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Papers by Carlos Ferrayoli
… of pharmaceutical and …, 2004
A fast, reliable and specific method for the screening, confirmation, determination and quantitat... more A fast, reliable and specific method for the screening, confirmation, determination and quantitation of salbutamol enantiomers was developed and validated. The described procedure includes a single robust chiral HPLC determination employing a Teicoplanin ...
Bioscience, Biotechnology, and Biochemistry, 2002
Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitore... more Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitored by an insect antifeedant bioassay, led to the isolation of meliartenin, a limonoid antifeedant, which existed as a mixture of two interchangeable isomers. At 4 mg W cm 2 and 1 mg W cm 2 , the isomeric mixture was as active as azadirachtin in strongly inhibiting the larval feeding of Epilachna paenulata Germ. (Coleoptera: Coccinellidae) and the polyphagous pest, Spodoptera eridania (Lepidoptera: Noctuidae), respectively.
Journal of Agricultural and Food Chemistry, 2003
Extracts from different parts of Melia azedarach L. were studied as potential antifungal agents f... more Extracts from different parts of Melia azedarach L. were studied as potential antifungal agents for selected phytopathogenic fungi. In a serial agar dilution method, hexanic and ethanolic extracts from fruit, seed kernels, and senescent leaves exhibited fungistatic activity against Aspergillus flavus,Diaporthe phaseolorum var. meridionales, Fusarium oxysporum, Fusarium solani, Fusarium verticillioides, and Sclerotinia sclerotiorum. Both hexanic extract from senescent leaves and ethanolic extract from seed kernel were highly effective on all tested fungi, with minimum inhibitory concentration (MIC) values ranging from 0.5 to 25 mg/mL and 0.5 to 5 mg/mL, respectively. In addition, all of the above-mentioned extracts showed fungicidal activity on these fungi, with ethanolic seed kernel extract being the most active. Three compounds displaying activity against F. verticillioides were isolated from the ethanolic seed kernel extract and were characterized as vanillin (1), 4-hydroxy-3-meth...
Tetrahedron, May 21, 1993
The reaction of 1-chloronaphthalenewith acetone (Za) and acetophenone (Zb) enolate ions was initi... more The reaction of 1-chloronaphthalenewith acetone (Za) and acetophenone (Zb) enolate ions was initiated by sodium amalgam [Na(Hg)] in liquid ammonia giving good yields of the substitution products 3a and 3b respectively. P-Chloroguinoline and 2-chloropyridine gave good yields of substitution product with Zb, and moderate to good yields with 2a. 4-Bromobeneophenone and la gave 78% of the substitution product 5. With aryl halides whose radical anions fragment fast and consequently close to the Na(Hg) surface, such as bromobenxene and p-bromoanisole, only dehalogenationptoducts were observed. However, when bensonitrile was used as a redox catalyst, about 50% of the substitution product 6 was obtained with p-bromoaniaole and 2a. However, with the more reactive carbanionic nucleophile, such as anthrone anion 4, good yields of the substitution product 7 were obtained with bromobenzene. In all these reactions neither reduction of the aromatic moiety nor the ketone functionality was observed. It is therefore suggested that Na(Hg) amalgam initiates these S%,,l reactions. The aromatic radical nucleophilic substitution, or Sm,l, has been shown to be an excellent means of affecting the nucleophilic substitution of unactivated aromatic compounds possessing suitable leaving groups. The mechanism of the reaction is a chain process, and the propagation steps are shown in Scheme I.' Scheme I depicts a nucleophilic substitution in which radicals and radical anions are intermediates. However, this chain process requires an initiation step. In a few systems, spontaneous electron transfer (ET) from the nucleophile to the substrate has been observed.3 When ET does not occur spontaneously, it can be induced by light,4 by solvated electrons in liquid aavaonia,' by cathodically generated electrons,6 or by certain inorganic salts.'
