New metabolites of Gibberella fujikuroi—I

Cross, B. E.; Galt, R. H. B.; Hanson, James R.

doi:10.1016/s0040-4020(01)92692-4

Cited by 73 publications

(21 citation statements)

References 19 publications

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“…We demonstrated that chokol K has a fungitoxic effect at ecologically relevant concentrations and that chokol K production is intrinsic to Epichloe¨. In fact, cyclonerodiol, a chemically related sesquiterpene that likely originates from the same biochemical pathway (Yue et al, 2000), is found to be widespread in fungi (Nozoe et al, 1970;Cross et al, 1971;Hanson et al, 1975;Ghisalberti & Rowland, 1993). This may suggest that at least part of the chokol K producing pathway is ancestral to fungi.…”

Section: Discussionmentioning

confidence: 74%

Ecological role of volatiles produced by EpichloÃ«: differences in antifungal toxicity

Steinebrunner¹,

Schiestl²,

Leuchtmann³

2008

FEMS Microbiology Ecology

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Species of Epichloë (Ascomycota, Clavicipitaceae) are endophytic symbionts of pooid grasses. Sexual reproduction of the fungus depends on gamete-transferring Botanophila flies, which in earlier studies were shown to be specifically attracted by the fungal volatiles chokol K and methyl (Z)-3-methyldodec-2-enoate. As several Epichloë volatiles are known to have antimicrobial properties, it was hypothesised that the original function of insect-attracting volatiles is microbial deterrence. However, the origin of volatile compounds and their toxicity within an ecological context has not yet been clarified. We examined the inhibitory effect of chokol K and methyl (Z)-3-methyldodec-2-enoate on mycoparasites, plant pathogenic fungi and on Epichloë itself at ecologically relevant concentrations, and assessed volatile production in pure cultures of Epichloë on complex and defined media supplemented with inorganic sources of carbon and nitrogen. Chokol K reduced the spore germination of all tested fungi, whereas methyl (Z)-3-methyldodec-2-enoate had no inhibitory effect. Moreover, only chokol K was produced in culture, confirming its fungal origin. Our findings are consistent with the proposed scenario that fungal volatile substances have followed an evolutionary pathway from defence to attraction.

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Section: Discussionmentioning

confidence: 74%

Ecological role of volatiles produced by EpichloÃ«: differences in antifungal toxicity

Steinebrunner¹,

Schiestl²,

Leuchtmann³

2008

FEMS Microbiology Ecology

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“…matthiola (Miersch et al, 1999)). However, the first description of JA-Ile and 9,10-dihydro-JA-Ile produced by F. fujikoroi and L. theobromae dates back to 1970-71 (Aldridge et al, 1971;Cross and Webster, 1970).…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Jasmonates from Linoleic Acid by the Fungus Fusarium oxysporum. Evidence for a Novel Allene Oxide Cyclase

Oliw

Hámberg

2019

Lipids

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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.

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“…The tropical plant pathogen L. theobromae and a few other fungi secrete JAs (25,26,48). A key intermediate in plant JA biosynthesis, 12-oxo-10,15(Z)-phytodienoic acid, was recently identified in the culture medium of L. theobromae (49).…”

Section: Discussionmentioning

confidence: 99%

“…JA is a prototype defense molecule of virtually all plants (18), but it can also be formed by fungi. Its biosynthesis by the tropical and devastating plant pathogen Lasiodiplodia theobromae was discovered more than 40 years ago (25,26). L. theobromae also oxidizes 18:2n-6 sequentially to 9R-HPODE and 9(10)-EODE by its 9R-DOX and AOS activities (27).…”

mentioning

confidence: 99%

Expression of Fusion Proteins of Aspergillus terreus Reveals a Novel Allene Oxide Synthase

Hoffmann

Jernerén

Oliw

2013

Journal of Biological Chemistry

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Background: Allene oxide synthases (AOS) of the CYP74 family are present in plants, but AOS of fungi have not been characterized. Results: Expression of dioxygenase-cytochrome P450 fusion proteins of Aspergillus terreus reveals a novel AOS. Conclusion: AOS of A. terreus forms compound II with catalytic similarities to CYP74 and CYP8A1. Significance: The fungal AOS protein sequence is unique with little homology to CYP74.

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New metabolites of Gibberella fujikuroi—I

Cited by 73 publications

References 19 publications

Ecological role of volatiles produced by EpichloÃ«: differences in antifungal toxicity

Ecological role of volatiles produced by EpichloÃ«: differences in antifungal toxicity

Biosynthesis of Jasmonates from Linoleic Acid by the Fungus Fusarium oxysporum. Evidence for a Novel Allene Oxide Cyclase

Expression of Fusion Proteins of Aspergillus terreus Reveals a Novel Allene Oxide Synthase

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