Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp

Amit Raj Sharma; Enjuro Harunari; Tao Zhou; Agus Trianto; Yasuhiro Igarashi

doi:10.3762/bjoc.15.225

Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp

Beilstein J Org Chem. 2019 Sep 30:15:2327-2332. doi: 10.3762/bjoc.15.225. eCollection 2019.

Authors

Amit Raj Sharma¹, Enjuro Harunari¹, Tao Zhou¹, Agus Trianto², Yasuhiro Igarashi¹

Affiliations

¹ Biotechnology Research Center and Department of Biotechnology, Toyama Prefectural University, 5180 Kurokawa, Imizu, Toyama 939-0398, Japan.
² Faculty of Fisheries and Marine Sciences, Diponegoro University, Tembalang Campus, St. Prof. Soedarto SH., Semarang 50275, Central Java, Indonesia.

Abstract

(2Z,4E)-3-Methyl-2,4-decadienoic acid (1) was identified as a major metabolite from a culture extract of a marine bacterium Microbulbifer which was collected from a stony coral Porites sp. NMR-based spectroscopic analysis revealed that 1 is an unsaturated fatty acid in which a methyl group is located in an uncommon position as a natural product. Feeding experiments of ¹³C-labeled precursors clarified that ʟ-methionine-derived methylation takes place at the carbon which is derived from the carbonyl carbon of acetate. Compound 1 showed weak growth inhibition against Saccharomyces cerevisiae.

Keywords: Microbulbifer; biosynthesis; fatty acid; marine bacteria; methylation.