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Molecules 2016, 21(1), 59; doi:10.3390/molecules21010059

Isolation and Biosynthetic Analysis of Haliamide, a New PKS-NRPS Hybrid Metabolite from the Marine Myxobacterium Haliangium ochraceum

1
Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan
2
Institute for Innovation, Ajinomoto Co., Inc., Kawasaki, Kanagawa 210-8681, Japan
3
R & D Planning Department, Ajinomoto Co., Inc., Chuo-ku, Tokyo 104-8315, Japan
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 11 November 2015 / Revised: 29 December 2015 / Accepted: 31 December 2015 / Published: 6 January 2016
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [874 KB, uploaded 6 January 2016]   |  

Abstract

Myxobacteria of marine origin are rare and hard-to-culture microorganisms, but they genetically harbor high potential to produce novel antibiotics. An extensive investigation on the secondary metabolome of the unique marine myxobacterium Haliangium ochraceum SMP-2 led to the isolation of a new polyketide-nonribosomal peptide hybrid product, haliamide (1). Its structure was elucidated by spectroscopic analyses including NMR and HR-MS. Haliamide (1) showed cytotoxicity against HeLa-S3 cells with IC50 of 12 μM. Feeding experiments were performed to identify the biosynthetic building blocks of 1, revealing one benzoate, one alanine, two propionates, one acetate and one acetate-derived terminal methylene. The biosynthetic gene cluster of haliamide (hla, 21.7 kbp) was characterized through the genome mining of the producer, allowing us to establish a model for the haliamide biosynthesis. The sulfotransferase (ST)-thioesterase (TE) domains encoded in hlaB appears to be responsible for the terminal alkene formation via decarboxylation. View Full-Text
Keywords: marine myxobacterium; Haliangium ochraceum; haliamide; polyketide; biosynthesis marine myxobacterium; Haliangium ochraceum; haliamide; polyketide; biosynthesis
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Sun, Y.; Tomura, T.; Sato, J.; Iizuka, T.; Fudou, R.; Ojika, M. Isolation and Biosynthetic Analysis of Haliamide, a New PKS-NRPS Hybrid Metabolite from the Marine Myxobacterium Haliangium ochraceum. Molecules 2016, 21, 59.

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