4-O-Acetylation and 3-O-Acetylation of Trichothecenes by Trichothecene 15-O-Acetyltransferase Encoded byFusarium Tri3

Tokai, Takeshi; Takahashi-Ando, Naoko; Izawa, Masako; Kamakura, Takashi; Yoshida, Minoru; Fujimura, Masatake; Kimura, Makoto

doi:10.1271/bbb.80501

Cited by 18 publications

(14 citation statements)

References 24 publications

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“…Four out of ten F. culmorum strains produced nivalenol/fusarenon X, while six, classified as the 3Ac-DON chemotype by PCR, produced high DON amounts, smaller amounts of 3Ac-DON and yet smaller amounts of 15Ac-DON. This behavior is common in strains belonging to the 3Ac-DON chemotype [22], because acetyltrichothecene esterase (a product of the gene, Tri8 ) is present in all three chemotypes; merely its activities towards C3 and C15 positions differ [23]. Similar to our results, ten F. culmorum strains belonging to the 3Ac-DON chemotype from France produced large amounts of DON [24].…”

Section: Resultssupporting

confidence: 81%

Study of Fungal Colonization of Wheat Kernels in Syria with a Focus on Fusarium Species

Alkadri

Nipoti

Döll

et al. 2013

IJMS

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Wheat is one of the main crops in Mediterranean countries, and its cultivation has an important role in the Syrian economy. In Syria, Fusarium head blight (FHB) has not been reported so far. Mycological analysis of 48 samples of wheat kernels collected from cultivation areas with different climatic conditions were performed in 2009 and 2010. Fungal isolates were identified at the genus level morphologically; Fusarium species were characterized morphologically and by species-specific PCR. The most frequent fungal genera found were Alternaria spp. and Cladosporium spp., with frequencies of 24.7% and 8.1%, respectively, while the frequency of Fusarium spp. was 1.5% of kernels. Most frequent Fusarium species were F. tricinctum (30% of all Fusarium isolates), F. culmorum (18%), F. equiseti (14%) and F. graminearum (13%). The mycotoxin production potential of selected Fusarium isolates was assessed by HPLC-MS analysis of rice cultures; chemotyping by PCR was carried out for comparison. All six F. graminearum strains tested produced small amounts (<3 mg/kg) of nivalenol (NIV). All ten F. culmorum strains tested produced large amounts of trichothecenes (>100 mg/kg); four strains produced NIV and six strains produced deoxynivalenol (DON) and 3-acetyl-deoxynivalenol (3Ac-DON). PCR chemotyping lead to an oversimplified picture, because all 3Ac-DON chemotype strains produced more DON than 3Ac-DON; furthermore, the strongest NIV producers produced significant amounts of DON. All tested strains of F. culmorum, F. graminearum, F. pseudograminearum (two strains) and most F. equiseti strains (five of six strains) produced zearalenone. Grains of durum wheat were more frequently colonized by Fusarium spp. than grains of soft wheat. Incidence of Fusarium spp. in irrigated fields was higher than in rainfed fields. The incidence of Fusarium strains producing mycotoxins raises concerns about the risk of Fusarium head blight to Syria and its consequences for public health.

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Section: Resultssupporting

confidence: 81%

Study of Fungal Colonization of Wheat Kernels in Syria with a Focus on Fusarium Species

Alkadri

Nipoti

Döll

et al. 2013

IJMS

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“…We propose that the C4 acylation activity is ancestral and C15 acylation is derived, because trichothecenes produced by fungi with a lineage A or B TRI cluster (i.e., Microcyclospora and Trichoderma ) have an acyl group at C4 but not at C15 ( Fig 10E ). The proposed ancestral and derived activities of Tri3 are consistent with the acquisition of C15 oxygenation in fungi with a lineage C and D TRI cluster ( Fig 10B ), because a hydroxyl group at C15 is a prerequisite for C15 acetylation catalyzed by the Fusarium Tri3 [ 33 , 64 ]. If the proposed ancestral and derived activities of Tri3 are correct, the low level of C4 acetylation activity reported for recombinant F .…”

Section: Discussionmentioning

confidence: 56%

“…If the proposed ancestral and derived activities of Tri3 are correct, the low level of C4 acetylation activity reported for recombinant F . graminearum Tri3 [ 64 ] indicates that some of the ancestral activity has been retained in this fungus.…”

