Biological Modification of Trichothecene Mycotoxins: Acetylation and Deacetylation of Deoxynivalenols by Fusarium spp

Yoshizawa, Takumi; Morooka, Nobuichi

doi:10.1128/aem.29.1.54-58.1975

Cited by 43 publications

(28 citation statements)

References 7 publications

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“…A similar trend was observed in DON-contaminated spikes, wherein the frequencies of 3-ADON were 16% (6 days), 19% (29 days), 3% (62 days) and 1% (107 days). Thus, the conversion of 4-ANIV and 3-ADON to the parent toxins was indicated in the spikes, supporting the author's previous hypothesis that the deacetylation in the field is induced by biological hydrolysis during the maturation of cereal grain, probably by host-plant enzymes 86) .…”

Section: Occurrence Of Mycotoxigenic Fusarium Species and Don/niv Onsupporting

confidence: 83%

“…The author first found the microbial acetylation at the C-3α position of DON with resting mycelia of F. nivale Fn2B (=F. kyushuense) 86) . The acetyl conjugation of T-2 toxin, HT-2 toxin and neosolaniol, each having a C-3α hydroxy group, was also studied by using mycelia of trichothecene-producing strains of F. graminearum, F. nivale (=F.…”

Section: Acetyl Conjugation Of Trichothecenes 97)mentioning

confidence: 99%

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Thirty-five Years of Research on Deoxynivalenol, a Trichothecene Mycotoxin: with Special Reference to Its Discovery and Co-occurrence with Nivalenol in Japan

Yoshizawa

2013

Food Safety

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Deoxynivalenol (DON), a trichothecene mycotoxin, was characterized together with nivalenol (NIV) from naturally infected wheat and barley grains of the 1970 epidemic in Kagawa ** , Japan. DON, 3-acetyl-DON (3-ADON) and 3,15-diacetyl-DON (3,15-DADON) were identified as metabolites of Fusarium roseum No.117 (=F. graminearum ATCC 28114), a toxic isolate from the cereals of the 1970 epidemic, and their toxicological properties in animals, including acute toxicity, emetic activity, and in vivo de-epoxydation metabolism into DOM-1 (deepoxy-DON), were elucidated. Natural co-occurrence of DON and NIV in the domestic cereals was found to be common not only in southern Japan but also in other regions, and the geographic difference in the occurrence of both toxins in Japan was elucidated. In terms of mycotoxigenicity, F. graminearum strains isolated from crop fields were divided into two types: DON-and NIV-producers, and DON-producer was further subdivided into two subtypes, 3-ADON-and 15-acetyl-DON-producers by biotransformation experiment of 3,15-DADON as a precursor. The geographic differences in the incidence of these producers in Japan were observed. Correlation between the incidence of the toxin producers and the occurrence of DON and NIV were investigated by field trials. For screening NIV alone or in combination with DON in cereals, specific monoclonal antibodies were produced, and practical ELISA kits were successfully developed. In relation to our previous findings, current advances in the molecular phylogenetic analysis of mycotoxigenic F. graminearum, the molecular genetics of trichothecene biosynthesis, among others, were briefly reviewed.

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Section: Occurrence Of Mycotoxigenic Fusarium Species and Don/niv Onsupporting

confidence: 83%

Section: Acetyl Conjugation Of Trichothecenes 97)mentioning

confidence: 99%

Thirty-five Years of Research on Deoxynivalenol, a Trichothecene Mycotoxin: with Special Reference to Its Discovery and Co-occurrence with Nivalenol in Japan

Yoshizawa

2013

Food Safety

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“…Growing mycelia of the fungus that had been grown on peptone-supplemented Czapek-Dox medium (pH 6.8) in a shaking flask at 20 C for 3 days were washed three times with 0.67 M phosphate buffer (pH 6.8). Deoxynivalenol (VII) and its derivatives were prepared as previously described (10,17,19). Fusarenon (II) and T-2 toxin (XIV) were isolated from peptone-supplemented Czapek-Dox media of F. nivale and F. solani, respectively, by the procedure described by Ueno et al (11,14).…”

Section: Methodsmentioning

confidence: 99%

“…thecenes by intact mycelia of F. nivale or F. solani was performed in sugar-free Czapek-Dox medium under the same conditions as previously described (19). Chemical transformation of trichothecenes was performed in methanolic ammonium hydroxide at 5 C for an appropriate period, and methanol was evaporated in vacuo.…”

Section: 'Iha3mentioning

confidence: 99%

Comparative Studies on Microbial and Chemical Modifications of Trichothecene Mycotoxins

Yoshizawa¹,

Morooka²

1975

Applied Microbiology

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The microbial modification of several trichothecene mycotoxins by trichothecene-producing strains of Fusarium nivale and F. solani was studied. These results were compared with the corresponding chemical modifications. The growing mycelia of Fusarium spp. did not convert 4,B-acetoxy-3a,7a,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one (fusarenon) into 3a,4f0,7a,15-tetrahydroxy-12,13-epoxy-trichothec-9-en-8-one (nivalenol), whereas 3a,4,,7a,15-tetraacetoxy-12,13-epoxytrichothec-9-en-8-one (tetraacetylnivalenol) was deacetylated to yield 3a-hydroxy-4j3,7a,15-triacetoxy-12,13-epoxytrichothec-9-en-8-one (4,7,15-triacetylnivalenol), which was resistant to further deacetylation. T-2 toxin was transformed into HT-2 toxin, and 8a-(3-methylbutyryloxy)-3a,4l,-15-triacetoxy-12,13-epoxytrichothec-9-en-8-one (T-2 acetate) was transformed into HT-2 toxin via T-2 toxin. Chemical modification with ammonium hydroxide converted tetraacetylnivalenol into fusarenon via 4,7,15-triacetylnivalenol. 3a,-7a,15-Triacetoxy-12,13-epoxytrichothec-9-en-8one (triacetyldeoxynivalenol) gave deacetylation products lacking the C-7 or C-15 acetyl group in addition to 7a,15-diacetoxy-3a-hydroxy-12,13-epoxytrichothec-9-en-8-one (7,15diacetyldeoxynivalenol). These results demonstrate the regio-selectivity in microbial modification of trichothecenes. Based on the results and available knowledge concerning the transformation of trichothecenes, mechanisms for biological modifications of these mycotoxins are postulated.

