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- Title
Isolation and Biosynthetic Analysis of Haliamide, a New PKS-NRPS Hybrid Metabolite from the Marine Myxobacterium Haliangium ochraceum.
- Authors
Yuwei Sun; Tomohiko Tomura; Junichi Sato; Takashi Iizuka; Ryosuke Fudou; Makoto Ojika
- 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.
- Subjects
BIOSYNTHESIS; MYXOBACTERALES; METABOLOMICS; PEPTIDES; DECARBOXYLATION
- Publication
Molecules, 2016, Vol 21, Issue 1, p59
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules21010059