Phenazinoates A‒E, five pairs of phenazine conjugates from a mangrove soil-derived Streptomyces strain OUCMDZ-4923

IF 4.9 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2026-03-04 DOI:10.1007/s13659-026-00597-0

Dongyang Wang, Peipei Liu, Yukang Gao, Linmeng Chen, Liping Wang, Ning Li, Weiming Zhu

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Abstract

Phenazinoates A–E (1–5), comprising five pairs of methyl saphenate conjugates with genistein, o-aminophenol, p-acetaminophenol and glycerol, were isolated from the fermentation broth of mangrove soil-derived Streptomyces sp. OUCMDZ-4923. Their structures were determined through comprehensive one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy, coupled with high-resolution electrospray ionization mass spectrometry. The absolute configurations of each isomer were established by comparing experimental electronic circular dichroism spectra with calculated counterparts. Based on the biosynthetic pathway analysis, compounds 1‒3 were semi-synthesized from the reactions of methyl (R)-saphenate with genistein, o-aminophenol, and o-formamidophenol, utilizing microwave-assisted solid acid catalysis. The compounds were resolved as enantiomerically pure forms and subsequently tested for antibacterial efficacy against six pathogenic bacteria. Phenazinoates A (1) and B (2) demonstrated bioactivity against four Gram-positive bacterial strains, with minimum inhibitory concentration values ranging from 0.78 to 3.13 μg/mL.

Graphical Abstract

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红树林土壤链霉菌OUCMDZ-4923的5对非那嗪偶联物a - e

从红树林土壤源Streptomyces sp. OUCMDZ-4923发酵液中分离得到5对甲基隐酸酯与染料木素、邻氨基酚、对乙酰氨基酚和甘油的偶联物Phenazinoates A-E（1-5）。通过综合一维和二维核磁共振波谱，结合高分辨率电喷雾电离质谱测定了它们的结构。通过比较实验电子圆二色性光谱和计算电子圆二色性光谱，确定了各异构体的绝对构型。在生物合成途径分析的基础上，利用微波辅助固体酸催化，由甲基(R)-隐酸酯与染料木黄酮、邻氨基酚和邻甲脒酚反应半合成化合物1 ~ 3。这些化合物被分解为对映体纯形式，随后测试了对六种致病菌的抗菌功效。Phenazinoates A(1)和B(2)对4种革兰氏阳性菌均有抑制作用，最小抑制浓度范围为0.78 ~ 3.13 μg/mL。图形抽象

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.