Plant Physiol.
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Piperonylic Acid, a Selective, Mechanism-Based Inactivator of the trans-Cinnamate 4-Hydroxylase: A New Tool to Control the Flux of Metabolites in the Phenylpropanoid Pathway1

Michel Schalk, Francisco Cabello-Hurtado, Marie-Agnès Pierrel, Rossitza Atanossova, Patrick Saindrenan, and Danièle Werck-Reichhart*

Département d'Enzymologie Cellulaire et Moléculaire (M.S., F.C.-H., D.W.-R.), and Département de Phytopathologie (M.-A.P., R.A., P.S.), Institut de Biologie Moléculaire des Plantes, Centre National de la Recherche Scientifique Unité Propre de Recherche 406, 28 rue Goethe, 67000 Strasbourg, France

Piperonylic acid (PA) is a natural molecule bearing a methylenedioxy function that closely mimics the structure of trans-cinnamic acid. The CYP73A subfamily of plant P450s catalyzes trans-cinnamic acid 4-hydroxylation, the second step of the general phenylpropanoid pathway. We show that when incubated in vitro with yeast-expressed CYP73A1, PA behaves as a potent mechanism-based and quasi-irreversible inactivator of trans-cinnamate 4-hydroxylase. Inactivation requires NADPH, is time dependent and saturable (KI = 17 µM, kinact = 0.064 min-1), and results from the formation of a stable metabolite-P450 complex absorbing at 427 nm. The formation of this complex is reversible with substrate or other strong ligands of the enzyme. In plant microsomes PA seems to selectively inactivate the CYP73A P450 subpopulation. It does not form detectable complexes with other recombinant plant P450 enzymes. In vivo PA induces a sharp decrease in 4-coumaric acid concomitant to cinnamic acid accumulation in an elicited tobacco (Nicotiana tabacum) cell suspension. It also strongly decreases the formation of scopoletin in tobacco leaves infected with tobacco mosaic virus.

1   This work was supported by a Ministére de la Recherche et de l'Enseignement Supériur grant to M.S. F.C.-H. was supported by a postdoctoral grant from the Spanish Ministerio de Agricultura, Pesca y Alimentación, and M.-A.P. was supported by the Bio Avenir program funded by Rhône-Poulenc, the Ministère de la Recherche et de l'Espace, and the Ministère de l'Industrie et du Commerce Extérieur.
*   Corresponding author; e-mail daniele.werck{at}ibmp-ulp.u-strasbg.fr; fax 33-3-88-35-84-84.

Plant Physiol. (1998) 118: 209-218
Copyright Clearance Center:   0032-0889/98/118//10
© 1998 American Society of Plant Physiologists




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