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

Claridge, C. A.; Schmitz, H

doi:10.1128/aem.37.4.693-696.1979

Cited by 11 publications

(8 citation statements)

References 5 publications

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“…A number of in vitro studies on the metabolism of TCTC in animals have shown that hydroxylases and esterases in the liver play an important role in diverse structures and their toxicities [Ohta et al, 1977[Ohta et al, , 1978Swanson and Corley, 1989;Ueno et al, 1983;Wei and Chu, 1985;Yoshizawa and Morooka, 19751. Fungal esterases from crude extracts or with whole mycelia have also been shown capable of hydrolyzing TCTC [Baldwin et a]., 1986;Claridge andSchmitz, 1978, 1979;Kotsonis and Ellison, 1975;Udell and Dewick, 1989;Yoshizawa and Morooka, 19751. Whereas both intracellular and extracellular esterases have been found, intracellular esterases were found to be primarily involved in the hydrolytic reactions [Udell and Dewick, 1989;Ueno et al, 1973;Yoshizawa and Morooka, 19751.…”

Section: Discussionmentioning

confidence: 99%

“…These toxicological effects are correlated with their chemical characteristics. Type A TCTCs possess hydroxyls or esterified hydroxyls at the C-3,4,7,8, or 15 positions; hydrolysis of the ester side chain generally results in a decrease of toxicity in experimental animals [Claridge andSchmitz, 1978,1979;Ueno, 1983;Yoshizawa and Morooka, 1975;Yoshizawa et al, 1980aYoshizawa et al, , 1980bYoshizawa et al, . 1982Swanson and Corley, 19891. Whereas metabolic hydrolysis of the ester bond of TCTCs by mammalian enzymes plays an important role in determining the toxicity of the toxin, the multiplicity of TCTCs produced by various fusaria was also attributed to the hydroxylase and esterase enzymes [Anonymous, 1983;Baldwin et al, 1986;Beeton and Bull, 1989;Desjardins et al, C 1996WileyLiss, Inc 1993Miller and Trenholm, 1994;Swanson and Corley, 1989;Udell and Dewick, 1989;Ueno, 19831.…”

Section: Introductionmentioning

confidence: 99%

“…In a previous study on the production of various type A TCTCs by Fusarium spororrichioides, we found that T-2 toxin was converted to more polar metabolites after prolonged incubation [Park and Chu, 19931. Although hydrolytic enzymes involved in acetylation and deacetylation of the ester side chain of TCTC have been studied in animal organs [Johnsen et al, 1986;Ohta et al, 1977Ohta et al, , 1978Ueno et al, 1973;Wu and Marletta, 19881 and bacteria [Beeton and Bull, 1989;Ueno et al, 1983;Yoshizawa et al, 1980a1, as well as intact fungal mycelium [Claridge andSchmitz, 1978, 1979;Kotsonis and Ellison, 1975;Yoshizawa and Morooka, 19751 and crude extract of fungus [Baldwin et al, 1986;Udell and Dewick, 1989;Yoshizawa and Luangpituksa, 19851, the enzymes involved in such reactions have not been well characterized. In the present study, a fungal esterase from E spororrichioides T-424 was partially purified and characterized.…”

Section: Introductionmentioning

confidence: 99%

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Partial purification and characterization of an esterase from fusarium sporotrichioides

Park

Chu

1996

Natural Toxins

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Kinetics analysis of the growth of Fusarium sporotrichioides T-424 at 15 degrees C and 25 degrees C in liquid culture for 35 days revealed that production of deacetylated trichothecenes was associated with an increased activity in fungal esterases. High temperature (25 degrees C) favored enzyme production and enhanced esterase activity. Electrophoresis of crude extracts from the mycelia of F. sporotrichioides T-424 with carboxylesterase staining revealed that several esterases were produced by the fungus. Four carboxylesterase isoenzymes (I-IV) were separated on a DEAE-Sephadex anion exchange column. Type (III) esterase, having activities with the substrate 4-nitrophenylacetate and acetanilide, as well as hydrolytic activity for T-2 toxin and acetyl-T-2 toxin, was partially purified with ammonium sulfate precipitation, immunoaffinity column chromatography, and DEAE-Sephadex A-50 chromatography. The esterase (III) had a molecular weight around 68 kDa in SDS-PAGE. For the deacylation of T-2 toxin and acetyl-T-2 toxin, type (III) esterase had a high specificity for the acetyl group at the C-3 and C-4 positions. The Km values for acetyl-T-2 and T-2 toxin were found to be 41.35 microM and 0.38 microM, respectively. The Km value for the acetyl group at C-3 is 110 times greater than for that at C-4.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Partial purification and characterization of an esterase from fusarium sporotrichioides

Park

Chu

1996

Natural Toxins

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

Cited by 11 publications

References 5 publications

Partial purification and characterization of an esterase from fusarium sporotrichioides

Partial purification and characterization of an esterase from fusarium sporotrichioides

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

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