AI Article Synopsis
- The study explored how lasiodiplodin (1) and its derivative (2) are made by using (13)C-labeled acetates in the fungus Lasiodiplodia theobromae.
- The labeling patterns were analyzed with (13)C-NMR and INADEQUATE techniques, confirming that both compounds are derived from octaketide biosynthesis.
- Additionally, the research proposed that highly reduced acyl intermediates are involved in synthesizing lasiodiplodins, supported by experiments with (2)H-labeled intermediates that showed successful incorporation into lasiodiplodin (1).
Article Abstract
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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| http://dx.doi.org/10.1271/bbb.80878 | DOI Listing |
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