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

  1. Shun SaitoORCID Logo,
  2. Kanji Indo,
  3. Naoya OkuORCID Logo,
  4. Hisayuki Komaki,
  5. Masashi Kawasaki and
  6. Yasuhiro Igarashi

Submitting author affiliation: Keio University, Hiyoshi, Kohoku-ku, Yokohama, Japan

Beilstein Arch. 2021, 202174. https://doi.org/10.3762/bxiv.2021.74.v1

Published 18 Oct 2021

  • Preprint

Abstract

A genome mining survey combined with metabolome analysis of publicly available strains identified Couchioplanessp. RD010705, a strain belonging to an underexplored genus of rare actinomycetes, as a producer of new metabolites. HPLC-DAD-guided 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 15 were weakly inhibitory against Kocuria rhizophila at MIC 100 mg/mL and none were cytotoxic against P388 at the same concentration.

Keywords: Couchioplanes; prenylated tryptophan; rare actinomycete; unsaturated fatty acid

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Saito, S.; Indo, K.; Oku, N.; Komaki, H.; Kawasaki, M.; Igarashi, Y. Beilstein Arch. 2021, 202174. doi:10.3762/bxiv.2021.74.v1

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