Melanogenesis and Melanin-Related Compounds: A Cosmetic Perspective

A special issue of Cosmetics (ISSN 2079-9284).

Deadline for manuscript submissions: closed (31 July 2019) | Viewed by 54542

Special Issue Editor


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Guest Editor
Department of Chemical Sciences, University of Naples “Federico II”, Via Cintia 4, I-80126 Naples, Italy
Interests: structural characterization, extraction, and evaluation/modulation of the antioxidant properties of natural phenolic compounds; exploitation of phenolic compounds, especially from agri-food by-products for the development of functional materials to be used in cosmetics, food packaging, and biomedicine; reactivity of natural phenolic compounds with reactive oxygen and nitrogen species and their manipulation/derivatization to improve their functional properties; evaluation of the antioxidant properties of phenolic compounds and of complex extracts/matrices using validated chemical assays; chemistry of melanin pigments
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Special Issue Information

Dear Colleagues,

Melanin pigments are one of the main determinants of skin and hair sensitivity to ultraviolet light and susceptibility to sun damage. Moreover, an overproduction or accumulation of melanins can lead to a local excess of pigmentation (hypermelanosis) associated with disorders such as melasma, lentigo, or postinflammatory hyperpigmentation, with a significant medical and aesthetic impact. Melanin pigments are produced in melanocytes by tyrosinase catalyzed oxidation of tyrosine, followed by a complex series of events that are regulated by either enzymatic or non-enzymatic factors. Recent advances in the chemistry of melanins have allowed one to disclose a number of important structure–property–function relationships that are of crucial relevance to the biological role of human pigments, including skin (photo) protection and UV-susceptibility. Two main groups of melanin pigments are found in humans: the black-to-dark brown eumelanins; and the lighter, yellowish-to-brown, sulfur-containing pheomelanins. The firsts are generated from the oxidative polymerization of 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA), derived from cyclization/oxidation of dopaquinone, whereas pheomelanins are produced when the addition of the thiol group of cysteine to dopaquinone occurs, leading to 5-S-cysteinyldopa as the major compound. Further oxidation of 5-S-cystenylopda leads to the formation of the pigments via benzothiazine intermediates. This Special Issue welcomes original research manuscripts on eumelanin and/or pheomelanin biosynthesis, which represent structures and properties of cosmetic relevance. Articles describing depigmenting activity (e.g., tyrosinase inhibition properties) of natural or synthetic compounds, as well as reviews describing the current state-of-the-art, are also welcome.

Dr. Lucia Panzella
Guest Editor

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Keywords

  • melanins
  • melanogenesis
  • eumelanins
  • pheomelanins
  • 5,6-dihydroxyindoles
  • 5-S-cysteinyldopa
  • antioxidant
  • tyrosinase
  • depigmenting agents
  • photoprotection

Published Papers (5 papers)

