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Microbial transformation of curvularin.
Jixun Zhan1, A A Leslie Gunatilaka
1Southwest Center for Natural Products Research and Commercialization, Office of Arid Lands Studies, College of Agriculture and Life Sciences, The University of Arizona, 250 East Valencia Road, Tucson, Arizona 85706-6800, USA.
Journal of Natural Products
|August 30, 2005
Summary
Beauveria bassiana ATCC 7159 transformed curvularin into three novel compounds through hydroxylation, glucosidation, and methylglucosidation. This fungus possesses constitutive enzymes for these transformations, as evidenced by metabolite 5 isolation without added substrate.
Area of Science:
- Microbiology
- Natural Product Chemistry
- Biotechnology
Background:
- Curvularin is a known natural product with potential biological activities.
- Microbial transformations are valuable tools for generating novel chemical entities from existing scaffolds.
Purpose of the Study:
- To investigate the microbial transformation of curvularin using Beauveria bassiana ATCC 7159.
- To identify and characterize new metabolites produced by the fungus.
- To explore the enzymatic capabilities of Beauveria bassiana ATCC 7159.
Main Methods:
- Incubation of curvularin with Beauveria bassiana ATCC 7159.
- Isolation and purification of metabolites using chromatographic techniques.
- Structure elucidation of new compounds via spectroscopic methods (e.g., NMR, MS).
Main Results:
- Three new curvularin derivatives were identified: curvularin-7-O-beta-D-glucopyranoside (2), curvularin-4'-O-methyl-7-O-beta-D-glucopyranoside (3), and 6-hydroxycurvularin-4'-O-methyl-6-O-beta-D-glucopyranoside (4).
- These metabolites resulted from hydroxylation, glucosidation, and methylglucosidation reactions.
- A fifth metabolite, 6-methyl-2,4-dihydroxyphenyl-4'-O-methyl-1-O-beta-D-glucopyranoside (5), was isolated from fermentation without added substrate.
Conclusions:
- Beauveria bassiana ATCC 7159 effectively transforms curvularin into novel glycosylated and hydroxylated derivatives.
- The fungus possesses constitutive hydroxylase, glucosyl transferase, and methylase enzymes, enabling complex metabolic modifications.
- This study expands the chemical diversity of curvularin analogues and highlights the biosynthetic potential of Beauveria bassiana.