title: Jasmonate-induced epoxidation of tabersonine by a cytochrome P-450 in hairy root cultures of Catharanthus roseus.
abstract: Methyl jasmonate, a chemical inducer of secondary metabolism, was shown to promote tabersonine 2 biosynthesis in hairy root cultures of Catharanthus roseus. Tabersonine 6,7-epoxidase activity was detected in total protein extract of jasmonate-induced hairy root cultures using labeled 14C-tabersonine 2. This enzyme converted tabersonine 2 to lochnericine 3 by selective epoxidation at positions 6 and 7 via a reaction dependent on NADPH and molecular oxygen. Carbon monoxide, clotrimazole, miconazole, and cytochrome C were shown to be strong inhibitors of the enzyme. The activity was found in microsomes, indicating that tabersonine 6,7-epoxidase was a cytochrome P-450-dependent monooxygenase.
authors.affiliation: Service de l'environnement et de l'énergie, Les Croisettes, CP 33 1066 Epalinges, Switzerland.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Rodriguez
authors.forename: Vincent
authors.initials: V
authors.lastname: Compagnon
authors.forename: Nicholas P
authors.initials: NP
authors.lastname: Crouch
authors.forename: Benoit
authors.initials: B
authors.lastname: St-Pierre
authors.forename: Vincenzo
authors.initials: V
authors.lastname: De Luca
mesh_terms: D000085:Acetates / Q000494:pharmacology*; D000470:Alkaloids / Q000737:chemistry* / Q000378:metabolism*; D002248:Carbon Monoxide / Q000494:pharmacology; D030008:Catharanthus / Q000201:enzymology* / Q000378:metabolism; D003517:Cyclopentanes / Q000494:pharmacology*; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D045304:Cytochromes c / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000494:pharmacology; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism; D006867:Hydrolases / Q000037:antagonists & inhibitors / Q000378:metabolism; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry* / Q000378:metabolism*; D008861:Microsomes / Q000201:enzymology; D009249:NADP / Q000378:metabolism; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000037:antagonists & inhibitors / Q000378:metabolism; D010100:Oxygen / Q000378:metabolism; D054883:Oxylipins; D018517:Plant Roots / Q000378:metabolism*; D011804:Quinolines / Q000737:chemistry* / Q000378:metabolism*
chemical_list: D000085:Acetates; D000470:Alkaloids; D003517:Cyclopentanes; D004791:Enzyme Inhibitors; D004852:Epoxy Compounds; D026121:Indole Alkaloids; D007211:Indoles; D054883:Oxylipins; D011804:Quinolines; C009373:tabersonine; D009249:NADP; D002248:Carbon Monoxide; D045304:Cytochromes c; C072239:methyl jasmonate; D003577:Cytochrome P-450 Enzyme System; D010088:Oxidoreductases; C023111:epoxidase; D006867:Hydrolases; D010100:Oxygen