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Molecules 2018, 23(6), 1415; https://doi.org/10.3390/molecules23061415

(2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells

1
Molecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, Korea
2
College of Pharmacy, Pusan National University, Busan 46241, Korea
*
Author to whom correspondence should be addressed.
Received: 11 May 2018 / Revised: 8 June 2018 / Accepted: 11 June 2018 / Published: 11 June 2018
(This article belongs to the Special Issue Design in Synthetic Biology)
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Abstract

Ultraviolet (UV) radiation exposure is the primary cause of extrinsic skin aging, which results in skin hyperpigmentation and wrinkling. In this study, we investigated the whitening effect of (2E,5E)-2,5-bis(3-hydroxy-4-methoxybenzylidene)cyclopentanone (BHCP) on B16F10 melanoma and its anti-wrinkle activity on Hs27 fibroblasts cells. BHCP was found to potently inhibit tyrosinase, with 50% inhibition concentration (IC50) values of 1.10 µM and 8.18 µM for monophenolase (l-tyrosine) and diphenolase (l-DOPA), and the enzyme kinetics study revealed that BHCP is a competitive-type tyrosinase inhibitor. Furthermore, BHCP significantly inhibited melanin content and cellular tyrosinase activity, and downregulated the levels of microphthalmia-associated transcription factor (MITF), phosphorylated levels of cAMP response element-binding (CREB) protein, and tyrosinase in α-melanocyte stimulating hormone (α-MSH)-induced B16F10 melanoma cells. Moreover, BHCP inhibited the phosphorylation of p65 and expression of matrix metalloproteinases (MMP-1, MMP-9, MMP-12, and MMP-13) in Hs27 fibroblasts stimulated with UV radiation. Therefore, our results demonstrate that BHCP may be a good candidate for the development of therapeutic agents for diseases associated with hyperpigmentation and wrinkling. View Full-Text
Keywords: (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene)cyclopentanone (BHCP); tyrosinase inhibitor; anti-melanogenesis; anti-wrinkle (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene)cyclopentanone (BHCP); tyrosinase inhibitor; anti-melanogenesis; anti-wrinkle
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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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Jung, H.J.; Lee, A.K.; Park, Y.J.; Lee, S.; Kang, D.; Jung, Y.S.; Chung, H.Y.; Moon, H.R. (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells. Molecules 2018, 23, 1415.

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