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

(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 locate...

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Autores principales: Sharma, Amit Raj, Harunari, Enjuro, Zhou, Tao, Trianto, Agus, Igarashi, Yasuhiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6808205/
https://www.ncbi.nlm.nih.gov/pubmed/31666867
http://dx.doi.org/10.3762/bjoc.15.225
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author Sharma, Amit Raj
Harunari, Enjuro
Zhou, Tao
Trianto, Agus
Igarashi, Yasuhiro
author_facet Sharma, Amit Raj
Harunari, Enjuro
Zhou, Tao
Trianto, Agus
Igarashi, Yasuhiro
author_sort Sharma, Amit Raj
collection PubMed
description (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 (13)C-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.
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spelling pubmed-68082052019-10-30 Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp. Sharma, Amit Raj Harunari, Enjuro Zhou, Tao Trianto, Agus Igarashi, Yasuhiro Beilstein J Org Chem Full Research Paper (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 (13)C-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. Beilstein-Institut 2019-09-30 /pmc/articles/PMC6808205/ /pubmed/31666867 http://dx.doi.org/10.3762/bjoc.15.225 Text en Copyright © 2019, Sharma et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Sharma, Amit Raj
Harunari, Enjuro
Zhou, Tao
Trianto, Agus
Igarashi, Yasuhiro
Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
title Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
title_full Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
title_fullStr Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
title_full_unstemmed Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
title_short Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp.
title_sort isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium microbulbifer sp.
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6808205/
https://www.ncbi.nlm.nih.gov/pubmed/31666867
http://dx.doi.org/10.3762/bjoc.15.225
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