Microbial and chemical transformations of some 12,13-epoxytrichothec-9,10-enes

Claridge, C. A.; Schmitz, H

doi:10.1128/aem.36.1.63-67.1978

Cited by 16 publications

(8 citation statements)

References 11 publications

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“…The biological 3α-O-acetylation of trichothecenes, diacetoxyscirpenol and 15-acetoxyscirpene-3,4-diol by trichothecene nonproducing fungi of Mucor mucedo and F. oxysporum f. sp. vasinfectum was reported 98,99) .…”

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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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: 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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“…We first found the microbial acetylation of trichothecenes in deoxynivalenol with resting mycelia of F. nivale, and the reaction occurred at C-3a position (12). Thereafter, Claridge and Schmitz (1,2) reported the biological 3a-O-acetylation of diacetoxyscirpenol and 15-acetoxyscirpene-3,4-diol by resting cells on Mucor mucedo and growing cells of F. oxysporum f. sp. vasinfectum.…”

Section: Discussionmentioning

confidence: 99%

Microbial acetyl conjugation of T-2 toxin and its derivatives

Yoshizawa¹,

Onomoto²,

Morooka³

1980

Appl Environ Microbiol

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The acetyl conjugation of T-2 toxin and its derivatives, the 12,13-epoxytrichothecene mycotoxins, was studied by using mycelia of trichothecene-producing strains of Fusarium graminearum, F. nivale, Calonectria nivalis, and F. sporotrichoides. T-2 toxin was efficiently converted into acetyl T-2 toxin by all strains except a T-2 toxin-producing strain of F. sporotrichoides, which hydrolyzed the substrate to HT-2 toxin and neosolaniol. HT-2 toxin was conjugated to 3-acetyl HT-2 toxin as an only product by mycelia of F. graminearum and C. nivalis, but was also resistant to conjugation by both F. nivale and F. sporotrichioides. Neosolaniol was also biotransformed selectively into 3-acetyl neosolaniol by F. graminearum. However, 3-acetyl HT-2 toxin was not acetylated by any of the strains under the conditions employed, but was hydrolyzed to HT-2 toxin by F. graminearum and F. nivale. This is the first report on the biological 3a-0-acetyl conjugation of T-2 toxin and its derivatives. T-2 toxin, 4,8,15-diacetoxy-8a-(3-methylbutyloxy)-3a-hydroxy-12,13-epoxytrichothec-9ene, is one of the most important trichothecene mycotoxins occurring naturally in agricultural products and associated with serious field toxicoses of humans and animals (5, 6). The metabolic fates of this toxin have been studied in fungi (12-14), livers (3, 9, 10), rats and mice (11), and chickens (T. Yoshizawa, S. P. Swanson, and C. J. Mirocha, submitted for publication). Up to

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“…This series contained triacetoxyscirpene, scirpenetriol, the three diacetoxyscirpenols, and two of the monoacetoxyscirpenediols, namely, 4-acetoxyscirpene-3,5-diol and 15-acetoxyscirpene-3,4-diol. We were unable to obtain the hitherto unknown 3-acetoxyscirpene-4,15-diol either by treatment of scirpenetriol with Mucor mucedo or of 3,15-diacetoxyscirpene-4-ol with Streptomyces griseus, two of the organisms previously reported to transform anguidine to the 4-and 15-acetoxy analogs (4).…”

mentioning

confidence: 93%

“…We have been studying the transformation of the antitumor antibiotic anguidine by both microbiological and chemical means, seeking one or more derivatives having enhanced in vivo chemotherapeutic properties. One such series of derivatives already has been prepared, and their antifungal and cytotoxic activities have been determined (4). This series contained triacetoxyscirpene, scirpenetriol, the three diacetoxyscirpenols, and two of the monoacetoxyscirpenediols, namely, 4-acetoxyscirpene-3,5-diol and 15-acetoxyscirpene-3,4-diol.…”

mentioning

confidence: 99%

Production of 3-acetoxyscirpene-4,15-diol from anguidine (4,15-diacetoxyscirpene-3-ol) by Fusarium oxysporum f.sp. vasinfectum

Claridge¹,

Schmitz²

1979

Appl Environ Microbiol

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Growing cells of Fusarium oxysporum f.sp. vasinfectum (ATCC 7808) formed 3-acetoxyscirpene-4,15-diol from anguidine (4,15-diacetoxyscirpene-3-ol) by way of the intermediates triacetoxyscirpene, 3,4-diacetoxyscirpene-15-ol and 3,15-diacetoxyscirpene-4-ol. The new 3-acetoxy analog was found to be less active than anguidine and the two other monoacetoxy derivatives when tested against a series of fungal strains and against HeLa cells in vitro.

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Microbial and chemical transformations of some 12,13-epoxytrichothec-9,10-enes

Cited by 16 publications

References 11 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

Microbial acetyl conjugation of T-2 toxin and its derivatives

Production of 3-acetoxyscirpene-4,15-diol from anguidine (4,15-diacetoxyscirpene-3-ol) by Fusarium oxysporum f.sp. vasinfectum

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