Zamora Rosario, Hidalgo Francisco J
Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Avenida Padre García Tejero 4, 41012 Sevilla, Spain.
Chem Res Toxicol. 2005 Feb;18(2):342-8. doi: 10.1021/tx049700y.
N-Substituted 2-pentylpyrrole formation has been related to the etiology or the consequences of several diseases in which lipid oxidation is involved. This study describes the formation of N-substituted 2-alkylpyrroles in the reaction of 4,5-epoxy-2-alkenals with amino compounds and suggests an alternative pathway for the formation of these compounds that are nowadays commonly accepted to be produced by reaction of the lipid oxidation product 4-hydroxy-2-nonenal with primary amino compounds. The described reaction constitutes a new route for pyrrole production in the lipid peroxidation pathway when it takes place in the presence of amino compounds and implies the loss of one carbon in the 4,5-epoxy-2-alkenal during the formation of the heterocyclic ring, which is proposed to be released as formaldehyde. This reaction also confirms the high reactivity of 4,5-epoxy-2-alkenals, which are usually found in smaller amounts than other lipid oxidation products. Their importance in vivo may be underappreciated in part as a consequence of this high reactivity that brings about their rapid disappearance.
N-取代的2-戊基吡咯的形成与几种涉及脂质氧化的疾病的病因或后果有关。本研究描述了4,5-环氧-2-烯醛与氨基化合物反应中N-取代的2-烷基吡咯的形成，并提出了这些化合物形成的另一种途径，目前普遍认为这些化合物是由脂质氧化产物4-羟基-2-壬烯醛与伯氨基化合物反应产生的。当该反应在氨基化合物存在下发生时，所描述的反应构成了脂质过氧化途径中吡咯产生的新途径，这意味着在杂环形成过程中4,5-环氧-2-烯醛中一个碳原子的损失，该碳原子被认为以甲醛形式释放。该反应还证实了4,5-环氧-2-烯醛的高反应活性，它们通常比其他脂质氧化产物的含量少。由于这种高反应活性导致它们迅速消失，它们在体内的重要性可能在一定程度上被低估了。
