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An allene oxide and 12-oxophytodienoic acid are key intermediates in jasmonic acid biosynthesis by Fusarium oxysporum
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
Karolinska Inst, Dept Med Biochem & Biophys, SE-17177 Stockholm, Sweden..
2017 (English)In: Journal of Lipid Research, ISSN 0022-2275, E-ISSN 1539-7262, Vol. 58, no 8, 1670-1680 p.Article in journal (Refereed) Published
Abstract [en]

Fungi can produce jasmonic acid (JA) and its isoleucine conjugate in large quantities, but little is known about the biosynthesis. Plants form JA from 18: 3n-3 by 13S-lipoxygenase (LOX), allene oxide synthase, and allene oxide cyclase. Shaking cultures of Fusarium oxysporum f.sp. tulipae released over 200 mg of jasmonates per liter. Nitrogen powder of the mycelia expressed 10R-dioxygenase-epoxy alcohol synthase activities, which was confirmed by comparison with the recombinant enzyme. The 13S-LOX of F. oxysporum could not be detected in the cell-free preparations. Incubation of mycelia in phosphate buffer with [17,17,18,18,18-2 H5] 18: 3n-3 led to biosynthesis of a [H-2(5)] 12-oxo-13-hydroxy-9Z, 15Z-octadecadienoic acid (. -ketol), [H-2(5)] 12-oxo-10,15Z-phytodienoic acid (12-OPDA), and [H-2(5)] 13-keto-and [H-2(5)] 13S-hydroxyoctadecatrienoic acids. The. -ketol consisted of 90% of the 13R stereoisomer, suggesting its formation by nonenzymatic hydrolysis of an allene oxide with 13S configuration. Labeled and unlabeled 12-OPDA were observed following incubation with 0.1 mM [H-2(5)] 18: 3n-3 in a ratio from 0.4: 1 up to 47: 1 by mycelia of liquid cultures of different ages, whereas 10 times higher concentration of [H-2(5)] 13S-hydroperoxyoctadecatrienoic acid was required to detect biosynthesis of [H-2(5)] 12-OPDA. The allene oxide is likely formed by a cytochrome P450 or catalase-related hydroperoxidase. We conclude that F. oxysporum, like plants, forms jasmonates with an allene oxide and 12-OPDA as intermediates.

Place, publisher, year, edition, pages
AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC , 2017. Vol. 58, no 8, 1670-1680 p.
Keyword [en]
cytochrome P450, epoxy alcohol synthase, fatty acid dioxygenase, jasmonates, lipids/oxidation, lipoxygenase, mass spectrometry, methods/high-performance liquid chromatography
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:uu:diva-333711DOI: 10.1194/jlr.M077305ISI: 000406686600017PubMedID: 28572515OAI: oai:DiVA.org:uu-333711DiVA: diva2:1157820
Funder
Swedish Research Council, K2013-67X-06523-31-3Knut and Alice Wallenberg Foundation, KAW 2004.0123
Available from: 2017-11-16 Created: 2017-11-16 Last updated: 2017-11-16Bibliographically approved

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