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Daniel Giddings Vassao - One of the best experts on this subject based on the ideXlab platform.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants. Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants.
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The phytopathogenic fungus Sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
'Springer Science and Business Media LLC', 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase
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metabolism of glucosinolate derived Isothiocyanates to glutathione conjugates in generalist lepidopteran herbivores
Insect Biochemistry and Molecular Biology, 2012Co-Authors: Katharina Schramm, Daniel Giddings VassaoAbstract:Abstract The defensive properties of the glucosinolate-myrosinase system in plants of the order Brassicales have been attributed to the formation of toxic Isothiocyanates generated upon tissue damage. Lepidopteran herbivores specialised on brassicaceous plants have been shown to possess biochemical mechanisms preventing the formation of Isothiocyanates. Yet, no such mechanisms are known for generalist lepidopterans which also occasionally but successfully feed on plants of the Brassicales. After feeding on Arabidopsis thaliana plants, faeces of Spodoptera littoralis larvae contained glutathione conjugate derivatives (cysteinylglycine- and cysteinyl-Isothiocyanate-conjugates) of the plant's major glucosinolate hydrolysis product, 4-methylsulfinylbutyl Isothiocyanate. When caterpillars fed on leaves of A . thaliana containing [ 14 C] 4 -methylsulfinylbutyl glucosinolate, more than half of the ingested radioactivity was excreted as the unmetabolised corresponding Isothiocyanate, and only 11% as glutathione conjugate derivatives. However, these conjugates were demonstrated to be the major metabolites of Isothiocyanates in S. littoralis , and their abundance was shown to correlate with the amount of Isothiocyanates ingested. Analysis of larval faeces from several species of generalist lepidopterans ( Spodoptera exigua , S. littoralis , Mamestra brassicae , Trichoplusia ni and Helicoverpa armigera ) fed on different Brassicaceae revealed that glutathione conjugates arise from a variety of aliphatic and aromatic Isothiocyanates derived from dietary glucosinolates.
Curt Wentrup - One of the best experts on this subject based on the ideXlab platform.
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Rearrangements of Acyl, Thioacyl, and Imidoyl (Thio)cyanates to Iso(thio)cyanates, Acyl Iso(thio)cyanates to (Thio)acyl Isocyanates, and Imidoyl Iso(thio)cyanates to (Thio)acyl Carbodiimides, RCX-YCN ⇌ RCX-NCY ⇌ RCY-NCX ⇌ RCY-XCN (X and Y = O, S, NR′
2016Co-Authors: Rainer Koch, Curt WentrupAbstract:Two types of rearrangements have been investigated computationally at the B3LYP/6-311+G(d,p) level. The activation barriers for rearrangement of acyl thiocyanates RCO–SCN to the corresponding Isothiocyanates RCO–NCS are 30–31 kcal/mol in agreement with the observation that the thiocyanates are in some cases isolable albeit very sensitive compounds. Alkoxycarbonyl-, (alkylthio)carbonyl- and carbamoyl thiocyanates are isolable and have higher calculated barriers (ca. 40 kcal/mol) toward rearrangement to Isothiocyanates, whereas all thioacyl thiocyanate derivatives are rather unstable compounds with barriers in the range 20–30 kcal/mol for rearrangement to the Isothiocyanates. Acyl-, alkoxycarbonyl-, and carbamoyl cyanates R–CO–OCN are predicted to be in some cases isolable compounds with barriers up to ca. 40 kcal/mol for rearrangement to the isocyanates RCO–NCO. All of the rearrangements of this type involve the HOMO of a nearly linear (thio)cyanate anion and the LUMO of the acyl cation, in particular the acyl CX π* orbital. The second type of rearrangement involves 1,3-shifts of the groups R attached to the (thio)acyl groups, that is, acyl Isothiocyanate–thioacyl isocyanate and imidoyl Isothiocyanate–thioacyl carbodiimide rearrangements. These reactions involve four-membered cyclic, zwitterionic transition states facilitated by lone pair–LUMO interactions between the migrating R group and the neighboring iso(thio)cyanate function. Combination of the two rearrangements leads to the general reaction scheme RCX–YCN ⇌ RCX–NCY ⇌ RCY–NCX ⇌ RCY–XCN (X and Y = O, S, NR′)
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rearrangements of acyl thioacyl and imidoyl thio cyanates to iso thio cyanates acyl iso thio cyanates to thio acyl isocyanates and imidoyl iso thio cyanates to thio acyl carbodiimides rcx ycn rcx ncy rcy ncx rcy xcn x and y o s nr
