The Experts below are selected from a list of 201 Experts worldwide ranked by ideXlab platform
Antonio Evidente - One of the best experts on this subject based on the ideXlab platform.
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inhibition of spore germination and appressorium formation of rust species by plant and fungal metabolites
Natural Product Communications, 2016Co-Authors: Eleonora Barilli, Alessio Cimmino, Marco Masi, Marco Evidente, Diego Rubiales, Antonio EvidenteAbstract:Eight fungal and plant metabolites belonging to different classes of naturally occurring compounds, a 24-oxa[14]-cytochalasan as Cytochalasin B (1), a trisubstituted isocoumarin as 6-hydroxymellein (2), a tetracyclic pimarane diterpene as sphaeropsidin A (3), a chalcone as cavoxin (4), a pentasubstituted benzofuranone as cyclopaldic acid (5), a bicyclic-sesquiterpene as inuloxin A (6), a epipolythiopiperazine as gliotoxin (7) and a cyclohexene epoxide as epiepoformin (8), were tested for their effectiveness in reducing early stages of development of several major rust fungi from the genera Puccinia and Uromyces. Spore germination and appressoria formation were assessed on pre-treated detached leaves, under controlled conditions. Among the various metabolites evaluated, compounds 5 and 8 were the most effective in inhibiting fungal germination and penetration of all rust species studied at values comparable with those obtained by fungicide application, while compound 4 was phytotoxic to plant leaves at any concentration tested.
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In vitro growth inhibitory effects of Cytochalasins and derivatives in cancer cells.
Planta medica, 2010Co-Authors: Gwendoline Van Goietsenoven, Alessio Cimmino, Anna Andolfi, Véronique Mathieu, Florence Lefranc, Robert Kiss, Antonio EvidenteAbstract:The in vitro anticancer activity of eight natural Cytochalasins and three hemisynthetic derivatives of Cytochalasin B on six cancer cell lines was evaluated. The IC (50) in vitro growth inhibitory concentrations, as determined by an MTT colorimetric assay, ranged between 3 and 90 µM and did not relate to the intrinsic sensitivity of the cancer cell lines to proapoptotic stimuli. Structure activity relationship (SAR) analyses revealed that the presence of an unmodified hydroxyl group at C-7 of the perhydroisoinsolyl-1-one residue as well as the functionalities and the conformational freedom of the macrocycle are all important features for Cytochalasin-mediated anticancer activities in vitro. Computer-assisted phase-contrast microscopy revealed two groups of Cytochalasins, i.e., cytotoxic versus cytostatic ones. Our data open new possibilities for tuning Cytochalasin targets and developing nontoxic, cytostatic Cytochalasins to combat cancers associated with poor prognoses, such as those that display intrinsic resistance to proapoptotic stimuli.
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production of phytotoxins by phoma exigua var exigua a potential mycoherbicide against perennial thistles
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Alessio Cimmino, Anna Andolfi, Alexander Berestetskiy, Antonio EvidenteAbstract:The potential of the different Phoma exigua var. exigua strains for the biocontrol of the perennial weeds Sonchus arvensis and Cirsium arvense, occurring throughout temperate regions of the world, has been evaluated in previous studies. The majority of the above strains produced ascosonchine, a newly discovered enol tautomer of 4- pyridylpyruvic acid, whereas strains C-177 and S-9, though virulent to weeds, did not produce the above metabolite. In this study, it was demonstrated that the above two strains, grown in liquid and solid cultures, produced p-hydroxybenzaldehyde, Cytochalasins B, F, Z2 and Z3, and deoxaphomin. When assayed on the leaves of both C. arvense and S. arvensis, p-hydroxybenzaldehyde was inactive, whereas deoxaphomin demonstrated the highest level of toxicity on leaves of S. arvensis. Cytochalasin Z2 appeared to be the less toxic cytochalasan on both plants according to the lack of the secondary hydroxyl group on C-7. Production of Cytochalasins by P. exigua var. exigua strains isolated from C. arvense and S. arvensis is discussed in relation to chemotaxonomy and the biocontrol potential of the fungus.
