(±)-Talapyrones A−F: six pairs of dimeric polyketide enantiomers with unusual 6/6/6 and 6/6/6/5 ring systems from Talaromycesadpressus

IF 4.9 2区医学 Q1 INTEGRATIVE & COMPLEMENTARY MEDICINE

Chinese Journal of Natural Medicines Pub Date : 2025-08-01 DOI:10.1016/S1875-5364(25)60928-9

Meijia Zheng , Xinyi Zhao , Chenxi Zhou , Hong Liao , Qin Li , Yuling Lu , Bingbing Dai , Weiguang Sun , Ying Ye , Chunmei Chen , Yonghui Zhang , Hucheng Zhu

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Abstract

(±)-Talapyrones A−F (1−6), six pairs of dimeric polyketide enantiomers featuring unusual 6/6/6 and 6/6/6/5 ring systems, were isolated from the fungus Talaromyces adpressus. Their structures were determined by spectroscopic analysis and HR-ESI-MS data, and their absolute configurations were elucidated using a modified Mosher’s method and electronic circular dichroism (ECD) calculations. (±)-Talapyrones A−F (1−6) possess a 6/6/6 tricyclic skeleton, presumably formed through a Michael addition reaction between one molecule of α-pyrone derivative and one molecule of C₈ poly-β-keto chain. In addition, compounds 2/3 and 4/5 are two pairs of C-18 epimers, respectively. Putative biosynthetic pathways of 1−6 were discussed.

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（±）-Talapyrones A−F：来自Talaromycesadpressus的六对具有特殊6/6/6和6/6/6/5环体系的二聚体聚酮对映体

（±）-Talapyrones A−F（1−6）是从真菌Talaromyces adpressus中分离得到的六对二聚聚酮对映体，具有独特的6/6/6和6/6/6/5环体系。通过光谱分析和HR-ESI-MS数据确定了它们的结构，并利用改进的Mosher法和电子圆二色性（ECD）计算确定了它们的绝对构型。（±）-Talapyrones A−F（1−6）具有6/6/6三环骨架，可能是由1个α-吡酮衍生物分子与1个C8聚β-酮链分子的Michael加成反应形成的。另外，化合物2/3和4/5分别是两对C-18外映体。讨论了1 - 6可能的生物合成途径。

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.