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PubMed2006

Antifungal activity of thiophenes from Echinops ritro.

Extracts from 30 plants of the Greek flora were evaluated for their antifungal activity using direct bioautography assays with three Colletotrichum species. Among the bioactive extracts, the dichloromethane extract of the radix of Echinops ritro (Asteraceae) was the most potent. Bioassay-guided fractionation of this extract led to the isolation of eight thiophenes. Antifungal activities of isolated compounds together with a previously isolated thiophene from Echinops transiliensis were first evaluated by bioautography and subsequently evaluated in greater detail using a broth microdilution assay against plant pathogens Colletotrichum acutatum, Colletotrichum fragariae, Colletotrichum gloeosporioides, Botrytis cinerea, Fusarium oxysporum, Phomopsis viticola, and Phomopsis obscurans. 5'-(3-Buten-1-ynyl)-2,2'-bithiophen (1), alpha-terthienyl (2), and 2-[pent-1,3-diynyl]-5-[4-hydroxybut-1-ynyl]thiophene (5) at 3 and 30 microM were active against all three Colletotrichum species, F. oxysporum, P. viticola, and P. obscurans.

Ascomycota↗
PubMed2006

Study of amine composition of botrytized grape berries.

Aliphatic primary and biogenic amines of grape varieties from two vintages were studied. We established that appearance and/or increase of both primary aliphatic and biogenic amines is due to microbiota living in/on grape berries. Aszú, gray rotten grapes infected mainly with Botrytis cinerea, grape berries infected mainly with Penicillium species, and intact grape berries were compared on the basis of amine composition using t-test, analysis of variance, and multivariate statistical analysis (principal component analysis and linear discriminant analysis). The amine composition and amine content of Aszú grapes were significantly different (p < 0.05) from those of intact grapes despite the effect of the vineyards and the vintages. Grape samples coming from the same growing location, intact, Aszú grapes, and grape berries infected mainly with Penicillium species could be separated from each other with multivariate statistical analysis. We distinguished intact, Aszú (noble rotten), and gray rotten berries from each other as well. Evaluating amine values of grape samples independently of the place of origin, the Aszú and green rotten berries could not be differentiated. The varieties and vineyards have affected the amine composition of Aszú grapes, while these effects on intact grapes appeared only slightly.

Biogenic Amines↗
PubMed2003

Chemical transformations on botryane skeleton. Effect on the cytotoxic activity.

Eighteen compounds with a botryane skeleton have been obtained through chemical transformations of various toxins from the fungus Botrytis cinerea. During the course of these transformations, the C-10 carbon of the botryane skeleton was found to exhibit an interesting high regioselectivity to oxidizing and reducing agents. In addition, the cytotoxicity of 27 botryane derivatives was determined in vitro against Hs578T, MDA-MB-231, HT-1080, U87-MG, IMR-90, and HUVEC cell lines. The results of this study confirm that the cytotoxicity of botrydial (1) and its derivatives is related to the presence of a 1,5-dialdehyde functionality.

Aldehydes↗
PubMed2004

Thiobutacin, a novel antifungal and antioomycete antibiotic from Lechevalieria aerocolonigenes.

A novel butanoic acid, thiobutacin (1), 4-(2-aminophenyl)-4-oxo-2-methylthiobutanoic acid (C11H13NO3S), was isolated from the culture broth of a soil actinomycete, Lechevalieria aerocolonigenes strain VK-A9. The structure of thiobutacin (1) was elucidated on the basis of the extensive 2D NMR spectral data including 1H-1H COSY, HMBC, HMQC, ROESY, and NOESY. Thiobutacin (1) showed antioomycete and antifungal activity against phytopathogenic Phytophthora capsici and Botrytis cinerea and the yeast Saccharomyces cerevisiae.

Actinomycetales↗
PubMed1998

The promoter of the plant defensin gene PDF1.2 from Arabidopsis is systemically activated by fungal pathogens and responds to methyl jasmonate but not to salicylic acid.

