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PubMed2005

Mycotoxin-producing and other fungi isolated from grapes for wine production, with particular emphasis on ochratoxin A.

Mycotoxins are toxic secondary metabolites produced by filamentous fungi that have been detected in food commodities, including grapes and wine. A survey was conducted to assess mycotoxin-producing fungi in grapes destined for wine production. The mycotoxigenic capacity of the isolates was tested in culture media. Grapes were analyzed by plating methods from 4 Portuguese wine-growing regions at 3 maturation stages (pea berry, early veraison and ripe berry) between 2001 and 2003. From the 10,602 strains detected and identified, the most frequent genera were Cladosporium (25%), Alternaria (24%), Botrytis (15%), Penicillium (9%) and Aspergillus (8%). Most (92.0%) were non-mycotoxigenic or produced mycotoxins of unknown relevance to health. Potential producers of ochratoxin A (OTA) (Aspergillus niger aggregate, 5.4%, Aspergillus carbonarius, 0.6%) and trichothecenes (Fusarium spp., 0.4%; Trichothecium roseum, 0.8%) were the most frequent mycotoxigenic species isolated from grapes. OTA was detected in all cultures of A. carbonarius and 4% of A. niger aggregate strains. There was potential for OTA and trichothecene production in grapes by A. carbonarius and T. roseum, respectively, prior to harvest time. Data presented herein indicate that A. carbonarius is most likely to occur in vineyards with Mediterranean climates, while T. roseum is more likely to occur in more temperate climates, and is associated with gray rot. The present work emphasizes the need to use grapes under good condition so as to reduce the risk of contamination with mycotoxigenic fungi and subsequent mycotoxin occurrence in wine.

Aspergillus↗
PubMed2003

Isolation of a large thaumatin-like antifungal protein from seeds of the Kweilin chestnut Castanopsis chinensis.

A protein with an N-terminal sequence showing a much lesser extent of homology than French bean and kiwi fruit thaumatin-like proteins (TLPs) to other TLPs, and possessing a molecular mass of 30 kDa which is considerably higher than those of previously reported TLPs, has been purified from the seeds of the chestnut Castanopsis chinensis Hance. The protein was unadsorbed on DEAE-cellulose in 10 mM Tris-HCl buffer (pH 7.3), and adsorbed on Affi-gel blue gel in the same buffer, on CM-cellulose in 10 mM ammonium acetate buffer (pH 4.5), and on Mono S in 20 mM ammonium acetate buffer (pH 5.5). A highly purified protein preparation was obtained after fractionation on the first three chromatographic media. Castanopsis TLP appeared as a single band (30 kDa) in sodium dodecyl sulfate-polyacrylamide gel electrophoresis and as a single peak (30 kDa) in gel filtration on Superdex 75 by fast protein liquid chromatography. The TLP exerted antifungal activity against Botrytis cinerea, Fusarium oxysporum, Mycosphaerella arachidicola, and Physalospora piricola, with an IC(50) of 0.5 microM against F. oxysporum. Castanopsis TLP was more potent than French bean and kiwi fruit TLPs in its antifungal activity toward F. oxysporum and M. arachidicola. The antifungal activity of Castanopsis TLP remained essentially unaltered after incubation at 40 degrees C for 10 min, was reduced after incubation at 60 degrees C, and disappeared after treatment at 80 degrees C. The antifungal activity underwent a decline after treatment with trypsin (enzyme:substrate ratio 1:100) at 37 degrees C for 1h but some activity remained. Castanopsis TLP exhibited a much more potent inhibitory activity on HIV-1 reverse transcriptase (IC(50) = 1.6 microM) than kiwi fruit TLP (IC(50) > or = 27 microM). Castanopsis TLP was obtained with a yield of 20 mg from 1 kg chestnut seeds.

Amino Acid Sequence↗
PubMed2003

Scarabaecin, a novel cysteine-containing antifungal peptide from the rhinoceros beetle, Oryctes rhinoceros.

