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PubMed2001

Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects.

Oxidative modification of low density lipoprotein (LDL) induced by free radicals is implicated in the development of atherosclerosis. The aim of the present study was to examine the ability of various pineal indoles in inhibiting LDL oxidation which is accompanied by an increase in mobility in agarose gel electrophoresis and by an augmented generation of thiobarbituric acid-reactive substance induced by Cu2+. It was found that the order of potencies in inhibiting malondialdehyde formation was 5-hydroxytryptamine (serotonin)>5-hydroxytryptophol and 5-hydroxyindole-3-acetic acid when tested at 4 mM. 5-methoxytryptamine was as effective as 5-hydroxytryptophol and 5-hydroxyindole-3-acetic acid when tested at 4 mM but was inactive at 1 mM. 5-methoxytryptophol was marginally active at 4 mM. Melatonin, 5-methoxyindole-3-acetic acid and 6-methoxy-2-benzoxazolinone were inactive even at 4 mM. The ranking of antioxidative potencies as reflected in the shift of mobility in agar gel electrophoresis was 5-hydroxytryptamine>5-methoxytryptamine>5-hydroxyindole-3-acetic acid and 5-methoxytryptophol>5-hydroxytryptophol and melatonin. Another aim of this investigation was to ascertain the action of the aforementioned pineal indoles on the enhanced lipid peroxidation brought about in the mouse kidney and liver by intraperitoneal administrations of carbon tetrachloride. It was found that all pineal indoles tested demonstrated an inhibitory effect in the kidney but not in the liver. 6-methox-2-benzoxazolinone and 5-methoxyindole-3-acetic acid exerted antifungal activity against Mycosphaerella arachidicola, Botrytis cinerea and Physalospora piricola. 6-methoxy-2-benzoxazolinone exhibited antibacterial activity against Proteus vulgaris and 5-methoxytryptamine against Staphylocccus aureus and Bacillus subtilis. Other pineal indoles did not possess antifungal or antibacterial action.

Animals↗
PubMed2005

Interactions between the mycoparasite Pythium oligandrum and two types of sclerotia of plant-pathogenic fungi.

The interactions between Pythium oligandrum hyphae and two types of sclerotia, i.e. the plano-convexoid sclerotium of Botrytis cinerea and the tuberoid sclerotium of Sclerotinia minor, were investigated by ultrastructural and cytochemical experiments. In the mycoparasitism of P. oligandrum, some differences in relation to sclerotium anatomy and the role of the rind layer in preventing invasion are documented. Both types of sclerotia showed neither alterations of the heavily melanised rind walls, nor direct rind wall penetration by P. oligandrum. This oomycete successfully entered B. cinerea sclerotia only through breaches at the junction of rind cells and corresponding to gaps in melanin deposits. On the other hand, none of these breaches was observed in the small sclerotia of S. minor, and P. oligandrum ingress in the sclerotia stopped at the inner rind layer. After the penetration of B. cinerea sclerotia by the mycoparasite, it extensively colonised the cortical and medulla areas by intercellular growth. The invaded tissues displayed pronounced alterations as well as some disorganisation of tissue in places. Colonisation was associated with severe chitin degradations of all host walls, which occurred even at some distance from P. oligandrum hyphae. The observation of wall thickenings in some P. oligandrum-hyphae suggests that the sclerotial cells constitute a harsh environment unsuitable for survival of the mycoparasite. These wall thickenings could be interpreted as P. oligandrum defence-like reactions.

Antibiosis↗
PubMed2001

Partitioning of monomethylmercury between freshwater algae and water.

Phytoplankton-water monomethylmercury (MeHg) partition constants (KpI) have been determined in the laboratory for two green algae Selenastrum capricornutum and Cosmarium botrytis, the blue-green algae Schizothrix calcicola, and the diatom Thallasiosira spp., algal species that are commonly found in natural surface waters. Two methods were used to determine KpI, the Freundlich isotherm method and the flow-through/dialysis bag method. Both methods yielded KpI values of about 10(6.6) for S. capricornutum and were not significantly different. The KpI for the four algae studied were similar except for Schizothrix, which was significantly lower than S. capricornutum. The KpI for MeHg and S. capricornutum (exponential growth) was not significantly different in systems with predominantly MeHgOH or MeHgCl species. This is consistent with other studies that show metal speciation controls uptake kinetics, but the reactivity with intracellular components controls steady-state concentrations. Partitioning constants determined with exponential and stationary phase S. capricornutum cells at the same conditions were not significantly different, while the partitioning constant for exponential phase, phosphorus-limited cells was significantly lower, suggesting that P-limitation alters the ecophysiology of S. capricornutum sufficiently to impact partitioning, which may then ultimately affect mercury levels in higher trophic species.

