Epoxidation of cis and trans Δ9‐unsaturated lauric acids by a cytochrome P‐450‐dependent system from higher plant microsomes

FEBS Letters

Durst, Francis¹  Pflieger, Philippe²  Mioskowski, Charles²  Weissbart, Daniel¹  Salaün, Jean-Pierre¹ 

[1]Laboratoire d'Enzymologie Cellulaire et Moléculaire, Université Louis Pasteur - CNRS UA 1182, 28, rue Goethe, F-67083 Strasbourg Cedex France

[2]Laboratoire de Chimie Bio-organique, Université Louis Pasteur - CNRS UA 31-Faculté de Pharmacie, 74 route du Rhin, F-67048 Strasbourg Cedex, France

关键词: Cytochrome P-450;    Epoxidation;    Hydroxylation;    Fatty acid;    Induction;    (Helianthus tuberosus);   

DOI  :  10.1016/0014-5793(89)80266-2

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

A new epoxygenase, differing in substrate and stereospecificity from those previously described in mammals, bacteria and Vicia faba, has been characterized in higher plants. A microsomal fraction from Jerusalem artichoke tubers which catalyses in-chain monohydroxylation of lauric acid has now been found to convert synthetic 9-dodecenoic acid (9-DDNA) to 9,10-epoxylauric acid. Epoxidation of the cis and trans isomers proceeds at similar rates affording the corresponding cis and trans epoxides. This reaction is dependent upon O₂ and NADPH and does not occur with boiled microsomes. Lauric acid, carbon monoxide and polyclonal antibody against NADPH-cytochrome P-450 reductase from Jerusalem artichoke inhibit epoxide formation. Compared to freshly sliced tuber tissues, epoxidation activity was strongly enhanced in tissues aged in 20 mM aminopyrine solution. The possibility that 9, 10-epoxidation of 9-DDNA is catalyzed by the cytochrome P-450 isoenzyme involved in lauric acid in-chain hydroxylation in this plant was investigated.

【 授权许可】

Unknown