Methylene-interrupted double bond in polyunsaturated fatty acid is an essential structure for metabolism by the fatty acid chain elongation system of rat liver

Tamotsu Tanaka, Toshinori Hattori, Maki Kouchi, Kaoru Hirano, Kiyoshi Satouchi
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引用次数: 30

Abstract

Some plant oils contain non-methylene-interrupted polyunsaturated fatty acids (NMIFAs). Pinolenic acid (all cis Δ-5,9,12/18:3) and columbinic acid (trans,cis,cis Δ-5,9,12/18:3) are NMIFAs that exist in pine seed oil and columbine seed oil, respectively. We investigated the double bond position of fatty acid recognized by the fatty acid chain elongation system (FACES) of rat liver using NMIFAs as experimental tools. In the total elongation assay, amounts of C2 unit chain-elongated metabolites of pinolenic acid and columbinic acid were 32% and 11%, respectively, compared to that of γ-linolenic (all cis Δ-6,9,12/18:3) as the substrate. In the condensation reaction assay, the rate limiting step of FACES, the conversion rates of pinolenic acid and columbinic acid to the corresponding C20 β-keto fatty acids were 19% and 9% of that of γ-linolenic acid, respectively. The formation of elongated metabolite of podocarpic acid (all cis Δ-5,11,14/20:3) was only 7% of that of arachidonic acid (all cis Δ-5,8,11,14/20:4). From these results it was concluded that the condensing enzyme of FACES could recognize the methylene-interrupted cis double bond structure vicinal to the carboxyl group in the fatty acid molecule.

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多不饱和脂肪酸中的亚甲基中断双键是大鼠肝脏脂肪酸链延伸系统代谢所必需的结构
一些植物油含有非亚甲基中断多不饱和脂肪酸(NMIFAs)。蒎酸(均为顺式Δ-5,9,12/18:3)和耧斗菜酸(反式,顺式,顺式Δ-5,9,12/18:3)分别是存在于松籽油和耧斗菜籽油中的NMIFAs。以NMIFAs为实验工具,研究了大鼠肝脏脂肪酸链延伸系统(FACES)识别的脂肪酸双键位置。在总伸长试验中,与γ-亚麻酸(均顺式Δ-6,9,12/18:3)作为底物相比,蒎烯酸和柱伦比酸的C2单位链伸长代谢物的数量分别为32%和11%。在缩合反应实验中,face的限速步骤、蒎烯酸和柱灯酸对相应的C20 β-酮脂肪酸的转化率分别为γ-亚麻酸的19%和9%。足香酸(全顺式Δ-5,11,14/20:3)的细长代谢物的形成仅为花生四烯酸(全顺式Δ-5,8,11,14/20:4)的7%。从这些结果可以看出,FACES的凝聚酶可以识别脂肪酸分子中羧基附近的亚甲基中断的顺式双键结构。
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