The plant defensin PDF1.2 has previously been shown to accumulate systemically via a salicylic acid-independent pathway in leaves of Arabidopsis upon challenge by fungal pathogens. To further investigate the signalling and transcriptional processes underlying plant defensin induction, a DNA fragment containing 1184 bp and 1232 bp upstream of the transcriptional and translational start sites, respectively, was cloned by inverse PCR. To test for promoter activity this DNA fragment was linked to the beta-glucuronidase (GUS)-encoding region of the UidA gene as a translational fusion and introduced into Arabidopsis ecotype C-24. Challenge of the transgenic plants with the fungal pathogens Alternaria brassicicola and Botrytis cinerea resulted in both local and systemic induction of the reporter gene. Wounding of the transgenic plants had no effect on GUS activity. Treatment of the transgenic plants with either jasmonates or the active oxygen generating compound paraquat strongly induced the reporter gene. In contrast, neither salicylate nor its functional analogues 2,6-dichloroisonicotinic acid and 1,2,3-benzothiodiazole-7-carbothioic acid S-methyl ester resulted in reporter gene induction. These results are consistent with the existence of a salicylic acid-independent signalling pathway, possibly involving jasmonates as regulators, that is triggered by pathogen challenge but not by wounding. The transgenic plants containing the PDF1.2-based promoter-reporter construct will provide useful tools for future genetic dissection of this novel systemic signalling pathway.

Acetates↗
PubMed1999

Gene encoding polygalacturonase inhibitor in apple fruit is developmentally regulated and activated by wounding and fungal infection.

A cDNA encoding polygalacturonase-inhibiting protein (PGIP) from mature apple fruit has been cloned and characterized. The open reading frame encodes a polypeptide of 330 amino acids, in which 24 amino acids at the N-terminus comprise the signal peptide. Apple PGIP contains 10 imperfect leucine-rich repeat sequence motifs averaging 24 amino acids in length. In addition to the 1.3 kb PGIP transcript, the cloned cDNA also hybridized to RNA molecules with sizes of 3.2 and 5.0 kb. Genomic DNA analysis revealed that the apple PGIP probably belongs to a small family of genes. PGIP transcript levels varied in fruit collected at different maturities, suggesting the gene is developmentally regulated. Very high PGIP transcript levels were detected in decayed areas and the tissue adjacent to the inoculation sites of Penicillium expansum and Botrytis cinerea. However, no increase in the amount of PGIP transcript in tissue distant from the decayed region was observed. Wounding on fruit also induced PGIP gene expression but to a much lessser extent when compared with decayed areas. After storage at 0 degrees C for 1 month, the abundance of PGIP transcript in ripe fruit was substantially increased. The PGIP gene in immature and ripe fruit was rapidly up-regulated by fungal infections, while in stored fruit the induction was very limited and concurred with an increase of fruit susceptibility to fungal colonization. Since PGIP gene expression is regulated by fruit development and responds to wounding, fungal infection and cold storage, these observations suggest that apple PGIP may have multiple roles during fruit development and stress response.

Amino Acid Sequence↗
PubMed1999

Characterization of a pine multigene family containing elicitor-responsive stilbene synthase genes.

Young pine seedlings respond to environmental stress by induced synthesis of pinosylvin, a stilbene phytoalexin. Heartwood of pine trees is characterized by a high content of pinosylvin. The formation of pinosylvin from cinnamoyl-CoA and three molecules malonyl-CoA catalysed by pinosylvin synthase is typical of the genus Pinus. Its enzyme activity not detectable in unstressed seedlings is substantially increased upon application of stimuli like UV-light or infection with the phytopathogenic fungus Botrytis cinerea. A genomic DNA library was screened with pinosylvin synthase cDNA pSP-54 as a probe. Ten clones were isolated and grouped into five subclasses according to the size of their introns. After subcloning into plasmid T7T3, four different members of the five gene subclasses were characterized by sequencing. Emphasis was put on isolating various promoters and analyzing and comparing their responsiveness. The amino acid sequences deduced from genes PST-1, PST-2, PST-3 and PST-5 shared an overall identity of more than 95%. In gene PST-5, the putative translation start site ATG was replaced by CTG. While promoter regions near the TATAA box were almost identical PST-1, PST-2 and PST-3, further upstream sequences differed substantially. Differences in promoter strength were analysed both in transgenic tobacco plants and by transient expression in tobacco protoplasts. Constructs used contained the bacterial beta-glucuronidase under the control of the promoters of pine genes PST-1, PST-2 and PST-3. Upon treatment with UV light or fungal elicitor, the promoter of PST-1 showed highest responsiveness and led to tissue-specific expression in vascular bundles. The data suggest that in pine the gene product of PST-1 is responsible for both the stress response in seedlings and pinosylvin formation in the heartwood.

Acyltransferases↗
PubMed1999

Plants ectopically expressing the iron-binding protein, ferritin, are tolerant to oxidative damage and pathogens.