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Research

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12 pages, 2388 KiB  
Communication
Calebin-A, a Curcuminoid Analog Inhibits α-MSH-Induced Melanogenesis in B16F10 Mouse Melanoma Cells
by Shilpi Goenka, Kalyanam Nagabhushanam, Muhammed Majeed and Sanford R. Simon
Cosmetics 2019, 6(3), 51; https://doi.org/10.3390/cosmetics6030051 - 19 Aug 2019
Cited by 9 | Viewed by 7813
Abstract
Hyperpigmentation skin disorders comprise melasma, age spots, and post-inflammatory hyperpigmentation. They are characterized by an aberrant upregulation of melanin pigment and pose a significant burden aesthetically. Calebin-A (CBA) is a natural curcuminoid analog derived from turmeric root (Curcuma longa) but, unlike [...] Read more.
Hyperpigmentation skin disorders comprise melasma, age spots, and post-inflammatory hyperpigmentation. They are characterized by an aberrant upregulation of melanin pigment and pose a significant burden aesthetically. Calebin-A (CBA) is a natural curcuminoid analog derived from turmeric root (Curcuma longa) but, unlike curcumin, it has not been explored yet for anti-melanogenic activity. Hence, in the current study, we studied CBA for its effects on α-melanocyte stimulating hormone (αMSH)-stimulated melanogenesis in B16F10 mouse melanoma cells. Our results showed that CBA (20 μM) significantly suppressed αMSH-stimulated melanogenesis after 48 h treatment. The underlying mechanisms of CBA’s anti-melanogenic activity were studied, and it was shown that CBA did not affect either intracellular tyrosinase activity or the direct activity of tyrosinase enzyme. Additionally, CBA did not affect intracellular α-glucosidase activity but significantly inhibited direct α-glucosidase activity. CBA also directly scavenged 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radicals, consistent with potent antioxidant activity but did not inhibit intracellular reactive oxygen species (ROS). CBA increased acidification of cellular organelles and inhibited maturation of melanosomes by significantly reducing the number of mature melanosomes. Our results indicate that CBA may hold promise as a pigmentation inhibitor for hyperpigmentation disorders for cosmetic use by targeting pathways other than tyrosinase inhibition. Further studies to delineate the molecular signaling mechanism of melanogenesis inhibition and test anti-melanogenesis efficacy of CBA in human skin melanocytes and skin equivalents are warranted. Full article
(This article belongs to the Special Issue Melanogenesis and Melanin-Related Compounds: A Cosmetic Perspective)
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10 pages, 735 KiB  
Article
Use of Vegetable Oils to Improve the Sun Protection Factor of Sunscreen Formulations
by Lucia Montenegro and Ludovica Maria Santagati
Cosmetics 2019, 6(2), 25; https://doi.org/10.3390/cosmetics6020025 - 08 Apr 2019
Cited by 17 | Viewed by 12598
Abstract
Some vegetable oils have many biological properties, including UV-absorbing capacity. Therefore, their use has been suggested to reduce the content of organic UV-filters in sunscreen products. In this work, we investigated the feasibility of developing oil-based vehicles with a high sun protection factor [...] Read more.
Some vegetable oils have many biological properties, including UV-absorbing capacity. Therefore, their use has been suggested to reduce the content of organic UV-filters in sunscreen products. In this work, we investigated the feasibility of developing oil-based vehicles with a high sun protection factor (SPF) using pomegranate oil (PMG) and shea oil (BPO) in association with different percentages of organic UV-filters (octyl– methoxycinnamate, butyl methoxydibenzoylmethane, and bemotrizinol). We characterized the spreadability, occlusion factor, pH, and required hydrophilic lipophilic balance of the resulting formulations, and did not observe relevant differences due to the incorporation of vegetable oils. The in vitro spectrophotometric determinations of SPF values highlighted that the addition of BPO (1% (w/w)) and PMG (1% (w/w)) resulted in an increase in SPF in comparison with the same formulations that contained only organic UV-filters. The SPF increase was more significant for the formulations that contained lower amounts of organic UV-filters. The results of this study supported the hypothesis that including suitable vegetable oils in sunscreen formulations could be a promising strategy to design products with a lower content of organic UV-filters. Full article
(This article belongs to the Special Issue Melanogenesis and Melanin-Related Compounds: A Cosmetic Perspective)
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13 pages, 2510 KiB  
Article
Efficacy and Safety of an Oral Nutritional (Dietary) Supplement Containing Pinus pinaster Bark Extract and Grape Seed Extract in Combination with a High SPF Sunscreen in the Treatment of Mild-to-Moderate Melasma: A Prospective Clinical Study
by Sonia Aladrén, Aurora Garre, Palmira Valderas-Martínez, Jaime Piquero-Casals and Corinne Granger
Cosmetics 2019, 6(1), 15; https://doi.org/10.3390/cosmetics6010015 - 01 Mar 2019
Cited by 10 | Viewed by 11169
Abstract
Background: Melasma is a common hyperpigmentation disorder, characterized by light-to-dark brown patches, usually distributed on sun-exposed areas of the body. The objective of this study was to evaluate the efficacy and tolerability of an oral nutritional supplement containing Pinus pinaster and Grape seed [...] Read more.
Background: Melasma is a common hyperpigmentation disorder, characterized by light-to-dark brown patches, usually distributed on sun-exposed areas of the body. The objective of this study was to evaluate the efficacy and tolerability of an oral nutritional supplement containing Pinus pinaster and Grape seed extract, vitamins and minerals, used concomitantly with a high SPF sunscreen in 30 women with mild-to-moderate facial melasma. Methods: Efficacy was assessed by measurement of the Melasma Area and Severity Index (MASI), instrumental analysis of the lesions (Mexameter®, VISIA®)) and Patient’s and Physician’s Global Assessment (PGA). Results: The MASI score decreased significantly compared with baseline at days 28, 56, and 84. Mexameter® analysis showed a significant decrease of ∆M (difference in the melanin index between melasma and adjacent area). VISIA® results also showed a reduction in the number and areas of UV pigmented spots and in the areas of melasma overtime. Both the Patient’s and Physician’s Global Assessment showed that the product led to an improvement of the lesions in terms of depigmentation and had positive cosmetic features without adverse events. Conclusion: The oral supplement subject of this study in combination with high SPF sunscreen was effective and well-tolerated for treatment of mild to moderate facial melasma. Full article
(This article belongs to the Special Issue Melanogenesis and Melanin-Related Compounds: A Cosmetic Perspective)
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9 pages, 1458 KiB  
Article
Inonotus obliquus Extract as An Inhibitor of α-MSH-Induced Melanogenesis in B16F10 Mouse Melanoma Cells
by Eun Ji Lee and Hwa Jun Cha
Cosmetics 2019, 6(1), 9; https://doi.org/10.3390/cosmetics6010009 - 10 Feb 2019
Cited by 42 | Viewed by 7025
Abstract
Melanogenesis is a biosynthetic pathway that produces the pigment melanin in human skin. The catalyzation of the key enzyme tyrosinase is the first step in melanogenesis, and the downregulation of tyrosinase enzyme activity is the most reported method for inhibiting melanogenesis. Hyperpigmentation is [...] Read more.
Melanogenesis is a biosynthetic pathway that produces the pigment melanin in human skin. The catalyzation of the key enzyme tyrosinase is the first step in melanogenesis, and the downregulation of tyrosinase enzyme activity is the most reported method for inhibiting melanogenesis. Hyperpigmentation is an important issue in the cosmetic industry, and there is great demand for melanogenesis inhibitors. In the present study, we demonstrated the anti-melanogenic effect of Inonotus obliquus in alpha-melanocyte-stimulating hormone (α-MSH)-induced B16F10 mouse melanoma cells and identified it as a new melanogenesis inhibitor. Comparing the B16F10 cells treated with the control and the Inonotus obliquus extract, we identified the melanin contents, mRNA and protein expression of tyrosinase, tyrosinase activity, and microphthalmia-associated transcription factor (Mitf) activity using a constructed plasmid. Through these experiments, we confirmed that Inonotus obliquus extract inhibits melanin synthesis by downregulating the activity and expression of tyrosinase. Furthermore, we revealed that tyrosinase expression is regulated by Inonotus obliquus extract via the repression of Mitf transcriptional activity. Thus, in this study, we found that Inonotus obliquus extract has anti-melanogenic effects via the suppression of melanin synthesis. Taken together, we demonstrated that Inonotus obliquus extract is a good potential candidate for use as a natural source for the therapeutic treatment of hyperpigmentation and for applications in whitening cosmetic products. Full article
(This article belongs to the Special Issue Melanogenesis and Melanin-Related Compounds: A Cosmetic Perspective)
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Review

