Document Detail

Biosynthesis of resorcylic acid lactone lasiodiplodin in Lasiodiplodia theobromae.
MedLine Citation:
PMID:  19420710     Owner:  NLM     Status:  MEDLINE    
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.
Takasumi Kashima; Kosaku Takahashi; Hideyuki Matsuura; Kensuke Nabeta
Publication Detail:
Type:  Journal Article     Date:  2009-05-07
Journal Detail:
Title:  Bioscience, biotechnology, and biochemistry     Volume:  73     ISSN:  1347-6947     ISO Abbreviation:  Biosci. Biotechnol. Biochem.     Publication Date:  2009 May 
Date Detail:
Created Date:  2009-05-25     Completed Date:  2009-08-28     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9205717     Medline TA:  Biosci Biotechnol Biochem     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  1118-22     Citation Subset:  IM    
Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Sapporo, Japan.
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MeSH Terms
Acetates / chemistry
Ascomycota / metabolism*
Carbon Isotopes / chemistry
Deuterium / chemistry
Hydroxybenzoic Acids / chemistry*
Magnetic Resonance Spectroscopy
Staining and Labeling
Zearalenone / analogs & derivatives*,  biosynthesis,  chemistry
Reg. No./Substance:
0/Acetates; 0/Carbon Isotopes; 0/Hydroxybenzoic Acids; 0/lasiodiplodin; 17924-92-4/Zearalenone; 7782-39-0/Deuterium

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