| Biosynthesis of resorcylic acid lactone lasiodiplodin in Lasiodiplodia theobromae. | |
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MedLine Citation:
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PMID: 19420710 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The biosynthesis of lasiodiplodin (1) and its (5S)-5-hydroxylated derivative (2) were investigated by the administration of (13)C-labeled acetates to Lasiodiplodia theobromae. The labeling patterns of biosynthetically (13)C-labeled 1 and 2 were determined by (13)C-NMR and INADEQUATE spectra, demonstrating the octaketide origins of 1 and 2. Taking into account the biosynthetic study of resorcylic acid lactones, the involvement of highly reduced acyl intermediates in the biosynthesis of lasiodiplodins was presumed; thus, we synthesized (2)H-labeled hypothetical acyl intermediates of 1, 9-hydroxydecanoic acid (4) and its N-acetylcysteamine thioester (SNAC, 5). When L. theobromae was incubated with 5 mM of a (2)H-labeled intermediate, the (2)H-label from the intermediate was incorporated at the expected position of 1. These incorporation studies revealed that 1 was produced via a pathway which closely resembles that of resorcylic acid lactone biosynthesis. |
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Authors:
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Takasumi Kashima; Kosaku Takahashi; Hideyuki Matsuura; Kensuke Nabeta |
Publication Detail:
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Type: Journal Article Date: 2009-05-07 |
Journal Detail:
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Title: Bioscience, biotechnology, and biochemistry Volume: 73 ISSN: 1347-6947 ISO Abbreviation: Biosci. Biotechnol. Biochem. Publication Date: 2009 May |
Date Detail:
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Created Date: 2009-05-25 Completed Date: 2009-08-28 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9205717 Medline TA: Biosci Biotechnol Biochem Country: Japan |
Other Details:
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Languages: eng Pagination: 1118-22 Citation Subset: IM |
Affiliation:
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Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Sapporo, Japan. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acetates
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chemistry Ascomycota / metabolism* Carbon Isotopes / chemistry Deuterium / chemistry Hydroxybenzoic Acids / chemistry* Magnetic Resonance Spectroscopy Staining and Labeling Zearalenone / analogs & derivatives*, biosynthesis, chemistry |
| Chemical | |
Reg. No./Substance:
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0/Acetates; 0/Carbon Isotopes; 0/Hydroxybenzoic Acids; 0/lasiodiplodin; 17924-92-4/Zearalenone; 7782-39-0/Deuterium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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