Bioconversion of 6-Hydroxyflavanone: Isolation, Characterization and Bioactivity Evaluation of Eleven Phase I and Phase II Microbial Metabolites

Flavonoids are important polyphenolic phytochemicals found in fruits, vegetables and many dietary supplements. Described as health promoting and disease preventing, flavonoids are associated with a wide range of biological activities. Since flavonoids are exceedingly efficient in a variety of biological processes, their use in regularly consumed dietary supplements should be considered with caution. Flavonoids are known to interact with cytochromes P450 (CYPs). Depending upon their structures and concentration flavonoids can either inhibit or activate human CYPs. This underscores the importance of determining the metabolic pathways of flavonoids. Microorganisms are good predictors of mammalian drug metabolites with the ability to yield sufficient quantities of metabolites for structure analysis and further pharmacological evaluation [1]. 6-Hydroxyflavanone (1) was screened using 40 organisms. Eleven metabolites were identified using four selected cultures to isolate the maximum number of metabolites. Structures of the metabolic products were elucidated by means of spectroscopic data analysis. None of the metabolites tested showed antibacterial, antifungal and antimalarial activities against selected organisms.

P59, Fig. 1: Microbial Metabolites of
6-Hydroxyflavanone

Acknowledgements: This work was supported, in part by the United States Department of Agriculture, Agricultural Research Specific Cooperative Agreement No. 58 – 6408 – 02 – 1-612. References: [1] Davis PJ, (1987) “Antibiotics and Microbial Transformation,” ed. By Lamba SS, Walker CA, CRC, Boca Raton, Florida, pp. 47 – 70.