7 results on '"Fabrizio Freda"'
Search Results
2. Phytotoxic Activity and Structure–Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)
- Author
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Marco Masi, Fabrizio Freda, Suzette Clement, Alessio Cimmino, Massimo Cristofaro, Susan Meyer, and Antonio Evidente
- Subjects
buffelgrass ,Cochliobolus australiensis ,radicinin ,derivatives ,SAR ,leaf puncture bioassay ,phytotoxicity ,Organic chemistry ,QD241-441 - Abstract
Radicinin (1), is a fungal dihydropyranopyran-4,5-dione isolated together with some analogues, namely 3-epi-radicinin, radicinol, 3-epi-radicinol, and cochliotoxin (2−5), from the culture filtrates of the fungus Cochliobolus australiensis, a foliar pathogen of buffelgrass (Cenchrus ciliaris), an invasive weed in North America. Among the different metabolites 1 showed target-specific activity against the host plant and no toxicity on zebrafish embryos, promoting its potential use to develop a natural bioherbicide formulation to manage buffelgrass. These data and the peculiar structural feature of 1 suggested to carry out a structure-activity relationship study, preparing some key hemisynthetic derivatives and to test their phytotoxicity. In particular, p-bromobenzoyl, 5-azidopentanoyl, stearoyl, mesyl and acetyl esters of radicinin were semisynthesized as well as the monoacetyl ester of 3-epi-radicinin, the diacetyl esters of radicinol and its 3 epimer, and two hexa-hydro derivatives of radicinin. The spectroscopic characterization and the activity by leaf puncture bioassay against buffelgrass of all the derivatives is reported. Most of the compounds showed phytotoxicity but none of them had comparable or higher activity than radicinin. Thus, the presence of an α,β unsaturated carbonyl group at C-4, as well as, the presence of a free secondary hydroxyl group at C-3 and the stereochemistry of the same carbon proved to be the essential feature for activity.
- Published
- 2019
- Full Text
- View/download PDF
3. Radicinin, a Fungal Phytotoxin as a Target-Specific Bioherbicide for Invasive Buffelgrass (Cenchrus ciliaris) Control
- Author
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Marco Masi, Fabrizio Freda, Felicia Sangermano, Viola Calabrò, Alessio Cimmino, Massimo Cristofaro, Susan Meyer, and Antonio Evidente
- Subjects
buffelgrass ,foliar pathogens ,Cochliobolus australiensis ,Pyricularia grisea ,phytotoxins ,epi-pyriculol ,radicinin ,Organic chemistry ,QD241-441 - Abstract
The fungal pathogens Cochliobolus australiensis and Pyricularia grisea have recently been isolated from diseased leaves of buffelgrass (Cenchrus ciliaris) in its North American range, and their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides against this invasive weed was investigated. Fourteen secondary metabolites obtained from in vitro cultures of these two pathogens were tested by leaf puncture assay on the host plant at different concentrations. Radicinin and (10S, 11S)-epi-pyriculol proved to be the most promising compounds. Thus, their phytotoxic activity was also evaluated on non-host indigenous plants. Radicinin demonstrated high target-specific toxicity on buffelgrass, low toxicity to native plants, and no teratogenic, sub-lethal, or lethal effects on zebrafish (Brachydanio rerio) embryos. It is now under consideration for the development of a target-specific bioherbicide to be used against buffelgrass in natural systems where synthetic herbicides cause excessive damage to native plants.
- Published
- 2019
- Full Text
- View/download PDF
4. Synthesis and Herbicidal Activity Against Buffelgrass (Cenchrus ciliaris) of (±)-3-deoxyradicinin
- Author
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Marco Masi, Maria Sabrina Ciccone, Antonio Evidente, Fabrizio Freda, Patrizia Scafato, Giulia Marsico, Massimo Cristofaro, Stefano Superchi, Marsico, G., Ciccone, M. S., Masi, M., Freda, F., Cristofaro, M., Evidente, A., Superchi, S., and Scafato, P.
