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6. ��9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology

Author

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

Subjects
570 Life sciences, biology, 610 Medicine & health
Abstract

The cis-stereoisomers of ��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 ��9-cis-THC (3) occurs in cannabis fiber hemp in the concentration range of (-)-��9-trans-THC [(-)-1], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural ��9-cis-THC (3) is scalemic (ca. 80-90% enantiomeric purity), and the absolute configuration of the major enantiomer was established as 6aS,10aR [(-)-3] by chiral chromatographic comparison with a sample available by asymmetric synthesis. The major enantiomer, (-)-��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 "��9-THC and isomers" and needs therefore revision, or at least a more specific wording, to account for the presence of ��9-cis-THCs [(+)-3 and (-)-3] in cannabis fiber hemp varieties.

Published
2021
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8. 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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9. Biosurfactants

Author

Martinotti, Maria Giovanna, primary, Allegrone, Gianna, additional, Cavallo, Massimo, additional, and Fracchia, Letizia, additional

Published
2013
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17. Medical-Grade Silicone Coated with Rhamnolipid R89 Is Effective against Staphylococcus spp. Biofilms

Author

Ceresa, Chiara, primary, Tessarolo, Francesco, additional, Maniglio, Devid, additional, Tambone, Erica, additional, Carmagnola, Irene, additional, Fedeli, Emanuele, additional, Caola, Iole, additional, Nollo, Giandomenico, additional, Chiono, Valeria, additional, Allegrone, Gianna, additional, Rinaldi, Maurizio, additional, and Fracchia, Letizia, additional

Published
2019
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20. Determination of melatonin content of different varieties of hemp (Cannabis sativaL.) by liquid chromatography tandem mass spectrometry

Author

Allegrone, Gianna, Razzano, Federica, Pollastro, Federica, and Grassi, Gianpaolo

Abstract

Melatonin (N-acetyl-5-methoxytryptamine), was first isolated in the bovine pineal gland, and then was discovered in bacteria, algae and higher plants. Melatonin concentrations in plants differ from species to species, among varieties within the same species and also within different organs or tissues of a given plant as roots, leaves, fruits, flowers, and seeds. Although the presence of melatonin in plants seems to be a universal trait, there is still lack of information on its occurrence in several plants, in particular in hemp (Cannabis sativaL.). The aim of this study was to develop a method to quantitate melatonin in the aerial parts of the plant, constituted of leaves and flower heads, and in the seeds, of four different hemp varieties using liquid chromatography–tandem mass spectrometry (LC–ESI/MS/MS). A sample preparation procedure with methanol extraction followed by solid-phase clean-up protocol was set up for melatonin extraction and a LC–ESI/MS/MS method in single reaction monitoring (SRM) was used for its determination. Chromatographic separation was achieved on a C18 column using a gradient elution with acetonitrile–buffer ammonium formate/formic acid system. The developed method, validated as per International Conference on Harmonization guidelines, was successfully applied to analyze hemp samples varieties belonging to fiber-type or drug-type chemotypes. The melatonin was found to accumulate highly in seeds in the range 13.43–30.40 ng g−1while the content in the aerial parts was assessed in the range 1.16–4.85 ng g−1. No correlation was found between the melatonin levels detected in aerial parts and seeds in each hemp variety and the concentration of specific cannabinoids in the same variety.

Published
2019
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22. The high-resolution crystal structure of periplasmicHaemophilus influenzaeNAD nucleotidase reveals a novel enzymatic function of human CD73 related to NAD metabolism

Author

Garavaglia, Silvia, primary, Bruzzone, Santina, additional, Cassani, Camilla, additional, Canella, Laura, additional, Allegrone, Gianna, additional, Sturla, Laura, additional, Mannino, Elena, additional, Millo, Enrico, additional, De Flora, Antonio, additional, and Rizzi, Menico, additional

Published
2011
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27. Impurity analysis of retinoic acid samples

Author

Allegrone, Gianna, primary, Brenna, Elisabetta, additional, Fronza, Giovanni, additional, Fuganti, Claudio, additional, Giovenzana, Tommaso, additional, Malpezzi, Luciana, additional, Barlocchi, Enrico, additional, and Pellegatta, Cesare, additional

Published
2005
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32. Stereochemistry of the microbial generation of .delta.-decanolide, .gamma.-dodecanolide, and .gamma.-nonanolide from C18 13-hydroxy, C18 10-hydroxy, and C19 14-hydroxy unsaturated fatty acids

Author

Cardillo, Rosanna, primary, Fronza, Giovanni, additional, Fuganti, Claudio, additional, Grasselli, Piero, additional, Mele, Andrea, additional, Pizzi, Domenica, additional, Allegrone, Gianna, additional, Barbeni, Massimo, additional, and Pisciotta, Antonella, additional

Published
1991
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34. LCESIMSMS characterisation of lipopeptide biosurfactants produced by the Bacillus licheniformisV9T14 strain

Author

Pecci, Ylenia, Rivardo, Fabrizio, Martinotti, Maria Giovanna, and Allegrone, Gianna

