Cited by 136melanin and skin pigmentationSkin Protection and AgingCircadian rhythm and melatonin

Photodegradation of Eumelanin and Pheomelanin and Its Pathophysiological Implications

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Ito, Shosuke, Wakamatsu, Kazumasa, Sarna, Tadeusz·2018·Photochemistry and Photobiology

Abstract

Eumelanin is photoprotective for pigmented tissues while pheomelanin is phototoxic. In this review, we summarize current understanding of how eumelanin and pheomelanin structures are modified by ultraviolet A (UVA) and also by visible light and how reactive oxygen species participate in those processes. Alkaline hydrogen peroxide oxidation was employed to characterize eumelanin and benzothiazole‐type pheomelanin, giving pyrrole‐2,3,5‐tricarboxylic acid (PTCA) and thiazole‐2,4,5‐tricarboxylic acid (TTCA), respectively. Reductive hydrolysis with hydroiodic acid gives 4‐amino‐3‐hydroxyphenylalanine (4‐AHP) from the benzothiazine moiety of pheomelanin. The results show that the photoaging of eumelanin gives rise to free PTCA (produced by peroxidation in situ) and pyrrole‐2,3,4,5‐tetracarboxylic acid (PT e CA, produced by cross‐linking). The TTCA/4‐AHP ratio increases with photoaging, indicating the conversion of benzothiazine to the benzothiazole moiety. Analysis of those markers and their ratios show that both eumelanin and pheomelanin in human retinal pigment epithelium melanosomes undergo extensive structural modifications due to their lifelong exposure to blue light. Using synthetic melanins, we also found that singlet oxygen, in addition to superoxide anions, is photogenerated and quenched upon UVA irradiation. The (patho)physiological significance of those findings is discussed in relation to the tanning process, to melanomagenesis in the skin and to age‐related macular degeneration in the eyes.

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  • BT-pheomelanin is produced primarily by the oxidation of 5-S-cysteinyl dopa and converted to BZ-pheomelanin during photolysis or upon exposure to UVA or heat.

    “It is established that BT-pheomelanin is produced primarily by the oxidation of 5- S -cysteinyl dopa and converted to BZ-pheomelanin during photolysis or upon exposure to UVA or heat [ 28 , 29 , 49 , 50 ].”

    From Differential Induction of Reactive Oxygen Species and Expression of Antioxidant Enzymes in Human Melanocytes Correlate with Melanin Content: Implications on the Response to Solar UV and Melanoma Susceptibility (2022) · cites this paper as [50]

    The Introduction describes pheomelanin as arising from oxidative polymerization of both 5-S- and 2-S-cysteinyldopa; it does not establish that 5-S-cysteinyldopa is the primary precursor. The Photodegradation section (p. 411) supports conversion of benzothiazine (BT) to benzothiazole (BZ) under UVA irradiation, but the passages found do not establish heat as another cause of that conversion. (LLM, conf=0.86)

    Experimental — accuracy not yet measured
  • Some of these compounds are present in human plasma at 0.1-300 μM.

    “Some of these compounds are present in human plasma at 0.1-300 μM (130).”

    From Chemiexcitation: Mammalian Photochemistry in the Dark<sup>†</sup> (2023) · cites this paper as [130]

    The Introduction discusses melanin composition in human epidermis, and the Conclusions describe melanin measurements in hair and retinal pigment epithelium; neither gives concentrations in human plasma. Searches for “human plasma 0.1-300 μM,” “plasma,” and “300 μM” found no passage addressing the claimed range. (LLM, conf=0.75)

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Authors
Ito, S., Wakamatsu, K., & Sarna, T.
Affiliations
  • Fujita Health University (JP)
  • Jagiellonian University (PL)
Corresponding author
Ito, Shosuke
Venue
Photochemistry and Photobiology
Publisher
Wiley
Published
2017-10-26
Volume
94
Issue
3
Pages
409-420
ISSN
  • 0031-8655 (ISSN-L)
  • 1751-1097
OpenAlex
W2753682339
Cited by
136
References
90
Citations by year
2026: 16 · 2025: 18 · 2024: 21 · 2023: 19 · 2022: 16 · 2021: 17 · 2020: 11 · 2019: 13 · 2018: 5
FWCI
0.93
Type
journal article
Language
en
Open access
Locations
  • Photochemistry and Photobiology (publishedVersion)
  • PubMed (publishedVersion)
  • Jagiellonian University Repository (Jagiellonian University) (submittedVersion, cc-by-nc-nd)
Funders
  • Japan Society for the Promotion of Science (23591659 and 26461705)
  • Narodowe Centrum Nauki (2013/08/A/NZ1/00194)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Cell Biology › melanin and skin pigmentation
  • Health Sciences › Medicine › Dermatology › Skin Protection and Aging
  • Life Sciences › Neuroscience › Endocrine and Autonomic Systems › Circadian rhythm and melatonin
Keywords
eumelanin, pheomelanin, photodegradation, UVA, visible light, reactive oxygen species, benzothiazine, melanosomes, retinal pigment epithelium, blue light, singlet oxygen, superoxide, tanning, melanomagenesis, age-related macular degeneration, photoaging
MeSH terms
Carboxylic Acids, Eye, Humans, Hydrogen Peroxide, Light, Melanins, Pyrroles, Skin, Thiazoles, Tyrosine, Ultraviolet Rays, Skin Aging, Reactive Oxygen Species, Melanosomes, Retinal Pigment Epithelium

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