Document Detail

Novel pathway for N1-acetyl-5-methoxykynuramine: UVB-induced liberation of carbon monoxide from precursor N1-acetyl-N2-formyl-5-methoxykynuramine.
MedLine Citation:
PMID:  18194200     Owner:  NLM     Status:  MEDLINE    
Irradiation of the melatonin metabolite N(1)-acetyl-N(2)-formyl-5-methoxykynuramine (AFMK) with UV light of 254 nm causes the release of carbon monoxide (CO) and, thus, deformylation to N(1)-acetyl-5-methoxykynuramine (AMK). Liberation of CO was demonstrated by reduction of PdCl(2) to metallic palladium, under avoidance of actions by other reductants. Photochemical AMK formation was not due to UV-induced hydroxyl radicals, because the reaction also took place with high efficiency in ethanol and 2-propanol. Moreover, AMK was generated from AFMK by UVB on a dry thin layer chromatographic plate. Although AMK seems to be the major primary product generated by UVB radiation, prolonged exposure of AFMK led to various other products, especially formed by destruction of AMK, as shown by irradiation of this latter compound. With regard to the demonstration of melatonin in skin and substantial amounts of AFMK in keratinocytes, these findings may be of dermatologic relevance.
Katinka Seever; Rüdiger Hardeland
Publication Detail:
Type:  Journal Article     Date:  2008-01-09
Journal Detail:
Title:  Journal of pineal research     Volume:  44     ISSN:  1600-079X     ISO Abbreviation:  J. Pineal Res.     Publication Date:  2008 May 
Date Detail:
Created Date:  2008-04-15     Completed Date:  2008-07-15     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8504412     Medline TA:  J Pineal Res     Country:  Denmark    
Other Details:
Languages:  eng     Pagination:  450-5     Citation Subset:  IM    
Johann Friedrich Blumenbach Institute of Zoology and Anthropology, University of Göttingen, Göttingen, Germany.
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MeSH Terms
Carbon Monoxide / chemistry*
Hydroxyl Radical / chemistry
Kynuramine / analogs & derivatives*,  chemistry
Melatonin / chemistry
Ultraviolet Rays*
Reg. No./Substance:
3352-57-6/Hydroxyl Radical; 363-36-0/Kynuramine; 52450-38-1/N-acetyl-N-formyl-5-methoxykynurenamine; 52450-39-2/N-acetyl-5-methoxy kynurenamine; 630-08-0/Carbon Monoxide; 73-31-4/Melatonin

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