Synthesis of novel azo-resveratrol,azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors |
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Authors: | Yu Min Song Young Mi Ha Jin-Ah Kim Ki Wung Chung Yohei Uehara Kyung Jin Lee Pusoon Chun Youngjoo Byun Hae Young Chung Hyung Ryong Moon |
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Affiliation: | 1. Molecular Inflammation Research Center for Aging Intervention (MRCA), College of Pharmacy, Pusan National University, Busan 609-735, Republic of Korea;2. College of Pharmacy, Inje University, Gimhae, Gyeongnam 621-749, Republic of Korea;3. College of Pharmacy, Korea University, Chungnam 339-700, Republic of Korea |
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Abstract: | Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 μM, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC50 value of IC50 = 36.28 ± 0.72 μM, comparable to that of resveratrol, a well-known tyrosinase inhibitor. |
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