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“…Recently, we found that T-2 toxin is converted to HT-2 toxin (3,4-dihydroxy-15-acetoxy-8-isovaleroxy-12,13-epoxy-A9-trichothecene) in F. poae (NRRL 3287) liquid cultures (manuscript submitted for publication). The isolation of acetyl T-2 toxin from the same strain of F. poae, and the recent work by Yoshizawa and Morooka (10) showing that the 3-acetoxy group of 3a,7a,15-triacetoxy-12,13-epoxytrichothec-9ene-one is particularly susceptible to enzymatic hydrolysis by Fusarium solani, have led us to suspect that acetyl T-2 toxin is the immediate biogenetic precursor of T-2 toxin. If this is the case, any observed T-2 toxicosis associated with F. poae (= F. tricinctum) contamination of field samples may well be dependent upon the relative efficiency of C-3 deacetylation in acetyl T-2 toxin.…”

mentioning

confidence: 99%

Isolation of Acetyl T-2 Toxin from Fusarium poae

Kotsonis¹,

Ellison²,

Smalley³

1975

Applied Microbiology

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Acetyl T-2 toxin (3,4,15-triacetoxy-8-isovaleroxy-12,13-epoxy-A9-trichothecene) was isolated and characterized as a naturally occurring emetic trichothecene from liquid cultures of Fusarium poae (NRRL 3287). Acetyl T-2 toxin was shown to be much less toxic than T-2 toxin in pigeon assays.Emesis has frequently been reported as a distinct toxicosis associated with the contamination of cereals by Fusarium species (5). Researchers in Japan (7, 8) and the U.S. (2) have implicated Fusarium-elaborated trichothecenes as causal agents. Their hypothesis has been supported by the identification of emetic trichothecenes in field samples of moldy cereals (3,9).Early investigations of moldy cereal emesis carried out by Prentice and Dickson (4) demonstrated that several Fusarium species including F. poae (NRRL 3287) (= F. tricinctum, according to Synder and Hansen [6]) produced emetic substances. They reported the presence of two emetic substances. One was free from harmful side effects at doses of 100 ,ug or less in pigeons, and the second one caused emesis and death at a comparable dose. In an earlier examination of F. poae (NRRL 3287) metabolites, we isolated T-2 toxin (3-hydroxy-4,15-diacetoxy-8isovaleroxy-12,13-epoxy-A9-trichothecene) and suggested it as the lethal emetic described by Prentice and Dickson (4). We report here our reexamination ofF. poae (NRRL 3287) metabolites and the isolation and characterization of acetyl T-2 toxin (Fig. 1).F. poae was grown as an agitated culture (300 rpm, New Brunswick Gyrotatory Shaker) in 14 2-liter flasks, each containing 500 ml of Richards solution (0.1 M potassium nitrate nitrogen source), for 4 weeks.The contents of the 14 culture flasks were filtered through Whatman no. 2 paper, and the filtrate was adjusted to pH 9.0 with saturated sodium carbonate followed by five extractions with chloroform. The chloroform layers were combined, dried over sodium sulfate, and evaporated in vacuo (40 C) to give an oily residue (861 mg) that was biologically active. Additional active material (86 mg) was obtained by extraction of the mycelial residue with water for 8 h followed by chloroform extraction as before.Column chromatography of the material recovered from the filtrate (662 mg) on silica gel (Merck E.M., 120 g, 2.7 by 46 cm) was effected with ethyl acetate-Skelly B (85:15) with 1.0-ml (tubes 1 to 232) and 1.7-ml (tubes 233 to 300) fractions being collected. The eluate was combined into 6 fractions (A --F) for bioassay. Fraction D (tubes 200 to 287, 145 mg), clearly the most active fraction, was purified by preparative thin-layer chromatography on 2-mm Brinkman F-254 silical gel plates with ethyl acetate. The isolated oil (59 mg) was nearly pure T-2 toxin (2). Fraction B (tubes 134-163, 113 mg) was rechromatographed on silica gel (20 g, 1.2 by 58 cm) with ethyl acetate-Skelly B (85:15) and 0.5-ml fractions were collected. Tubes 37 to 80 afforded a crude material 'Which was tentatively identified as a trichothecene. Further purification of this material by column chromatography was affecte...

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Biological Modification of Trichothecene Mycotoxins: Acetylation and Deacetylation of Deoxynivalenols by Fusarium spp

Cited by 43 publications

References 7 publications

Thirty-five Years of Research on Deoxynivalenol, a Trichothecene Mycotoxin: with Special Reference to Its Discovery and Co-occurrence with Nivalenol in Japan

Thirty-five Years of Research on Deoxynivalenol, a Trichothecene Mycotoxin: with Special Reference to Its Discovery and Co-occurrence with Nivalenol in Japan

Comparative Studies on Microbial and Chemical Modifications of Trichothecene Mycotoxins

Isolation of Acetyl T-2 Toxin from Fusarium poae

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