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      N-(4-methoxyphenyl) caffeamide-induced melanogenesis inhibition mechanisms

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          Abstract

          Background

          The derivative of caffeamide exhibits antioxidant and antityrosinase activity. The activity and mechanism of N-(4-methoxyphenyl) caffeamide (K36E) on melanogenesis was investigated.

          Methods

          B16F0 cells were treated with various concentrations of K36E; the melanin contents and related signal transduction were studied. Western blotting assay was applied to determine the protein expression, and spectrophotometry was performed to identify the tyrosinase activity and melanin content.

          Results

          Our results indicated that K36E reduced α-melanocyte-stimulating hormone (α-MSH)-induced melanin content and tyrosinase activity in B16F0 cells. In addition, K36E inhibited the expression of phospho-cyclic adenosine monophosphate (cAMP)-response element-binding protein, microphthalmia-associated transcription factor (MITF), tyrosinase, and tyrosinase-related protein-1 (TRP-1). K36E activated the phosphorylation of protein kinase B (AKT) and glycogen synthase kinase 3 beta (GSK3β), leading to the inhibition of MITF transcription activity. K36E attenuated α-MSH induced cAMP pathways, contributing to hypopigmentation.

          Conclusions

          K36E regulated melanin synthesis through reducing the expression of downstream proteins including p-CREB, p-AKT, p-GSK3β, tyrosinase, and TRP-1, and activated the transcription factor, MITF. K36E may have the potential to be developed as a skin whitening agent.

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          Most cited references46

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          Human skin pigmentation: melanocytes modulate skin color in response to stress.

          All organisms, from simple invertebrates to complex human beings, exist in different colors and patterns, which arise from the unique distribution of pigments throughout the body. Pigmentation is highly heritable, being regulated by genetic, environmental, and endocrine factors that modulate the amount, type, and distribution of melanins in the skin, hair, and eyes. In addition to its roles in camouflage, heat regulation, and cosmetic variation, melanin protects against UV radiation and thus is an important defense system in human skin against harmful factors. Being the largest organ of the body that is always under the influence of internal and external factors, the skin often reacts to those agents by modifying the constitutive pigmentation pattern. The focus of this review is to provide an updated overview of important physiological and biological factors that increase pigmentation and the mechanisms by which they do so. We consider endocrine factors that induce temporary (e.g., during pregnancy) or permanent (e.g., during aging) changes in skin color, environmental factors (e.g., UV), certain drugs, and chemical compounds, etc. Understanding the mechanisms by which different factors and compounds induce melanogenesis is of great interest pharmaceutically (as therapy for pigmentary diseases) and cosmeceutically (e.g., to design tanning products with potential to reduce skin cancer risk).
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            Central role of p53 in the suntan response and pathologic hyperpigmentation.

            UV-induced pigmentation (suntanning) requires induction of alpha-melanocyte-stimulating hormone (alpha-MSH) secretion by keratinocytes. alpha-MSH and other bioactive peptides are cleavage products of pro-opiomelanocortin (POMC). Here we provide biochemical and genetic evidence demonstrating that UV induction of POMC/MSH in skin is directly controlled by p53. Whereas p53 potently stimulates the POMC promoter in response to UV, the absence of p53, as in knockout mice, is associated with absence of the UV-tanning response. The same pathway produces beta-endorphin, another POMC derivative, which potentially contributes to sun-seeking behaviors. Furthermore, several instances of UV-independent pathologic pigmentation are shown to involve p53 "mimicking" the tanning response. p53 thus functions as a sensor/effector for UV pigmentation, which is a nearly constant environmental exposure. Moreover, this pathway is activated in numerous conditions of pathologic pigmentation and thus mimics the tanning response.
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              Hypopigmenting agents: an updated review on biological, chemical and clinical aspects.

