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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Anticarcinogenic Agents / chemistry*
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Anticarcinogenic Agents / pharmacology
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Caffeic Acids / chemistry*
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Caffeic Acids / pharmacology
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Decarboxylation
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Flavonoids*
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Glutathione / chemistry*
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Hydrogen-Ion Concentration
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Nitrites / chemistry*
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Nitrosation / drug effects
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Nuclear Magnetic Resonance, Biomolecular
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Oximes / chemical synthesis
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Phenols / chemistry
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Phenols / pharmacology
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Polymers / chemistry
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Polymers / pharmacology
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Polyphenols
Substances
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Anticarcinogenic Agents
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Caffeic Acids
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Flavonoids
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Nitrites
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Oximes
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Phenols
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Polymers
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Polyphenols
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Glutathione
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caffeic acid