title: Inhibitory activity of novel kojic acid derivative containing trolox moiety on melanogenesis.
abstract: A novel kojic acid derivative containing a trolox moiety, (±)-5-hydroxy-4-oxo-4H-pyran-2-yl methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate (3a), was synthesized. The two biologically active compounds, namely, kojic acid and trolox, were conjugated via an ester bond as they are expected to behave synergistically. The antioxidant activity and the tyrosinase inhibitory activity of this novel kojic acid derivative on melanogenesis were evaluated. Compound 3a exhibited potent tyrosinase inhibitory activity and radical scavenging activity. Limited structure-activity relationship (SAR) investigations indicated that the tyrosinase inhibitory activities may originate from the kojic acid moiety, and the radical scavenging activity may be due to the phenolic hydroxyl group of trolox. Compound 3a also exhibited potent depigmenting activity in a cell-based assay. The limited SAR investigations revealed that the depigmenting activity of 3a may be due to the synergistic activities of kojic acid and its trolox moiety.
authors.affiliation: Kyung Hee University Skin Biotechnology Center, Suwon, Republic of Korea.
authors.forename: Soo Mi
authors.initials: SM
authors.lastname: Ahn
authors.forename: Ho Sik
authors.initials: HS
authors.lastname: Rho
authors.forename: Heung Soo
authors.initials: HS
authors.lastname: Baek
authors.forename: Yung Hyup
authors.initials: YH
authors.lastname: Joo
authors.forename: Yong Deog
authors.initials: YD
authors.lastname: Hong
authors.forename: Song Seok
authors.initials: SS
authors.lastname: Shin
authors.forename: Young-Ho
authors.initials: YH
authors.lastname: Park
authors.forename: Soo Nam
authors.initials: SN
authors.lastname: Park
mesh_terms: D000818:Animals; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001665:Binding Sites; D002454:Cell Differentiation; D002839:Chromans / Q000737:chemistry*; D003198:Computer Simulation; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008544:Melanocytes / Q000166:cytology / Q000187:drug effects*; D051379:Mice; D008810:Mice, Inbred C57BL; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C570589:5-hydroxy-4-oxo-4H-pyran-2-yl methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate; D001578:Benzopyrans; D002839:Chromans; D016166:Free Radical Scavengers; D011753:Pyrones; C011890:kojic acid; D014442:Monophenol Monooxygenase; C010643:6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid