(2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells
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...
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MDPI AG
2018-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/23/6/1415 |
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| author | Hee Jin Jung A Kyoung Lee Yeo Jin Park Sanggwon Lee Dongwan Kang Young Suk Jung Hae Young Chung Hyung Ryong Moon |
| author_facet | Hee Jin Jung A Kyoung Lee Yeo Jin Park Sanggwon Lee Dongwan Kang Young Suk Jung Hae Young Chung Hyung Ryong Moon |
| author_sort | Hee Jin Jung |
| collection | DOAJ |
| description | 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. |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T19:06:05Z |
| publishDate | 2018-06-01 |
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| series | Molecules |
| spelling | doaj.art-ad5df8d9ba5e4495b7afe07052f074632022-12-22T03:20:01ZengMDPI AGMolecules1420-30492018-06-01236141510.3390/molecules23061415molecules23061415(2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast CellsHee Jin Jung0A Kyoung Lee1Yeo Jin Park2Sanggwon Lee3Dongwan Kang4Young Suk Jung5Hae Young Chung6Hyung Ryong Moon7Molecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaMolecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaMolecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaMolecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaMolecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaMolecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaMolecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaMolecular Inflammation Research Center for Aging Intervention (MRCA), Pusan National University, Busan 46241, KoreaUltraviolet (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.http://www.mdpi.com/1420-3049/23/6/1415(2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene)cyclopentanone (BHCP)tyrosinase inhibitoranti-melanogenesisanti-wrinkle |
| spellingShingle | Hee Jin Jung A Kyoung Lee Yeo Jin Park Sanggwon Lee Dongwan Kang Young Suk Jung Hae Young Chung Hyung Ryong Moon (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 (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene)cyclopentanone (BHCP) tyrosinase inhibitor anti-melanogenesis anti-wrinkle |
| title | (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells |
| title_full | (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells |
| title_fullStr | (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells |
| title_full_unstemmed | (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells |
| title_short | (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene) cyclopentanone Exerts Anti-Melanogenesis and Anti-Wrinkle Activities in B16F10 Melanoma and Hs27 Fibroblast Cells |
| title_sort | 2e 5e 2 5 bis 3 hydroxy 4 methoxybenzylidene cyclopentanone exerts anti melanogenesis and anti wrinkle activities in b16f10 melanoma and hs27 fibroblast cells |
| topic | (2E,5E)-2,5-Bis(3-hydroxy-4-methoxybenzylidene)cyclopentanone (BHCP) tyrosinase inhibitor anti-melanogenesis anti-wrinkle |
| url | http://www.mdpi.com/1420-3049/23/6/1415 |
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