Inhibitory activity of novel kojic acid derivative containing trolox moiety on melanogenesis |
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Authors: | Ahn Soo Mi Rho Ho Sik Baek Heung Soo Joo Yung Hyup Hong Yong Deog Shin Song Seok Park Young-Ho Park Soo Nam |
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Institution: | aKyung Hee University Skin Biotechnology Center, Suwon, Republic of Korea;bAmorePacific R&D Center, Yongin 446-729, Republic of Korea;cDepartment of Fine Chemistry, Seoul National University of Science and Technology, Seoul 139-743, Republic of Korea |
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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. |
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Keywords: | Kojic acid Trolox Tyrosinase DPPH Depigmentation |
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