A novel antifungal peptide, scarabaecin (4080Da), was isolated from the coconut rhinoceros beetle, Oryctes rhinoceros. Scarabaecin cDNA was cloned by reverse transcriptase-polymerase chain reactions (RT-PCR) using a primer based on the N-terminal amino acid sequence. The amino acid sequence deduced from scarabaecin cDNA showed no significant similarity to those of reported proteins. Chemically synthesized scarabaecin indicated antifungal activity against phytopathogenic fungi such as Pyricularia oryzae, Rhizoctonia solani, and Botrytis cinerea, but not against phytopathogenic bacteria. It showed weak activity against Bauberia bassiana, an insect pathogenic fungus, and Staphylococcus aureus, a pathogenic bacterium. Scarabaecin showed chitin binding property and its K(d) was 1.315 microM. A comparison of putative chitin-binding domains among scarabaecin, invertebrate, and plant chitin-binding proteins suggests that scarabaecin is a new member of chitin-binding antimicrobial proteins.

Amino Acid Sequence↗
PubMed2003

Dendrocin, a distinctive antifungal protein from bamboo shoots.

An antifungal protein, with a molecular weight of 20 kDa and an inhibitory action on mycelial growth in the fungi Fusarium oxysporum, Botrytis cincerea, and Mycosphaerella arachidicola, was isolated from fresh bamboo shoots. The protein, designated dendrocin, was unadsorbed on DEAE-cellulose and adsorbed on Affi-gel blue gel and CM-Sepharose. Dendrocin showed only limited similarity in N-terminal sequence to thaumatin-like proteins, unlike other thaumatin-like proteins which closely resemble each other. Its molecular weight was also lower than those of the previously reported thaumatin-like proteins. The protein was devoid of hemagglutinating and ribonuclease activities found in some antifungal proteins.

Amino Acid Sequence↗
PubMed2002

Five disulfide bridges stabilize a hevein-type antimicrobial peptide from the bark of spindle tree (Euonymus europaeus L.).

A small 45 amino acid residue antifungal polypeptide was isolated from the bark of spindle tree (Euonymus europaeus L.). Though the primary structure of this so-called E. europaeus chitin-binding protein or Ee-CBP is highly similar to the hevein domain, it distinguishes itself from most previously identified hevein-type antimicrobial peptides (AMP) by the presence of two extra cysteine residues that form an extra disulfide bond. Due to these five disulfide bonds Ee-CBP is a remarkably stable protein. Agar diffusion and microtiterplate assays demonstrated that Ee-CBP is a potent antimicrobial protein. IC(50)-values as low as 1 microg/ml were observed for the fungus Botrytis cinerea. Comparative assays further demonstrated that Ee-CBP is a stronger inhibitor of fungal growth than Ac-AMP2 from Amaranthus caudatus seeds, which is considered one of the most potent antifungal hevein-type plant proteins.

Amino Acid Sequence↗
PubMedDate not supplied

Isolation and bioactivities of epidioxysterol from the tunicate Cynthia savignyi.

From a hexane extract of the tunicate Cynthia savignyi, collected in Morocco, epidioxysterol or 5,8-alpha-epidioxy-5alpha-cholest-6-en-3beta-ol has been isolated. This is the first example of epidioxysterol found in the tunicate C. savignyi. The structure of epidioxysterol has been characterised by NMR data (1H, 13C and 2D). Epidioxysterol possesses antifungal activity against three tomato pathogenic fungi: Botrytis cinerea, Fusarium oxysporum and Verticillium albo atrum and antibacterial activity against Agrobacterium tumefaciens, Escherichia coli, Staphylococcusfaecalis, Staphylococcus aureus and Pseudomonas aeruginosa and cytotoxicity against Artemia salina larvae.

Animals↗
PubMed2003

Cynthichlorine: a bioactive alkaloid from the tunicate Cynthia savignyi.

From ether extracts of the tunicate Cynthia savignyi, collected in Morocco, a new alkaloid-cynthichlorine-has been isolated. The structure of cynthichlorine has been characterized by extensive 2D-NMR data. Cynthichlorine possesses antifungal activity against two tomato pathogenic fungi: Botrytis cinerea and Verticillium albo atrum and antibacterial activity against Agrobacterium radiobacter, Escherichia coli and Pseudomonas aeruginosa and cytotoxicity against Artemia salina larvae.

