Search results for "Guignardia"
showing 5 items of 5 documents
Assignment of Configuration in a Series of Dioxolanone-Type Secondary Metabolites fromGuignardia bidwellii- A Comparison of VCD and ECD Spectroscopy
2013
The absolute configurations of a series of phytotoxic dioxolanone-type secondary metabolites isolated from culture filtrates of the grape black rot fungus Guignardia bidwellii were determined by vibrational circular dichroism (VCD) spectroscopy in the mid-IR frequency range. Comparison of the recorded data with DFT calculations showed good agreement between experiment and theory for VCD, whereas electronic circular dichroism (ECD) data for the compounds matched poorly with the predicted spectra obtained by time-dependent DFT (TDDFT) calculations at the same level of theory.
Phytotoxic dioxolanone-type secondary metabolites from Guignardia bidwellii.
2012
Phenguignardic acid was recently described as a phytotoxic secondary metabolite from submerged cultures of the grape black rot fungus Guignardia bidwellii. Since the production rate of this natural product in submerged culture is very low, fermentation optimisation was carried out. The optimisation of cultivation conditions led to the identification of seven secondary metabolites, structurally related to guignardic acid, a known secondary metabolite from Guignardia species containing a dioxolanone moiety. All metabolites presented here have not been described to date and are presumably biosynthesised via deamination products of amino acids, such as phenylalanine, valine, tyrosine, and alani…
Total Synthesis of (+)-Phenguignardic Acid, a Phytotoxic Metabolite ofGuignardia bidwellii
2013
(+)-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.
Phenguignardic acid and guignardic acid, phytotoxic secondary metabolites from Guignardia bidwellii.
2012
Bioactivity-guided isolation led to the identification of phenguignardic acid (2), a new phytotoxic secondary metabolite from submerged cultures of grape black rot fungus, Guignardia bidwellii. The compound is structurally related to guignardic acid (1), a dioxolanone moiety-containing metabolite isolated previously from Guignardia species. However, in contrast to guignardic acid, which is presumably synthesized from deamination products of valine and phenylalanine, the biochemical precursor for the biosynthesis of the new phytotoxin appears to be exclusively phenylalanine. Guignardic acid was also found in extracts of cultures from Guignardia bidwellii. The phytotoxic activities of both co…
ChemInform Abstract: Total Synthesis of (+)-Phenguignardic Acid, a Phytotoxic Metabolite of Guignardia bidwellii
2014
(+)-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.