Phenolic and heterocyclic metabolite profiles of the grapevine pathogen Eutypa lata

Mahoney, Noreen; Lardner, Richard; Molyneux, Russell J.; Scott, Eileen S.; Smith, Leverett R.; Schoch, Thomas K.

doi:10.1016/s0031-9422(03)00337-6

Cited by 48 publications

(53 citation statements)

References 23 publications

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“…The phytotoxicity of E. lata metabolites was tested in a leaf disk bioassay on “ Cabernet Sauvignon ” leaves (Figure 3A) [28]. Activity at 50 μg/mL of metabolites 1, 2, and 9-12 (Figure 2) indicated that neither eutypinol nor siccayne were phytotoxic; while eutypine, benzofuran, eulatinol, and eulatacromene ( 1, 9, 11 and 12 , Figure 2) had a toxic effect, producing necrotic spots on the leaves (Figure 3A).…”

Section: Eutypa Diebackmentioning

confidence: 99%

“…However eulatachromene ( 12 , Figure 2) was also examined for toxicity at various concentrations from 10 to 100 μg/mL. At its lowest concentration, 12 (Figure 2) caused necrosis on some disks, and at its highest concentration it caused necrosis on all disks (Figure 3B) [28]. …”

Section: Eutypa Diebackmentioning

confidence: 99%

“…(A) Comparison, after 24 h and at 50 μg/mL, of the toxicity of the methanol control (C) and of the primary metabolites eutypine 1 , eutypinol 2 , 2- iso -propenyl-5-formylbenzofuran 9 , siccayene 10 , eulatinol 11 , and eulatachromene 12 , in a grape leaf bioassay; ( B ) comparison, after 24 h and at 10, 25, 50 and 100 μg/mL, of phytotoxicity of the methanol control ( C ) and eulatachromene ( 12 ) (redrawn with modifications from Figure 5 in [28]).…”

Section: Eutypa Diebackmentioning

confidence: 99%

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Phytotoxins Produced by Fungi Associated with Grapevine Trunk Diseases

Andolfi

Mugnai

Luque

et al. 2011

Toxins

154

180

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Up to 60 species of fungi in the Botryosphaeriaceae family, genera Cadophora, Cryptovalsa, Cylindrocarpon, Diatrype, Diatrypella, Eutypa, Eutypella, Fomitiporella, Fomitiporia, Inocutis, Phaeoacremonium and Phaeomoniella have been isolated from decline-affected grapevines all around the World. The main grapevine trunk diseases of mature vines are Eutypa dieback, the esca complex and cankers caused by the Botryospheriaceae, while in young vines the main diseases are Petri and black foot diseases. To understand the mechanism of these decline-associated diseases and the symptoms associated with them, the toxins produced by the pathogens involved in these diseases were isolated and characterised chemically and biologically. So far the toxins of only a small number of these decline fungi have been studied. This paper presents an overview of the toxins produced by the most serious of these vine wood pathogens: Eutypa lata, Phaeomoniella chlamydospora, Phaeoacremonium aleophilum and some taxa in the Botryosphaeriaceae family, and examines how these toxins produce decline symptoms. The chemical structure of these metabolites and in some cases their vivotoxin nature are also discussed.

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Section: Eutypa Diebackmentioning

confidence: 99%

Section: Eutypa Diebackmentioning

confidence: 99%

Section: Eutypa Diebackmentioning

confidence: 99%

See 1 more Smart Citation

Phytotoxins Produced by Fungi Associated with Grapevine Trunk Diseases

Andolfi

Mugnai

Luque

et al. 2011

Toxins

154

180

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“…Indeed, the chemical structures of secreted toxins, as well as of the products of cell wall degrading activities, have been described for some trunk pathogens [14–16]. For example, degradation of cellulose and xyloglucans, and secretion of oxidases that might participate in the breakdown of wall-bound lignin, were detected in wood colonized by the Eutypa dieback pathogen Eutypa lata .…”

