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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

Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan
Institute for Innovation, Ajinomoto Co., Inc., Kawasaki, Kanagawa 210-8681, Japan
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]   |  


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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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