Alkaloids↗
PubMedDate not supplied

Synthesis and antifungal activity of new N-isoxazolyl-2-iodobenzamides.

N-Isoxazolyl-2-iodobenzamides 3 and 9, with a benodanil-like structure, were synthesized by refluxing in acetic acid the corresponding benzotriazinones 2 and 8 with potassium iodide for 1 h with the aim to ascertain if they were active as fungicides against Phytophthora citricola Saw., Botrytis cinerea Pers., Rhizoctonia sp. and Alternaria sp. Among the tested iodo derivatives, compounds 3b and 9a possess interesting activities against the aforesaid fungal strains in several cases similar to that of benodanil I taken as reference drug.

Benzamides↗
PubMed2001

Purification of allivin, a novel antifungal protein from bulbs of the round-cloved garlic.

A novel antifungal protein, designated allivin, was isolated from bulbs of the round-cloved garlic Allium sativum var. round clove with a procedure involving ion exchange chromatography on DEAE-cellulose, affinity chromatography on Affi-gel blue gel, ion exchange chromatography on CM-Sepharose and FPLC-gel filtration on Superdex 75. Allivin possessed an N-terminal sequence demonstrating very little similarity to sequences of Allium sativum chitinases and ribosome inactivating proteins. Allivin exhibited a molecular weight of 13 kDa in gel filtration and SDS-polyacrylamide gel electrophoresis. It displayed antifungal activity against Botrytis cinerea, Mycosphaerella arachidicola and Physalospora piricola. It inhibited translation in a cell-free rabbit reticulocyte system with an IC50 of 1.6 microM.

Amino Acid Sequence↗
PubMed2002

Isolation of a new cyclophilin-like protein from chickpeas with mitogenic, antifungal and anti-HIV-1 reverse transcriptase activities.

A protein designated chickpea cyclophilin-like antifungal protein (CLAP) was isolated from seeds of the chickpea (Cicer arietinum). Chickpea CLAP was characterized by a molecular weight of 18 kDa and an N-terminal sequence homologous to cyclophilins. The protein was isolated with a procedure involving affinity chromatography on Affi-gel blue gel and ion exchange chromatography on CM-Sepharose. In addition to an inhibitory effect on the growth of fungi including Rhizoctonia solani, Mycosphaerella arachidicola and Botrytis cinerea, the protein was capable of inhibiting human immunodeficiency virus-1 reverse transcriptase. Chickpea CLAP did not possess lectin and ribonuclease activities but it weakly inhibited translation in a rabbit reticulocyte lysate system. The protein stimulated 3H-thymidine incorporation by mouse splenocytes.

Amino Acid Sequence↗
PubMed2002

Isolation of a novel peroxidase from French bean legumes and first demonstration of antifungal activity of a non-milk peroxidase.

A novel antifungal protein with its N-terminal sequence bearing similarity to the C-terminal sequences of peroxidases was isolated from French bean legumes. The protein, which possessed a molecular weight of 37 kDa, was adsorbed on Affi-gel blue gel and CM-Sepharose. The protein exhibited peroxidase activity with a Km of 58 microM and a Vmax of 3.36 U/nmol. Optimal peroxidase activity was found at 22 degrees C and pH 4. It exerted antifungal activity against a variety of fungal species including Coprinus comatus, Mycosphaerella arachidicola, Fusarium oxysporum and Botrytis cinerea. It inhibited the activities of alpha-glucosidase and beta-glucosidase but was without any inhibitory effect on HIV-1 reverse transcriptase.

Amino Acid Sequence↗
PubMed2000

Fungicidal activity of natural and synthetic sesquiterpene lactone analogs.