Biotransformation↗
PubMed2002

Kinetics and uptake mechanisms for monomethylmercury between freshwater algae and water.

Uptake kinetics of monomethylmercury chloride (MeHgCl) were measured for two species of green algae (Selenastrum capricomutum and Cosmarium botrytis), one blue-green algae (Schizothrix calcicola), and one diatom (Thalassiosira weissflogii), algal species that are commonly found in natural surface waters. Species differences were found with the two green algae giving the highest uptake rates, and one of them (Cosmarium) showing differences between cultures having widely different cell age (exponential versus stationary), where increases in uptake rate for cells 30 days old were about 25 times greater than cells only 3 days old when weights of cells were considered. Both Schizothrix and Thalassiosira exhibited nearly the same lower uptake rates, approximately 20 times lower than the two green algal species. Experiments with photosystem inhibitors, uncouplers, gamma-radiation, light deprivation, and extended range uptake all point to an active transport mechanism for MeHgCl.

Chlorophyta↗
PubMed2001

Evidence for surfactant solubilization of plant epicuticular wax.

The solubilization of isolated, reconstituted tomato (Lycopersicon esculentum Mill.) fruit and broccoli (Brassica oleracaea var. botrytis L.) leaf epicuticular waxes (ECW) by nonionic octylphenoxypolyethoxy ethanol surfactant (Triton X-100) was demonstrated in a model system by TLC and fluorescence analysis using pyrene as a fluorescent probe. ECW was solubilized at or above the surfactant critical micelle concentration; solubilization increased with an increase in micelle concentration. As shown by the fluorescence quenching of pyrene, surfactant solubilization of the ECW increased rapidly for the first 12 h, then approached a plateau, increased linearly with an increase in temperature (22--32 degrees C), and decreased linearly with the log of the polyoxyethylene chain length (range 5--40 oxyethylenes). These data are discussed in relation to surfactant effects on phytotoxicity and performance of foliar spray application of agrochemicals.

Brassica↗
PubMed2000

Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation.

A method using HPLC analysis has been used to compare the level of resveratrol and its derivatives, piceid, pterostilbene and epsilon-viniferin, in grapevine berries of three Vitis vinifera varieties. The concentration of these compounds has been evaluated in healthy and Botrytis cinerea infected grape clusters, both in natural vineyard conditions and in response to UV elicitation.

Chromatography, High Pressure Liquid↗
PubMed2002

A mixed green vegetable and fruit beverage decreased the serum level of low-density lipoprotein cholesterol in hypercholesterolemic patients.

The effects of a canned mixed green vegetable and fruit beverage, containing broccoli (Brassica oleracea L. var. botrytis L.) and cabbage (Brassica oleracea L. var. capitata L.) as main materials, on serum lipid levels in hypercholesterolemic patients were investigated. Thirty-one adult subjects were administered two cans of the beverage (160 g/can) per day for 3 weeks. Their serum total cholesterol (TC) levels significantly decreased from 6.7 +/- 0.8 to 6.1 +/- 0.6 mmol/L, and, more strikingly, the level of low-density lipoprotein cholesterol (LDL-C) significantly decreased from 4.4 +/- 0.8 to 3.8 +/- 0.7 mmol/L. At 9 weeks after the cessation of the administration, these levels had returned to the preadministration levels. Furthermore, 14 other subjects who were administered one can of the sample for 12 weeks also showed a significant reduction in the levels of serum TC and LDL-C. Thus, daily consumption of this mixed green vegetable and fruit beverage may be useful in lowering serum TC and LDL-C levels in hypercholesterolemic patients.

Adult↗
PubMed2003

Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.

