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22 results on '"Pollastro, Federica"'

2. Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology

Author

Schafroth, Michael A., primary, Mazzoccanti, Giulia, additional, Reynoso-Moreno, Ines, additional, Erni, Reto, additional, Pollastro, Federica, additional, Caprioglio, Diego, additional, Botta, Bruno, additional, Allegrone, Gianna, additional, Grassi, Giulio, additional, Chicca, Andrea, additional, Gasparrini, Francesco, additional, Gertsch, Jürg, additional, Carreira, Erick M., additional, and Appendino, Giovanni, additional

Published
2021
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3. Correction to Anti-inflammatory Activity of Absinthin and Derivatives in Human Broncho-Epithelial Cells

Author

Talmon, Maria, primary, Bosso, Lorenza, additional, Quaregna, Martina, additional, Lopatriello, Annalisa, additional, Rossi, Silvia, additional, Gavioli, Daniele, additional, Marotta, Patrizia, additional, Caprioglio, Diego, additional, Boldorini, Renzo, additional, Miggiano, Riccardo, additional, Fresu, Luigia G., additional, and Pollastro, Federica, additional

Published
2020
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4. Anti-inflammatory Activity of Absinthin and Derivatives in Human Bronchoepithelial Cells

Author

Talmon, Maria, primary, Bosso, Lorenza, additional, Quaregna, Martina, additional, Lopatriello, Annalisa, additional, Rossi, Silvia, additional, Gavioli, Daniele, additional, Marotta, Patrizia, additional, Caprioglio, Diego, additional, Boldorini, Renzo, additional, Miggiano, Riccardo, additional, Fresu, Luigia G., additional, and Pollastro, Federica, additional

Published
2020
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5. The Oxidation of Phytocannabinoids to Cannabinoquinoids

Author

Caprioglio, Diego, primary, Mattoteia, Daiana, additional, Pollastro, Federica, additional, Negri, Roberto, additional, Lopatriello, Annalisa, additional, Chianese, Giuseppina, additional, Minassi, Alberto, additional, Collado, Juan A., additional, Munoz, Eduardo, additional, Taglialatela-Scafati, Orazio, additional, and Appendino, Giovanni, additional

Published
2020
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12. STAT-3 Inhibitory Bisabolanes from Carthamus glaucus

Author

Taglialatela-Scafati, Orazio, primary, Pollastro, Federica, additional, Cicione, Lavinia, additional, Chianese, Giuseppina, additional, Bellido, Maria Luz, additional, Munoz, Eduardo, additional, Özen, Hasan Çetin, additional, Toker, Zuhal, additional, and Appendino, Giovanni, additional

Published
2012
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16. Antimicrobial Phenolics and Unusual Glycerides from Helichrysum italicumsubsp. microphyllum

Author

Taglialatela-Scafati, Orazio, Pollastro, Federica, Chianese, Giuseppina, Minassi, Alberto, Gibbons, Simon, Arunotayanun, Warunya, Mabebie, Blessing, Ballero, Mauro, and Appendino, Giovanni

Abstract

During a large-scale isolation campaign for the heterodimeric phloroglucinyl pyrone arzanol (1a) from Helichrysum italicumsubsp. microphyllum, several new phenolics as well as an unusual class of lipids named santinols (5a–c, 6–8) have been characterized. Santinols are angeloylated glycerides characterized by the presence of branched acyl- or keto-acyl chains and represent a hitherto unreported class of plant lipids. The antibacterial activity of arzanol and of a selection of Helichrysumphenolics that includes coumarates, benzofurans, pyrones, and heterodimeric phloroglucinols was evaluated, showing that only the heterodimers showed potent antibacterial action against multidrug-resistant Staphylococcus aureusisolates. These observations validate the topical use of Helichrysumextracts to prevent wound infections, a practice firmly established in the traditional medicine of the Mediterranean area.

Published
2013
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17. Genepolide, a Sesterpene γ-Lactone with a Novel Carbon Skeleton from Mountain Wormwood (Artemisia umbelliformis)⊥

Author

Appendino, Giovanni, Taglialatela-Scafati, Orazio, Romano, Adriana, Pollastro, Federica, Avonto, Cristina, and Rubiolo, Patrizia

Abstract

The sesterpene γ-lactone genepolide (5) has been isolated from a Swiss horticultural variety of mountain wormwood (Artemisia umbelliformis) developed as a thujones-free alternative to native Western Alps wormwoods for the production of liqueurs. Genepolide is the formal Diels−Alder adduct of the exomethylene-γ-lactone costunolide (2) and the diene myrcene (6), two poorly reactive partners in cycloaddition reactions, and its structure was elucidated through a combination of spectroscopic methods. An investigation on the thermal stability of mixtures of 2and 6, as well as considerations on the sensitivity of 2to Brønsted and Lewis acids, suggests that 5is a genuine natural product and that the Swiss chemotype of A. umbelliformiscontains Diels−Alderase enzymatic activity that is lacking in native mountain wormwoods from Western Alps. Remarkable differences in thermal and acid-catalyzed reactions of the cyclodecadiene moiety of 2and 5suggest that quaternarization at C-11 has far-reaching effects on the reactivity of their homoconjugated medium-sized diene system. The wide occurrence of this structural motif in sesquiterpenoids makes this issue worth a systematic investigation.