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nonenolides and Cytochalasins with phytotoxic activity against cirsium arvense and sonchus arvensis a structure activity relationships study
Phytochemistry, 2008Co-Authors: Alexander Berestetskiy, Anna Andolfi, A I Dmitriev, Galina Mitina, Iosif Lisker, Antonio EvidenteAbstract:Abstract A structure–activity relationships study was conducted assaying 15 natural analogues and derivatives belonging to two groups of organic compounds, nonenolides and Cytochalasins, for their toxicity against the composite perennial weeds Cirsium arvense and Sonchus arvensis occurring through the temperate region of world. The toxic nonenolides (stagonolide, putaminoxin, pinolidoxin) and Cytochalasins (deoxaphomin, Cytochalasins A, B, F, T, Z2 and Z3) were isolated from phytopathogenic Stagonospora, Phoma and Ascochyta spp. The pinolidoxin (7,8-O,O′-diacetyl- and 7,8-O,O′-isopropylidene-pinolidoxin) and Cytochalasins B (21,22-dihydro-, 7-O-acetyl- and 7,20-O,O′-diacetyl-Cytochalasin B) derivatives were obtained by chemical modifications of the corresponding toxins. Among the 15 compounds tested, stagonolide and deoxaphomin proved to be the most phytotoxic to C. arvense and S. arvensis leaves, respectively. The tested phytotoxic nonenolides were stronger inhibitors of photosynthesis in C. arvense leaves than Cytochalasines A and B. Stagonolide had less effect on membrane permeability in C. arvense leaves than Cytochalasin B. Significant changes of light absorption by C. arvense leaves in visible and infrared spectra were caused by stagonolide. The functional groups and the conformational freedom of the ring, appear to be important structural features for the nonenolides toxicity, whereas and the presence of the hydroxy group at C-7, the functional group at C-20 and the conformational freedom of the macrocyclic ring are important for the Cytochalasins toxicity.
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Cytochalasins from Phoma exigua var. heteromorpha
Phytochemistry, 1991Co-Authors: Renato Capasso, Antonio Evidente, Maurizio VurroAbstract:Abstract Three further Cytochalasins from Phoma exigua var. heteromorpha , grown on wheat, were isolated and characterized by spectroscopic methods and by chemical correlation with Cytochalasin B. They were identified as Cytochalasin T, a new 24-oxa[14]cytochalasan, Cytochalasin F and 7- O -acetylCytochalasin B, both isolated for the first time from this fungus. Cytochalasin F showed significant activity in the brine shrimp assay and on tomato seedling growth.
Anna Andolfi - One of the best experts on this subject based on the ideXlab platform.
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In vitro growth inhibitory effects of Cytochalasins and derivatives in cancer cells.
Planta medica, 2010Co-Authors: Gwendoline Van Goietsenoven, Alessio Cimmino, Anna Andolfi, Véronique Mathieu, Florence Lefranc, Robert Kiss, Antonio EvidenteAbstract:The in vitro anticancer activity of eight natural Cytochalasins and three hemisynthetic derivatives of Cytochalasin B on six cancer cell lines was evaluated. The IC (50) in vitro growth inhibitory concentrations, as determined by an MTT colorimetric assay, ranged between 3 and 90 µM and did not relate to the intrinsic sensitivity of the cancer cell lines to proapoptotic stimuli. Structure activity relationship (SAR) analyses revealed that the presence of an unmodified hydroxyl group at C-7 of the perhydroisoinsolyl-1-one residue as well as the functionalities and the conformational freedom of the macrocycle are all important features for Cytochalasin-mediated anticancer activities in vitro. Computer-assisted phase-contrast microscopy revealed two groups of Cytochalasins, i.e., cytotoxic versus cytostatic ones. Our data open new possibilities for tuning Cytochalasin targets and developing nontoxic, cytostatic Cytochalasins to combat cancers associated with poor prognoses, such as those that display intrinsic resistance to proapoptotic stimuli.
