Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

Shun Saito, Kanji Indo, Naoya Oku, Hisayuki Komaki, Masashi Kawasaki, Yasuhiro Igarashi

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

A genome mining survey combined with metabolome analysis of publicly available strains identified Couchioplanes sp. RD010705, a strain belonging to an underexplored genus of rare actinomycetes, as a producer of new metabolites. HPLC-DADguided fractionation of its fermentation extracts resulted in the isolation of five new methyl-branched unsaturated fatty acids, (2E,4E)-2,4-dimethyl-2,4-octadienoic acid (1), (2E,4E)-2,4,7-trimethyl-2,4-octadienoic acid (2), (R)-(-)-phialomustin B (3), (2E,4E)-7-hydroxy-2,4-dimethyl-2,4-octadienoic acid (4), (2E,4E)-7-hydroxy-2,4,7-trimethyl-2,4-octadienoic acid (5), and one prenylated tryptophan derivative, 6-(3,3-dimethylallyl)-N-acetyl-L-tryptophan (6). The enantiomer ratio of 4 was determined to be approximately S/R = 56:44 by a recursive application of Trost's chiral anisotropy analysis and chiral HPLC analysis of its methyl ester. Compounds 1-5 were weakly inhibitory against Kocuria rhizophila at MIC 100 μg/mL and none were cytotoxic against P388 at the same concentration.

Original languageEnglish
Pages (from-to)2939-2949
Number of pages11
JournalBeilstein Journal of Organic Chemistry
Volume17
DOIs
Publication statusPublished - 2021

Keywords

  • Couchioplanes
  • Prenylated tryptophan
  • Rare actinomycete
  • Unsaturated fatty acid

ASJC Scopus subject areas

  • Organic Chemistry

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