Cyclic 3-hydroxymelatonin

A melatonin metabolite generated as a result of hydroxyl radical scavenging

D. X. Tan, L. C. Manchester, Russel J Reiter, B. F. Plummer

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

The pineal secretory product, melatonin, is a potent, endogenous hydroxyl radical (HȮ) scavenger. When melatonin was incubated in different in vitro cell-free HȮ-generating systems, a novel melatonin adduct was formed. The molecular weight of this new compound is 248. Its structure was found to be cyclic 3-hydroxymelatonin (3-OHM). A proposed reaction pathway suggests that 3-OHM is the footprint product of the interaction between melatonin with HȮ. 3-OHM was also detected in the urine of both rats and humans. This urinary metabolite is identical to the compound generated in the in vitro chemical reaction between HȮ and melatonin. This provides direct evidence that melatonin, under physiological conditions, functions as an antioxidant to detoxify the most reactive and cytotoxic endogenous HȮ. When exogenous melatonin was administered to young rats, urinary 3-OHM levels increased significantly in the treated rats compared to those in controls. This indicates that even in young animals there is insufficient endogenously produced melatonin to detoxify the basal levels of the toxic HȮ. The accumulated damage induced by the escaped HȮ that results when the HȮ avoids detoxification over the course of a life time may directly or indirectly accelerate aging and aging-related diseases.

Original languageEnglish (US)
Pages (from-to)70-74
Number of pages5
JournalBiological Signals and Receptors
Volume8
Issue number1-2
StatePublished - 1999

Fingerprint

Scavenging
Melatonin
Metabolites
Hydroxyl Radical
Rats
Aging of materials
Detoxification
Poisons
Chemical reactions
Animals
Antioxidants
Molecular Weight
Molecular weight
Urine

Keywords

  • Aging
  • Antioxidant
  • Cyclic 3-hydroxymelatonin
  • Hydroxyl radical
  • Melatonin
  • Metabolite

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

Cyclic 3-hydroxymelatonin : A melatonin metabolite generated as a result of hydroxyl radical scavenging. / Tan, D. X.; Manchester, L. C.; Reiter, Russel J; Plummer, B. F.

In: Biological Signals and Receptors, Vol. 8, No. 1-2, 1999, p. 70-74.

Research output: Contribution to journalArticle

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