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Enzymatic Potential of Mucor inaequisporus for Naringin Biotransformation, Accessed by Fractional Factorial Design and Mass Spectrometry Analysis

Enzo Monte Canedo, Taicia Pacheco Fill, Edenir Rodrigues Pereira-Filho and Edson Rodrigues-Filho

Whole cells of Mucor inaequisporus were used for biotransformation of the flavonoid naringin, as a green method for structural diversification of this class of natural product. The metabolism of the fungus was challenged against naringin under several culturing conditions, using statistical optimization. Eight parameters were evaluated comprising type and concentration of carbon source, substrate concentration, substrate addition time, shaking, luminosity, temperature and extraction time. Sixteen different culture conditions were tested in this screening. After LC-MS analysis, several biotransformation products were identified and naringenin was identified as the major product. Eleven biotransformation products were detected in Ft-HRMS analyses and identified as naringenin as major compound, 4’-methoxynaringenin, 4’-methoxynaringin, rhoifolin, apigenin, methoxyapigenin, acetylated naringin, and also two biflavonoids and two triflavonoids. Ft-HRMSn showed to be a powerful technique for structural elucidation of flavonoid biotransformation products. The fungus was capable to perform deglycosylation, reduction and O-methylation reactions at this substrate indicating good enzymatic potential, since these reactions weren’t observed before for this fungus-genus.

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