Total Synthesis and Antimicrobial Evaluation of Bisoflavolin D: A Novel Biflavonoid from Streptomyces sp.

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-07-30 DOI:10.1021/acs.jnatprod.5c00720

Na Wang, Zhengwen Li, Hefei Shi, Mengqi Wang, Yufei Che, Fei Tan, Chunran Zhang, Hongbo Dong

引用次数: 0

Abstract

Bisoflavolin D (1) is a structurally unique biflavonoid originally isolated from Streptomyces sp. strain HDN154127 and exhibits potent antibacterial activity. However, its extremely low natural abundance has limited further biological investigation. Herein, we report the first total synthesis of bisoflavolin D (1). The key steps of our synthesis include three Suzuki-Miyaura cross-coupling reactions to construct the isoflavone monomers and establish the C-3‴-C-8 linkage of the biflavonoid scaffold. Preliminary antimicrobial testing revealed moderate antibacterial activity against Gram-positive pathogens, with a notable synergistic effect observed between bisoflavolin D (1) and norfloxacin (FICI = 0.28) against methicillin-resistant Staphylococcus aureus, as well as with amikacin against Escherichia coli (FICI < 0.16). This work provides a foundation for further exploration of bisoflavolin D (1) and its potential as an antimicrobial agent.

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链霉菌中新型类黄酮生物黄素D的合成及抗菌性能评价

Bisoflavolin D(1)是从Streptomyces sp.菌株HDN154127中分离出来的一种结构独特的双黄酮，具有很强的抗菌活性。然而，其极低的自然丰度限制了进一步的生物学研究。本文首次报道了生物异黄酮素D(1)的全合成。我们合成的关键步骤包括三个Suzuki-Miyaura交叉偶联反应，以构建异黄酮单体和建立双类黄酮支架的C-3 -C-8连锁。初步抑菌试验显示，生物黄素D(1)与诺氟沙星（FICI = 0.28）对耐甲氧西林金黄色葡萄球菌有较强的协同作用，与阿米卡星（FICI < 0.16）对大肠杆菌有较强的协同作用。本研究为进一步探索生物异黄酮D(1)及其抗菌潜力奠定了基础。

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

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.