Fungicidal activity of 36 natural and synthetic sesquiterpene lactones with guaianolide, trans, trans-germacranolide, cis, cis-germacranolide, melampolide, and eudesmanolide carbon skeletons was evaluated against the phytopathogenic fungi Colletotrichum acutatum, C. fragariae, C. gloeosporioides, Fusarium oxysporum, Botrytis cinerea, and Phomopsis sp. Dose-response data for the active compounds dehydrozaluzanin C, dehydrocostuslactone, 5alpha-hydroxydehydrocostuslacone, costunolide, and zaluzanin C are presented. A new 96-well microbioassay procedure for fast and easy evaluation of antifungal activity was used to compare these compounds with commercial fungicide standards. Some structure-activity conclusions are also presented.

Antifungal Agents↗
PubMed2001

Stress induced carbazole phytoalexins in Glycosmis species.

Induced formation of a series of carbazole alkaloids was observed in leaves of Glycosmis parviflora and G. pentaphylla after wounding, UV-irradiation, and particularly after inoculation with the fungus Botrytis cinerea. Chemical variation between different provenances and even individuals of G. parviflora led to an accumulation of different derivatives from which three proved to be undescribed natural products. Their structures were identified by spectroscopic methods and named carbalexins A, B, and C. Bioautographic tests on TLC plates with Cladosporium herbarum exhibited strong antifungal activity for the new carbalexins as well as for the already known 2-hydroxy-3-methylcarbazole, but only weak effects for the pyranocarbazole glycoborinine. Detailed experiments with marked infection areas confirmed the restricted accumulation of carbazole derivatives which could not be detected in non-infected areas of the same leaf. Apart from carbazoles, in some individuals of G. parviflora an additional accumulation of the pyranoquinolones flindersine and methylflindersine was induced, which supports the already previously discussed biogenetic connections between carbazoles and prenylated quinolones.

Alkaloids↗
PubMed1999

Methoxybifurcarenone: an antifungal and antibacterial meroditerpenoid from the brown alga Cystoseira tamariscifolia.

A meroditerpenoid metabolite has been isolated from the brown alga Cystoseira tamariscifolia and characterized as methoxybifurcarenone, by spectral analysis. Methoxybifurcarenone possesses antifungal activity against three tomato pathogenic fungi: Botrytis cinerea, Fusarium oxysporum sp. mycopersici and Verticillium alboatrum and antibacterial activity against Agrobacterium tumefaciens and Escherichia coli.

Agrobacterium tumefaciens↗
PubMed2001

Effects of procymidone, fludioxonil and pyrimethanil on two non-target aquatic plants.

Procymidone, fludioxonil, and pyrimethanil are widely used to control the pathogenic fungus Botrytis cinerea in Champagne's vineyards. These fungicides may end up in surface waters and present potential risks for aquatic vascular plants and algae. Therefore, their toxicity was evaluated on Lemna minor and Scenedesmus acutus in six-day or 48-h tests, respectively. Based on growth and chlorophyll (Chl) content of L. minor and S. acutus cultures, the results showed that the alga was the most sensitive to the fungicides. Among the fungicides, pyrimethanil was the most toxic for L. minor, its nominal IC50 was 46.16 mg l(-1) and that of the other two was >100 mg l(-1). In contrast, pyrimethanil appeared the least toxic for S. acutus at low concentration, nominal IC50 were 22.81, 4.85, and 4.55 mg l(-1) for pyrimethanil, fludioxonil, and procymidone, respectively. Fate of the fungicides in the media was also investigated and acute toxicity of the agrochemicals is discussed in regard to concentration in the culture media. Poor solubility of procymidone and fludioxonil appeared to be partly responsible for the low toxicity of these fungicides. Based on these toxicity data and the concentrations found in ponds collecting vineyard runoff water, these pesticides should not impair the establishment of pioneer plants.

Agriculture↗
PubMed2002

Photosynthetic responses of Lemna minor exposed to xenobiotics, copper, and their combinations.

