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J. Biol. Chem., Vol. 280, Issue 43, 35881-35889, October 28, 2005

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Cloning, Functional Expression, and Characterization of CYP709C1, the First Sub-terminal Hydroxylase of Long Chain Fatty Acid in Plants

INDUCTION BY CHEMICALS AND METHYL JASMONATE^*

Sylvie Kandel1, Marc Morant2, Irène Benveniste, Elizabeth Blée, Danièle Werck-Reichhart, and Franck Pinot3

From the Département Réponse Métabolique à l'Environnement Biotique, IBMP-CNRS, UPR 2357, 28 Rue Goethe, F-67083 Strasbourg Cedex, France and Department of Plant Biology, The Royal Veterinary and Agricultural University, Thorvaldsensvej 40, Opgang 6-8, 2.Sal, DK-1871 Fredericksberg C, Copenhagen, Denmark

We cloned and characterized CYP709C1, a new plant cytochrome P450 belonging to the P450 family, that so far has no identified function except for clustering with a fatty acid metabolizing clade of P450 enzymes. We showed here that CYP709C1 is capable of hydroxylating fatty acids at the -1 and -2 positions. This work was performed after recoding and heterologous expression of a full-length cDNA isolated from a wheat cDNA library in an engineered yeast strain. Investigation on substrate specificity indicates that CYP709C1 metabolizes different fatty acids varying in their chain length (C12 to C18) and unsaturation. CYP709C1 is the first identified plant cytochrome P450 that can catalyze sub-terminal hydroxylation of C18 fatty acids. cis-9,10-Epoxystearic acid is metabolized with the highest efficiency, i.e. K_m(app) of 8 µM and V_max(app) of 328 nmol/min/nmol P450. This, together with the fact that wheat possesses a microsomal peroxygenase able to synthesize this compound from oleic acid, strongly suggests that it is a physiological substrate. Hydroxylated fatty acids are implicated in plant defense events. We postulated that CYP709C1 could be involved in plant defense by producing such compounds. This receives support from the observation that (i) sub-terminal hydroxylation of 9,10-epoxystearic acid is induced (15-fold after 3 h) in microsomes of wheat seedlings treated with the stress hormone methyl jasmonate and (ii) CYP709C1 is enhanced at the transcriptional level by this treatment. CYP709C1 transcript also accumulated after treatment with a combination of the safener naphthalic acid anhydride and phenobarbital. This indicates a possible detoxifying function for CYP709C1 that we discussed.

Received for publication, January 25, 2005 , and in revised form, July 7, 2005.

^* The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

¹ Supported by the French Ministry of Research.

² Supported by Bayer CropScience and the "Association Nationale de la Recherche Technique."

³ To whom correspondence should be addressed: IBMP-CNRS UPR 2357, Institut de Botanique, 28 Rue Goethe, F-67083 Strasbourg Cedex, France. Tel.: 33-3-90-24-18-37; Fax: 33-3-90-24-19-21; E-mail: franck.pinot{at}bota-ulp.u-strasbg.fr.

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