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Quinomycins with an unusual N-methyl-3-methylsulfinyl-alanine residue from a Streptomyces sp


Four new echinomycin congeners, quinomycins M−P (14) were isolated from the cultures of the soil-derived Streptomyces sp. CPCC205575. The planar structures were determined by comprehensive analyses of NMR and HRESIMS/MS data. The absolute configurations were elucidated by the advanced Marfey’s method combined with biosynthetic gene analysis. Compounds 14 represent the first examples of quinomycin-type natural products with the sulfur atom at the N,S-dimethylcysteine residue oxidized as a sulfoxide group forming the unusual N-methyl-3-methylsulfinyl-alanine residue. Bioassay results revealed that the oxidation of the sulfur atom at the Cys or Cys′ residues led to dramatic decrease of cytotoxicity and antimicrobial activity.

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This work was financially supported by the National Natural Science Foundation of China (Grant no. 82273830) and CAMS Innovation Fund for Medical Sciences (CIFMS, 2021-I2M-1-055).

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Correspondence to Shuzhen Chen, Yan Li or Maoluo Gan.

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Wang, A., Li, S., Wei, Y. et al. Quinomycins with an unusual N-methyl-3-methylsulfinyl-alanine residue from a Streptomyces sp. J Antibiot (2024).

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