Biosynthesis of resorcylic acid lactone lasiodiplodin in Lasiodiplodia theobromae

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, demonstrat...

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Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2009-05, Vol.73 (5), p.1118-1122
Main Authors: Kashima, T.(Hokkaido Univ., Sapporo (Japan)), Takahashi, K, Matsuura, H, Nabeta, K
Format: Article
Language:English
Subjects:
Acetates - chemistry
Ascomycota - metabolism
Biological and medical sciences
BIOSINTESIS
BIOSYNTHESE
BIOSYNTHESIS
BOTRYODIPLODIA THEOBROMAE
Carbon Isotopes - chemistry
Deuterium - chemistry
Fundamental and applied biological sciences. Psychology
Hydroxybenzoates - chemistry
LACTONAS
LACTONE
LACTONES
Lasiodiplodia theobromae
lasiodiplodin
Magnetic Resonance Spectroscopy
METABOLITE
METABOLITES
METABOLITOS
resorcylic acid lactone
Staining and Labeling
TECHNIQUE DES TRACEURS
TECNICAS DE TRAZADORES
TRACER TECHNIQUES
Zearalenone - analogs & derivatives
Zearalenone - biosynthesis
Zearalenone - chemistry
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Summary: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.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.80878