Abstract

Lipopeptide biosurfactants produced by the Bacillus licheniformisV9T14 strain showed an interesting antiadhesion activity against biofilm formation of human pathogenic bacterial strains. The chemical characterisation of the crude extract of V9T14 strain was first developed through electrospray ionisation mass spectrometry ESIMS and ESIMSMS direct infusions: two sets of molecular ion species belonging to the fengycin and surfactin families were revealed and their structures defined, interpreting their product ion spectra. The LCESIMS analysis of the crude extract allowed to separate in different chromatogram ranges the homologues and the isoforms of the two lipopeptide families. The extract was then fractionated by silica gel chromatography in two main fractions, I and II. The purified biosurfactants were analysed through a new, rapid and suitable LCESIMSMS method, which allowed characterising the composition and the structures of the produced lipopeptides. LCESIMSMS analysis of fraction I showed the presence of C13, C14and C15surfactin homologues, whose structures were confirmed by the product ion spectra of the sodiated molecules M Naat mz1030, 1044 and 1058. LCESIMSMS analysis of fraction II confirmed the presence of two main fengycin isoforms, with the protonated molecules M Hat mz1478 and 1506 corresponding to C17fengycin A and C17fengycin B, respectively. Other homologues C14to C16 were revealed and confirmed as belonging to fengycin A or B according to the retention times and the product ions generated, although with the same nominal mass. Finally, a relative percentage content of each homologue for both lipopeptides families in the whole extract was proposed. Copyright © 2010 John Wiley & Sons, Ltd.

Published
2010
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37. Helichrysum microphyllum subsp. tyrrhenicum : a possible correlation between small volatile compounds and phloroglucinol content.

Author

Pantusa C, Rinaldi M, Salamone S, Sanna C, Allegrone G, and Pollastro F

Abstract

The chemical composition of the flowered aerial parts of four samples of Helichrysum microphyllum subsp. tyrrhenicum collected in South-West Sardinia was investigated with a combined focus on volatile constituents and phloroglucinols to find a possible correlation with the presence of arzanol endowed with the major anti-inflammatory activity. The volatile constituents were analysed by GC-MS as EO-HD and with HS-SPME identifying a total of 95 compounds of which 70 and 77 by EO-HD and HS-SPME respectively. The profile of the non-volatile phloroglucinols was investigated by HPLC-MS/MS. Arzanol concentrations ranged from 2.79 to 21.87 mg/g, helipyrone showed the same trend but in lower concentration. Surprisingly, leaves and stems contain higher concentration of phloroglucinols than the flowers. The concentration of arzanol was positively correlated to the one of γ-curcumene and ethylpyrone in the EO, while a negative correlation was observed with the monoterpene limonene and linalool as well as with the sesquiterpene 5-eudesmen-11-ol.

Published
2024
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38. 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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39. The high-resolution crystal structure of periplasmic Haemophilus influenzae NAD nucleotidase reveals a novel enzymatic function of human CD73 related to NAD metabolism.

Author

Garavaglia S, Bruzzone S, Cassani C, Canella L, Allegrone G, Sturla L, Mannino E, Millo E, De Flora A, and Rizzi M

Subjects
Adenosine Diphosphate, Amino Acid Sequence, Animals, Bacterial Proteins genetics, Binding Sites, COS Cells, Chlorocebus aethiops, Cloning, Molecular, Crystallization, Haemophilus influenzae genetics, Haemophilus influenzae metabolism, Humans, Models, Molecular, Molecular Sequence Data, NAD metabolism, Nicotinamide Mononucleotide metabolism, Nucleotidases genetics, Protein Conformation, Pyrophosphatases genetics, Zinc chemistry, 5'-Nucleotidase metabolism, Bacterial Proteins metabolism, Gene Expression Regulation, Bacterial physiology, Haemophilus influenzae enzymology, Nucleotidases metabolism, Pyrophosphatases metabolism
Abstract

Haemophilus influenzae is a major pathogen of the respiratory tract in humans that has developed the capability to exploit host NAD(P) for its nicotinamide dinucleotide requirement. This strategy is organized around a periplasmic enzyme termed NadN (NAD nucleotidase), which plays a central role by degrading NAD into adenosine and NR (nicotinamide riboside), the latter being subsequently internalized by a specific permease. We performed a biochemical and structural investigation on H. influenzae NadN which determined that the enzyme is a Zn2+-dependent 5'-nucleotidase also endowed with NAD(P) pyrophosphatase activity. A 1.3 Å resolution structural analysis revealed a remarkable conformational change that occurs during catalysis between the open and closed forms of the enzyme. NadN showed a broad substrate specificity, recognizing either mono- or di-nucleotide nicotinamides and different adenosine phosphates with a maximal activity on 5'-adenosine monophosphate. Sequence and structural analysis of H. influenzae NadN led us to discover that human CD73 is capable of processing both NAD and NMN, therefore disclosing a possible novel function of human CD73 in systemic NAD metabolism. Our data may prove to be useful for inhibitor design and disclosed unanticipated fascinating evolutionary relationships.

Published
2012
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