- Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin
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The synthesis of several sulfates of trichothecene mycotoxins is presented. Deoxynivalenol (DON) and its acetylated derivatives were synthesized from 3-acetyldeoxynivalenol (3ADON) and used as substrate for sulfation in order to reach a series of five different DON-based sulfates as well as T2-toxin-3-sulfate. These substances are suspected to be formed during phase-II metabolism in plants and humans. The sulfation was performed using a sulfuryl imidazolium salt, which was synthesized prior to use. All protected intermediates and final products were characterized via NMR and will serve as reference materials for further investigations in the fields of toxicology and bioanalytics of mycotoxins.
- Fruhmann, Philipp,Skrinjar, Philipp,Weber, Julia,Mikula, Hannes,Warth, Benedikt,Sulyok, Michael,Krska, Rudolf,Adam, Gerhard,Rosenberg, Erwin,Hametner, Christian,Fr?hlich, Johannes
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p. 5260 - 5266
(2014/07/08)
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- Sulfation of deoxynivalenol, its acetylated derivatives, and T2-toxin
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The synthesis of several sulfates of trichothecene mycotoxins is presented. Deoxynivalenol (DON) and its acetylated derivatives were synthesized from 3-acetyldeoxynivalenol (3ADON) and used as substrate for sulfation in order to reach a series of five different DON-based sulfates as well as T2-toxin-3-sulfate. These substances are suspected to be formed during phase-II metabolism in plants and humans. The sulfation was performed using a sulfuryl imidazolium salt, which was synthesized prior to use. All protected intermediates and final products were characterized via NMR and will serve as reference materials for further investigations in the fields of toxicology and bioanalytics of mycotoxins.
- Fruhmann, Philipp,Skrinjar, Philipp,Weber, Julia,Mikula, Hannes,Warth, Benedikt,Sulyok, Michael,Krska, Rudolf,Adam, Gerhard,Rosenberg, Erwin,Hametner, Christian,Fr?hlich, Johannes
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p. 5260 - 5266
(2014/12/10)
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- Structure-activity relationships of trichothecene toxins in an Arabidopsis thaliana leaf assay
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Many Fusarium species produce trichothecenes, sesquiterpene epoxides that differ in patterns of oxygenation and esterification at carbon positions C-3, C-4, C-7, C-8, and C-15. For the first comprehensive and quantitative comparison of the effects of oxygenation and esterification on trichothecene phytotoxicity, we tested 24 precursors, intermediates, and end products of the trichothecene biosynthetic pathway in an Arabidopsis thaliana detached leaf assay. At 100 μM, the highest concentration tested, only the trichothecene precursor trichodiene was nontoxic. Among trichothecenes, toxicity varied more than 200-fold. Oxygenation at C-4, C-8, C-7/8, or C-15 was, on average, as likely to decrease as to increase toxicity. Esterification at C-4, C-8, or C-15 generally increased toxicity. Esterification at C-3 increased toxicity in one case and decreased toxicity in three of eight cases tested. Thus, the increase in structural complexity along the trichothecene biosynthetic pathway in Fusarium is not necessarily associated with an increase in phytotoxicity.
- Desjardins, Anne E.,McCormick, Susan P.,Appell, Michael
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p. 6487 - 6492
(2008/09/19)
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- Trichothecene mycotoxin interconversions: Partial syntheses of calonectrin and deoxynivalenol, and of a trichothecene epi-epoxide, 3α,4β,15-triacetoxy-12,13-epi-epoxytrichothec-9-ene
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The partial syntheses of two trichothecenes, calonectrin (4β,15-diacetoxy-12,13-epoxytrichothec-9-ene) and deoxynivalenol (3α,7α,15-trihydroxy-12,13-epoxytrichothec-9-ene), from a readily available trichothecene, anguidine (4β,15-diacetoxy-3α-hydroxy-12,13-epoxytrichothec-9-ene) are described. In addition, and in order to provide further insight into the mode of action of the trichothecene mycotoxins, 3α,4β,15-tricetoxy-12,13-epi-epoxytrichothec-9-ene, of the first semisynthetic trichothecene epi-epoxides, has been prepared and its X-ray crystal structure determined. In significant contrast to its natural isomer, epi-epoxide proved to be biologically inactive.
- Cameron,Colvin
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p. 887 - 895
(2007/10/02)
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- PARTIAL SYNTHESES OF THE TRICHOTHECENE MYCOTOXINS, CALONECTRIN AND DEOXYNIVALENOL
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The partial syntheses of two trichothecenes, calonectrin (1) and deoxynivalenol (2), from a readily available derivative of the trichothecene, anguidine, are described.The methodology used should be applicable to the provision of other less abundant trichothecenes.
- Colvin, Ernest W.,Cameron, Stuart
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p. 493 - 496
(2007/10/02)
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- Phytotoxic Compound Produced by Fusarium equiseti. Part 8. Acid Catalysed Rearrangement of 12,13-Epoxytrichothec-9-enes
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The acid catalysed rearrangement of 12,13-epoxytrichothec-9-enes to give biologically inactive 10,13-cyclotrichothecane or apotrichothec-9-ene products depends on the substitution pattern of both rings A and C.The former rearrangement is adversely affected by 8α-substitution and by the presence of a 4,15-macrolide ring; the latter rearrangement by 7α- and by 3α-substitution.Compared with the trichothecene, the greater flexibility of the apotrichothecene skeleton is reflected in the range of values for the ring C vicinal coupling constants in the 1H n.m.r. spectra.
- Grove, John Frederick
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p. 647 - 654
(2007/10/02)
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