Squalene as a Target Molecule in Skin Hyperpigmentation Caused by Singlet Oxygen

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  • Ryu Akemi
    Research Laboratories, KOSÉ Corporation
  • Arakane Kumi
    Research Laboratories, KOSÉ Corporation
  • Koide Chiharu
    Research Laboratories, KOSÉ Corporation
  • Arai Hiroyuki
    Department of Health Chemistry, Graduate School of Pharmaceutical Sciences, The University of Tokyo
  • Nagano Tetsuo
    Laboratory of Chemistry and Biology, Graduate School of Pharmaceutical Sciences, The University of Tokyo

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Based on our previous finding (Biochem. Biophys. Res. Commun., 223, 578—582, 1996) of singlet oxygen generation from coproporphyrin excreted on the skin surface from Propionibacterium acnes, we hypothesized that singlet oxygen formed in this way under UV exposure would promote peroxidation of skin surface lipids. We found that squalene was oxidized efficiently by singlet oxygen derived from coproporphyrin under UV exposure, and that the rate constant of squalene peroxidation by singlet oxygen was ten-fold higher than that of other skin surface lipids examined. The reaction was promoted more efficiently by UVA than by UVB. Furthermore, we found that topical application of squalene peroxide induced skin hyperpigmentation through increasing prostaglandin E2 release from keratinocytes in guinea pigs. These results suggest that squalene peroxide formation by singlet oxygen plays a key role in photo-induced skin damage.

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