The effects on the photosynthetic process of copper and pesticides, used in vineyards, and their combinations, were investigated by measuring different chlorophyll fluorescence parameters in Lemna minor. Cu and flumioxazin had a severe impact on duckweed since a decrease in their photosynthetic capacity was detected after 24h of exposure to 200 and 1 microg.L(-1), respectively. However, fungicides used to control Botrytis cinerea (procymidone, pyrimethanil, and fludioxonil) seem to have no marked effects on duckweed even at very high concentrations (50 mg.L(-1)). Analysis of the combinations between copper (200 microg.L(-1)) and pesticides revealed different patterns of response: a synergistic effect was observed when Cu(2+) was added to flumioxazin (1 microg.L(-1)). In contrast, an antagonism was detected when duckweed was exposed to a mixture of Cu(2+) and fludioxonil or procymidone. However, these interactions always tended toward additivity when pesticide concentrations increased. Additivity was also observed for the Cu(2+)-pyrimethanil mixture at each fungicide concentration.

Araceae↗
PubMed2002

Validity of detection of microbial growth in buildings by trained dogs.

Microbial growth in buildings may evoke respiratory and other symptoms in the occupants and promote decay of construction materials. The decay in wood is usually caused by dry-rot fungus, leading to the decomposition of cellulose and lignin. There are also some mold fungi and bacteria that can use wood as a nutrient. In this study, two trained dogs were used to detect microbial growth present in buildings. The rot fungi Serpula lacrymans, Coniophora puteana and Antrodia sinuosa were used in the training. In addition to decay samples, pieces of healthy birch, pine and imbued wood were used as controls. Another experiment was made using bacteria (Streptomyces sp.). In these experiments, a total of 100 decay, 75 control and 25 bacteria samples were used. The dogs detected 75% of the decay and 60% of the bacteria samples. Some (0-24%) control samples were also expressed as positive. Since the dogs identified also the bacteria samples without any specific training, a new test with some mold strains (Cladosporium, Botrytis, Trichoderma, Penicillium, Aspergillus) was carried out. The dogs found all the decay, mold and bacteria samples but only one sample of healthy wood. The use of dogs to detect mold or decay damage appears to have high specificity and high positive predictive value, but low sensitivity.

Animals↗
PubMed2002

Thiourea derivatives and their nickel(II) and platinum(II) complexes: antifungal activity.

We have synthesized two thiourea derivatives of methyl anthranilate (1, 2) and their complexes with nickel (3) and platinum(II) (4). We have also prepared the complexes of nickel(II) with two benzoylthiourea derivatives (5, 6). The obtained compounds were characterized by elemental analysis, spectroscopic methods (FT-IR, UV-vis, NMR), mass spectrometry and thermal analysis. Compound 1, C(20)H(23)N(3)O(2)S, crystallizes in monoclinic space group P21/n, with Z=4, and unit cell parameters, a=8.8042(4) A, b=7.6608(3) A, c=28.834(2) A, alpha=gamma=90 degrees, beta=90.94(1) degrees. Compound 2, C(20)H(21)N(3)O(3)S, crystallizes in monoclinic space group P21/c, with Z=4, and unit cell parameters, a=7.7345(4) A, b=8.6715(4) A, c=29.113(2) A, alpha=gamma=90 degrees, beta=90.67(1) degrees. Compound 5, C(24)H(30)N(4)NiO(2)S(2), crystallizes in monoclinic space group P21/n, with Z=4, and unit cell parameters, a=10.4317(8) A, b=18.517(2) A, c=13.299(1) A, alpha=gamma=90 degrees, beta=104.53(1) degrees. Compound 6, C(25)H(28)Cl(2)N(4)NiO(4)S(2), crystallizes with a molecule of CH(2)Cl(2) in triclinic space group P-1, with Z=2, and unit cell parameters, a=10.362(1) A, b=11.849(2) A, c=12.536(2) A, alpha=90.04(2) degrees, beta=84.73(1) degrees, gamma=113.43(2) degrees. Compounds 1 and 2 show antifungal activity against the major pathogens responsible for important plant diseases (Botrytis cinerea, Colletotrichum fragariae, Fusarium oxysporum and Phoma betae). The antifungal activity is practically the same for morpholine and ethyl derivatives.

Antifungal Agents↗