Structures and Biosynthetic Pathway of Coprisamides C and D, 2-Alkenylcinnamic Acid-Containing Peptides from the Gut Bacterium of the Carrion Beetle Silpha perforata

J Nat Prod. 2021 Feb 26;84(2):239-246. doi: 10.1021/acs.jnatprod.0c00864. Epub 2021 Jan 26.

Abstract

Coprisamides C and D (1 and 2) were isolated from a gut bacterium, Micromonospora sp. UTJ3, of the carrion beetle Silpha perforata. Based on the combined analysis of UV, MS, and NMR spectral data, the planar structures of 1 and 2 were elucidated to be unreported derivatives of coprisamides A and B, cyclic depsipeptides bearing a 2-alkenylcinnamic acid unit and the unusual amino acids β-methylaspartic acid and 2,3-diaminopropanoic acid. The absolute configuration of 1 was determined using the advanced Marfey's method, phenylglycine methyl ester derivatization, and J-based configuration analysis. The biosynthetic gene clusters for the coprisamides were investigated based on genomic data from coprisamide-producing strains Micromonospora sp. UTJ3 and Streptomyces sp. SNU533. Coprisamide C (1) was active against the Mycobacterium tuberculosis mc2 6230 strain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biosynthetic Pathways
  • Cinnamates
  • Coleoptera / microbiology*
  • Depsipeptides / biosynthesis
  • Depsipeptides / chemistry*
  • Gastrointestinal Microbiome*
  • Microbial Sensitivity Tests
  • Micromonospora / chemistry*
  • Molecular Structure
  • Multigene Family
  • Mycobacterium tuberculosis / drug effects
  • Peptides, Cyclic / biosynthesis
  • Peptides, Cyclic / chemistry*
  • Republic of Korea
  • Secondary Metabolism

Substances

  • Cinnamates
  • Depsipeptides
  • Peptides, Cyclic
  • cinnamic acid