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

doi:10.1007/s13659-026-00597-0

Natural Products and Bioprospecting ›› 2026, Vol. 16 ›› Issue (3): 42-42.DOI: 10.1007/s13659-026-00597-0

• ORIGINAL ARTICLES • Previous Articles

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

Dongyang Wang^1,3,4, Peipei Liu¹, Yukang Gao¹, Linmeng Chen¹, Liping Wang^3,4, Ning Li⁵, Weiming Zhu^1,2

1. Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, Ministry of Education of China, Ocean University of China, Qingdao 266003, China;
2. Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, China;
3. Natural Product Research Center of Guizhou Province, Guiyang 550014, China;
4. State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Guizhou Medical University, Guiyang 550014, China;
5. Biology Institute, Engineering Research Center of Zebrafish Models for Human Diseases and Drug Screening of Shandong Province, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250103, China

Received:2025-11-04 Online:2026-06-24
Contact: Weiming Zhu,E-mail:weimingzhu@ouc.edu.cn
Supported by:
This work was financially supported by the National Key Research and Development Program of China (No. 2022YFC2804100), the National Natural Science Foundation of China (No. 82473838), and Guizhou Provincial Basic Research Program (Natural Science) (No. QKHJC MS[2025]117).

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

Dongyang Wang^1,3,4, Peipei Liu¹, Yukang Gao¹, Linmeng Chen¹, Liping Wang^3,4, Ning Li⁵, Weiming Zhu^1,2

1. Key Laboratory of Marine Drugs, School of Medicine and Pharmacy, Ministry of Education of China, Ocean University of China, Qingdao 266003, China;
2. Laboratory for Marine Drugs and Bioproducts, Qingdao Marine Science and Technology Center, Qingdao 266237, China;
3. Natural Product Research Center of Guizhou Province, Guiyang 550014, China;
4. State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine, Guizhou Medical University, Guiyang 550014, China;
5. Biology Institute, Engineering Research Center of Zebrafish Models for Human Diseases and Drug Screening of Shandong Province, Qilu University of Technology (Shandong Academy of Sciences), Jinan 250103, China

通讯作者: Weiming Zhu,E-mail:weimingzhu@ouc.edu.cn
基金资助:
This work was financially supported by the National Key Research and Development Program of China (No. 2022YFC2804100), the National Natural Science Foundation of China (No. 82473838), and Guizhou Provincial Basic Research Program (Natural Science) (No. QKHJC MS[2025]117).

Abstract

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.

Key words: Mangrove actinobacteria, Streptomyces sp., Phenazine conjugates, Structure elucidation, Antibacterial activity

摘要： 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.

关键词: Mangrove actinobacteria, Streptomyces sp., Phenazine conjugates, Structure elucidation, Antibacterial activity

Dongyang Wang, Peipei Liu, Yukang Gao, Linmeng Chen, Liping Wang, Ning Li, Weiming Zhu. Phenazinoates A-E, five pairs of phenazine conjugates from a mangrove soil-derived Streptomyces strain OUCMDZ-4923[J]. Natural Products and Bioprospecting, 2026, 16(3): 42-42.

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

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

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