Phytotoxic dioxolanone-type secondary metabolites from Guignardia bidwellii

Buckel, Iris; Molitor, Daniel; Liermann, Johannes C.; Sandjo, Louis P.; Berkelmann-Löhnertz, Beate; Opatz, Till; Thines, Eckhard

doi:10.1016/j.phytochem.2013.01.004

Cited by 26 publications

(36 citation statements)

References 16 publications

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“…The fungus Guignardia bidwellii is the causal agent of grape black rot, a devastating disease that threatens vineyards in, for example, the Moselle and Nahe region and the Middle Rhine valley in Germany. We have recently elucidated the structures of eight dioxolanone‐type secondary metabolites isolated from culture filtrates of G. bidwellii 10,11. These compounds have in common a core structure similar to that of the previously known metabolite12 guignardic acid ( 1 , Figure 1) and differ only in the substituents at C‐2 and the carboxylate function.…”

Section: Resultsmentioning

confidence: 97%

Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si₂W₁₈O₆₂]⁸⁻ and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds

Minato

Suzuki

Kamata

et al. 2014

Chemistry A European J

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The design of structurally well-defined anionic molecular metal-oxygen clusters, polyoxometalates (POMs), leads to inorganic receptors with unique and tunable properties. Herein, an α-Dawson-type silicotungstate, TBA8[α-Si2W18O62]⋅3 H2O (II) that possesses a -8 charge was successfully synthesized by dimerization of a trivacant lacunary α-Keggin-type silicotungstate TBA4H6[α-SiW9O34]⋅2 H2O (I) in an organic solvent. POM II could be reversibly protonated (in the presence of acid) and deprotonated (in the presence of base) inside the aperture by means of intramolecular hydrogen bonds with retention of the POM structure. In contrast, the aperture of phosphorus-centered POM TBA6[α-P2W18O62]⋅H2O (III) was not protonated inside the aperture. The density functional theory (DFT) calculations revealed that the basicities and charges of internal μ3-oxygen atoms were increased by changing the central heteroatoms from P(5+) to Si(4+), thereby supporting the protonation of II. Additionally, II showed much higher catalytic performance for the Knoevenagel condensation of ethyl cyanoacetate with benzaldehyde than I and III.

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Section: Resultsmentioning

confidence: 97%

Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si₂W₁₈O₆₂]⁸⁻ and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds

Minato

Suzuki

Kamata

et al. 2014

Chemistry A European J

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“…On the other hand, comparison of the ECD spectra of natural 2 and the spectra of ( S )‐ 1 reported by Heerklotz et al4 (data not shown) suggested the R configuration for 2 , because all the bands were inverted (Table 1). The inversion of the ECD bands was thus caused either by the exchange of the ester group in 2 for the methyl group in 9 or by the presence of the benzyl residue in 2 instead of the isopropyl group in 1 6,11…”

Section: Resultsmentioning

confidence: 99%

“…The major phytotoxic metabolite of G. bidwellii is ( S )‐guignardic acid ( 1 , Figure 1),4 but its congener phenguignardic acid ( 2 )5 shows an even more pronounced effect. Alaguignardic acid ( 3 ),6 another metabolite of G. bidwellii , shows nearly the same phytotoxic activity as 1 . Compounds 1 – 3 presumably originate from amino acid metabolism (Scheme ); their putative precursors would be the oxidative deamination products of valine, alanine, and phenylalanine (dimethylpyruvic acid, pyruvic acid, and phenylpyruvic acid), respectively 7…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of (+)‐Phenguignardic Acid, a Phytotoxic Metabolite of Guignardia bidwellii

2013

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(+)‐Phenguignardic acid, a phytotoxic metabolite of the grape black rot fungus Guignardia bidwellii was synthesized, as well as its enantiomer, in eight steps from (R)‐phenyllactic acid and 3‐phenylprop‐2‐yn‐1‐ol. The formation of the carboxylate at a late stage, to avoid enolization of the precursor used in the central acetalization step, proved to be crucial. The synthesis of the natural product allowed the unabiguous assignment of its hitherto unknown absolute configuration.

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“…The necrotic spots resulting from black rot infections led to the hypothesis that the pathogens produce phytotoxic compounds. Recently, several compounds with phytotoxic properties were isolated from fungal cultures and characterized (Molitor et al ., 2012 b ; Sommart et al ., ; Buckel et al ., ). In‐depth knowledge on these compounds may stimulate the development of a new generation of herbicides of biological origin.…”

Section: Introductionmentioning

confidence: 97%

Epidemiology, identification and disease management of grape black rot and potentially useful metabolites of black rot pathogens for industrial applications – a review

Molitor

Beyer²

2014

Annals of Applied Biology

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Phyllosticta ampelicida (teleomorph: Guignardia bidwellii) is the fungal plant pathogen that causes black rot on grapevine. It is able to infect all green, expanding grape tissues. Black rot poses a threat to both yield and wine quality; a severe attack can virtually cause a complete crop loss. The fungus is native to North America, and was spread to Europe at the end of the 19th century. With the beginning of the 21st century, an increasing importance of the disease was observed in several European winegrowing regions. Successful black rot control strategies combine sanitary measures, cultural techniques, growing cultivars with reduced susceptibility and the use of effective fungicides. Berries are most susceptible to infections between flowering and bunch closure and consequently, fungicide applications against black rot need to focus on this period. In this paper, forecast models and decision support systems that help to achieve satisfactory control with a minimum of fungicide input are presented. Black rot in grapevine was reported to be well controlled in field experiments by a broad range of fungicide classes including quinone outside inhibitors (98 ± 3% efficacy), demethylation inhibitors (98 ± 3% efficacy) and dithiocarbamates (92 ± 7% efficacy). Average efficacies of other fungicide classes tested so far ranged from 32 to 69%; meta data on the efficacy of fungicides in numerous field trials are given. At present, black rot causes major problems primarily if vineyard management and fungicide use were reduced or abandoned. Organically managed vineyards are highly affected. Hence, site and cultivar selection as well as cultural measures are of the highest importance especially in organic viticulture. Recent studies showed that some strains formerly classified as G. bidwellii in fact belong to a distinct species (P. parthenocissi). Black rot pathogens produce some phytotoxic secondary metabolites, such as phenguignardic acid, guignardic acid, alaguignardic acid and the guignardianones A, E and F, which could stimulate the development of new herbicides of natural origin.

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Phytotoxic dioxolanone-type secondary metabolites from Guignardia bidwellii

Cited by 26 publications

References 16 publications

Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si₂W₁₈O₆₂]⁸⁻ and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds

Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si₂W₁₈O₆₂]⁸⁻ and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds

Total Synthesis of (+)‐Phenguignardic Acid, a Phytotoxic Metabolite of Guignardia bidwellii

Epidemiology, identification and disease management of grape black rot and potentially useful metabolites of black rot pathogens for industrial applications – a review

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Phytotoxic dioxolanone-type secondary metabolites from Guignardia bidwellii

Cited by 26 publications

References 16 publications

Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si2W18O62]8− and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds

Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si2W18O62]8− and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds

Total Synthesis of (+)‐Phenguignardic Acid, a Phytotoxic Metabolite of Guignardia bidwellii

Epidemiology, identification and disease management of grape black rot and potentially useful metabolites of black rot pathogens for industrial applications – a review

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Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si₂W₁₈O₆₂]⁸⁻ and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds

Synthesis of α‐Dawson‐Type Silicotungstate [α‐Si₂W₁₈O₆₂]⁸⁻ and Protonation and Deprotonation Inside the Aperture through Intramolecular Hydrogen Bonds