Spencertoxin and spencer acid, new phytotoxic derivatives of diacrylic acid and dipyridinbutan-1,4-diol produced by Spencermartinsia viticola, a causal agent of grapevine Botryosphaeria dieback in Australia

Reveglia, Pierluigi; Savocchia, Sandra; Billones‐Baaijens, Regina; Masi, Marco; Evidente, Antonio

doi:10.1016/j.arabjc.2018.01.014

Cited by 15 publications

(14 citation statements)

References 17 publications

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“…4-Hydroxybenzaldehyde (2) was first reported as phytotoxin produced by Phaeomoniella chlamydospora involved in the esca complex disease of grapevine (Tabacchi et al 2000) and later from Spencermartinsia viticola, one of the causal agents of grapevine Botryosphaeria dieback in Australia (Reveglia et al 2018). p-Cresol (3), which has been recently isolated from the culture of Clostridium difficile, a Gram-positive spore-forming anaerobe and a major cause of antibiotic-associated diarrhoea.1had bacteriostatic activity against microorganisms including Escherichia coli, Klebsiella oxytoca and Bacteroides thetaiotaomicron (Passmore et al 2018).…”

Section: Resultsmentioning

confidence: 99%

Phytotoxic metabolites produced by Diaporthe eres involved in cane blight of grapevine in Italy

Reveglia¹,

Pacetti

Masi³

et al. 2019

Natural Product Research

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Grapevine trunk diseases (GTDs) are one of the most serious biotic stresses affecting this important crop. Among them a range of diseases were identified and associated to a plethora of phytopathogenic fungi, including species of Diaporthe. Diaporthe eres was recently identified as one of the species involved in cane blight of grapevine. The ability of a strain of this fungus isolated from infected grapevine plant in Italy to produce in vitro phytotoxic metabolites was investigated. Five phytotoxic metabolites were identified by their physical and spectroscopic properties as 4-hydroxybenzaldehyde, 4-hydroxybenzoic acid, nectriapyrone, p-cresol and tyrosol. When tested on grapevine leaf disks and by leaf absorption, 4-hydroxybenzoic acid induced symptoms on both disks and leaves, 4-hydroxybenzaldehyde and p-cresol showed, respectively, phytotoxicity on leaf disks and on the leaf absorption bioassay.

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Section: Resultsmentioning

confidence: 99%

Phytotoxic metabolites produced by Diaporthe eres involved in cane blight of grapevine in Italy

Reveglia¹,

Pacetti

Masi³

et al. 2019

Natural Product Research

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“…Both metabolites showed strong phytotoxicity on Vitis lambrausca and Vitis vinifera cv. Shiraz by grapevine leaf assay [ 163 ].…”

Section: Phenols and Phenolic Acidsmentioning

confidence: 99%

Phytotoxic Secondary Metabolites from Fungi

Xue

Shen

et al. 2021

Toxins

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Fungal phytotoxic secondary metabolites are poisonous substances to plants produced by fungi through naturally occurring biochemical reactions. These metabolites exhibit a high level of diversity in their properties, such as structures, phytotoxic activities, and modes of toxicity. They are mainly isolated from phytopathogenic fungal species in the genera of Alternaria, Botrytis, Colletotrichum, Fusarium, Helminthosporium, and Phoma. Phytotoxins are either host specific or non-host specific phytotoxins. Up to now, at least 545 fungal phytotoxic secondary metabolites, including 207 polyketides, 46 phenols and phenolic acids, 135 terpenoids, 146 nitrogen-containing metabolites, and 11 others, have been reported. Among them, aromatic polyketides and sesquiterpenoids are the main phytotoxic compounds. This review summarizes their chemical structures, sources, and phytotoxic activities. We also discuss their phytotoxic mechanisms and structure–activity relationships to lay the foundation for the future development and application of these promising metabolites as herbicides.

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“…As previously mentioned, together with the vascular necrosis, during the whole assay period it was observed that many of the grapevine plants exhibited certain foliar symptoms (Figure 1f,g), probably due to a long-dispersal action of phytotoxins produced by the inoculated pathogens. The production of such type of secondary metabolites by these and other GTD-related fungi is well known [7,[47][48][49]. Among these, low molecular weight lipophilic phytotoxins (for example, naphthalenone pentaketides, melleins and polyphenols) produced by the different Bot taxa could be responsible for the observed symptoms (i.e., moderate to severe withering and necrotic spots).…”

Section: In Vivo Testsmentioning

confidence: 99%

On the Applicability of Chitosan Oligomers-Amino Acid Conjugate Complexes as Eco-Friendly Fungicides against Grapevine Trunk Pathogens

et al. 2021

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In a context in which the incidence and severity of grapevine fungal diseases is increasing as a result of both climate change and modern management culture practices, reducing the excessive use of phytosanitary products in viticulture represents a major challenge. Specifically, grapevine trunk diseases (GTDs), caused by several complexes of wood decay or xylem-inhabiting fungi, pose a major challenge to vineyard sustainability. In this study, the efficacy of chitosan oligomers (COS)–amino acid conjugate complexes against three fungal species belonging to the Botryosphaeriaceae family (Neofusicoccum parvum, Diplodia seriata, and Botryosphaeria dothidea) was investigated both in vitro and in planta. In vitro tests led to EC50 and EC90 effective concentrations in the 254.6−448.5 and 672.1−1498.5 µg·mL−1 range, respectively, depending on the amino acid involved in the conjugate complex (viz. cysteine, glycine, proline or tyrosine) and on the pathogen assayed. A synergistic effect between COS and the amino acids was observed against D. seriata and B. dothidea (synergy factors of up to 2.5 and 2.8, respectively, according to Wadley’s method). The formulations based on COS and on the conjugate complex that showed the best inhibition rates, COS−tyrosine, were further investigated in a greenhouse trial on grafted vines of two varieties (”Tempranillo” on 775P and “Garnacha” on 110R rootstock), artificially inoculated with the mentioned three Botryosphaeriaceae species. The in planta bioassay revealed that the chosen formulations induced a significant decrease in disease severity against N. parvum and B. dothidea. In summary, the reported conjugate complexes may be promising enough to be worthy of additional examination in larger field trials.

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Spencertoxin and spencer acid, new phytotoxic derivatives of diacrylic acid and dipyridinbutan-1,4-diol produced by Spencermartinsia viticola, a causal agent of grapevine Botryosphaeria dieback in Australia

Cited by 15 publications

References 17 publications

Phytotoxic metabolites produced by Diaporthe eres involved in cane blight of grapevine in Italy

Phytotoxic metabolites produced by Diaporthe eres involved in cane blight of grapevine in Italy

Phytotoxic Secondary Metabolites from Fungi

On the Applicability of Chitosan Oligomers-Amino Acid Conjugate Complexes as Eco-Friendly Fungicides against Grapevine Trunk Pathogens

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