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production of phytotoxins by phoma exigua var exigua a potential mycoherbicide against perennial thistles
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Alessio Cimmino, Anna Andolfi, Alexander Berestetskiy, Antonio EvidenteAbstract:The potential of the different Phoma exigua var. exigua strains for the biocontrol of the perennial weeds Sonchus arvensis and Cirsium arvense, occurring throughout temperate regions of the world, has been evaluated in previous studies. The majority of the above strains produced ascosonchine, a newly discovered enol tautomer of 4- pyridylpyruvic acid, whereas strains C-177 and S-9, though virulent to weeds, did not produce the above metabolite. In this study, it was demonstrated that the above two strains, grown in liquid and solid cultures, produced p-hydroxybenzaldehyde, Cytochalasins B, F, Z2 and Z3, and deoxaphomin. When assayed on the leaves of both C. arvense and S. arvensis, p-hydroxybenzaldehyde was inactive, whereas deoxaphomin demonstrated the highest level of toxicity on leaves of S. arvensis. Cytochalasin Z2 appeared to be the less toxic cytochalasan on both plants according to the lack of the secondary hydroxyl group on C-7. Production of Cytochalasins by P. exigua var. exigua strains isolated from C. arvense and S. arvensis is discussed in relation to chemotaxonomy and the biocontrol potential of the fungus.
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nonenolides and Cytochalasins with phytotoxic activity against cirsium arvense and sonchus arvensis a structure activity relationships study
Phytochemistry, 2008Co-Authors: Alexander Berestetskiy, Anna Andolfi, A I Dmitriev, Galina Mitina, Iosif Lisker, Antonio EvidenteAbstract:Abstract A structure–activity relationships study was conducted assaying 15 natural analogues and derivatives belonging to two groups of organic compounds, nonenolides and Cytochalasins, for their toxicity against the composite perennial weeds Cirsium arvense and Sonchus arvensis occurring through the temperate region of world. The toxic nonenolides (stagonolide, putaminoxin, pinolidoxin) and Cytochalasins (deoxaphomin, Cytochalasins A, B, F, T, Z2 and Z3) were isolated from phytopathogenic Stagonospora, Phoma and Ascochyta spp. The pinolidoxin (7,8-O,O′-diacetyl- and 7,8-O,O′-isopropylidene-pinolidoxin) and Cytochalasins B (21,22-dihydro-, 7-O-acetyl- and 7,20-O,O′-diacetyl-Cytochalasin B) derivatives were obtained by chemical modifications of the corresponding toxins. Among the 15 compounds tested, stagonolide and deoxaphomin proved to be the most phytotoxic to C. arvense and S. arvensis leaves, respectively. The tested phytotoxic nonenolides were stronger inhibitors of photosynthesis in C. arvense leaves than Cytochalasines A and B. Stagonolide had less effect on membrane permeability in C. arvense leaves than Cytochalasin B. Significant changes of light absorption by C. arvense leaves in visible and infrared spectra were caused by stagonolide. The functional groups and the conformational freedom of the ring, appear to be important structural features for the nonenolides toxicity, whereas and the presence of the hydroxy group at C-7, the functional group at C-20 and the conformational freedom of the macrocyclic ring are important for the Cytochalasins toxicity.
Maurizio Vurro - One of the best experts on this subject based on the ideXlab platform.
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Isolation of Cytochalasins A and B fromAscochyta lathyri.
Mycotoxin research, 1992Co-Authors: Maurizio Vurro, Renato Capasso, M. C. Zonno, And Antonio Evidente, A BottaiicoAbstract:The possible presence of toxic metabolites in the culture extracts of 24Ascochyta strains, grown on autoclaved wheat, was ascertained by the use of the biological assay on brine shrimps (Artemia salina). Only in the culture extract ofA lathyri, that showed a very high toxicity, the presence of Cytochalasins A and B was revealed by tlc,1H nmr and fab-mass spectra. SinceA heteromorpha, previously described as the firstAscochyta species to produce Cytochalasins, has been reclassified asPhoma exigua varheteromorpha, this is therefore the first report on the Cytochalasin production by a trueAscochyta species.
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Cytochalasins from Phoma exigua var. heteromorpha
Phytochemistry, 1991Co-Authors: Renato Capasso, Antonio Evidente, Maurizio VurroAbstract:Abstract Three further Cytochalasins from Phoma exigua var. heteromorpha , grown on wheat, were isolated and characterized by spectroscopic methods and by chemical correlation with Cytochalasin B. They were identified as Cytochalasin T, a new 24-oxa[14]cytochalasan, Cytochalasin F and 7- O -acetylCytochalasin B, both isolated for the first time from this fungus. Cytochalasin F showed significant activity in the brine shrimp assay and on tomato seedling growth.
