Browse

Activation of the Maillard Reaction Product 5-(Hydroxymethyl)furfural to Strong Mutagens via Allylic Sulfonation and Chlorination

Cited 107 time in Web of Science Cited 105 time in Scopus
Authors
Surh, Young-Joon; Tannenbaum, Steven R.
Issue Date
1994-05
Citation
Chemical Research in Toxicology, Vol.7 No.3, pp.313-318
Abstract
5-(Hydroxymethyl)furfural (HMF), one of the major intermediate products in the Maillard reaction, is present in a wide variety of foods. This aldehyde is formed as a decomposition product of glucose and fructose in foodstuffs subject to cooking or heat sterilization. It has been found to possess mutagenic and DNA strand-breaking activity. However, the mechanisms by which HMF exerts its genotoxicity remain unclear. The present study was undertaken to determine if HMF could be metabolically activated via esterification of the allylic hydroxyl group. In support of this concept, the chemically synthesized sulfuric acid ester, 5-[(sulfooxy)methyl]furfural (SMF), exhibited direct mutagenicity at both thymidine kinase and hypoxanthine-guanine phosphoribosyltransferase loci in human lymphoblasts. This reactive ester also induced 8-azaguanine-resistant mutants in Salmonella typhimurium TM677 in a dose-dependent manner. The intrinsic mutagenicity pf SMF was enhanced by addition of extra chloride ion to the assay medium. The model allylic derivative, 5-(chloromethyl)furfural, was also mutagenic and cytotoxic in bacteria, but much more active than the sulfuric acid ester in this regard. In contrast to (sulfooxy)methyl and chloromethyl derivatives of HMF, 2-[(sulfooxy)-methyl]- and 2-(chloromethyl)furans which lack the aldehyde functionality did not exhibit significant mutagenicity. Rodent hepatic cytosols contained sulfotransferase activity responsible for the formation of the reactive allylic sulfuric acid ester metabolite from HMF.
ISSN
0893-228X
URI
https://hdl.handle.net/10371/172671
DOI
https://doi.org/10.1021/tx00039a007
Files in This Item:
There are no files associated with this item.
Appears in Collections:
Graduate School of Convergence Science and Technology (융합과학기술대학원)Dept. of Molecular and Biopharmaceutical Sciences (분자의학 및 바이오제약학과)Journal Papers (저널논문_분자의학 및 바이오제약학과)
  • mendeley

Items in S-Space are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse