Coprisamides A and B, new branched cyclic peptides from a gut bacterium of the dung beetle Copris tripartitus

Org Lett. 2015 Mar 6;17(5):1272-5. doi: 10.1021/acs.orglett.5b00249. Epub 2015 Feb 16.

Abstract

Coprisamides A and B (1 and 2) were isolated from a bacterium in the gut of the dung beetle Copris tripartitus. Spectroscopic analysis revealed that the planar structures of 1 and 2 are novel cyclic heptapeptides bearing unusual units, such as β-methylaspartic acid and 2,3-diaminopropanoic acid branched to valine and 2-heptatrienyl cinnamic acid. Absolute configurations were established by chemical derivatization and chiroptical spectroscopy. The coprisamides displayed significant activity for induction of quinone reductase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bacterial Physiological Phenomena / drug effects*
  • Coleoptera / microbiology*
  • Feces
  • Molecular Structure
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / isolation & purification
  • Streptomyces / chemistry*
  • beta-Alanine / analogs & derivatives*
  • beta-Alanine / chemistry

Substances

  • Peptides, Cyclic
  • coprisamide A
  • coprisamide B
  • beta-Alanine
  • 2,3-diaminopropionic acid