1-hydroxy-7-oxolavanducyanin and Δ7″,8″-6″-hydroxynaphthomevalin from Streptomyces sp. CPCC 203577

Abstract

Lavanducyanin is a bioactive phenazine-containing secondary metabolite, and naphthomevalin is an antibacterial polyketide secondary metabolite. Herein, new analogues of lavanducyanin (2) and of naphthomevalin (4), together with lavanducyanin (1) and naphthomevalin (3), were identified from Streptomyces sp. CPCC 203577, an actinomycete soil isolate. The structures of 2 and 4 were elucidated as 1-hydroxy-7-oxolavanducyanin and Δ7″,8″-6″-hydroxynaphthomevalin, respectively, by 1D and 2D NMR. Antibacterial assays revealed that 2 had significant but reduced anti-Gram-positive bacterial activity compared with 1, and 4 was devoid of anti-Gram-positive bacterial activity. This indicated that the phenazinone nucleus in lavanducyanin and the monoterpene side chain in naphthomevalin might be important for their anti-Gram-positive bacterial activity. Compounds 14 were all inactive against Gram-negative bacteria.

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Acknowledgements

The authors thank Nuclear Magnetic Resonance Center (Institute of Materia Medica, CAMS & PUMC) and Analytical Center of Drugs (Institute of Medicinal Biotechnology, CAMS & PUMC) for the NMR and MS analyses. This work was supported by CAMS Initiative for Innovative Medicine (CAMS-I2M-3-012) and National Infrastructure of Microbial Resources (No. NIMR-2018-3).

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Correspondence to Bingya Jiang or Linzhuan Wu.

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Li, S., Hu, X., Li, L. et al. 1-hydroxy-7-oxolavanducyanin and Δ7″,8″-6″-hydroxynaphthomevalin from Streptomyces sp. CPCC 203577. J Antibiot 73, 324–328 (2020). https://doi.org/10.1038/s41429-020-0282-9

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