Journal of Agricultural and Food Chemistry, 2005
In the continuous search for antifungal compounds from plants, the hydroxycoumarin scopoletin (1)... more In the continuous search for antifungal compounds from plants, the hydroxycoumarin scopoletin (1) was isolated from seed kernels of Melia azedarach L. from which three other compounds, vanillin (2), 4-hydroxy-3-methoxycinnamaldehyde (3), and (+/-) pinoresinol (4), have also been isolated. Guided fractionation through autobiography on TLC using Fusarium verticillioides (Saccardo) Nirenberg as test organism led to the isolation of 1, which exhibited a minimum inhibitory concentration (MIC) of 1.50 mg/mL in the microbroth dilution method. Despite its own weak activity, when the coumarin was combined with the above-mentioned compounds, a strong enhancement of the antifungal effect was observed, even showing a complete inhibition in the growth of the pathogen when 1 was added at a concentration of up to 5% of its MIC value. The same level of effectiveness was observed when the synthetic antifungal agents Mancozeb and Carboxin were each combined with compounds 1-4, in which cases it became possible to decrease the effective concentrations of these commercial compounds by up to 2.5 and 3%, respectively.
Bioscience, …, 2002
Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitore... more Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitored by an insect antifeedant bioassay, led to the isolation of meliartenin, a limonoid antifeedant, which existed as a mixture of two interchangeable isomers. At 4 μg/cm 2 and ...
Journal of chemical …, 2005
Journal of the American …, 2007
Phytochemistry, 2017
Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, aga... more Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination (ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum (monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum (ECg50 = 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulating the root growth of P. miliaceum seedlings, with an ECr50 of 1.0 mM. Char...
Fitoterapia, 2007
Aerial parts of 27 plant species native to Argentina were tested in anti-insect, germination inhi... more Aerial parts of 27 plant species native to Argentina were tested in anti-insect, germination inhibition and bactericide bio-assays. In antifeedant assays on Epilachna paenulata larvae, 11 species showed strong feeding deterrent effects (higher than 90% at 200 μg/cm 2 ). Twelve plants strongly inhibited the germination of Avena sativa seeds, but only six inhibited Raphanus sativum germination at 10 mg/ml. Four plants showed complete growth inhibition of Escherichia coli at a concentration of 2 mg/ml.
… of pharmaceutical and …, 2004
A fast, reliable and specific method for the screening, confirmation, determination and quantitat... more A fast, reliable and specific method for the screening, confirmation, determination and quantitation of salbutamol enantiomers was developed and validated. The described procedure includes a single robust chiral HPLC determination employing a Teicoplanin ...
Bioscience, Biotechnology, and Biochemistry, 2002
Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitore... more Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitored by an insect antifeedant bioassay, led to the isolation of meliartenin, a limonoid antifeedant, which existed as a mixture of two interchangeable isomers. At 4 mg W cm 2 and 1 mg W cm 2 , the isomeric mixture was as active as azadirachtin in strongly inhibiting the larval feeding of Epilachna paenulata Germ. (Coleoptera: Coccinellidae) and the polyphagous pest, Spodoptera eridania (Lepidoptera: Noctuidae), respectively.
Journal of Agricultural and Food Chemistry, 2003
Extracts from different parts of Melia azedarach L. were studied as potential antifungal agents f... more Extracts from different parts of Melia azedarach L. were studied as potential antifungal agents for selected phytopathogenic fungi. In a serial agar dilution method, hexanic and ethanolic extracts from fruit, seed kernels, and senescent leaves exhibited fungistatic activity against Aspergillus flavus,Diaporthe phaseolorum var. meridionales, Fusarium oxysporum, Fusarium solani, Fusarium verticillioides, and Sclerotinia sclerotiorum. Both hexanic extract from senescent leaves and ethanolic extract from seed kernel were highly effective on all tested fungi, with minimum inhibitory concentration (MIC) values ranging from 0.5 to 25 mg/mL and 0.5 to 5 mg/mL, respectively. In addition, all of the above-mentioned extracts showed fungicidal activity on these fungi, with ethanolic seed kernel extract being the most active. Three compounds displaying activity against F. verticillioides were isolated from the ethanolic seed kernel extract and were characterized as vanillin (1), 4-hydroxy-3-meth...
