Phytotoxic metabolites from Neofusicoccum parvum, a pathogen of Botryosphaeria dieback of grapevine.
Liquid chromatography-diode array screening of the organic extract of the cultures of 13 isolates of the fungus Neofusicoccum parvum, the main causal agent of botryosphaeria dieback of grapevine, showed similar metabolites. One strain was selected for further chemical studies and led to the isolation and characterisation of 13 metabolites. Structures were elucidated through spectroscopic analyses, including one- and two-dimensional NMR and mass spectrometry, and through comparison to literature data. The isolated compounds belong to four different chemical families: five metabolites, namely, (-)-terremutin (1), (+)-terremutin hydrate (2), (+)-epi-sphaeropsidone (3) (-)-4-chloro-terremutin hydrate (4) and(+)-4-hydroxysuccinate-terremutin hydrate (5), belong to the family of dihydrotoluquinones; two metabolites, namely, (6S,7R) asperlin (6) and (6R,7S)-dia-asperlin (7), belong to the family of epoxylactones; four metabolites, namely, (R)-(-)-mellein (8), (3R,4R)-4-hydroxymellein (9), (3R,4S)-4-hydroxymellein (10) (R)(-)-3-hydroxymellein (11), belong to the family of dihydroisocoumarins; and two of the metabolites, namely, 6-methyl-salicylic acid (12) and 2-hydroxypropyl salicylic acid (13), belong to the family of hydroxybenzoic acids. We determined the phytotoxic activity of the isolated metabolites through a leaf disc assay and the expression of defence-related genes in Vitis vinifera cells cv. Chardonnay cultured with (-)-terremutin (1), the most abundant metabolite. Finally, analysis of the brown stripes of grapevine wood from plants showing botryosphaeria dieback symptoms revealed the presence of two of the isolated phytotoxins.
Department of Biology, University of Fribourg, Ch. du Musée 10, 1700 Fribourg, Switzerland. Electronic address: eliane.abou-mansour@unifr.ch.
Eliane
E
Abou-Mansour
Department of Biology, University of Fribourg, Ch. du Musée 10, 1700 Fribourg, Switzerland.
Jean-Luc
JL
Débieux
Laboratoire Vigne Biotechnologie et Environnement EA 3991, Université de Haute-Alsace, 33, rue de Herrlisheim, BP 68008 Colmar Cedex, France.
Montserrat
M
Ramírez-Suero
Laboratoire Vigne Biotechnologie et Environnement EA 3991, Université de Haute-Alsace, 33, rue de Herrlisheim, BP 68008 Colmar Cedex, France.
Mélanie
M
Bénard-Gellon
Laboratoire Stress Défense et Reproduction des Plantes EA 4707, Université de Reims Champagne-Ardenne, UFR Sciences, Moulin de la Housse, 51687 Reims Cedex 2, France.
Maryline
M
Magnin-Robert
Department of Biology, University of Fribourg, Ch. du Musée 10, 1700 Fribourg, Switzerland; Laboratoire Stress Défense et Reproduction des Plantes EA 4707, Université de Reims Champagne-Ardenne, UFR Sciences, Moulin de la Housse, 51687 Reims Cedex 2, France.
Alessandro
A
Spagnolo
Laboratoire Vigne Biotechnologie et Environnement EA 3991, Université de Haute-Alsace, 33, rue de Herrlisheim, BP 68008 Colmar Cedex, France.
Julie
J
Chong
Laboratoire Vigne Biotechnologie et Environnement EA 3991, Université de Haute-Alsace, 33, rue de Herrlisheim, BP 68008 Colmar Cedex, France.
Sibylle
S
Farine
Laboratoire Vigne Biotechnologie et Environnement EA 3991, Université de Haute-Alsace, 33, rue de Herrlisheim, BP 68008 Colmar Cedex, France.
Christohpe
C
Bertsch
Department of Biology, University of Fribourg, Ch. du Musée 10, 1700 Fribourg, Switzerland.
Floriane
F
L'Haridon
Department of Biology, University of Fribourg, Ch. du Musée 10, 1700 Fribourg, Switzerland.
Mario
M
Serrano
Laboratoire Stress Défense et Reproduction des Plantes EA 4707, Université de Reims Champagne-Ardenne, UFR Sciences, Moulin de la Housse, 51687 Reims Cedex 2, France.
Florence
F
Fontaine
Institut Supérieur d'Agronomie, Tapada da Ajuda, Lisbonne, Portugal.
Cecilia
C
Rego
Institut Français de la Vigne et du Vin Pôle Rhône-Méditerranée, France, Domaine de Donadille, 30230 Rodilhan, France.
Philippe
P
Larignon
D001203:Ascomycota / Q000737:chemistry*; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D010935:Plant Diseases / Q000382:microbiology*; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism; D027843:Vitis / Q000382:microbiology*
D003603:Cytotoxins; D011809:Quinones; C009401:terremutin
Botryosphaeria dieback; Defence gene expression; Dihydrotoluquinones; Epoxylactones; Esca; Isocoumarins; Neofusicoccum parvum; Phytotoxins; Vitis vinifera cells (calli)