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Molecules 2015, 20(9), 16933-16945; doi:10.3390/molecules200916933

Synthesis and Biological Evaluation of Resveratrol Derivatives as Melanogenesis Inhibitors

1
College of Pharmacy, Chungbuk National University, Cheongju, Chungbuk 28644, Korea
2
RNS Inc., Yuseong-Gu, Daejeon 34182, Korea
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 15 June 2015 / Revised: 2 September 2015 / Accepted: 10 September 2015 / Published: 17 September 2015
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [907 KB, uploaded 17 September 2015]   |  

Abstract

Resveratrol (1), a naturally occurring stilbene compound, has been suggested as a potential whitening agent with strong inhibitory activity on melanin synthesis. However, the use of resveratrol in cosmetics has been limited due to its chemical instability and poor bioavailability. Therefore, resveratrol derivatives were prepared to improve bioavailability and anti-melanogenesis activity. Nine resveratrol derivatives including five alkyl ether derivatives with C2H5, C4H9, C5H11, C6H13, and C8H17 (2a2e) and four ester derivatives with CH3, CH=C(CH3)2, CH(C2H5)C4H9, C7H15 (3a3d) were newly synthesized and their effect on melanin synthesis were assessed. All the synthetic derivatives efficiently reduced the melanin content in α-MSH stimulated B16F10 melanoma cells. Further investigation showed that the inhibitory effect of 2a on melanin synthesis was achieved not by the inhibition of tyrosinase activity but by the inhibition of melanogenic enzyme expressions such as tyrosinase and tyrosinase-related protein (TRP)-1. Our synthetic resveratrol derivatives have more lipophilic properties than resveratrol by the addition of alkyl or acyl chains to free hydroxyl moiety of resveratrol; thus, they are expected to show better bioavailability in skin application. Therefore, we suggest that our synthetic resveratrol derivatives might be promising candidates for better practical application to skin-whitening cosmetics. View Full-Text
Keywords: melanin; resveratrol derivatives; tyrosinase; tyrosinase-related protein (TRP)-1 melanin; resveratrol derivatives; tyrosinase; tyrosinase-related protein (TRP)-1
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Liu, Q.; Kim, C.; Jo, Y.H.; Kim, S.B.; Hwang, B.Y.; Lee, M.K. Synthesis and Biological Evaluation of Resveratrol Derivatives as Melanogenesis Inhibitors. Molecules 2015, 20, 16933-16945.

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