Journal
PHYTOCHEMISTRY
Volume 89, Issue -, Pages 96-103Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2013.01.004
Keywords
Guignardia bidwellii; Botryosphaeriaceae; Vitis vinifera (cv. Riesling); Vitaceae; Grape black rot; Phytotoxins; Dioxolanone; Guignardic acid; Phenguignardic acid
Categories
Funding
- state of Rheinland-Pfalz
- Naturstoffzentrum Rheinland-Pfalz
- BASF SE
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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 alanine. Four of the seven compounds showed phytotoxic activity. Based on the structures determined by NMR spectroscopy a preliminary structure activity relationship indicated a free carboxyl group as presumably required for the phytotoxic activity. (C) 2013 Elsevier Ltd. All rights reserved.
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