Phytotoxic Fungal Exopolysaccharides Produced by Fungi Involved in Grapevine Trunk Diseases

Cimmino, Alessio; Cinelli, Tamara; Evidente, Marco; Masi, Marco; Mugnai, Laura; Silva, Marcondes A; Michereff, Sami Jorge; Surico, Giuseppe; Evidente, Antonio

doi:10.1177/1934578x1601101015

Cited by 8 publications

(16 citation statements)

References 20 publications

(36 reference statements)

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“…The ethanolic phases were recovered and the precipitates resuspended and again precipitated as above. The polysaccharide content of the precipitates was measured following a recently described procedure . The standards of jasmonic acid ( 6 ), cis -(3 R ,4 R )- and trans -(3 R ,4 S )-(−)-4-hydroxymelleins ( 2 and 3 ), scytalone, and isosclerone were compared by TLC analysis with the residues obtained from both ethanolic phases.…”

Section: Methodsmentioning

confidence: 99%

“…The polysaccharide content of the precipitates was measured following a recently described procedure. 31 The standards of jasmonic acid (6), cis-(3R,4R)-and trans-(3R,4S)-(−)-4-hydroxymelleins (2 and 3), scytalone, and isosclerone were compared by TLC analysis with the residues obtained from both ethanolic phases. The samples containing jasmonic acid were also analyzed by LC/MS.…”

Section: ■ Introductionmentioning

confidence: 99%

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Phytotoxic Lipophilic Metabolites Produced by Grapevine Strains of Lasiodiplodia Species in Brazil

Cimmino¹,

Cinelli

Masi³

et al. 2017

J. Agric. Food Chem.

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Phytotoxic metabolites produced in liquid culture by six species of Lasiodiplodia isolated in Brazil and causing Botryosphaeria dieback of grapevine were chemically identified. As ascertained by LC/MS, L. brasiliense, L. crassispora, L. jatrophicola, and L. pseudotheobromae produced jasmonic acid, and L. brasiliense synthesized, besides jasmonic acid, also (3R,4S)-4-hydroxymellein. L. euphorbicola and L. hormozganensis produced some low molecular weight lipophilic toxins. Specifically, L. euphorbicola produced (−)-mellein, (3R,4R)-(−)-and (3R,4S)-(−)-4-hydroxymellein, and tyrosol, and L. hormozganensis synthesized tyrosol and p-hydroxybenzoic acid. This is the first report on the production of the above cited metabolites from L. euphorbicola and L. hormozganensis. The phytotoxic activity of the metabolites produced is also discussed and related to the symptoms these pathogens cause in the grapevine host plants.

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Section: Methodsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Phytotoxic Lipophilic Metabolites Produced by Grapevine Strains of Lasiodiplodia Species in Brazil

Cimmino¹,

Cinelli

Masi³

et al. 2017

J. Agric. Food Chem.

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“…Those obtained by N. parvum were characterized as a mannan with a backbone consisting of (1→6)-linked mannopyranose units almost all branched at the 2 position, whereby the arms are made up of 2- and/or 3-linked units. When adsorbed by detached grapevine leaves, these EPS induced likewise reddening and withering depending on the tested concentration and time from absorption [ 19 ]. The EPSs produced by P. chlamydospora were also used to develop a flow cytometry method that unequivocally identifies some of the toxic metabolites.…”

Section: Introductionmentioning

confidence: 99%

Polysaccharide Based Polymers Produced by Scabby Cankered Cactus Pear (Opuntia ficus-indica L.) Infected by Neofusicoccum batangarum: Composition, Structure, and Chemico-Physical Properties

Santagata

Cimmino²,

Poggetto

et al. 2022

Biomolecules

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Neofusiccocum batangarum is the causal agent of scabby canker of cactus pear (Opuntia ficus-indica L.). The symptoms of this disease are characterized by crusty, perennial cankers, with a leathery, brown halo. Characteristically, a viscous polysaccharide exudate, caking on contact with air, leaks from cankers and forms strips or cerebriform masses on the surface of cactus pear cladodes. When this polysaccharide mass was partial purified, surprisingly, generated a gel. The TLC analysis and the HPLC profile of methyl 2-(polyhydroxyalkyl)-3-(o-tolylthiocarbomoyl)-thiazolidine-4R-carboxylates obtained from the mixture of monosaccharides produced by acid hydrolysis of the three EPSs examined in this research work [the polysaccharide component of the exudate (EPSC) and the EPSs extracted from asymptomatic (EPSH) and symptomatic (EPSD) cladodes] showed the presence of d-galactose, l-rhamnose, and d-glucose in a 1:1:0.5 ratio in EPSC while d-galactose, l-rhamnose, d-glucose, and d-xylose at the same ratio were observed in EPSH and EPSD. The presence of uronic acid residues in EPSC was also showed by solid state NMR and IR investigation. Furthermore, this manuscript reports the chemical-physical characterization of the gel produced by the infected cactus pear.