Transgenic tobacco plants that synthesize alfalfa ferritin in vegetative tissues--either in its processed form in chloroplasts or in the cytoplasmic nonprocessed form--retained photosynthetic function upon free radical toxicity generated by iron excess or paraquat treatment. Progeny of transgenic plants accumulating ferritin in their leaves exhibited tolerance to necrotic damage caused by viral (tobacco necrosis virus) and fungal (Alternaria alternata, Botrytis cinerea) infections. These transformants exhibited normal photosynthetic function and chlorophyll content under greenhouse conditions. We propose that by sequestering intracellular iron involved in generation of the very reactive hydroxyl radicals through a Fenton reaction, ferritin protects plant cells from oxidative damage induced by a wide range of stresses.

Alternaria↗
PubMed2001

Role of botrytized grape micro-organisms in SO2 binding phenomena.

AIMS: The purpose of this work was to study the involvement of micro-organisms, which develop together with Botrytis cinerea on grapes, in the SO2 binding power of musts. METHODS AND RESULTS: Yeasts and bacteria were involved. Most bacteria were acetic acid bacteria, mainly of the Gluconobacter genus. Unlike oxidative yeasts, Gluconobacter produce gluconic acid (in balance with delta-gluconolactone) from glucose, 5-oxofructose from fructose and dihydroxyacetone from glycerol. Production of carbonyl compounds from other sugars and polyols was not detected or was very weak. CONCLUSION: Acetic acid bacteria are responsible for the increases in SO2 binding power of musts from botrytized grapes by oxidizing the three main sugars of these grapes. SIGNIFICANCE AND IMPACT OF THE STUDY: Up to 80% of the SO2 binds with products of Gluconobacter which easily grow on 'botrytized' grapes. Depending on climatic conditions, some vintages are particularly difficult to stabilize.

Acetic Acid↗
PubMed2002

Improvement of Candida sake biocontrol activity against post-harvest decay by the addition of ammonium molybdate.

AIM: To improve the efficacy of Candida sake by adding ammonium molybdate to control post-harvest decay in Golden Delicious apples. METHODS AND RESULTS: In laboratory trials, C. sake 2 x 10(6) cfu ml(-)1 plus 5 mmol l(-1) ammonium molybdate greatly reduced Penicillium expansum, Botrytis cinerea or Rhizopus stolonifer in apples stored at 20 degrees C for 7 days, and reduced by more than 90% blue and grey mould in apples stored at 1 degrees C for 60 days. The consistency of these results was maintained in semi-commercial trials at 1 degrees C in air and in a low oxygen atmosphere for 120 days. The pre-harvest application of C. sake 2 x 10(7) cfu ml(-1) plus 1 mmol l(-1) ammonium molybdate did not improve post-harvest biocontrol of blue mould. The population of C. sake significantly decreased in the presence of ammonium molybdate in apple wounds. CONCLUSION: The addition of ammonium molybdate at 5 mmol l(-1) to C. sake enhanced the efficacy of the antagonist to control post-harvest diseases on apples. SIGNIFICANCE AND IMPACT OF THE STUDY: Ammonium molybdate significantly reduces the amount of C. sake biomass required to achieve post-harvest disease control, with a consequent reduction in costs. This may be useful in the industrial production of C. sake.

Antibiosis↗
PubMed2002

Resveratrol acts as a natural profungicide and induces self-intoxication by a specific laccase.

The grapevine (Vitis) secondary metabolite resveratrol is considered a phytoalexin, which protects the plant from Botrytis cinerea infection. Laccase activity displayed by the fungus is assumed to detoxify resveratrol and to facilitate colonization of grape. We initiated a functional molecular genetic analysis of B. cinerea laccases by characterizing laccase genes and evaluating the phenotype of targeted gene replacement mutants. Two different laccase genes from B. cinerea were characterized, Bclcc1 and Bclcc2. Only Bclcc2 was strongly expressed in liquid cultures in the presence of either resveratrol or tannins. This suggested that Bclcc2, but not Bclcc1, plays an active role in the oxidation of both resveratrol and tannins. Gene replacement mutants in the Bclcc1 and Bclcc2 gene were made to perform a functional analysis. Only Bclcc2 replacement mutants were incapable of converting both resveratrol and tannins. When grown on resveratrol, both the wild type and the Bclcc1 replacement mutant showed inhibited growth, whereas Bclcc2 replacement mutants were unaffected. Thus, contrary to the current theory, BcLCC2 does not detoxify resveratrol but, rather, converts it into compounds that are more toxic for the fungus itself. The Bclcc2 gene was expressed during infection of B. cinerea on a resveratrol-producing host plant, but Bclcc2 replacement mutants were as virulent as the wild-type strain on various hosts. The activation of a plant secondary metabolite by a pathogen introduces a new dimension to plant-pathogen interactions and the phytoalexin concept.