              An overview of agents causing hypopigmentation in human skin is presented. The review is organized to put forward groups of biological and chemical agents. Their mechanisms of action cover (i) tyrosinase inhibition, maturation and enhancement of its degradation; (ii) Mitf inhibition; (iii) downregulation of MC1R activity; (iv) interference with melanosome maturation and transfer; (v) melanocyte loss, desquamation and chemical peeling. Tyrosinase inhibition is the most common approach to achieve skin hypopigmentation as this enzyme catalyses the rate-limiting step of pigmentation. Despite the large number of tyrosinase inhibitors in vitro, only a few are able to induce effects in clinical trials. The gap between in-vitro and in-vivo studies suggests that innovative strategies are needed for validating their efficacy and safety. Successful treatments need the combination of two or more agents acting on different mechanisms to achieve a synergistic effect. In addition to tyrosinase inhibition, other parameters related to cytotoxicity, solubility, cutaneous absorption, penetration and stability of the agents should be considered. The screening test system is also very important as keratinocytes play an active role in modulating melanogenesis within melanocytes. Mammalian skin or at least keratinocytes/melanocytes co-cultures should be preferred rather than pure melanocyte cultures or soluble tyrosinase.
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                Author and article information

                Contributors
                kuoyh@mail.cmu.edu.tw
                ben00691206@hotmail.com
                wu.poyuan@gmail.com
                cswu@mail.cmu.edu.tw
                pjsung@nmmba.gov.tw
                yihlin@asia.edu.tw
                +886-4-22053366-5302 , hmchiang@mail.cmu.edu.tw
                Journal
                BMC Complement Altern Med
                BMC Complement Altern Med
                BMC Complementary and Alternative Medicine
                BioMed Central (London )
                1472-6882
                23 January 2017
                23 January 2017
                2017
                : 17
                : 71
                Affiliations
                [1 ]ISNI 0000 0001 0083 6092, GRID grid.254145.3, Department of Chinese Pharmaceutical Sciences and Chinese Medicine Resources, , China Medical University, ; Taichung, 404 Taiwan
                [2 ]ISNI 0000 0000 9263 9645, GRID grid.252470.6, Department of Biotechnology, , Asia University, ; Taichung, 413 Taiwan
                [3 ]ISNI 0000 0001 0083 6092, GRID grid.254145.3, Department of Cosmeceutics, , China Medical University, ; Taichung, 404 Taiwan
                [4 ]ISNI 0000 0004 0572 9415, GRID grid.411508.9, Department of Dermatology, , China Medical University Hospital, ; Taichung, 404 Taiwan
                [5 ]ISNI 0000 0001 0083 6092, GRID grid.254145.3, School of Medicine, , China Medical University, ; Taichung, 404 Taiwan
                [6 ]ISNI 0000 0004 0638 9483, GRID grid.452856.8, , National Museum of Marine Biology and Aquarium, ; Pingtung, 944 Taiwan
                Article
                1554
                10.1186/s12906-016-1554-6
                5259883
                28114924
                7645bdaf-815a-415b-9b96-a9c68caf3645
                © The Author(s). 2017

                Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License ( http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver ( http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.

                History
                : 27 July 2016
                : 28 December 2016
                Funding
                Funded by: the Ministry of Science and Techenology
                Award ID: NSC100-2320-B-039-002-MY3; MOST104-2320-B-039-006
                Award Recipient :
                Funded by: Taiwan Ministry of Health and Welfare Clinical Trial and Research Center of Excellence
                Award ID: MOHW104-TDU-B-212-113002
                Funded by: FundRef http://dx.doi.org/10.13039/501100007300, China Medical University ;
                Award ID: CMU102-ASIA-18
                Award Recipient :
                Categories
                Research Article
                Custom metadata
                © The Author(s) 2017

                Complementary & Alternative medicine
                n-(4-methoxyphenyl) caffeamide,melanogenesis,propolis,microphthalmia-associated transcription factor,camp response element-binding protein,glycogen synthase kinase 3 beta

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