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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
Published on: September 25, 2017
The catecholic antioxidant piceatannol is an effective nitrosation inhibitor via an unusual double bond nitration
Maria De Lucia1, Lucia Panzella, Orlando Crescenzi
1Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Via Cintia, I-80126 Naples, Italy.
Abstract:
Piceatannol (1) was found to be more effective than caffeic acid, an established antinitrosating agent, in inhibiting N-nitrosation of 2,3-diaminonaphthalene. Product analysis of the reaction mixture of 1 (20 microM) with nitrite ions (80 microM) at pH 3.0 and at 37 degrees C showed conversion to a single major nitration product, (E)-3,3',4,5'-tetrahydroxy-beta-nitrostilbene (2) (68% yield). This would result from an unexpected nitration at the double bond sector via the 4-phenoxyl radical, which was analyzed at the unrestricted DFT level.
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