Deinococcucins A-D, Aminoglycolipids from Deinococcus sp., a Gut Bacterium of the Carpenter Ant Camponotus japonicus

J Nat Prod. 2017 Nov 22;80(11):2910-2916. doi: 10.1021/acs.jnatprod.7b00426. Epub 2017 Nov 1.

Abstract

Four new aminoglycolipids, deinococcucins A-D (1-4), were discovered from a Deinococcus sp. strain isolated from the gut of queen carpenter ants, Camponotus japonicus. The structures of deinococcucins A-D were elucidated as a combination of N-acetyl glucosamine, 2,3-dihydroxypropanoic acid, and an alkyl amine with a C16 or C17 hydrocarbon chain primarily based on 1D and 2D NMR and mass spectroscopic data. The exact location of the olefinic double bond in deinococcucins C and D (3 and 4) was assigned based on the liquid chromatography-mass spectroscopy data obtained after olefin metathesis. The absolute configurations of the N-acetyl glucosamine and 2,3-dihydroxy moieties were determined through gas chromatography-mass spectroscopy analysis of authentic samples and phenylglycine methyl ester-derivatized products, respectively. Deinococcucins A and C displayed significant induction of quinone reductase in murine Hepa-1c1c7 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ants / microbiology*
  • DNA, Bacterial
  • Deinococcus / chemistry*
  • Gastrointestinal Microbiome
  • Glycolipids / chemistry
  • Glycolipids / isolation & purification*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phylogeny

Substances

  • DNA, Bacterial
  • Glycolipids
  • deinococcucin A
  • deinococcucin C