New phenylbutenoids and terpene glycosides from Ginkgo biloba leaves

IF 4 2区 医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE Chinese Journal of Natural Medicines Pub Date : 2024-02-01 DOI:10.1016/S1875-5364(24)60588-1
Zeshi SUN , Shan LIN , Zhi-Li WU , Hong-Yuan DONG , Xi-Ke XU , Hui-Liang LI , Jinxin WANG
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Abstract

Our continued works on the chemical constituents of Ginkgo biloba (G. biloba) leaves has led to the isolation of two novel phenylbutenoids (1, 2), along with five previously unidentified terpene glycosides (3–7). Among them, compounds 1 and 2 represent unique (Z)-phenylbutenoids, 3–6 are megastigmane glycosides, and 7 is identified as a rare bilobanone glycoside (Fig. 1). This study marks the first reported isolation of phenylbutenoid and bilobanone glycoside from G. biloba. The chemical structures of these compounds were elucidated through extensive spectroscopic analysis, including HR-ESI-MS and various 1D and 2D NMR experiments. Furthermore, the absolute configurations of these molecules were determined using Mosher's method, ECD experiments, and Cu-Kα X-ray crystallographic analyses.

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银杏叶中新的苯基丁烯酸类和萜烯苷类化合物
我们对银杏叶化学成分的持续研究,分离出了两种新的苯基丁烯酸类化合物(1、2),以及五种以前未被发现的萜烯苷类化合物(3-7)。其中,化合物 1 和 2 代表独特的 (Z)-phenylbutenoids 类化合物,3-6 是巨石榴烯苷,而 7 则被鉴定为罕见的双苯乙酮苷(图 1)。这项研究首次报道了从双叶鹅掌楸中分离出苯基丁烯酸和双叶鹅掌楸酮苷。通过广泛的光谱分析,包括 HR-ESI-MS 以及各种一维和二维核磁共振实验,阐明了这些化合物的化学结构。此外,还利用莫舍方法、ECD 实验和 Cu-Kα X 射线晶体学分析确定了这些分子的绝对构型。
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来源期刊
Chinese Journal of Natural Medicines
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.
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