Published
2009
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18. Turmeric Sesquiterpenoids: Expeditious Resolution, Comparative Bioactivity, and a New Bicyclic Turmeronoid

Author

Giovanni Appendino, Danilo Del Prete, Orazio Taglialatela-Scafati, Estrella Millán, Eduardo Muñoz, Federica Pollastro, Paolo Luciano, Juan A. Collado, Giuseppina Chianese, Del Prete, Danilo, Millán, Estrella, Pollastro, Federica, Chianese, Giuseppina, Luciano, Paolo, Collado, Juan A., Munoz, Eduardo, Appendino, Giovanni, and TAGLIALATELA SCAFATI, Orazio

Subjects
STAT3 Transcription Factor, Curcumin, Resolution (mass spectrometry), Anti-Inflammatory Agents, Pharmaceutical Science, 010402 general chemistry, 01 natural sciences, Analytical Chemistry, Comparative evaluation, chemistry.chemical_compound, Mice, Structure-Activity Relationship, Bicycloturmeronol, Curcuma, Drug Discovery, Organic chemistry, Animals, Humans, Luciferases, Pharmacology, Bicyclic molecule, biology, Molecular Structure, 010405 organic chemistry, Tumor Necrosis Factor-alpha, Organic Chemistry, NF-kappa B, biology.organism_classification, 0104 chemical sciences, Rhizome, Complementary and alternative medicine, chemistry, Italy, TURMERIC OIL, Indonesia, turmerone, anti-inflammatory, bisabolane, NF-kB, STAT3, NIH 3T3 Cells, Molecular Medicine, Sesquiterpenes, HeLa Cells
Abstract

An expeditious strategy to resolve turmerone, the lipophilic anti-inflammatory principle of turmeric (Curcuma longa), into its individual bisabolane constituents (ar-, α-, and β-turmerones, 2-4, respectively) was developed. The comparative evaluation of these compounds against a series of anti-inflammatory targets (NF-κB, STAT3, Nrf2, HIF-1α) evidenced surprising differences, providing a possible explanation for the contrasting data on the activity of turmeric oil. Differences were also evidenced in the profile of more polar bisabolanes between the Indian and the Javanese samples used to obtain turmerone, and a novel hydroxylated bicyclobisabolane ketol (bicycloturmeronol, 8) was obtained from a Javanese sample of turmeric. Taken together, these data support the view that bisabolane sesquiterpenes represent an important taxonomic marker for turmeric and an interesting class of anti-inflammatory agents, whose strict structure-activity relationships are worth a systematic evaluation.

Published
2016

19. Δ 9 - cis -Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology.

Author

Schafroth MA, Mazzoccanti G, Reynoso-Moreno I, Erni R, Pollastro F, Caprioglio D, Botta B, Allegrone G, Grassi G, Chicca A, Gasparrini F, Gertsch J, Carreira EM, and Appendino G

Subjects
Animals, Cannabis chemistry, Dronabinol chemistry, Male, Mice, Mice, Inbred BALB C, Molecular Structure, Stereoisomerism, Cannabinoids agonists, Dronabinol pharmacology
Abstract

The cis -stereoisomers of Δ 9 -THC [(-)- 3 and (+)- 3 ] were identified and quantified in a series of low-THC-containing varieties of Cannabis sativa registered in Europe as fiber hemp and in research accessions of cannabis. While Δ 9 - cis -THC ( 3 ) occurs in cannabis fiber hemp in the concentration range of (-)-Δ 9 - trans -THC [(-)- 1 ], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural Δ 9 - cis -THC ( 3 ) is scalemic (ca. 80-90% enantiomeric purity), and the absolute configuration of the major enantiomer was established as 6a S ,10a R [(-)- 3 ] by chiral chromatographic comparison with a sample available by asymmetric synthesis. The major enantiomer, (-)-Δ 9 - cis -THC [(-)- 3 ], was characterized as a partial cannabinoid agonist in vitro and elicited a full tetrad response in mice at 50 mg/kg doses. The current legal discrimination between narcotic and non-narcotic cannabis varieties centers on the contents of "Δ 9 -THC and isomers" and needs therefore revision, or at least a more specific wording, to account for the presence of Δ 9 - cis -THCs [(+)- 3 and (-)- 3 ] in cannabis fiber hemp varieties.

Published
2021
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20. Iodine-Promoted Aromatization of p-Menthane-Type Phytocannabinoids.