Section: Introductionmentioning

confidence: 99%

Distinctive expansion of gene families associated with plant cell wall degradation, secondary metabolism, and nutrient uptake in the genomes of grapevine trunk pathogens

et al. 2015

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BackgroundTrunk diseases threaten the longevity and productivity of grapevines in all viticulture production systems. They are caused by distantly-related fungi that form chronic wood infections. Variation in wood-decay abilities and production of phytotoxic compounds are thought to contribute to their unique disease symptoms. We recently released the draft sequences of Eutypa lata, Neofusicoccum parvum and Togninia minima, causal agents of Eutypa dieback, Botryosphaeria dieback and Esca, respectively. In this work, we first expanded genomic resources to three important trunk pathogens, Diaporthe ampelina, Diplodia seriata, and Phaeomoniella chlamydospora, causal agents of Phomopsis dieback, Botryosphaeria dieback, and Esca, respectively. Then we integrated all currently-available information into a genome-wide comparative study to identify gene families potentially associated with host colonization and disease development.ResultsThe integration of RNA-seq, comparative and ab initio approaches improved the protein-coding gene prediction in T. minima, whereas shotgun sequencing yielded nearly complete genome drafts of Dia. ampelina, Dip. seriata, and P. chlamydospora. The predicted proteomes of all sequenced trunk pathogens were annotated with a focus on functions likely associated with pathogenesis and virulence, namely (i) wood degradation, (ii) nutrient uptake, and (iii) toxin production. Specific patterns of gene family expansion were described using Computational Analysis of gene Family Evolution, which revealed lineage-specific evolution of distinct mechanisms of virulence, such as specific cell wall oxidative functions and secondary metabolic pathways in N. parvum, Dia. ampelina, and E. lata. Phylogenetically-informed principal component analysis revealed more similar repertoires of expanded functions among species that cause similar symptoms, which in some cases did not reflect phylogenetic relationships, thereby suggesting patterns of convergent evolution.ConclusionsThis study describes the repertoires of putative virulence functions in the genomes of ubiquitous grapevine trunk pathogens. Gene families with significantly faster rates of gene gain can now provide a basis for further studies of in planta gene expression, diversity by genome re-sequencing, and targeted reverse genetic approaches. The functional validation of potential virulence factors will lead to a more comprehensive understanding of the mechanisms of pathogenesis and virulence, which ultimately will enable the development of accurate diagnostic tools and effective disease management.Electronic supplementary materialThe online version of this article (doi:10.1186/s12864-015-1624-z) contains supplementary material, which is available to authorized users.

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“…Several acetylenic phenols and chromene metabolites were isolated from this fungus and some of them have proved to be toxic. [4][5][6] One of the Eutypa-like isolates, named as FED-3, has been studied to characterize its metabolites. This paper report the identification of the new sesquiterpene (1R,4S,5S,7R,10R)-10-hydroxyguaianol 10-O--mannopyranoside (1), and 3-hydroxy-5-phenylmethyl-(3S,5R)-tetrahydrofuran-2-one (2), isolated from the Eutypa-like strain FED-3.…”

Section: Introductionmentioning

confidence: 99%

A new guaiane mannoside from a Eutypa-like fungus isolated from Murraya paniculata in Brazil

Souza¹,

Rodrigues‐Filho²,

Souza³

et al. 2008

J. Braz. Chem. Soc.

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Um fungo semelhante aos do gênero Eutypa foi isolado da madeira do caule de Murraya paniculata. Cultivado em meio líquido, o fungo produziu o novo sesquiterpeno do tipo guaiano (1R,4S,5S,7R,10R)-10-hidroxiguaianol-10-O--manopiranosídeo e um diastereômero da harzialactona A, a 3-hidróxi-5-fenilmetil-(3S,5R)-tetraidrofuran-2-ona, obtida pela primeira vez como produto natural. As estruturas desses metabólitos foram elucidadas com base na análise dos seus respectivos dados espectroscópicos.A Eutypa-like fungus was isolated from the stems of Murraya paniculata. The fungus was cultivated in liquid medium and produced the new guaiane-type sesquiterpenoid (1R,4S,5S,7R,10R)-10-hydroxyguaianol 10-O--mannopyranoside and the 3-hydroxy-5-phenylmethyl-(3S,5R)-tetrahydrofuran-2-one, a diastereomer of harzialactone A, obtained for the first time from a natural source. The structures of these metabolites were elucidated based on analysis of their spectroscopic data.

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Phenolic and heterocyclic metabolite profiles of the grapevine pathogen Eutypa lata

Cited by 48 publications

References 23 publications

Phytotoxins Produced by Fungi Associated with Grapevine Trunk Diseases

Phytotoxins Produced by Fungi Associated with Grapevine Trunk Diseases

Distinctive expansion of gene families associated with plant cell wall degradation, secondary metabolism, and nutrient uptake in the genomes of grapevine trunk pathogens

A new guaiane mannoside from a Eutypa-like fungus isolated from Murraya paniculata in Brazil

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