Fungicidal activity of Curcuma longa rhizome-derived materials against Botrytis cineria, Erysiphe graminis, Phytophthora infestans, Puccinia recondita, Pyricularia oryzae, and Rhizoctonia solani was tested using a whole plant method in vivo. It was compared with synthetic fungicides and four commercially available compounds derived from C. longa. The response varied with the tested plant pathogen. At 1000 mg/L, the hexane extract of C. longa showed fungicidal activities against E.graminis, P. infestans, and R. solani, and the ethyl acetate extract of C. longa showed fungicidal activities against B. cineria, P. infestans, Pu. recondita, and R. solani. Curcumin was isolated from the ethyl acetate fraction using chromatographic techniques and showed fungicidal activities against P. infestans, Pu. recondita, and R. solani with 100, 100, and 63% control values at 500 mg/L and 85, 76, and 45% control values at 250 mg/L, respectively. In the test with components derived from C. longa, turmerone exhibited weak activity against E. graminis, but no activity was observed from treatments with borneol, 1,8-cineole, sabinene, and turmerone. In comparison, potent fungicidal activity with chlorothalonil against P. infestans at 50 mg/L and dichlofluanid against B. cinerea at 50 mg/L was exhibited. These results may be an indication of at least one of the fungicidal actions of curcumin derived from C. longa.

Curcuma↗
PubMed2002

Biodegradation of ochratoxin A by fungi isolated from grapes.

Ochratoxin A is a mycotoxin present in several food products for which levels should be reduced. Chemical, physical, and biological methods have been proposed for the detoxification of mycotoxins, biological methods being the more promising ones. In this report, filamentous fungi isolated from Portuguese grapes were assessed for ochratoxin A degradation capabilities. It was observed that 51 of the 76 tested strains, predominantly aspergillus species, were able to degrade more than 80% of ochratoxin A added to the culture medium and that the most potent species (more than 95% of initial amount) were the black aspergilli, A. clavatus, A. ochraceus, A. versicolor, and A. wentii. Other fungi frequently isolated from grapes, such as Alternaria, Botrytis, Cladosporium, and Penicillium, also showed significant degradation capabilities. It was observed that the compounds obtained from the degradation of ochratoxin A by black aspergilli and by A. ochraceus and A. wentii strains were different.

Aspergillus↗
PubMed2004

Structure-activity relationships of derivatives of fusapyrone, an antifungal metabolite of Fusarium semitectum.

Fusapyrone (1) and deoxyfusapyrone (2) are two 3-substituted-4-hydroxy-6-alkyl-2-pyrones isolated from Fusarium semitectum that have considerable antifungal activity against molds. Because of their low zootoxicity and selective action they are potentially utilizable along with biocontrol yeasts for control of postharvest crop diseases. Seven derivatives of 1 (3 and 5-10) and one derivative of 2 (4) were obtained by chemical modifications of the glycosyl residue, the 2-pyrone ring, the aliphatic chain, or a combination thereof, and a structure-activity correlation study was carried out with regard to their zootoxicity and antifungal activity. Derivatives 7-10, as well as 1, were slightly zootoxic in Artemia salina (brine shrimp) bioassays, whereas pentaacetylation of 1 into 3, 5, and 6 resulted in a strong increase in toxicity. Compound 4, the tetraacetyl derivative of 2, was as toxic as 2. Because the structural changes of 1 that resulted in an increase of biological activity in A. salina bioassay were those that affected mainly the water solubility of the molecule, it appears that toxicity is related to hydrophobicity. Compounds 1 and 2 showed strong antifungal activity toward Botrytis cinerea, Aspergillus parasiticus, and Penicilliun brevi-compactum (minimum inhibitory concentration at 24 h = 0.78-6.25 microg/mL). Among derivatives 3-10, only compounds 7, 9, and 10 retained some activity, limited to B. cinerea and at high concentration (25-50 microg/mL). None of the compounds 1-10 inhibited the growth of the biocontrol yeasts Pichia guilliermondii and Rhodotorula glutinis at the highest concentration tested (50 microg/mL).

Animals↗
PubMed2005

Synthesis and fungicidal activity of novel 2-oxocycloalkylsulfonylureas.

A series of 2-oxocycloalkylsulfonylureas (2) have been synthesized in a six-step, three-pot reaction sequence from readily available cyclododecanone, cycloheptanone, and cyclohexanone. Their structures were confirmed by IR, 1H NMR, and elemental analysis. The bioassay indicated that some of them possess certain fungicidal activity against Gibberella zeae Petch. In general, compounds containing a 12-membered ring (2A) are more active than those containing a 6- or 7-membered ring (2B, 2C). In the series 2A, the compounds in which R is a disubstituted phenyl or pyrimidyl showed better activity than those in which R is a monosubstituted phenyl or pyrimidyl, and aryl-substituted compounds have somewhat higher activity than those substituted by pyrimidyl. The further bioassay showed that the representative of 2A, 2A15, has good fungicidal activities against not only G. zeae Petch but also Botrytis cinerea Pers, Colletotrichum orbiculare Arx, Pythium aphanidermatum Fitzp, Fusarium oxysporum Schl. f. sp. Vasinfectum, etc.

