title: Nitrite-mediated decarboxylative conjugation of caffeic acid with glutathione under mildly acidic conditions.
abstract: 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.
authors.affiliation: Department of Organic Chemistry and Biochemistry, University of Naples 'Federico II', Via Cinthia 4, Italy.
authors.forename: Lucia
authors.initials: L
authors.lastname: Panzella
authors.forename: Alessandra
authors.initials: A
authors.lastname: Napolitano
authors.forename: Marco
authors.initials: M
authors.lastname: d'Ischia
mesh_terms: 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
chemical_list: D016588:Anticarcinogenic Agents; D002109:Caffeic Acids; D005419:Flavonoids; D009573:Nitrites; D010091:Oximes; D010636:Phenols; D011108:Polymers; D059808:Polyphenols; D005978:Glutathione; C040048:caffeic acid