title: Synthesis, antioxidant capacity, and structure-activity relationships of tri-O-methylnorbergenin analogues on tyrosinase inhibition.
abstract: A series of tri-O-methylnorbergenin analogues 1-9 were synthesized and their antioxidant activities and inhibitory effects on tyrosinase were evaluated. Among tested analogues, compound 4 bearing cathechol moiety exhibited greater antioxidant activity and excellent inhibition on tyrosinase with IC50 value of 9.1 μM, comparable to that of corresponding positive controls. The inhibition mechanism analysis of compound 4 demonstrated that it was a mixed-type inhibitor on tyrosinase. These results suggest that these compounds may serve as a useful clue for further designing and development of novel potential tyrosinase inhibitors.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, 3-4-1 Kowakae, Higashiosaka-shi, Osaka 577-8502, Japan.
authors.forename: Yusei
authors.initials: Y
authors.lastname: Kashima
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Miyazawa
mesh_terms: D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D062385:Hydroxybenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D049934:Isocoumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D011485:Protein Binding / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: C000589836:11-O-protocatechuoyl-tri-O-methylnorbergenin; D000975:Antioxidants; D001578:Benzopyrans; D004791:Enzyme Inhibitors; D062385:Hydroxybenzoates; D049934:Isocoumarins; C063922:norbergenin; D014442:Monophenol Monooxygenase
keywords: Antioxidant; Bergenin; Structure–activity relationship; Tri-O-methylnorbergenin analogues; Tyrosinase inhibitor