儿茶酚类抗氧化剂白皮杉醇通过一种不同寻常的双键硝化作用，是一种有效的亚硝化抑制剂。

The catecholic antioxidant piceatannol is an effective nitrosation inhibitor via an unusual double bond nitration.

作者信息

De Lucia Maria, Panzella Lucia, Crescenzi Orlando, Napolitano Alessandra, Barone Vincenzo, d'Ischia Marco

机构信息

Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Via Cintia, I-80126 Naples, Italy.

出版信息

Bioorg Med Chem Lett. 2006 Apr 15;16(8):2238-42. doi: 10.1016/j.bmcl.2006.01.043. Epub 2006 Feb 7.

DOI:10.1016/j.bmcl.2006.01.043

PMID:16455243

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.

摘要

已发现白藜芦醇（1）在抑制2,3 - 二氨基萘的N - 亚硝化反应方面比已确定的抗亚硝化剂咖啡酸更有效。在pH 3.0和37℃下，1（20微摩尔）与亚硝酸根离子（80微摩尔）反应混合物的产物分析表明转化为单一主要硝化产物，（E）-3,3',4,5'-四羟基-β-硝基芪（2）（产率68%）。这是通过4 - 苯氧基自由基在双键区域意外硝化产生的，该自由基在无限制密度泛函理论（DFT）水平上进行了分析。