Biosynthesis of jasmonic acid in a plant pathogenic fungus, Lasiodiplodia theobromae

Tsukada, K.; Takahashi, Kosaku; Nabeta, Kensuke

doi:10.1016/j.phytochem.2010.09.013

Cited by 63 publications

(46 citation statements)

References 19 publications

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“…Racemic 9-and 13-HPODE were obtained by photo Fungal pathogens may secrete LOXs during invasive growth to generate reactive oxygen species and lysis of membranes. Fungal LOXs may also regulate biosynthesis of secondary metabolites and toxins, including biosynthesis of jasmonates ( 11,(13)(14)(15)(16)(17).…”

Section: Methodsmentioning

confidence: 99%

Manganese lipoxygenase of F. oxysporum and the structural basis for biosynthesis of distinct 11-hydroperoxy stereoisomers

Wennman

Magnuson

Hámberg

et al. 2015

Journal of Lipid Research

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This article is available online at http://www.jlr.org Lipoxygenases (LOXs) belong to a common gene family ( 1, 2 ). The catalytic domain is formed by ␣ -helices, which harbor fi ve metal ligands. The 3D structure is known for over 10 enzymes from plants, animals, and bacteria with 13 S -LOX of soybean LOX-1 (sLOX-1) and 8 R -LOX of Plexaura homomalla as old and new prototypes ( 3-5 ). The latter was recently crystallized with its substrate in the active site ( 5 ). Information on the active site and reaction mechanism has also been gained by site-directed mutagenesis and by analysis of various substrates, deuterated fatty acids, and LOX inhibitors ( 1, 6 ). With few exceptions, LOXs oxidize polyunsaturated fatty acids with one or more cis , cis-1,4-pentadiene units to hydroperoxides, which in many cases are precursors of biological mediators ( 1, 6, 7 ). Mammalian LOXs initiate biosynthesis of leukotrienes and epoxy alcohols, which are involved in allergic infl ammation, asthma, formation of the skin-water barrier, and cancer development ( 6,8 ). Plant LOXs form jasmonates and related oxylipins with functions in defense against pathogens and in wound healing ( 9,10 ).The N-terminal parts of mammalian and plant LOXs usually consist of ␤ -sheets with homology to polycystin-1/ LOX/ ␣ -toxin (PLAT) domains with regulatory functions. The N-terminal domains of fungal LOXs lack this homology, but they often contain a secretion signal ( 11, 12 ). Abbreviations: Af-MnLOX, Aspergillus fumigatus manganese lipoxygenase; Cg-MnLOX, Colletotrichum gloeosporioides manganese lipoxygenase; CP, chiral phase; EPR, electron paramagnetic resonance; FeLOX, iron lipoxygenase; Fo-MnLOX, Fusarium oxysporum manganese lipoxygenase; HPODE, hydroperoxyoctadecadienoic acid; 9 S -H(P)ODE, 9 S -hydro(pero) xy-10 E ,12 Z -octadecadienoic acid; 11 S -H(P)ODE, 11 S -hydro(pero)xy-9 Z ,12 Z -octadecadienoic acid; 13 R -H(P)ODE, 13 R -hydro(pero)xy-9 Z ,11 Eoctadecadienoic acid; HPOTrE, hydroperoxyoctadecatrienoic acid; 9 S -H(P)OTrE, 9 S -hydro(pero)xy-10 E ,12 Z ,15Z-octadecatrienoic acid; 11 R -H(P)OTrE, 11 R -hydro(pero)xy-9 Z ,12 Z ,15 Z -octadecatrienoic acid; 13 R -H(P)OTrE, 13 R -hydro(pero)xy-9 Z ,11 E ,15Z-octadecatrienoic acid; ICP-AES, inductively coupled plasma atomic emission spectroscopy; LOX, lipoxygenase; MnLOX, manganese lipoxygenase; Mo-MnLOX, Magnaporthe oryzae manganese lipoxygenase; RP, reversed phase; sLOX-1, soybean lipoxygenase-1; TPP, triphenylphosphine . Abstract The biosynthesis of jasmonates in plants is

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Section: Methodsmentioning

confidence: 99%

Manganese lipoxygenase of F. oxysporum and the structural basis for biosynthesis of distinct 11-hydroperoxy stereoisomers

Wennman

Magnuson

Hámberg

et al. 2015

Journal of Lipid Research

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“…It is possible that the fi rst steps of biosynthesis of the fi ve-membered ring of JA occur by the same mechanism as in plants: oxidation and transformation of 18:3n-3 by 13 S -LOX, allene oxide synthase (AOS), and allene oxide cyclase. This is supported by the identical absolute confi guration of plant and fungal JA and its metabolites ( 11,14 ), the detection of 12-oxo-phytodienoic acid as a metabolite of L. theobromae ( 15 ), and the recent characterization of 13 S -LOX of F. oxysporum ( 16 ). Aspergillus terreus does not form JA, but this fungus oxidizes 18:2n-6 sequentially to 9 R -hydroperoxy-10( E ),12( Z )-octadecadienoic acid (HPODE) and an allene oxide, 9 R (10)-epoxy-11,(12 Z )-octadecadienoic acid [9 R (10)-EODE] ( 17 ).…”

Section: Methodsmentioning

confidence: 75%

Discovery of a linoleate 9S-dioxygenase and an allene oxide synthase in a fusion protein of Fusarium oxysporum

Hoffmann

Oliw

2013

Journal of Lipid Research

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“…Lasiodiplodia theobromae and a few other fungal pathogens overproduce jasmonic acid to induce pathological plant growth (45). Fungal jasmonates may be formed by the biochemical pathway in plants, but details are lacking (8,46). The fungal repertoire of oxylipins likely participates in the struggle between the pathogen and its host, as well as in reproduction and development (1).…”

Section: Discussionmentioning

confidence: 99%

A new class of fatty acid allene oxide formed by the DOX-P450 fusion proteins of human and plant pathogenic fungi, C. immitis and Z. tritici

Oliw

Aragó

Chen

et al. 2016

Journal of Lipid Research

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Biosynthesis of jasmonic acid in a plant pathogenic fungus, Lasiodiplodia theobromae

Cited by 63 publications

References 19 publications

Manganese lipoxygenase of F. oxysporum and the structural basis for biosynthesis of distinct 11-hydroperoxy stereoisomers

Manganese lipoxygenase of F. oxysporum and the structural basis for biosynthesis of distinct 11-hydroperoxy stereoisomers

Discovery of a linoleate 9S-dioxygenase and an allene oxide synthase in a fusion protein of Fusarium oxysporum

A new class of fatty acid allene oxide formed by the DOX-P450 fusion proteins of human and plant pathogenic fungi, C. immitis and Z. tritici

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