- Subjects
0106 biological sciences ,buffelgrass ,(±)-3-deoxyradicinin ,Pharmaceutical Science ,01 natural sciences ,Article ,Deoxyradicinin ,Analytical Chemistry ,lcsh:QD241-441 ,phytotoxins ,Phytotoxin ,lcsh:Organic chemistry ,Cenchrus ciliaris ,bioherbicides ,Drug Discovery ,Physical and Theoretical Chemistry ,Buffelgra ,biology ,Herbicides ,010405 organic chemistry ,Cenchrus ,Organic Chemistry ,biology.organism_classification ,0104 chemical sciences ,radicinin ,Agronomy ,Pyrones ,Bioherbicides ,Buffelgrass ,Phytotoxins ,Radicinin ,Chemistry (miscellaneous) ,Molecular Medicine ,Phytotoxicity ,Bioherbicide ,010606 plant biology & botany - Abstract
A novel synthetic strategy for obtainment of (±, )-3-deoxyradicinin (2) is reported. This synthetic methodology is more efficient than those previously reported in the literature and also shows higher versatility towards the introduction of different side-chains at both C-7 and C-2. The obtained compound (±, )-2 shows phytotoxicity against the grass-weed buffelgrass comparable to that of the natural phytotoxin radicinin (1). Therefore, (±, )-2 can constitute a more practical synthetic alternative to 1 as bioherbicide for buffelgrass control.
- Published
- 2019
- Full Text
- View/download PDF
5. Phytotoxic Activity and Structure-Activity Relationships of Radicinin Derivatives against the Invasive Weed Buffelgrass (Cenchrus ciliaris)
- Author
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Fabrizio Freda, Susan E. Meyer, Marco Masi, Suzette Clement, Alessio Cimmino, Massimo Cristofaro, Antonio Evidente, Masi, M., Freda, F., Clement, S., Cimmino, A., Cristofaro, M., Meyer, S., and Evidente, A.
- Subjects
Pharmaceutical Science ,Plant Weeds ,phytotoxicity ,01 natural sciences ,Analytical Chemistry ,chemistry.chemical_compound ,Drug Discovery ,Alkaloid ,Bioassay ,Toxins ,biology ,Molecular Structure ,Chemistry ,Cenchrus ,Cochliobolus australiensis ,leaf puncture bioassay ,Chemistry (miscellaneous) ,Cochliobolus australiensi ,Molecular Medicine ,Phytotoxicity ,Epimer ,Mitosporic Fungi ,Bioherbicide ,SAR ,buffelgrass ,derivatives ,radicinin ,Alkaloids ,Ascomycota ,North America ,Pyrones ,Toxins, Biological ,Structure-Activity Relationship ,Cenchru ,Fungus ,010402 general chemistry ,Article ,lcsh:QD241-441 ,Cenchrus ciliaris ,lcsh:Organic chemistry ,Botany ,derivative ,Physical and Theoretical Chemistry ,Pyrone ,Plant Weed ,010405 organic chemistry ,Organic Chemistry ,buffelgra ,biology.organism_classification ,Biological ,Diacetyl ,0104 chemical sciences ,Weed - Abstract
Radicinin (1), is a fungal dihydropyranopyran-4,5-dione isolated together with some analogues, namely 3-epi-radicinin, radicinol, 3-epi-radicinol, and cochliotoxin (2&ndash, 5), from the culture filtrates of the fungus Cochliobolus australiensis, a foliar pathogen of buffelgrass (Cenchrus ciliaris), an invasive weed in North America. Among the different metabolites 1 showed target-specific activity against the host plant and no toxicity on zebrafish embryos, promoting its potential use to develop a natural bioherbicide formulation to manage buffelgrass. These data and the peculiar structural feature of 1 suggested to carry out a structure-activity relationship study, preparing some key hemisynthetic derivatives and to test their phytotoxicity. In particular, p-bromobenzoyl, 5-azidopentanoyl, stearoyl, mesyl and acetyl esters of radicinin were semisynthesized as well as the monoacetyl ester of 3-epi-radicinin, the diacetyl esters of radicinol and its 3 epimer, and two hexa-hydro derivatives of radicinin. The spectroscopic characterization and the activity by leaf puncture bioassay against buffelgrass of all the derivatives is reported. Most of the compounds showed phytotoxicity but none of them had comparable or higher activity than radicinin. Thus, the presence of an &alpha, &beta, unsaturated carbonyl group at C-4, as well as, the presence of a free secondary hydroxyl group at C-3 and the stereochemistry of the same carbon proved to be the essential feature for activity.
- Published
- 2019
6. Radicinin, a fungal phytotoxin as a target-specific bioherbicide for invasive buffelgrass (cenchrus ciliaris) control
- Author
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Felicia Sangermano, Massimo Cristofaro, Susan E. Meyer, Marco Masi, Fabrizio Freda, Viola Calabrò, Alessio Cimmino, Antonio Evidente, Masi, Marco, Freda, Fabrizio, Sangermano, Felicia, Calabrò, Viola, Cimmino, Alessio, Cristofaro, Massimo, Meyer, Susan, Evidente, Antonio, Masi, M., Freda, F., Sangermano, F., Calabro, V., Cimmino, A., Cristofaro, M., Meyer, S., and Evidente, A.
