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Biosynthesis of Jasmonates from Linoleic Acid by the Fungus Fusarium oxysporum. Evidence for a Novel Allene Oxide Cyclase
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences. Uppsala Univ, Dept Pharmaceut Biosci, Div Biochem Pharmacol, Husargatan 3,Box 591, SE-75124 Uppsala, Sweden.
Karolinska Inst, Dept Med Biochem & Biophys, Stockholm, Sweden.
2019 (English)In: Lipids, ISSN 0024-4201, E-ISSN 1558-9307, Vol. 54, no 9, p. 543-556Article in journal (Refereed) Published
Abstract [en]

Fusarium oxysporum f. sp. tulipae (FOT) secretes (+)‐7‐iso‐jasmonoyl‐(S)‐isoleucine ((+)‐JA‐Ile) to the growth medium together with about 10 times less 9,10‐dihydro‐(+)‐7‐iso‐JA‐Ile. Plants and fungi form (+)‐JA‐Ile from 18:3n‐3 via 12‐oxophytodienoic acid (12‐OPDA), which is formed sequentially by 13S‐lipoxygenase, allene oxide synthase (AOS), and allene oxide cyclase (AOC). Plant AOC does not accept linoleic acid (18:2n‐6)‐derived allene oxides and dihydrojasmonates are not commonly found in plants. This raises the question whether 18:2n‐6 serves as the precursor of 9,10‐dihydro‐JA‐Ile in Fusarium, or whether the latter arises by a putative reductase activity operating on the n‐3 double bond of (+)‐JA‐Ile or one of its precursors. Incubation of pentadeuterated (d5) 18:3n‐3 with mycelia led to the formation of d5‐(+)‐JA‐Ile whereas d5‐9,10‐dihydro‐JA‐Ile was not detectable. In contrast, d5‐9,10‐dihydro‐(+)‐JA‐Ile was produced following incubation of [17,17,18,18,18‐2H5]linoleic acid (d5‐18:2n‐6). Furthermore, 9(S),13(S)‐12‐oxophytoenoic acid, the 15,16‐dihydro analog of 12‐OPDA, was formed upon incubation of unlabeled or d5‐18:2n‐6. Appearance of the α‐ketol, 12‐oxo‐13‐hydroxy‐9‐octadecenoic acid following incubation of unlabeled or [13C18]‐labeled 13(S)‐hydroperoxy‐9(Z),11(E)‐octadecadienoic acid confirmed the involvement of AOS and the biosynthesis of the allene oxide 12,13(S)‐epoxy‐9,11‐octadecadienoic acid. The lack of conversion of this allene oxide by AOC in higher plants necessitates the conclusion that the fungal AOC is distinct from the corresponding plant enzyme.

Place, publisher, year, edition, pages
2019. Vol. 54, no 9, p. 543-556
Keywords [en]
Allene oxide cyclase, Cytochrome P-450, Jasmonates, Lipids, oxidation, Lipoxygenase, Mass spectrometry, Methods, HPLC
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:uu:diva-394973DOI: 10.1002/lipd.12180ISI: 000485944300004PubMedID: 31353474OAI: oai:DiVA.org:uu-394973DiVA, id: diva2:1360181
Funder
Swedish Research Council, K2013-67X-06523-31-3Knut and Alice Wallenberg Foundation, KAW 2004.0123Available from: 2019-10-11 Created: 2019-10-11 Last updated: 2019-10-11Bibliographically approved

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