Piceatannol (1) was more effective than caffeic acid, an established antinitrosating agent, in inhibiting N-nitrosation of 2,3-diaminonaphthalene. Product anal. of the reaction mixt. of 1 (20 mM) with nitrite ions (80 mM) at pH 3.0 and at 37 showed conversion to a single major nitration product, (E)-3,3',4,5'-tetrahydroxy-b-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.
The catecholic antioxidant piceatannol is an effective nitrosation inhibitor via an unusual double bond nitration / DE LUCIA, Maria; Panzella, Lucia; Crescenzi, Orlando; Napolitano, Alessandra; Barone, Vincenzo; D'Ischia, Marco. - In: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS. - ISSN 0960-894X. - STAMPA. - 16:8(2006), pp. 2238-2242. [10.1016/j.bmcl.2006.01.043]
The catecholic antioxidant piceatannol is an effective nitrosation inhibitor via an unusual double bond nitration.
PANZELLA, LUCIA;CRESCENZI, ORLANDO;NAPOLITANO, ALESSANDRA;BARONE, VINCENZO;D'ISCHIA, MARCO
2006
Abstract
Piceatannol (1) was more effective than caffeic acid, an established antinitrosating agent, in inhibiting N-nitrosation of 2,3-diaminonaphthalene. Product anal. of the reaction mixt. of 1 (20 mM) with nitrite ions (80 mM) at pH 3.0 and at 37 showed conversion to a single major nitration product, (E)-3,3',4,5'-tetrahydroxy-b-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
