Journal
MARINE BIOTECHNOLOGY
Volume 16, Issue 4, Pages 412-422Publisher
SPRINGER
DOI: 10.1007/s10126-014-9557-0
Keywords
Manzamine; Fusarium spp.; Biotransformation; Metabolism; Resistance
Funding
- NCCIH NIH HHS [R01 AT007318] Funding Source: Medline
- NIAID NIH HHS [R01 AI036596] Funding Source: Medline
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As a part of our continuing investigation of the manzamine alkaloids we studied the in vitro activity of the beta-carboline containing manzamine alkaloids against Fusarium solani, Fusarium oxysporium, and Fusarium proliferatum by employing several bioassay techniques including one-dimensional direct bioautography, dilution, and plate susceptibility, and microtiter broth assays. In addition, we also studied the metabolism of the manzamine alkaloids by Fusarium spp. in order to facilitate the redesign of the compounds to prevent resistance of Fusarium spp. through metabolism. The present research reveals that the manzamine alkaloids are inactive against Fusarium spp. and the fungi transform manzamines via hydrolysis, reduction, and a retro Pictet-Spengler reaction. This is the first report to demonstrate an enzymatically retro Pictet-Spengler reaction. The results of this study reveal the utility of the rational design of metabolically stable antifungal agents from this class and the development of manzamine alkaloids as antimalarial drugs through the utilization of Fusarium's metabolic products to reconstruct the molecule.
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