1-Nitrosomelatonin is a spontaneous NO-releasing compound.
Melatonin (N-acetyl-5-methoxytryptamin), the main hormone secreted by the pineal gland in mammals, is nitrosated by nitrite at acidic pH and by NO in the presence of oxygen under neutral conditions. Melatonin is also partly converted to 1-nitrosomelatonin by oxoperoxonitrate (ONOO-, peroxynitrite) in phosphate-buffered solutions at pH 7-10 [Blanchard, B., et al. (2000) Journal of Pineal Research 29, 184-192]. In the present report, we show that 1-nitrosomelatonin in turn behaves as an NO-donor regenerating melatonin. NO-release is evidenced by the formation of nitrite in phosphate-buffered solutions and oxidation of HbO2. No peroxynitrite was formed during that decomposition because serotonin used as a probe was converted only to 4-nitroso-serotonin as expected for a true NO-donor [Blanchard, B., et al. (2001) Free Radical Research, 34, 177-188]. The spontaneous decay of 1-nitrosomelatonin is not affected by GSH and metallic ions but its decomposition is accelerated in acidic pH or in the presence of NADH or ascorbate. Furthermore, melatonin is partially or entirely recovered in the absence or presence of ascorbate, respectively. A homolytic cleavage of 1-nitrosomelatonin is strongly suggested and discussed. Formation of 1-nitrosomelatonin from melatonin and reactive nitrogen species (RNS) followed by its decay into NO demonstrates that melatonin could reduce these RNS to NO.
Blanchard-Fillion
B
B
Institut de Chimie des Substances Naturelles, CNRS SCUPR 2301, Gif-sur-Yvette, France.
Servy
C
C
Ducrocq
C
C
D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D008550:Melatonin / Q000031:analogs & derivatives* / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*; D009609:Nitrous Oxide / Q000737:chemistry*; D026361:Reactive Nitrogen Species / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013997:Time Factors
D009603:Nitroso Compounds; D026361:Reactive Nitrogen Species; D008550:Melatonin; D009609:Nitrous Oxide