Amino Acid Sequence↗
PubMed2002

Constitutive expression of ETHYLENE-RESPONSE-FACTOR1 in Arabidopsis confers resistance to several necrotrophic fungi.

Infection of a plant by a pathogen induces a variety of defense responses that imply the action of several signaling molecules, including salicylic acid (SA), jasmonic acid (JA) and ethylene (E). Here we describe the role of ETHYLENE-RESPONSE-FACTOR1 (ERF1) as a regulator of ethylene responses after pathogen attack in Arabidopsis. The ERF1 transcript is induced on infection by Botrytis cinerea, and overexpression of ERF1 in Arabidopsis is sufficient to confer resistance to necrotrophic fungi such as B. cinerea and Plectosphaerella cucumerina. A positive co-operation between E and SA pathways was observed in the plant response to P. cucumerina. Infection by Pseudomonas syringae tomato DC3000, however, does not affect ERF1 expression, and activation of ethylene responses by ERF1 overexpression in Arabidopsis plants reduces tolerance against this pathogen, suggesting negative crosstalk between E and SA signaling pathways, and demonstrating that positive and negative interactions between both pathways can be established depending on the type of pathogen.

Arabidopsis↗
PubMed2003

Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants.

Lipid peroxidation may be initiated either by lipoxygenases or by reactive oxygen species (ROS). Enzymatic oxidation of alpha-linolenate can result in the biosynthesis of cyclic oxylipins of the jasmonate type while free-radical-catalyzed oxidation of alpha-linolenate may yield several classes of cyclic oxylipins termed phytoprostanes in vivo. Previously, we have shown that one of these classes, the E1-phytoprostanes (PPE1), occurs ubiquitously in plants. In this work, it is shown that PPE1 are converted to novel cyclopentenone A1- and B1-phytoprostanes (PPA1 and PPB1) in planta. Enhanced formation of PPE1, PPA1, and PPB1 is observed after peroxide stress in tobacco cell cultures as well as after infection of tomato plants with a necrotrophic fungus, Botrytis cinerea. PPA1 and PPB1 display powerful biologic activities including activation of mitogen-activated protein kinase (MAPK) and induction of glutathione-S-transferase (GST), defense genes, and phytoalexins. Data collected so far infer that enhanced phytoprostane formation is a general consequence of oxidative stress in plants. We propose that phytoprostanes are components of an oxidant-injury-sensing, archaic signaling system that serves to induce several plant defense mechanisms.

Arabidopsis↗
PubMed1998

Trichoderma/pathogen interactions: measurement of antagonistic chemicals produced at the antagonist/pathogen interface using a tubular bioassay.

A tubular bioassay was used to measure analytically the local production and concentration of the antifungal Trichoderma secondary metabolite 6-n-pentyl-2H-pyran-2-one (6PAP) at the Trichoderma antagonist/pathogen interface. 6PAP levels significantly increased in the presence of the pathogen Botrytis cinerea, typically 300-700%, and were highest near the pathogen source. The level of response for a particular Trichoderma isolate was found to vary with the test organism used. Two products produced by biotransformation of 6PAP by B. cinerea in response to the interaction were also detected.

Antibiosis↗
PubMed2002

High-oxygen and high-carbon dioxide containing atmospheres inhibit growth of food associated moulds.

AIMS: The objective of this study was to determine the relationship between the growth of three foodborne fungi and high-oxygen modified atmosphere. METHODS AND RESULTS: Petri dishes were incubated in a series of connected flasks, which were placed in a climatized room and flushed continuously with the desired gas atmosphere. A combination of 80% oxygen and 20% carbon dioxide resulted in reduced growth of Rhizopus stolonifer, Botrytis cinerea and Penicillium discolor compared with ambient atmosphere conditions. Combining 80% oxygen and 20% carbon dioxide at 10 degrees C arrested growth of B. cinerea for 17 d while an elevated carbon dioxide concentration only inhibited growth up to 11 d. In addition, the peroxidase activity was doubled at 80% oxygen and decreased when 10% carbon dioxide was present. IMPACT OF THE STUDY: This study demonstrates the potential use of elevated oxygen levels in a modified atmosphere to inhibit food-associated mould growth.