Tetrahedron, May 21, 1993
The reaction of 1-chloronaphthalenewith acetone (Za) and acetophenone (Zb) enolate ions was initi... more The reaction of 1-chloronaphthalenewith acetone (Za) and acetophenone (Zb) enolate ions was initiated by sodium amalgam [Na(Hg)] in liquid ammonia giving good yields of the substitution products 3a and 3b respectively. P-Chloroguinoline and 2-chloropyridine gave good yields of substitution product with Zb, and moderate to good yields with 2a. 4-Bromobeneophenone and la gave 78% of the substitution product 5. With aryl halides whose radical anions fragment fast and consequently close to the Na(Hg) surface, such as bromobenxene and p-bromoanisole, only dehalogenationptoducts were observed. However, when bensonitrile was used as a redox catalyst, about 50% of the substitution product 6 was obtained with p-bromoaniaole and 2a. However, with the more reactive carbanionic nucleophile, such as anthrone anion 4, good yields of the substitution product 7 were obtained with bromobenzene. In all these reactions neither reduction of the aromatic moiety nor the ketone functionality was observed. It is therefore suggested that Na(Hg) amalgam initiates these S%,,l reactions. The aromatic radical nucleophilic substitution, or Sm,l, has been shown to be an excellent means of affecting the nucleophilic substitution of unactivated aromatic compounds possessing suitable leaving groups. The mechanism of the reaction is a chain process, and the propagation steps are shown in Scheme I.' Scheme I depicts a nucleophilic substitution in which radicals and radical anions are intermediates. However, this chain process requires an initiation step. In a few systems, spontaneous electron transfer (ET) from the nucleophile to the substrate has been observed.3 When ET does not occur spontaneously, it can be induced by light,4 by solvated electrons in liquid aavaonia,' by cathodically generated electrons,6 or by certain inorganic salts.'
Journal of Agricultural and Food Chemistry, 2005
In the continuous search for antifungal compounds from plants, the hydroxycoumarin scopoletin (1)... more In the continuous search for antifungal compounds from plants, the hydroxycoumarin scopoletin (1) was isolated from seed kernels of Melia azedarach L. from which three other compounds, vanillin (2), 4-hydroxy-3-methoxycinnamaldehyde (3), and (+/-) pinoresinol (4), have also been isolated. Guided fractionation through autobiography on TLC using Fusarium verticillioides (Saccardo) Nirenberg as test organism led to the isolation of 1, which exhibited a minimum inhibitory concentration (MIC) of 1.50 mg/mL in the microbroth dilution method. Despite its own weak activity, when the coumarin was combined with the above-mentioned compounds, a strong enhancement of the antifungal effect was observed, even showing a complete inhibition in the growth of the pathogen when 1 was added at a concentration of up to 5% of its MIC value. The same level of effectiveness was observed when the synthetic antifungal agents Mancozeb and Carboxin were each combined with compounds 1-4, in which cases it became possible to decrease the effective concentrations of these commercial compounds by up to 2.5 and 3%, respectively.
Bioscience, …, 2002
Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitore... more Systematic fractionation of a fruit extract from Argentine Melia azedarach L., which was monitored by an insect antifeedant bioassay, led to the isolation of meliartenin, a limonoid antifeedant, which existed as a mixture of two interchangeable isomers. At 4 μg/cm 2 and ...
Journal of chemical …, 2005
Journal of the American …, 2007
Phytochemistry, 2017
Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, aga... more Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination (ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum (monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum (ECg50 = 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulating the root growth of P. miliaceum seedlings, with an ECr50 of 1.0 mM. Char...
Fitoterapia, 2007
Aerial parts of 27 plant species native to Argentina were tested in anti-insect, germination inhi... more Aerial parts of 27 plant species native to Argentina were tested in anti-insect, germination inhibition and bactericide bio-assays. In antifeedant assays on Epilachna paenulata larvae, 11 species showed strong feeding deterrent effects (higher than 90% at 200 μg/cm 2 ). Twelve plants strongly inhibited the germination of Avena sativa seeds, but only six inhibited Raphanus sativum germination at 10 mg/ml. Four plants showed complete growth inhibition of Escherichia coli at a concentration of 2 mg/ml.