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Sunlight, melanogenesis and radicals in the skin

  • Free Radicals, Antioxidants, Skin Cancer and Related Diseases Symposium Held at the 78th AOCS Annual Meeting in New Orieans, Louisiana, May 1987
  • Published:
Lipids

Abstract

Melanocytes are cells of neural crest origin residing at the dermal-epidermal juncture. They produce specialized organelles called melanosomes within which the biochemical processes of melanization occurs. UV radiation is capable of inducing melanogenesis and, during the biosynthesis of melanins, several of the putative precursors “leak out” of the melanosome and can be detected in the skin, serum and urine of individuals undergoing active melanogenesis. Most notable are the cysteinyldopas (formed by nucleophilic addition of cysteine to dopaquinone) and several dihydroxyindoles (formed by intramolecular cyclization of dopaquinone). These catechols often are methylated in the melanocyte to afford a mixture of the monomethoxy derivatives and, in some cases, the dimethoxy species.

Recent investigations in our laboratories have demonstrated that the cysteinyldopas, dihydroxyindoles, and their various methylated derivatives are photochemically unstable. Irradiation with biologically relevant ultraviolet radiation (i.e. wavelengths >300 nm) results in the rapid destruction of the precursors/metabolites and the production of a variety of free radical species. The photochemistry and potential photobiological significance of melanogenic intermediates is discussed.

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Abbreviations

COMT:

catechol-O-methyl transferase

DCD:

2,5-S,S′-dicysteinyldopa

DHI:

5,6-dihydroxyindole

DHICA:

5,6-dihydroxyindole-2-carboxylic acid

DMICA:

5,6-dimethoxyindole-2-carboxylic acid

DMPO:

5,5-dimethyl-1-pyrollineN-oxide

5(or 6)-HMICA:

5(or 6)-monomethoxyindole-2-carboxylic acid

PUVA:

8-methoxypsoralen plus UVA

5SCS:

5-S-cysteinyldopa

UVA:

(B, C) ultraviolet light in the A (B or C) region, 400–320 nm (320–280 nm or <280 nm)

ESR:

electron spin resonance

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Authors and Affiliations

  1. Division of Environmental Chemistry, School of Hygiene and Public Health, The Johns Hopkins University, 21205, Baltimore, MD

    Miles R. Chedekel & Lisa Zeise

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  1. Miles R. Chedekel
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Chedekel, M.R., Zeise, L. Sunlight, melanogenesis and radicals in the skin. Lipids 23, 587–591 (1988). https://doi.org/10.1007/BF02535602

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  • DOI: https://doi.org/10.1007/BF02535602

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