Citation

Chang TS, Lin MY, Lin HJ. Journal of Cosmetic Science 2010; 61(3): 205-210.

Copyright

(Copyright © 2010)

DOI

unavailable

PMID

20587349

Abstract

A biotransformed metabolite of naringenin was isolated from the fermentation broth of Aspergillus oryzae, fed with naringenin, and identified as 8-hydroxynaringenin based on the mass and (1)H- and (13)C-NMR spectral data. The compound showed characteristics of both an irreversible inhibitor and a substrate of mushroom tyrosinase in preincubation and HPLC analysis. These results demonstrate that 8-hydroxynaringenin belongs to a suicide substrate of mushroom tyrosinase. The partition ratio between the compound's molecules in the formation of product and in the inactivation of the enzyme was determined to be 283 +/- 21. The present study's results, together with our previous findings, which proved that both 8-hydroxydaidzein and 8-hydroxygenistein are suicide substrates of mushroom tyrosinase, show that 7,8,4'-trihydroxyl functional groups on flavonoids' skeletons play important roles in producing suicide substrate properties toward mushroom tyrosinase.

Language: en

Keywords

Mass Spectrometry; Nuclear Magnetic Resonance, Biomolecular; Aspergillus oryzae; Monophenol Monooxygenase; Flavanones