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33 pages, 4343 KiB  
Review
Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances
by Lucia Panzella and Alessandra Napolitano
Cosmetics 2019, 6(4), 57; https://doi.org/10.3390/cosmetics6040057 - 01 Oct 2019
Cited by 119 | Viewed by 14570
Abstract
One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic [...] Read more.
One of the most common approaches for control of skin pigmentation involves the inhibition of tyrosinase, a copper-containing enzyme which catalyzes the key steps of melanogenesis. This review focuses on the tyrosinase inhibition properties of a series of natural and synthetic, bioinspired phenolic compounds that have appeared in the literature in the last five years. Both mushroom and human tyrosinase inhibitors have been considered. Among the first class, flavonoids, in particular chalcones, occupy a prominent role as natural inhibitors, followed by hydroxystilbenes (mainly resveratrol derivatives). A series of more complex phenolic compounds from a variety of sources, first of all belonging to the Moraceae family, have also been described as potent tyrosinase inhibitors. As to the synthetic compounds, hydroxycinnamic acids and chalcones again appear as the most exploited scaffolds. Several inhibition mechanisms have been reported for the described inhibitors, pointing to copper chelating and/or hydrophobic moieties as key structural requirements to achieve good inhibition properties. Emerging trends in the search for novel skin depigmenting agents, including the development of assays that could distinguish between inhibitors and potentially toxic substrates of the enzyme as well as of formulations aimed at improving the bioavailability and hence the effectiveness of well-known inhibitors, have also been addressed. Full article
(This article belongs to the Special Issue Melanogenesis and Melanin-Related Compounds: A Cosmetic Perspective)
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