Section: Discussionmentioning

confidence: 99%

Evolution of structural diversity of trichothecenes, a family of toxins produced by plant pathogenic and entomopathogenic fungi

et al. 2018

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Trichothecenes are a family of terpenoid toxins produced by multiple genera of fungi, including plant and insect pathogens. Some trichothecenes produced by the fungus Fusarium are among the mycotoxins of greatest concern to food and feed safety because of their toxicity and frequent occurrence in cereal crops, and trichothecene production contributes to pathogenesis of some Fusarium species on plants. Collectively, fungi produce over 150 trichothecene analogs: i.e., molecules that share the same core structure but differ in patterns of substituents attached to the core structure. Here, we carried out genomic, phylogenetic, gene-function, and analytical chemistry studies of strains from nine fungal genera to identify genetic variation responsible for trichothecene structural diversity and to gain insight into evolutionary processes that have contributed to the variation. The results indicate that structural diversity has resulted from gain, loss, and functional changes of trichothecene biosynthetic (TRI) genes. The results also indicate that the presence of some substituents has arisen independently in different fungi by gain of different genes with the same function. Variation in TRI gene duplication and number of TRI loci was also observed among the fungi examined, but there was no evidence that such genetic differences have contributed to trichothecene structural variation. We also inferred ancestral states of the TRI cluster and trichothecene biosynthetic pathway, and proposed scenarios for changes in trichothecene structures during divergence of TRI cluster homologs. Together, our findings provide insight into evolutionary processes responsible for structural diversification of toxins produced by pathogenic fungi.

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“…For preparation of the 3‐deCAL and 15‐deacetylcalonectrin (15‐deCAL) standards, CAL standard was incubated in 50 mM Tris–HCl at pH 11.2 for 72 h. The reaction products containing a mixture of 3‐deCAL and 3,15‐dideacetylcalonectrin were purified by TLC, and the latter was enzymatically re‐acetylated at C‐3 (Kimura et al ., ) to produce 15‐deCAL. The structures of 3‐deCAL and 15‐deCAL were confirmed by comparison of the LC–MS/MS spectrum to that of CAL standard after enzymatic acetylations with TRI101p and TRI3p (Tokai et al ., ), respectively. 3,4,15‐triacetylnivalenol (3,4,15‐triANIV) was prepared by 3‐ O ‐acetylation of 4,15‐diANIV and purified as described above.…”

Section: Methodsmentioning

confidence: 95%

Hydroxylations of trichothecene rings in the biosynthesis of Fusarium trichothecenes: evolution of alternative pathways in the nivalenol chemotype

Maeda

Tanaka

Sugiura

et al. 2016

Environmental Microbiology

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Fusarium sporotrichioides genes FsTri11, FsTri13, and FsTri1 encode cytochrome P450 monooxygenases (CYPs) responsible for hydroxylations at C-15, C-4, and C-8 of the trichothecene skeleton, respectively. However, the corresponding genes of nivalenol (NIV)-chemotype Fusarium graminearum remain to be functionally elucidated. In this study, we characterized the roles of these CYPs in NIV biosynthesis. Analyses of the metabolites of the F. graminearum Fgtri11 mutant, a disruptant of FgTri11 encoding isotrichodermin (ITD) C-15 hydroxylase, revealed a small amount of NIV-type trichothecenes suggesting that an alternative C-15 hydroxylase partially complemented FgTRI11p. In contrast, the C-7/C-8 hydroxylations depended solely on FgTRI1p, as suggested by the metabolite profiles of the Fgtri11 Fgtri1 double gene disruptant. Disruption of FgTri1 in both the wild-type and Fgtri13 mutant backgrounds revealed that FgTRI13p exhibits marginal activity toward calonectrin (CAL) and that it was the only C-4 hydroxylase. In addition, feeding experiments demonstrated that the C-4 hydroxylation of a 7-hydroxytrichothecene lacking C-8 ketone was extremely limited. The marginal activity of FgTRI13p toward CAL was advantageous for the C-7/C-8 hydroxylation steps in NIV biosynthesis, as transformation of a C-4 oxygenated trichothecene lacking C-7/C-8 modifications into NIV-type trichothecenes was quite inefficient. The significance of hydroxylation steps in the evolution of Fusarium trichothecenes is discussed.

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4-O-Acetylation and 3-O-Acetylation of Trichothecenes by Trichothecene 15-O-Acetyltransferase Encoded byFusarium Tri3

Cited by 18 publications

References 24 publications

Study of Fungal Colonization of Wheat Kernels in Syria with a Focus on Fusarium Species

Study of Fungal Colonization of Wheat Kernels in Syria with a Focus on Fusarium Species

Evolution of structural diversity of trichothecenes, a family of toxins produced by plant pathogenic and entomopathogenic fungi

Hydroxylations of trichothecene rings in the biosynthesis of Fusarium trichothecenes: evolution of alternative pathways in the nivalenol chemotype

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