Alexander Berestetskiy - One of the best experts on this subject based on the ideXlab platform.
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production of phytotoxins by phoma exigua var exigua a potential mycoherbicide against perennial thistles
Journal of Agricultural and Food Chemistry, 2008Co-Authors: Alessio Cimmino, Anna Andolfi, Alexander Berestetskiy, Antonio EvidenteAbstract:The potential of the different Phoma exigua var. exigua strains for the biocontrol of the perennial weeds Sonchus arvensis and Cirsium arvense, occurring throughout temperate regions of the world, has been evaluated in previous studies. The majority of the above strains produced ascosonchine, a newly discovered enol tautomer of 4- pyridylpyruvic acid, whereas strains C-177 and S-9, though virulent to weeds, did not produce the above metabolite. In this study, it was demonstrated that the above two strains, grown in liquid and solid cultures, produced p-hydroxybenzaldehyde, Cytochalasins B, F, Z2 and Z3, and deoxaphomin. When assayed on the leaves of both C. arvense and S. arvensis, p-hydroxybenzaldehyde was inactive, whereas deoxaphomin demonstrated the highest level of toxicity on leaves of S. arvensis. Cytochalasin Z2 appeared to be the less toxic cytochalasan on both plants according to the lack of the secondary hydroxyl group on C-7. Production of Cytochalasins by P. exigua var. exigua strains isolated from C. arvense and S. arvensis is discussed in relation to chemotaxonomy and the biocontrol potential of the fungus.
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nonenolides and Cytochalasins with phytotoxic activity against cirsium arvense and sonchus arvensis a structure activity relationships study
Phytochemistry, 2008Co-Authors: Alexander Berestetskiy, Anna Andolfi, A I Dmitriev, Galina Mitina, Iosif Lisker, Antonio EvidenteAbstract:Abstract A structure–activity relationships study was conducted assaying 15 natural analogues and derivatives belonging to two groups of organic compounds, nonenolides and Cytochalasins, for their toxicity against the composite perennial weeds Cirsium arvense and Sonchus arvensis occurring through the temperate region of world. The toxic nonenolides (stagonolide, putaminoxin, pinolidoxin) and Cytochalasins (deoxaphomin, Cytochalasins A, B, F, T, Z2 and Z3) were isolated from phytopathogenic Stagonospora, Phoma and Ascochyta spp. The pinolidoxin (7,8-O,O′-diacetyl- and 7,8-O,O′-isopropylidene-pinolidoxin) and Cytochalasins B (21,22-dihydro-, 7-O-acetyl- and 7,20-O,O′-diacetyl-Cytochalasin B) derivatives were obtained by chemical modifications of the corresponding toxins. Among the 15 compounds tested, stagonolide and deoxaphomin proved to be the most phytotoxic to C. arvense and S. arvensis leaves, respectively. The tested phytotoxic nonenolides were stronger inhibitors of photosynthesis in C. arvense leaves than Cytochalasines A and B. Stagonolide had less effect on membrane permeability in C. arvense leaves than Cytochalasin B. Significant changes of light absorption by C. arvense leaves in visible and infrared spectra were caused by stagonolide. The functional groups and the conformational freedom of the ring, appear to be important structural features for the nonenolides toxicity, whereas and the presence of the hydroxy group at C-7, the functional group at C-20 and the conformational freedom of the macrocyclic ring are important for the Cytochalasins toxicity.
Jin-ming Gao - One of the best experts on this subject based on the ideXlab platform.
