Phenguignardic acid and guignardic acid, phytotoxic secondary metabolites from Guignardia bidwellii.
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 compounds were assessed in plant assays using either detached vine leaves or intact plants. Antimicrobial and cytotoxic activities of phenguignardic acid were determined.
Department Environment and Agro-Biotechnologies,  Centre de Recherche Public-Gabriel Lippmann , 41 Rue du Brill, L-4422 Belvaux, Luxembourg.
Daniel
D
Molitor
Johannes C
JC
Liermann
Beate
B
Berkelmann-Löhnertz
Iris
I
Buckel
Till
T
Opatz
Eckhard
E
Thines
D004148:Dioxolanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D018515:Plant Leaves / Q000382:microbiology; D027843:Vitis / Q000382:microbiology*
D004148:Dioxolanes; C575776:guignardic acid; C575777:phenguignardic acid