Journal of Organic Chemistry, 2013Co-Authors: Rainer Koch, Curt WentrupAbstract:Two types of rearrangements have been investigated computationally at the B3LYP/6-311+G(d,p) level. The activation barriers for rearrangement of acyl thiocyanates RCO-SCN to the corresponding Isothiocyanates RCO-NCS are 30-31 kcal/mol in agreement with the observation that the thiocyanates are in some cases isolable albeit very sensitive compounds. Alkoxycarbonyl-, (alkylthio)carbonyl- and carbamoyl thiocyanates are isolable and have higher calculated barriers (ca. 40 kcal/mol) toward rearrangement to Isothiocyanates, whereas all thioacyl thiocyanate derivatives are rather unstable compounds with barriers in the range 20-30 kcal/mol for rearrangement to the Isothiocyanates. Acyl-, alkoxycarbonyl-, and carbamoyl cyanates R-CO-OCN are predicted to be in some cases isolable compounds with barriers up to ca. 40 kcal/mol for rearrangement to the isocyanates RCO-NCO. All of the rearrangements of this type involve the HOMO of a nearly linear (thio)cyanate anion and the LUMO of the acyl cation, in particular the acyl =X π* orbital. The second type of rearrangement involves 1,3-shifts of the groups R attached to the (thio)acyl groups, that is, acyl Isothiocyanate-thioacyl isocyanate and imidoyl Isothiocyanate-thioacyl carbodiimide rearrangements. These reactions involve four-membered cyclic, zwitterionic transition states facilitated by lone pair-LUMO interactions between the migrating R group and the neighboring iso(thio)cyanate function. Combination of the two rearrangements leads to the general reaction scheme RCX-YCN ⇌ RCX-NCY ⇌ RCY-NCX ⇌ RCY-XCN (X and Y = O, S, NR′).
Jingyuan Chen - One of the best experts on this subject based on the ideXlab platform.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants. Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase.
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The phytopathogenic fungus Sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
'Springer Science and Business Media LLC', 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase
Chhana Ullah - One of the best experts on this subject based on the ideXlab platform.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants. Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase.
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The phytopathogenic fungus Sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
'Springer Science and Business Media LLC', 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase
Franziska Beran - One of the best experts on this subject based on the ideXlab platform.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants.
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the phytopathogenic fungus sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
Nature Communications, 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Brassicales plants produce glucosinolates and myrosinases that generate toxic Isothiocyanates conferring broad resistance against pathogens and herbivorous insects. Nevertheless, some cosmopolitan fungal pathogens, such as the necrotrophic white mold Sclerotinia sclerotiorum, are able to infect many plant hosts including glucosinolate producers. Here, we show that S. sclerotiorum infection activates the glucosinolate-myrosinase system, and Isothiocyanates contribute to resistance against this fungus. S. sclerotiorum metabolizes Isothiocyanates via two independent pathways: conjugation to glutathione and, more effectively, hydrolysis to amines. The latter pathway features an Isothiocyanate hydrolase that is homologous to a previously characterized bacterial enzyme, and converts Isothiocyanate into products that are not toxic to the fungus. The Isothiocyanate hydrolase promotes fungal growth in the presence of the toxins, and contributes to the virulence of S. sclerotiorum on glucosinolate-producing plants. Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase.
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The phytopathogenic fungus Sclerotinia sclerotiorum detoxifies plant glucosinolate hydrolysis products via an Isothiocyanate hydrolase
'Springer Science and Business Media LLC', 2020Co-Authors: Jingyuan Chen, Franziska Beran, Chhana Ullah, Michael Reichelt, Jonathan Gershenzon, Almuth Hammerbacher, Zhiling Yang, Daniel Giddings VassaoAbstract:Some plants produce toxic Isothiocyanates that protect them against pathogens. Here, Chen et al. show that the plant pathogenic fungus Sclerotinia sclerotiorum converts Isothiocyanates into non-toxic compounds via glutathione conjugation and, more effectively, via hydrolysis to amines using an Isothiocyanate hydrolase