Fungi↗
PubMed2005

Adsorption-desorption dynamics of cyprodinil and fludioxonil in vineyard soils.

Cyprodinil and fludioxonil are new-generation fungicides that are employed to protect grapevines from botrytis and various rots. In this work, their adsorption and desorption dynamics in eight vineyard soils from Galicia (northwestern Spain) were examined in batch and column experiments. Both fungicides exhibited linear adsorption isotherms, with more ready adsorption (greater Kd) of fludioxonil. Kd values for cyprodinil were significantly correlated with soil organic matter content (r 2= 0.675, p < 0.01). Both pesticides exhibited adsorption-desorption hysteresis, but desorption was easier and more variable for cyprodinil (12-21%, RSD = 17%) than for fludioxonil (3-5%, RSD = 13%) and appeared to depend on the formation of irreversible bonds in the former case and on poor solubility in the latter. A linear adsorption model involving nonequilibrium conditions and an irreversible adsorption term was found to reproduce transport behavior accurately.

Adsorption↗
PubMed2004

Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi.

The fungicidal activities of Cassia tora extracts and their active principles were determined against Botrytis cineria, Erysiphe graminis, Phytophthora infestans, Puccinia recondita, Pyricularia grisea, and Rhizoctonia solani using a whole plant method in vivo and were compared with synthetic fungicides and three commercially available anthraquinones. The responses varied with the plant pathogen tested. At 1 g/L, the chloroform fraction of C. tora showed a strong fungicidal activity against B. cinerea, E. graminis, P. infestans, and R. solani. Emodin, physcion, and rhein were isolated from the chloroform fraction using chromatographic techniques and showed strong and moderate fungicidal activities against B. cinerea, E. graminis, P. infestans, and R. solani. Furthermore, aloe-emodin showed strong and moderate fungicidal activities against B. cinerea and R. solani, respectively, but did not inhibit the growth of E. graminis, P. infestans, P. recondita, and Py. grisea. Little or no activity was observed for anthraquinone and anthraquinone-2-carboxylic acid when tested at 1 g/L. Chlorothalonil and dichlofluanid as synthetic fungicides were active against P. infestans and B. cinerea at 0.05 g/L, respectively. Our results demonstrate the fungicidal actions of emodin, physcion, and rhein from C. tora.

Anthraquinones↗
PubMed2005

Improvement of table grapes quality and safety by the combination of modified atmosphere packaging (MAP) and eugenol, menthol, or thymol.

Table grape is a nonclimacteric fruit that shows a rapid loss of quality during storage and is very susceptible to colonization by fungi, especially Botrytis cinerea, which is considered the most important disease of this commodity. To solve this problem, synthetic fungicides have been used, although legal restrictions and consumer's concern demand the search of other safe means. In the present paper, and as an alternative of synthetic fungicides, an active packaging to improve MAP effectiveness on preserving table grape (cv. Crimson Seedless) quality and safety was developed by the addition of 0.5 mL of eugenol, thymol, or menthol inside the packages. Packages were stored at 1 degree C for 35 days. The final gas composition inside the packages was 1.4-2.0 and 10.0-14.5 kPa of CO(2) and O(2), respectively, with no significant slight differences among treatments. Results showed that the addition of eugenol, thymol, or menthol improved the beneficial effect of MAP in terms of delaying weight loss and color changes, retarding degrees Brix/acidity ratio evolution, and maintaining of firmness. Thereafter, these treatments showed additional benefit in terms of delayed rates of rachis deterioration and berry decay. Finally, the total viable counts for both mesophilic aerobics and especially yeast and molds were significantly reduced in the grapes packaged with the natural antimicrobial compounds. All of the above effects led to maintenance of table grape quality and safety for longer storage periods (3 additional weeks as compared to controls under MAP only).

Carbon Dioxide↗
PubMed2005

Isolation and identification of antifungal and antialgal alkaloids from Haplophyllum sieversii.