Atmosphere↗
PubMed2002

Pananotin, a potent antifungal protein from roots of the traditional chinese medicinal herb Panax notoginseng.

The roots of the sanchi ginseng, Panax notoginseng, were extracted with an aqueous buffer. The extract was chromatographed on a CM-cellulose column to remove extraneous unadsorbed proteins. The adsorbed fraction was dialyzed and chromatographed on Affi-gel blue gel. The adsorbed fraction was again collected, dialyzed and applied on a column of Mono S. The second peak was dialyzed and chromatographed on an FPLC-gel filtration Superdex 75 column. An antifungal protein with an N-terminal sequence similar to those of chitinases was isolated from the first peak which had a molecular mass of 35 kDa. The sequence was distinctive in that the third and ninth highly conserved N-terminal residues (C and G) were replaced by H and M, respectively. The protein inhibited mycelial growth in Coprinus comatus, Physalospora piricola, Botrytis cinerea, and Fusarium oxysporum with an IC 50 of 100 nM, 1 microM, 630 nM and 560 nM, respectively. It inhibited cell-free translation with an IC 50 of 630 nM. Its antifungal and translation-inhibitory activities were more potent than those of previously reported antifungal proteins. It inhibited human immunodeficiency virus-1 reverse transcriptase by 35.8 % at 12.6 microM and 24.7 % at 1.26 microM.

Amino Acid Sequence↗
PubMed2003

Five components of the ethylene-response pathway identified in a screen for weak ethylene-insensitive mutants in Arabidopsis.

Five ethylene-insensitive loci (wei1-wei5) were identified by using a low-dose screen for "weak" ethylene-insensitive mutants. wei1, wei2, and wei3 seedlings showed hormone insensitivity only in roots, whereas wei4 and wei5 displayed insensitivity in both roots and hypocotyls. The genes corresponding to wei1, wei4, and wei5 were isolated using a positional cloning approach. The wei1 mutant harbored a recessive mutation in TIR1, which encodes a component of the SCF protein ubiquitin ligase involved in the auxin response. wei4, a dominant mutant, resulted from a mutation in the ethylene receptor ERS, whereas wei5, a semidominant mutant, was caused by a mutation in the EIN3-related transcription factor gene EIL1. The simultaneous loss of functional WEI5EIL1 and EIN3 nearly completely abolished the ethylene response in etiolated seedlings, and adult plants were highly susceptible to infection by the necrotrophic fungal pathogen Botrytis cinerea. Moreover, wei5eil1 ein3 double mutants were able to fully suppress constitutive signaling caused by ctr1, suggesting a synergistic interaction among these gene products. Unlike previously known root ethylene-insensitive mutants, wei2 and wei3 were not affected in their response to auxin and showed a normal response to gravity. Genetic mapping studies indicate that wei2 and wei3 correspond to previously unidentified ethylene pathway genes that may control cell-elongation processes functioning at the intersection of the ethylene and auxin response pathways.

Alleles↗
PubMed2003

Interplay of the Arabidopsis nonhost resistance gene NHO1 with bacterial virulence.

It is poorly understood why a particular plant species is resistant to the vast majority of potential pathogens that infect other plant species, a phenomenon referred to as "nonhost" resistance. Here, we show that Arabidopsis NHO1, encoding a glycerol kinase, is required for resistance to and induced by Pseudomonas syringae isolates from bean and tobacco. NHO1 is also required for resistance to the fungal pathogen Botrytis cinerea, indicating that NHO1 is not limited to bacterial resistance. Strikingly, P. s. pv. tomato DC3000, an isolate fully virulent on Arabidopsis, actively suppressed the NHO1 expression. This suppression is abolished in coi1 plants, indicating that DC3000 required an intact jasmonic acid signaling pathway in the plant to suppress NHO1 expression. Constitutive overexpression of NHO1 led to enhanced resistance to this otherwise virulent bacterium. The presence of avrB in DC3000, which activates a cultivar-specific "gene-for-gene" resistance in Arabidopsis, restored the induction of NHO1 expression. Thus, NHO1 is deployed for both general and specific resistance in Arabidopsis and targeted by the bacterium for parasitism.

Amino Acid Sequence↗