Chemistry:6-Hydroxymelatonin

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6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin.[1] 6-Hydroxymelatonin is produced as a result of the enzymatic conversion of melatonin through hydroxylation.[2] Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors.[3][4] It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin.[5][6]

Role in metabolism

The determination of 6-OHM in human urine has been used to track the metabolism and excretion of melatonin using LC-MS/MS, providing quantifiable insights into circadian rhythm regulation and its oxidative role as a biomarker.[7] 6-OHM is one of four of the primary metabolic products of melatonin in the liver and is also a byproduct of its breakdown due to exposure to light. It is known to be very effective in protecting cells from oxidative damage caused by ultraviolet (UV) radiation.[8] Based on comparisons with other melatonin-related compounds, it is suggested that the protective effects of 6-OHM in mitigating oxidative stress are primarily attributed to their ability to scavenge free radicals.[9]

See also

References

  1. ↑ "Melatonin metabolism in the central nervous system". Curr Neuropharmacol 8 (3): 168–81. 2010. doi:10.2174/157015910792246164. PMID 21358968. 
  2. ↑ Magliocco, G.; Le Bloc'h, F.; Thomas, A.; Desmeules, J.; Daali, Y. (2021-09-01). "Simultaneous determination of melatonin and 6-hydroxymelatonin in human overnight urine by LC-MS/MS" (in en). Journal of Chromatography 1181. doi:10.1016/j.jchromb.2021.122938. PMID 34521018. https://linkinghub.elsevier.com/retrieve/pii/S1570023221004190. 
  3. ↑ "Pharmacology and function of melatonin receptors". FASEB J. 2 (12): 2765–73. 1988. doi:10.1096/fasebj.2.12.2842214. PMID 2842214. 
  4. ↑ Browning, Christopher; Beresford, Isabel; Fraser, Neil; Giles, Heather (2000). "Pharmacological characterization of human recombinant melatonin mt1and MT2receptors". British Journal of Pharmacology 129 (5): 877–886. doi:10.1038/sj.bjp.0703130. ISSN 0007-1188. PMID 10696085. 
  5. ↑ "Melatonin: new places in therapy". Biosci. Rep. 27 (6): 299–320. 2007. doi:10.1007/s10540-007-9052-1. PMID 17828452. 
  6. ↑ "N-Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin". J Phys Chem B 119 (27): 8535–43. 2015. doi:10.1021/acs.jpcb.5b04920. PMID 26079042. 
  7. ↑ Magliocco, G.; Le Bloc'h, F.; Thomas, A.; Desmeules, J.; Daali, Y. (2021-09-01). "Simultaneous determination of melatonin and 6-hydroxymelatonin in human overnight urine by LC-MS/MS" (in en). Journal of Chromatography B 1181. doi:10.1016/j.jchromb.2021.122938. PMID 34521018. https://linkinghub.elsevier.com/retrieve/pii/S1570023221004190. 
  8. ↑ Maharaj, Deepa S.; Anoopkumar-Dukie, Shailendra; Glass, Beverley D.; Antunes, Edith M.; Lack, Barbara; Walker, Roderick B.; Daya, Santy (2002-04-30). "The identification of the UV degradants of melatonin and their ability to scavenge free radicals". Journal of Pineal Research 32 (4): 257–261. doi:10.1034/j.1600-079x.2002.01866.x. ISSN 0742-3098. PMID 11982796. https://doi.org/10.1034/j.1600-079x.2002.01866.x. 
  9. ↑ Álvarez-Diduk, Ruslán; Galano, Annia; Tan, Dun Xian; Reiter, Russel J. (2015-07-09). "N -Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin" (in en). The Journal of Physical Chemistry B 119 (27): 8535–8543. doi:10.1021/acs.jpcb.5b04920. ISSN 1520-6106. PMID 26079042. https://pubs.acs.org/doi/10.1021/acs.jpcb.5b04920. 



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