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“…parvum can produce a plethora of low-molecular-weight compounds that showed toxic effects on grapevine and tomato leaves and grapevine calli. , Recently, exopolysaccharides have been obtained from the culture filtrates of an isolate of N. parvum and tested on grapevine leaves, showing different degrees of toxicity . However, more in-depth investigations are required to understand the effective role of these extracellular compounds in the disease development and symptom expression.…”

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“…5,10 Recently, exopolysaccharides have been obtained from the culture filtrates of an isolate of N. parvum and tested on grapevine leaves, showing different degrees of toxicity. 11 However, more in-depth investigations are required to understand the effective role of these extracellular compounds in the disease development and symptom expression. Investigations by Beńard-Gellon et al 7 showed that N. parvum produced aggressive extracellular proteins, causing necrosis and inducing an upregulation of grapevine defense genes.…”

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Phytotoxic Metabolites from Three Neofusicoccum Species Causal Agents of Botryosphaeria Dieback in Australia, Luteopyroxin, Neoanthraquinone, and Luteoxepinone, a Disubstituted Furo-α-pyrone, a Hexasubstituted Anthraquinone, and a Trisubstituted Oxepi-2-one from Neofusicoccum luteum

et al. 2020

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Different phytotoxic metabolites were isolated from the organic extract of Neofusicoccum luteum, Neofusicoccum australe, and Neofusicoccum parvum, causal agents of Botryosphaeria dieback in Australia. N. luteum produced a new disubstituted furo-α-pyrone, a hexasubstituted anthraquinone, and a trisubstituted oxepi-2(7H)-one, luteopyroxin (4), neoanthraquinone (5), and luteoxepinone (7), respectively, together with the known (±)-nigrosporione (6), tyrosol ( 8), (R)-(−)-mellein (1), and (3R,4S)-(−)and (3R,4R)-(−)-4-hydroxymellein (2 and 3). The three melleins and tyrosol were also produced by N. parvum, while N. australe produced (R)-(−)-mellein (1), neoanthraquinone (5), tyrosol (8), and p-cresol (9). Luteopryoxin (4), neoanthraquinone (5), and luteoxepinone (7) were characterized by analyses of physical data, essentially one-and two-dimensional nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry. The relative and absolute configurations of luteopyroxin (4) were determined by nuclear Overhauser effect spectroscopy and experimental and calculated electronic circular dichroism data. When assayed on grapevine leaves, neoanthraquinone (5) showed the highest toxic effect, causing severe shriveling and withering. Luteopyroxin (4), nigrosporione (6), and luteoxepinone (7) also showed different degrees of toxicity, while p-cresol (9) displayed low phytotoxicity.

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Phytotoxic Fungal Exopolysaccharides Produced by Fungi Involved in Grapevine Trunk Diseases

Abstract: This paper reports the isolation and chemical and biological characterization of exopolysaccharides produced by phytopathogenic fungi belonging to different genera and inducing various diseases on grapevine. Their role in the phytopathogenic processes is also discussed.

Cited by 8 publications

References 20 publications

Phytotoxic Lipophilic Metabolites Produced by Grapevine Strains of Lasiodiplodia Species in Brazil

Phytotoxic Lipophilic Metabolites Produced by Grapevine Strains of Lasiodiplodia Species in Brazil

Polysaccharide Based Polymers Produced by Scabby Cankered Cactus Pear (Opuntia ficus-indica L.) Infected by Neofusicoccum batangarum: Composition, Structure, and Chemico-Physical Properties

Phytotoxic Metabolites from Three Neofusicoccum Species Causal Agents of Botryosphaeria Dieback in Australia, Luteopyroxin, Neoanthraquinone, and Luteoxepinone, a Disubstituted Furo-α-pyrone, a Hexasubstituted Anthraquinone, and a Trisubstituted Oxepi-2-one from Neofusicoccum luteum

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