Author

Pollastro F, Caprioglio D, Marotta P, Moriello AS, De Petrocellis L, Taglialatela-Scafati O, and Appendino G

Subjects
Cannabidiol chemistry, Cannabidiol pharmacology, Cannabinoid Receptor Agonists pharmacology, Cannabinoids chemistry, Cannabinoids pharmacology, Cannabinol chemistry, Cannabinol pharmacology, Cannabis chemistry, Cell Line, Dronabinol chemistry, Dronabinol pharmacology, HEK293 Cells, Humans, TRPA1 Cation Channel metabolism, TRPV Cation Channels metabolism, Cannabinoid Receptor Agonists chemistry, Iodine chemistry
Abstract

Treatment with iodine cleanly converts various p-menthane-type phytocannabinoids and their carboxylated precursors into cannabinol (CBN, 1a). The reaction is superior to previously reported protocols in terms of simplicity and substrate range, which includes not only tricyclic tetrahydrocannabinols such as Δ 9 -THC (2a) but also bicyclic phytocannabinoids such as cannabidiol (CBD, 3a). Lower homologues from the viridin series (2c and 3c, respectively) afforded cannabivarin (CBV), a non-narcotic compound that, when investigated against a series of ionotropic (thermo-TRPs) biological end-points of phytocannabinoids, retained the submicromolar TRPA1-activating and TRPM8-inhibiting properties of CBN, while also potently activating TRPV2. Treatment with iodine provides an easy access to CBN (1a) from crude extracts and side-cuts of the purification of Δ 9 -THC and CBD from respectively narcotic Cannabis sativa (marijuana) and fiber hemp, substantially expanding the availability of this compound and, in the case of fiber hemp, dissecting it from narcotic phytocannabinoids.

Published
2018
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21. Antimicrobial phenolics and unusual glycerides from Helichrysum italicum subsp. microphyllum.

Author

Taglialatela-Scafati O, Pollastro F, Chianese G, Minassi A, Gibbons S, Arunotayanun W, Mabebie B, Ballero M, and Appendino G

Subjects
Anti-Bacterial Agents chemistry, Glycerides chemistry, Mediterranean Region, Methicillin-Resistant Staphylococcus aureus drug effects, Microbial Sensitivity Tests, Molecular Structure, Phenols chemistry, Phloroglucinol chemistry, Phloroglucinol isolation & purification, Phloroglucinol pharmacology, Pyrones chemistry, Anti-Bacterial Agents isolation & purification, Anti-Bacterial Agents pharmacology, Glycerides isolation & purification, Glycerides pharmacology, Helichrysum chemistry, Phenols isolation & purification, Phenols pharmacology, Phloroglucinol analogs & derivatives, Pyrones isolation & purification, Pyrones pharmacology
Abstract

During a large-scale isolation campaign for the heterodimeric phloroglucinyl pyrone arzanol (1a) from Helichrysum italicum subsp. microphyllum, several new phenolics as well as an unusual class of lipids named santinols (5a-c, 6-8) have been characterized. Santinols are angeloylated glycerides characterized by the presence of branched acyl- or keto-acyl chains and represent a hitherto unreported class of plant lipids. The antibacterial activity of arzanol and of a selection of Helichrysum phenolics that includes coumarates, benzofurans, pyrones, and heterodimeric phloroglucinols was evaluated, showing that only the heterodimers showed potent antibacterial action against multidrug-resistant Staphylococcus aureus isolates. These observations validate the topical use of Helichrysum extracts to prevent wound infections, a practice firmly established in the traditional medicine of the Mediterranean area.

Published
2013
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22. Genepolide, a sesterpene gamma-lactone with a novel carbon skeleton from mountain wormwood (Artemisia umbelliformis).

Author

Appendino G, Taglialatela-Scafati O, Romano A, Pollastro F, Avonto C, and Rubiolo P

Subjects
Italy, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Sesquiterpenes chemistry, Sesquiterpenes isolation & purification, Stereoisomerism, Artemisia chemistry, Lactones chemistry, Lactones isolation & purification, Terpenes chemistry, Terpenes isolation & purification
Abstract

The sesterpene gamma-lactone genepolide (5) has been isolated from a Swiss horticultural variety of mountain wormwood (Artemisia umbelliformis) developed as a thujones-free alternative to native Western Alps wormwoods for the production of liqueurs. Genepolide is the formal Diels-Alder adduct of the exomethylene-gamma-lactone costunolide (2) and the diene myrcene (6), two poorly reactive partners in cycloaddition reactions, and its structure was elucidated through a combination of spectroscopic methods. An investigation on the thermal stability of mixtures of 2 and 6, as well as considerations on the sensitivity of 2 to Brønsted and Lewis acids, suggests that 5 is a genuine natural product and that the Swiss chemotype of A. umbelliformis contains Diels-Alderase enzymatic activity that is lacking in native mountain wormwoods from Western Alps. Remarkable differences in thermal and acid-catalyzed reactions of the cyclodecadiene moiety of 2 and 5 suggest that quaternarization at C-11 has far-reaching effects on the reactivity of their homoconjugated medium-sized diene system. The wide occurrence of this structural motif in sesquiterpenoids makes this issue worth a systematic investigation.

Published
2009
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