title: The identification of the UV degradants of melatonin and their ability to scavenge free radicals.
abstract: Ultraviolet (UV) light is known to induce the generation of free radicals in biological tissues such as skin. Of these free radicals, the O2-. and particularly the.OH radical can induce cellular damage including lipid peroxidation. Thus, the use of antioxidants to prevent such damage induced by UV irradiation has received much attention recently. One such antioxidant, which has the potential to be incorporated into sunscreens, is the pineal secretory product melatonin. One of the concerns of using melatonin in sunscreens is its photostability. In the present study, we investigated the photostability of melatonin subjected to UV irradiation. In addition, we used liquid chromatography mass spectrometry (LC-MS) to identify the degradants and we also assessed the ability of the degradants to inhibit O2-. generation as well as lipid peroxidation in rat brain homogenate. The results show that UV irradiation of melatonin (0.1 mg/mL) using a 400-W lamp for 2 hr caused a significant decline of melatonin to 18% of its original concentration after 20 min, with the decline continuing until the melatonin concentration reaches zero at 120 min. The LC-MS results show that the degradants of melatonin are 6-hydroxymelatonin and N1-acetyl-N2-formyl-5-methoxykynurenamine (AFMK). These degradants were able to provide equipotent activity against potassium cyanide (KCN)-induced superoxide generation compared to non-irradiated melatonin. Thus, the study shows that although melatonin is rapidly degraded by UV irradiation, the degradants retain antioxidant activity, making melatonin a likely candidate for inclusion in sunscreens.
authors: Faculty of Pharmacy, Rhodes University, Grahamstown, South Africa.
authors: Deepa S
authors: DS
authors: Maharaj
authors: Shailendra
authors: S
authors: Anoopkumar-Dukie
authors: Beverley D
authors: BD
authors: Glass
authors: Edith M
authors: EM
authors: Antunes
authors: Barbara
authors: B
authors: Lack
authors: Roderick B
authors: RB
authors: Walker
authors: Santy
authors: S
authors: Daya
mesh_terms: D000818:Animals; D002853:Chromatography, Liquid; D016166:Free Radical Scavengers / Q000378:metabolism*; D015227:Lipid Peroxidation; D008297:Male; D013058:Mass Spectrometry; D008550:Melatonin / Q000378:metabolism*; D051381:Rats; D017208:Rats, Wistar; D014466:Ultraviolet Rays
chemical_list: D016166:Free Radical Scavengers; D008550:Melatonin