Identifying 8-hydroxynaringenin as a suicide substrate of mushroom tyrosinase
A biotransformed metabolite of naringenin was isolated from the fermentation broth of Aspergillus oryzae, fed with naringenin, and identifi ed as 8-hydroxynaringenin based on the mass and 1H- and 13C-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 fi ndings, which proved that both 8-hydroxydaidzein and 8-hydroxygenistein are suicide substrates of mushroom tyrosinase, show that 7,8,4′-trihydroxyl functional groups on fl avonoids’ skeletons play important roles in producing suicide substrate properties toward mushroom tyrosinase.
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Document Type: Abstract
Publication date: December 1, 2010