Melanogenesis from 5-hydroxytryptamine, 5,6- and 5,7-dihydroxytryptamines. An in vitro study using MALDI-TOF.

The role of tyrosinase and peroxidase in melanogenesis of 5-hydroxytryptamine, 5,6- and 5,7-dihydroxytryptamines was investigated by matrix-assisted laser desorption/ionization mass spectrometry. Each enzyme was incubated with the tryptamine derivatives and samples were drawn at various times, ultrafiltered and immediately lyophilized. The results indicated that peroxidase promotes oligomerization of 5-HT with fast kinetics but with yields lower than those achieved by tyrosinase. 5,6- and 5,7-DHT formed low molecular mass oligomers in the presence of peroxidase alone. The addition of hydrogen peroxide evidences different reactivity of the two isomers: 5,6-DHT formed immediately a black precipitate while oligomers of the molecule itself and of its oxidation products were detectable for 5,7-DHT.