Biosynthesis of the mycotoxin tenuazonic acid by a fungal NRPS–PKS hybrid enzyme

Yun, Choong-Soo; Motoyama, Takayuki; Osada, Hiroyuki

doi:10.1038/ncomms9758

Cited by 121 publications

(129 citation statements)

References 64 publications

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“…1). Further secondary metabolites previously described to be produced by the rice blast fungus, for example, pyrichalasin H [31], pyriculol [32] or tenuazonic acid [12][13][14], were not found in this study. Based on considerations concerning the chemical structure of pyriculol, we searched for PKS-encoding genes in the genome of M. oryzae.…”

Section: Discussioncontrasting

confidence: 73%

“…Additional studies have identified other metabolites produced by Magnaporthe strains, i.e. tenuazonic acid and Magtoxin [10,[12][13][14]. Tenuazonic acid is a mycotoxin synthesized by various plant pathogenic fungi.…”

Section: Introductionmentioning

confidence: 99%

“…Tenuazonic acid is a mycotoxin synthesized by various plant pathogenic fungi. The biosynthesis was hypothesized in M. oryzaefrom isoleucine and acetoacetyl-CoA by TeA synthetase 1 (TAS1) [14]. Furthermore, metabolome studies resulted in varieties of metabolites, i.e.…”

Section: Introductionmentioning

confidence: 99%

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Unravelling the biosynthesis of pyriculol in the rice blast fungus Magnaporthe oryzae

et al. 2017

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Pyriculol was isolated from the rice blast fungus Magnaporthe oryzae and found to induce lesion formation on rice leaves. These findings suggest that it could be involved in virulence. The gene MoPKS19 was identified to encode a polyketide synthase essential for the production of the polyketide pyriculol in the rice blast fungus M. oryzae. The transcript abundance of MoPKS19 correlates with the biosynthesis rate of pyriculol in a time-dependent manner. Furthermore, gene inactivation of MoPKS19 resulted in a mutant unable to produce pyriculol, pyriculariol and their dihydro derivatives. Inactivation of a putative oxidase-encoding gene MoC19OXR1, which was found to be located in the genome close to MoPKS19, resulted in a mutant exclusively producing dihydropyriculol and dihydropyriculariol. By contrast, overexpression of MoC19OXR1 resulted in a mutant strain only producing pyriculol. The MoPKS19 cluster, furthermore, comprises two transcription factors MoC19TRF1 and MoC19TRF2, which were both found individually to act as negative regulators repressing gene expression of MoPKS19. Additionally, extracts of DMopks19 and DMoC19oxr1 made from axenic cultures failed to induce lesions on rice leaves compared to extracts of the wild-type strain. Consequently, pyriculol and its isomer pyriculariol appear to be the only lesioninducing secondary metabolites produced by M. oryzae wild-type (MoWT) under these culture conditions. Interestingly, the mutants unable to produce pyriculol and pyriculariol were as pathogenic as MoWT, demonstrating that pyriculol is not required for infection.

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Section: Discussioncontrasting

confidence: 73%

Section: Introductionmentioning

confidence: 99%

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Unravelling the biosynthesis of pyriculol in the rice blast fungus Magnaporthe oryzae

et al. 2017

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“…Melanin, a polyketide compound, is biosynthesized by the PKS ALB1/MGG_07219 and modifying enzymes . Tenuazonic acid is biosynthesized by a unique NRPS–PKS enzyme: TAS1/MGG_07803 . Pyriculols are polyketide compounds, and the identification of the pyriculol biosynthetic gene cluster containing the PKS gene MoPKS19 / MGG_10912 was reported recently .…”

Section: Introductionmentioning

confidence: 99%

“…We have previously found that knockout of the HOG MAP kinase gene OSM1 , which works downstream of the TCS, can activate the production of tenuazonic acid in P. oryzae . Herein, we show that the production of other secondary metabolites can be activated by double gene knockout of OSM1 and PoYPD1 ( MoYPD1 ), which encodes an HPt.…”

Section: Introductionmentioning

confidence: 99%

Induction of Nectriapyrone Biosynthesis in the Rice Blast Fungus Pyricularia oryzae by Disturbance of the Two‐Component Signal Transduction System

et al. 2019

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Most fungal secondary metabolism genes are poorly expressed under laboratory conditions. Nectriapyrones are known as secondary metabolites produced mainly by symbiotic fungi, including endophytes and plant pathogens. Herein, we show the induction of nectriapyrone production in the rice blast fungus Pyricularia oryzae. The two‐component signal transduction system was disturbed by disrupting OSM1 and PoYPD1, which encoded a HOG MAP kinase and a His‐containing phosphotransfer (HPt) protein, respectively. This induced the production of two polyketide compounds: nectriapyrone and its hydroxylated analogue. The nectriapyrone biosynthetic gene cluster consists of a polyketide synthase gene (NEC1) and an O‐methyltransferase gene (NEC2). Overexpression of the two genes induced overproduction of nectriapyrone and five nectriapyrone analogues, including a new derivative. Nectriapyrone production was not required for the infection of rice. The structure of nectriapyrone is similar to that of the germicidins produced by Streptomyces spp., and nectriapyrone inhibited the growth of Streptomyces griseus.

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Bacterial Alkaloids Prevent Amoebal Predation

et al. 2016

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Bacterial defense mechanisms have evolved to protect bacteria against predation by nematodes, predatory bacteria, or amoebae. We identified novel bacterial alkaloids (pyreudiones A–D) that protect the producer, Pseudomonas fluorescens HKI0770, against amoebal predation. Isolation, structure elucidation, total synthesis, and a proposed biosynthetic pathway for these structures are presented. The generation of P. fluorescens gene‐deletion mutants unable to produce pyreudiones rendered the bacterium edible to a variety of soil‐dwelling amoebae.

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Biosynthesis of the mycotoxin tenuazonic acid by a fungal NRPS–PKS hybrid enzyme

Cited by 121 publications

References 64 publications

Unravelling the biosynthesis of pyriculol in the rice blast fungus Magnaporthe oryzae

Unravelling the biosynthesis of pyriculol in the rice blast fungus Magnaporthe oryzae

Induction of Nectriapyrone Biosynthesis in the Rice Blast Fungus Pyricularia oryzae by Disturbance of the Two‐Component Signal Transduction System

Bacterial Alkaloids Prevent Amoebal Predation

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