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Cytochalasins and an abietane type diterpenoid with allelopathic activities from the endophytic fungus xylaria species
Journal of Agricultural and Food Chemistry, 2019Co-Authors: Wenbo Han, Jian Xiao, Gennaro Pescitelli, Yijie Zhai, Yuqi Gao, Huiyi Zhou, Jin-ming GaoAbstract:Bioactivity-guided isolation of the cultures of the endophytic fugus Xylaria sp. XC-16 residing in a deciduous tree Toona sinensis led to the discovery of four new allelochemicals (1-4), including three Cytochalasins, epoxyCytochalasin Z17 (1), epoxyCytochalasin Z8 (2), and epoxyrosellichalasin (3), and an abietane-type diterpenoid, hydroxyldecandrin G (4), along with four known analogues, 10-phenyl-[12]-Cytochalasins Z16 (5) and Z17 (6), Cytochalasin K (7), and Cytochalasin E (8). The structures of these compounds were elucidated by comprehensive spectroscopic methods, and their absolute configurations were determined by electronic circular dichroism (CD) and X-ray diffraction. All of the chemicals were tested for their allelopathic effects on turnip ( Raphanus sativus) and wheat ( Triticum aestivum). Notably, compounds 3, 4, and 7 strongly inhibited wheat shoot elongation, and compounds 5, 7, and 8 inhibited wheat root elongation, showing comparable IC50 values to the positive control glyphosate. Meanwhile, compound 8 was a potential inhibitor on turnip root elongation, with an IC50 value of 1.57 ± 0.21 μM, which was 50-fold more potent than glyphosate. Nevertheless, compounds 5 and 7 stimulated turnip shoot elongation at lower concentrations.
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Cytochalasins and an Abietane-Type Diterpenoid with Allelopathic Activities from the Endophytic Fungus Xylaria Species
2019Co-Authors: Wenbo Han, Jian Xiao, Gennaro Pescitelli, Yijie Zhai, Yuqi Gao, Huiyi Zhou, Jin-ming GaoAbstract:Bioactivity-guided isolation of the cultures of the endophytic fugus Xylaria sp. XC-16 residing in a deciduous tree Toona sinensis led to the discovery of four new allelochemicals (1–4), including three Cytochalasins, epoxyCytochalasin Z17 (1), epoxyCytochalasin Z8 (2), and epoxyrosellichalasin (3), and an abietane-type diterpenoid, hydroxyldecandrin G (4), along with four known analogues, 10-phenyl-[12]-Cytochalasins Z16 (5) and Z17 (6), Cytochalasin K (7), and Cytochalasin E (8). The structures of these compounds were elucidated by comprehensive spectroscopic methods, and their absolute configurations were determined by electronic circular dichroism (CD) and X-ray diffraction. All of the chemicals were tested for their allelopathic effects on turnip (Raphanus sativus) and wheat (Triticum aestivum). Notably, compounds 3, 4, and 7 strongly inhibited wheat shoot elongation, and compounds 5, 7, and 8 inhibited wheat root elongation, showing comparable IC50 values to the positive control glyphosate. Meanwhile, compound 8 was a potential inhibitor on turnip root elongation, with an IC50 value of 1.57 ± 0.21 μM, which was 50-fold more potent than glyphosate. Nevertheless, compounds 5 and 7 stimulated turnip shoot elongation at lower concentrations
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Characterization of Cytochalasins from the endophytic Xylaria sp. and their biological functions.
Journal of agricultural and food chemistry, 2014Co-Authors: Qiang Zhang, Jian Xiao, Qing-qing Sun, Jian-chun Qin, Gennaro Pescitelli, Jin-ming GaoAbstract:Bioassay-guided fractionation of the fermentation extract of Xylaria sp. XC-16, an endophyte from Toona sinensis led to the isolation of two new cytochalasans Cytochalasin Z27, 1, and Cytochalasin Z28, 2, along with three known compounds seco-Cytochalasin E, 3, and Cytochalasin Z18, 4, and Cytochalasin E, 5. The structures of 1 and 2 were elucidated by spectroscopic and electronic circular dichroism methods. Compound 5 was shown to be potently cytotoxic against brine shrimp (LC50 = 2.79 μM), comparable to that of the positive agent toosendanin (LC50 = 4.03 μM), and also exhibited potential phytotoxic effects on Lactuca sativa and Raphanus sativus L. seedlings, which are higher than that of the positive control glyphosate. Additionally, the fungicidal effect of 2 against the phytopathogen Gibberella saubinetti was better than that of hymexazol. This is the first report of the three types of Cytochalasins present in genus Xylaria. A structure–phytotoxicity activity relationship is also discussed.
