Phytotoxic dioxolanones are potential virulence factors in the infection process of Guignardia bidwellii

Buckel, Iris; Andernach, Lars; Schüffler, Anja; Piepenbring, Meike; Opatz, Till; Thines, Eckhard

doi:10.1038/s41598-017-09157-6

Cited by 12 publications

(23 citation statements)

References 25 publications

(37 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…have been reported to have a similar metabolomic profile, including the dioxolanone phytotoxins which are regarded as potential virulence factors. However, one of these products, guignardic acid, has also been reported from P. capitalensis [80]. Biosynthetic abilities by endophytic strains of the latter species also refer to meroterpenes, such as compounds in the guignardone series [81][82][83][84] and the manginoids [85].…”

Section: Biotechnological Implicationsmentioning

confidence: 99%

Endophytic Fungi of Citrus Plants

Nicoletti

2019

Agriculture

View full text Add to dashboard Cite

Besides a diffuse research activity on drug discovery and biodiversity carried out in natural contexts, more recently, investigations concerning endophytic fungi have started considering their occurrence in crops based on the major role that these microorganisms have been recognized to play in plant protection and growth promotion. Fruit growing is particularly involved in this new wave, by reason that the pluriannual crop cycle likely implies a higher impact of these symbiotic interactions. Aspects concerning occurrence and effects of endophytic fungi associated with citrus species are revised in the present paper.Agriculture 2019, 9, 247 2 of 13 similar but fast-growing, and producing conidia embedded within a thicker mucoid sheath [4][5][6][7][8]. The latter, characterized as a different species (Phyllosticta capitalensis), are known to be ubiquitous as endophytes in woody plants, having been reported from at least 70 botanical families [6,9,10]. Guignardia endophyllicola, treated as a separate species in a work also emphasizing its widespread endophytic occurrence [11], is at present recognized as a synonym. Differences between the two sister species also concern their metagenetic cycle. In fact, it has been ascertained that P. citricarpa is heterothallic, while P. capitalensis is homothallic [8]. This consolidated taxonomic distinction supports the exclusion from quarantine measures of plant material harbouring P. capitalensis. To this purpose, several rapid PCR assays have been developed [12][13][14][15][16][17][18][19][20]. The applicative use of these assays has enabled to exclude the presence of the pathogen in New Zealand, unlike what was previously assumed [21], and has supported the hypothesis of the possible endophytic occurrence of P. citricarpa in asymptomatic Citrus spp., as pointed out by several investigations (Table 1). Moreover, the two species have been clearly differentiated on account of their enzymatic profiles, with a higher expression of amylases, endoglucanases, and pectinases in P. citricarpa, suggesting a likely involvement of these enzymes in the pathogenic aptitude of the CBS agent [22]. Differences in terms of pathogenesis-related proteins have been confirmed after the genome sequencing of the two species, disclosing a higher number of coding sequences in P. citricarpa (15,206 versus 14,797). Such a difference has been interpreted considering the presence of growth and developmental genes involved in the expression of pathogenicity [23].The issue of detection of contaminated material imported from areas where the pathogen is endemic has also prompted investigations concerning the assortment of Phyllosticta spp. able to colonize citrus plants in either symptomatic or latent courses. Several revisions have been published [17,24], and novel species characterized, which consistently enlarge the citrus-associated consortium within this widespread genus. Particularly, the pathogenic P. citriasiana from south-east Asia [25], P. citrichinaensis from China [26], P. citrimaxima from Thailand...

show abstract

Section: Biotechnological Implicationsmentioning

confidence: 99%

Endophytic Fungi of Citrus Plants

Nicoletti

2019

Agriculture

View full text Add to dashboard Cite

show abstract

“…have been reported to have a similar metabolomic profile, including the dioxolanone phytotoxins which are regarded as potential virulence factors. However one of these products, guignardic acid, has been also reported from P. capitalensis [80]. Biosynthetic abilities by endophytic strains of the latter species also refer to meroterpenes, such as compounds in the guignardone series [81][82][83][84] and the manginoids [85].…”

Section: Biotechnological Implicationsmentioning

confidence: 99%

Endophytic Fungi of Citrus Plants

Nicoletti¹

2019

Preprint

View full text Add to dashboard Cite

Besides a diffuse research activity on drug discovery and biodiversity carried out in natural contexts, more recently investigations concerning endophytic fungi have started considering their occurrence in crops based on the major role that these microorganisms have been recognized to play in plant protection and growth promotion. Fruit growing is particularly involved in this new wave, by reason that the pluriannual crop cycle implies a likely higher impact of these symbiotic interactions. Aspects concerning occurrence and effects of endophytic fungi associated with citrus species are revised in the present paper.

show abstract

“…The investigation of dioxolanone as a virulence factor in four species of Phyllosticta were performed by Buckel et al [5]. The authors demonstrated that phenguignardic acid (1c) and guignardic acid are involved in the development of grape black rot, a serious disease in grapes.…”

Section: Introductionmentioning

confidence: 99%

“…S1). The chemical structure of the new metabolite (1a) was determined by cumulative 1D and 2D NMR spectroscopy, high resolution mass spectrometry (HRMS), chemical synthesis and by comparison with related structures [5][6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

“…Phenguignardic acid butyl ester (1a) is closely related to compound phenguignardic acid (1c), with a butoxy group attached at 16-position (instead of an OH group, Fig. 1), and phenguignardic acid (1c) was described as an important virulence factor in the grape black rot disease development, caused by Guignardia bidwellii (P. ampelicida) [5]. Interestingly, the mechanism of action of this class of compounds remains unknown, and some authors suggested that these compounds could be used as an herbicide, because of their non-host specific toxicity [14].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Secondary metabolites produced by the citrus phytopathogen Phyllosticta citricarpa

et al. 2019

View full text Add to dashboard Cite

The isolation and structure elucidation of one new fungal metabolite, phenguignardic acid butyl ester (1a), and four previously reported metabolites (1b, 2a, 3-4) from the citrus phytopathogen Phyllosticta citricarpa LGMF06 are described. The new dioxolanone phenguignardic acid butyl ester (1a) had low phytotoxic activity in citrus leaves and fruits (at dose of 100 μg), and its importance as virulence factor in citrus black spot disease needs to be further addressed. Beside the phytotoxic analysis, we also evaluated the antibacterial (against methicillin sensitive and resistant Staphylococcus aureus) and cytotoxic (A549 non-small cell lung cancer, PC3 prostate cancer and HEL 299 normal epithelial lung) activities of the isolated compounds, which revealed that compounds 1a, 1b and 2a were responsible for the antibacterial activity of this strain.

show abstract

Phytotoxic dioxolanones are potential virulence factors in the infection process of Guignardia bidwellii

Cited by 12 publications

References 25 publications

Endophytic Fungi of Citrus Plants

Endophytic Fungi of Citrus Plants

Endophytic Fungi of Citrus Plants

Secondary metabolites produced by the citrus phytopathogen Phyllosticta citricarpa

Contact Info

Product

Resources

About