Bioassay-guided fractionation of the hexane/ethyl acetate/water (H/EtOAc/H2O) crude extract of the aerial parts of Haplophyllum sieversii was performed because of preliminary screening data that indicated the presence of growth inhibitory components against Colletotrichum fragariae, Colletotrichum gloeosporioides, and Colletotrichum acutatum. Fractionation was directed using bioautographical methods resulting in the isolation of the bioactive alkaloids flindersine, anhydroevoxine, haplamine, and a lignan eudesmin. These four compounds were evaluated for activity against C. fragariae, C. gloeosporioides, C. acutatum, Botrytis cinerea, Fusarium oxysporum, and Phomopsis obscurans in a dose-response growth-inhibitory bioassay at 50.0, 100.0, and 150.0 microM. Of the four compounds tested, flindersine demonstrated the highest level of antifungal activity. Additionally, flindersine, eudesmin, and haplamine were screened against the freshwater phytoplanktons Oscillatoria perornata, Oscillatoria agardhii, Selenastrum capricornutum, and Pseudanabaena sp. (strain LW397). Haplamine demonstrated selective inhibition against the odor-producing cyanobacterium O. perornata compared to the activity against the green alga S. capricornutum, with lowest observed effect concentration values of 1.0 and 10.0 microM, respectively.

Alkaloids↗
PubMed2006

Controlled atmosphere storage of wild strawberry fruit (Fragaria vesca L.).

Controlled atmosphere storage technology to extend the shelf life of "Reina de los Valles" wild strawberry fruit (Fragaria vesca L.) was studied. Fruits were stored at 3 degrees C for three weeks in different atmosphere compositions: 0.05% CO2/21% O2 (air), 3% CO2/18% O2, 6% CO2/15% O2, 10% CO2/11% O2, and 15% CO2/6% O2. The effect of gas composition on soluble solids content, titrable acidity, pH, off-flavor, aroma volatiles, and consumer preference was monitored. The result showed that the 10% CO2/11% O2 combination can efficiently prolong the shelf life of wild strawberries by maintaining the quality parameters within acceptable values, through inhibiting the development of Botrytis cinerea, without significantly modifying consumer acceptance.

Carbon Dioxide↗
PubMed2006

Isolation and antifungal and antioomycete activities of staurosporine from Streptomyces roseoflavus strain LS-A24.

The actinomycete strain LS-A24 active against some plant fungal and oomycete pathogens was isolated from a soil sample of the Sunghwan Lake in Korea. The cell wall composition and spore shape of strain LS-A24 were LL-diaminopimelic acid and spiral type, respectively. On the basis of the physiological and biochemical characteristics and 16S ribosomal DNA sequence analysis, strain LS-A24 was identical to Streptomyces roseoflavus. An antifungal and antioomycete antibiotic was isolated from LS-A24 using various chromatographic procedures. The molecular formular of the antibiotic was determined to be C(28)H(26)N(4)O(3), and on the basis of the NMR data, the antibiotic was confirmed to be staurosporine, 2,3,10,11,12,13-hexahydro-10R-methoxy-9S-methyl-11R-methylamino-9S,13R-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one. Staurosporine completely inhibited the mycelial growth of Colletotrichum orbiculare, Phytophthora capsici, Rhizoctonia solani, Botrytis cinerea, and Cladosporium cucumerinum with minimum inhibitory concentration (MIC) values of 1-50 microg/mL for MICs. Staurosporine also was active against Saccharomyces cerevisiae, Bacillus subtilis ssp. subtilis, and Xanthomonas vesicatoria. Staurosporine and the commercial fungicide metalaxyl inhibited the development of Phytophthora blight on pepper plants. However, the control efficacy of staurosporine against the Phytophthora disease was somewhat less than that of metalaxyl. This is the first study to isolate staurosporine from S. roseoflavus and demonstrate its in vitro and in vivo antioomycete activity against P. capsici.

Fungicides, Industrial↗
PubMed2006

Biodegradation of the fungicide iprodione by Zygosaccharomyces rouxii strain DBVPG 6399.

Iprodione is a contact fungicide used to control several pathogens such as Botrytis cinerea, Monilia, and Sclerotinia. This paper reports the ability of an iprodione-resistant strain of Zygosaccharomyces rouxii to degrade iprodione at a concentration of 1 mg L(-1). The yeast Z. rouxii was chosen also for its ability to grow at high osmolarity. Also of note is that in bioremediation situations and in the food industry such resistance could be important. The kinetic and metabolic behaviors of the fungicide in the media are described. The results show a new transformation pathway of iprodione by the yeast leading to the formation of N-(3,5-dichlorophenyl)-2,4-dioxoimidazoline, 3-isopropylhydantoin, and 3,5-dichloroaniline. These compounds were identified by 1H NMR, 13C NMR, and GC-MS analyses. This study provides a basis to employ yeast strains in biodegradation studies in relation to their ability in the disappearance and degradation of xenobiotics into simpler molecules.

Aminoimidazole Carboxamide↗