Formation of adrenochrome from epinephrine by myeloperoxidase via a free radical: Its biological significance.

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Adrenochrome, 2, 3-dihydro-3-hydroxy-1-methyl-1H-indole-5, 6-dione, is an unstable red compound formed by the oxidation of epinephrine, (R) -4- [1-hydroxy-2- (methylamino) ethyl] -1, 2-benzenediol. A red pigment was generated during the reaction between epinephrine and hydrogen peroxide by myeloperoxidase via a short-lived intermediate having a free radical detected by electron paramagnetic (spin) resonance spectroscopy, possibly o-semiquinone free radical of the substrate (epinephrine), in a moderately alkaline pH buffer solution. The light absorption peaks of the pigment at 220, 302 and 485 nm were identical with those of adrenochrome, and the Rf-value of the pigment on thin layer chromatography was consistent with that of standard adrenochrome. From these findings, the pigment was concluded to be adrenochrome. The biological significance of the formation of adrenochrome by the myeloperoxidase system <I>in vivo</I> might relate to a possible role in the body's self-defense system: myeloperoxidase released from neutrophils may catalyze the conversion of epinephrine to adrenochrome at a site of trauma or phlogosis, and this adrenochrome would promote wound healing through the formation of a blood clot and/or scab by radical polymerization of body-fluid components around the affected part, resulting in acceleration of hemostasis.
歯科基礎医学会の論文