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Identifying 8‐hydroxynaringenin as a suicide substrate of mushroom tyrosinase
Author(s) -
Chang T.S.,
Lin M.Y.,
Lin H.J.
Publication year - 2010
Publication title -
international journal of cosmetic science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.532
H-Index - 62
eISSN - 1468-2494
pISSN - 0142-5463
DOI - 10.1111/j.1468-2494.2010.00619_1.x
Subject(s) - mushroom , mushroom poisoning , tyrosinase , chemistry , medicine , humanities , art , biochemistry , food science , enzyme
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.