Nitrite-mediated decarboxylative conjugation of caffeic acid with glutathione under mildly acidic conditions.
In acetate buffer, pH 4, at room temperature, nitrite ions can mediate an unusual decarboxylative conjugation of caffeic acid with glutathione leading to novel isomeric 2-(3,4-dihydroxyphenyl)-2-S-glutathionylacetaldehyde oximes. These results hint at a possible role of endogenous and/or dietary glutathione in the mechanisms by which caffeic acid can affect the burden of carcinogenic N-nitroso compounds in the digestive tract.
Panzella
Lucia
L
Department of Organic Chemistry and Biochemistry, University of Naples 'Federico II', Via Cinthia 4, Italy.
Napolitano
Alessandra
A
d'Ischia
Marco
M
D016588:Anticarcinogenic Agents / Q000737:chemistry* / Q000494:pharmacology; D002109:Caffeic Acids / Q000737:chemistry* / Q000494:pharmacology; D003653:Decarboxylation; D005419:Flavonoids; D005978:Glutathione / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009573:Nitrites / Q000737:chemistry*; D015538:Nitrosation / Q000187:drug effects; D019906:Nuclear Magnetic Resonance, Biomolecular; D010091:Oximes / Q000138:chemical synthesis; D010636:Phenols / Q000737:chemistry / Q000494:pharmacology; D011108:Polymers / Q000737:chemistry / Q000494:pharmacology; D059808:Polyphenols
D016588:Anticarcinogenic Agents; D002109:Caffeic Acids; D005419:Flavonoids; D009573:Nitrites; D010091:Oximes; D010636:Phenols; D011108:Polymers; D059808:Polyphenols; D005978:Glutathione; C040048:caffeic acid