- Subjects
Embryo, Nonmammalian ,Pharmaceutical Science ,Cochliobolus australiensis ,Fatty Alcohol ,01 natural sciences ,Analytical Chemistry ,Drug Discovery ,Phytotoxins ,Zebrafish ,Buffelgra ,Nonmammalian ,biology ,Cenchrus ,food and beverages ,Native plant ,Embryo ,Chemistry (miscellaneous) ,Benzaldehydes ,Toxicity ,Cochliobolus australiensi ,Molecular Medicine ,Herbicide ,Fatty Alcohols ,Bioherbicide ,Pyricularia grisea ,Radicinin ,Cenchru ,Buffelgrass ,epi-pyriculol ,lcsh:QD241-441 ,Phytotoxin ,lcsh:Organic chemistry ,Cenchrus ciliaris ,Botany ,Foliar pathogens ,Animals ,Physical and Theoretical Chemistry ,Pyrone ,Foliar pathogen ,010405 organic chemistry ,Animal ,Herbicides ,Drug Discovery3003 Pharmaceutical Science ,fungi ,Epi-pyriculol ,Organic Chemistry ,Benzaldehyde ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Pyrones ,Weed - Abstract
The fungal pathogens Cochliobolus australiensis and Pyricularia grisea have recently been isolated from diseased leaves of buffelgrass (Cenchrus ciliaris) in its North American range, and their ability to produce phytotoxic metabolites that could potentially be used as natural herbicides against this invasive weed was investigated. Fourteen secondary metabolites obtained from in vitro cultures of these two pathogens were tested by leaf puncture assay on the host plant at different concentrations. Radicinin and (10S, 11S)-epi-pyriculol proved to be the most promising compounds. Thus, their phytotoxic activity was also evaluated on non-host indigenous plants. Radicinin demonstrated high target-specific toxicity on buffelgrass, low toxicity to native plants, and no teratogenic, sub-lethal, or lethal effects on zebrafish (Brachydanio rerio) embryos. It is now under consideration for the development of a target-specific bioherbicide to be used against buffelgrass in natural systems where synthetic herbicides cause excessive damage to native plants.
- Published
- 2019
7. α-Costic acid, a plant sesquiterpene with acaricidal activity against Varroa destructor parasitizing the honey bee
- Author
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Antonio Evidente, Ernesto Santoro, Alessio Cimmino, Fabrizio Freda, Massimo Cristofaro, Marco Masi, Stefano Superchi, Cimmino, A., Freda, F., Santoro, E., Superchi, S., Evidente, A., Cristofaro, M., Masi, M., Cimmino, Alessio, Freda, Fabrizio, Santoro, Ernesto, Superchi, Stefano, Evidente, Antonio, Cristofaro, Massimo, and Masi, Marco
- Subjects
sesquiterpene ,Perennial plant ,Plant Science ,Biology ,Sesquiterpene ,01 natural sciences ,Biochemistry ,Mediterranean Basin ,Analytical Chemistry ,α-costic acid ,chemistry.chemical_compound ,sesquiterpenes ,Botany ,Dittrichia viscosa ,Parasite hosting ,absolute configuration ,acaricidal activity ,chiroptical spectroscopy ,Varroa destructor ,010405 organic chemistry ,Organic Chemistry ,fungi ,food and beverages ,Honey bee ,Native plant ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,chemistry - Abstract
The organic extract of the aerial parts of Dittrichia viscosa, a perennial native plant of the Mediterranean basin, showed a significant acaricidal activity against Varroa destructor, the parasite mite of Apis mellifera, commonly called honey bee. Among the metabolites isolated from the organic extract of this Asteraceae, α-costic acid showed to be one of the compounds responsible for the toxic activity exhibited by the crude plant extract on this parasite mite species. In addition to the toxic effect a clear acaricidal response has been recorded when the parasitic mite was exposed to 1 mg/mL concentration of α-costic acid while no effects have been showed on honey bees using the same compound at the same concentration. This finding suggests a potential use of α-costic acid to control Varroa mites. The possibility to reliably achieve absolute configuration of α-costic acid by DFT computational analysis of chiroptical spectra has been also demonstrated.†
- Published
- 2019
- Full Text
- View/download PDF
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