Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 61, Issue 27, Pages 6597-6603Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf401585f
Keywords
hydroxypyridinone; kojic acid; tyrosinase inhibitor
Funding
- Zhejiang Provincial National Natural Science Foundation of China [LY12B02014]
- National Natural Science Foundation of China [20972138]
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A range of hydroxypyridinone-L-phenylalanine conjugates were synthesized starting from kojic acid. Their tyrosinase activity was determined, and it was found that one of the compounds ((S)-(5-(benzyloxy)-1-octyl-4-oxo-1,4-dihydropyridin-2-yl)methyl 2-amino-3-phenylpropanoate, 5e) showed potent inhibitory effect against mushroom tyrosinase, the IC50 values for monophenolase and diphenolase activities being 12.6 and 4.0 mu M, respectively. It was also demonstrated that these conjugates are mixed-type inhibitors, suggesting they could bind to both the free enzyme and the enzyme substrate complexes. MTT assay indicated that Se was nontoxic to three cell lines. This compound may find applications in food preservation and cosmetics.
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