiomers or diastereoisomers via chiral resolution, and their structures were determined based on extensive spectroscopic data. Their absolute configurations were determined by hydrolysis, comparison of experimental and calculated electronic circular dichroism (ECD) data, and single-crystal X-ray diffraction analysis. The isolates were evaluated for their ability to inhibit nitric oxide (NO) production in RAW264.7 cells. Among them, syringaresinol (5) exhibited prominent inhibition activity, with an IC₅₀ value of 28.4 ± 3.0 μmol·L⁻¹, and there was a slight difference between 5a, 5b and the racemic mixture 5.

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从铁皮石斛'Sonia'茎中提取的呋喃木脂素及其衍生物的手性解析。

五种新的呋喃木脂素及其衍生物：(-)-木脂素 I 4-O-β-D-吡喃葡萄糖苷(1a)、(+)-木脂素 I 4-O-β-D-吡喃葡萄糖苷(1b)、(+)-木脂素 I 7'-乙氧基-4-O-β-D-吡喃葡萄糖苷(2a)、(-)-glaberide I 7'-ethoxy-4-O-β-D-glucopyranoside (2b)、(-)-isoeucommin A (3b)以及 15 种已知的类似物都是从铁皮石斛'Sonia'的茎中分离出来的。通过手性解析，这些化合物被分为十对对映体或非对映异构体，并根据大量光谱数据确定了它们的结构。通过水解、比较实验和计算的电子圆二色性（ECD）数据以及单晶 X 射线衍射分析，确定了它们的绝对构型。对这些分离物抑制 RAW264.7 细胞产生一氧化氮（NO）的能力进行了评估。其中，丁香树脂醇（5）的抑制活性突出，其 IC50 值为 28.4 ± 3.0 μmol-L-1，且 5a、5b 和外消旋混合物 5 之间存在微小差异。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chinese Journal of Natural Medicines INTEGRATIVE & COMPLEMENTARY MEDICINE-PHARMACOLOGY & PHARMACY

CiteScore

7.50

自引率

4.30%

发文量

2235

期刊介绍： The Chinese Journal of Natural Medicines (CJNM), founded and sponsored in May 2003 by China Pharmaceutical University and the Chinese Pharmaceutical Association, is devoted to communication among pharmaceutical and medical scientists interested in the advancement of Traditional Chinese Medicines (TCM). CJNM publishes articles relating to a broad spectrum of bioactive natural products, leading compounds and medicines derived from Traditional Chinese Medicines (TCM). Topics covered by the journal are: Resources of Traditional Chinese Medicines; Interaction and complexity of prescription; Natural Products Chemistry (including structure modification, semi-and total synthesis, bio-transformation); Pharmacology of natural products and prescription (including pharmacokinetics and toxicology); Pharmaceutics and Analytical Methods of natural products.