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Title 

Flavonoids as mushroom tyrosinase inhibitors: a fluorescence quenching study

Authors 

Donghyun KimJiyeoun ParkJinhee KimC HanJ YoonN KimJ SeoChoong Hwan Lee

Publisher 

American Chemical Society

Issue Date 

2006

Citation 

Journal of Agricultural and Food Chemistry, vol. 54, no. 3, pp. 935-941

Keywords 

copper chelatorflavonoidsfluorescence quenchingtyrosinase inhibitorenzyme inhibitorflavonoidmonophenol monooxygenaseagaricalesamino acid sequencechemical structure

Abstract 

Flavonoids, a group of naturally occurring antioxidants and metal chelators, can be used as tyrosinase inhibitors due to their formation of copper-flavonoid complexes. Thus, to investigate the underlying inhibition mechanism, a large group of flavonoids from several major flavones and flavonols were tested using fluorescence quenching spectroscopy. In addition, large differences in the tyrosinase inhibitory activities and chelating capacities according to the location of the hydroxyl group(s) in combination with the A and B rings in the flavonoids were confirmed. Accordingly, the major conclusions from this work are as follows: (i) The tyrosinase inhibitory activity is not only dependent on the number of hydroxyl groups in the flavonoids, (ii) the enzyme is primarily quenched by the hydroxyl group(s) of A and B rings on the ether side of the flavonoids, and (iii) the tyrosinase inhibitory activity of 7,8,3′,4′-tetrahydroxyflavone is supported by a virtual model of docking with the mushroom tyrosinase, which depicts the quenching of the enzyme. The results also demonstrated that the dihydroxy substitutions in the A and B rings are crucial for Cu2+-chelate formation, thereby influencing the tyrosinase inhibitory activity.

ISSN 

0021-8561

Link 

http://dx.doi.org/10.1021/jf0521855

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2017-04-19


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