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      Cannabis sativa L. Inflorescences from Monoecious Cultivars Grown in Central Italy: An Untargeted Chemical Characterization from Early Flowering to Ripening

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          Abstract

          The chemical composition of the inflorescences from four Cannabis sativa L. monoecious cultivars (Ferimon, Uso-31, Felina 32 and Fedora 17), recently introduced in the Lazio Region, was monitored over the season from June to September giving indications on their sensorial, pharmaceutical/nutraceutical proprieties. Both untargeted (NMR) and targeted (GC/MS, UHPLC, HPLC-PDA/FD and spectrophotometry) analyses were carried out to identify and quantify compounds of different classes (sugars, organic acids, amino acids, cannabinoids, terpenoids, phenols, tannins, flavonoids and biogenic amines). All cultivars in each harvesting period showed a THC content below the Italian legal limit, although in general THC content increased over the season. Citric acid, malic acid and glucose showed the highest content in the late flowering period, whereas the content of proline drastically decreased after June in all cultivars. Neophytadiene, nerolidol and chlorogenic acid were quantified only in Felina 32 cultivar, characterized also by a very high content of flavonoids, whereas alloaromadendrene and trans-cinnamic acid were detected only in Uso-31 cultivar. Naringenin and naringin were present only in Fedora 17 and Ferimon cultivars, respectively. Moreover, Ferimon had the highest concentration of biogenic amines, especially in July and August. Cadaverine was present in all cultivars but only in September. These results suggest that the chemical composition of Cannabis sativa L. inflorescences depends on the cultivar and on the harvesting period. Producers can use this information as a guide to obtain inflorescences with peculiar chemical characteristics according to the specific use.

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          Hempseed as a nutritional resource: An overview

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            Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.

            Marijuana (Cannabis sativa) has long been known to contain antibacterial cannabinoids, whose potential to address antibiotic resistance has not yet been investigated. All five major cannabinoids (cannabidiol (1b), cannabichromene (2), cannabigerol (3b), Delta (9)-tetrahydrocannabinol (4b), and cannabinol (5)) showed potent activity against a variety of methicillin-resistant Staphylococcus aureus (MRSA) strains of current clinical relevance. Activity was remarkably tolerant to the nature of the prenyl moiety, to its relative position compared to the n-pentyl moiety (abnormal cannabinoids), and to carboxylation of the resorcinyl moiety (pre-cannabinoids). Conversely, methylation and acetylation of the phenolic hydroxyls, esterification of the carboxylic group of pre-cannabinoids, and introduction of a second prenyl moiety were all detrimental for antibacterial activity. Taken together, these observations suggest that the prenyl moiety of cannabinoids serves mainly as a modulator of lipid affinity for the olivetol core, a per se poorly active antibacterial pharmacophore, while their high potency definitely suggests a specific, but yet elusive, mechanism of activity.
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              Cannabidiol (CBD) and its analogs: a review of their effects on inflammation.

              First isolated from Cannabis in 1940 by Roger Adams, the structure of CBD was not completely elucidated until 1963. Subsequent studies resulted in the pronouncement that THC was the 'active' principle of Cannabis and research then focused primarily on it to the virtual exclusion of CBD. This was no doubt due to the belief that activity meant psychoactivity that was shown by THC and not by CBD. In retrospect this must be seen as unfortunate since a number of actions of CBD with potential therapeutic benefit were downplayed for many years. In this review, attention will be focused on the effects of CBD in the broad area of inflammation where such benefits seem likely to be developed. Topics covered in this review are; the medicinal chemistry of CBD, CBD receptor binding involved in controlling Inflammation, signaling events generated by CBD, downstream events affected by CBD (gene expression and transcription), functional effects reported for CBD and combined THC plus CBD treatment.
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                Author and article information

                Contributors
                Role: Academic Editor
                Journal
                Molecules
                Molecules
                molecules
                Molecules
                MDPI
                1420-3049
                20 April 2020
                April 2020
                : 25
                : 8
                : 1908
                Affiliations
                [1 ]Department of Chemistry and Technology of Drugs, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy; cinzia.ingallina@ 123456uniroma1.it (C.I.); simone.circi@ 123456uniroma1.it (S.C.); mattia.spano@ 123456uniroma1.it (M.S.); caterina.fraschetti@ 123456uniroma1.it (C.F.); antonello.filippi@ 123456uniroma1.it (A.F.); giulia.mazzoccanti@ 123456uniroma1.it (G.M.); francesco.gasparrini@ 123456uniroma1.it (F.G.); deborah.quaglio@ 123456uniroma1.it (D.Q.); bruno.botta@ 123456uniroma1.it (B.B.)
                [2 ]Institute for Biological Systems, Magnetic Resonance Laboratory “Segre-Capitani”, CNR, Via Salaria Km 29.300, 00015 Monterotondo, Italy; donatella.capitani@ 123456cnr.it
                [3 ]Department of Physiology and Pharmacology “V. Ersparmer”, Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy; antonella.disotto@ 123456uniroma1.it (A.D.S.); silvia.digiacomo@ 123456uniroma1.it (S.D.G.)
                [4 ]Department of Agriculture and Forest Sciences, University of Tuscia, Via San Camillo de Lellis snc, 01100 Viterbo, Italy; campigli@ 123456unitus.it
                [5 ]Department of Pharmacy, University “G. d’Annunzio” of Chieti-Pescara, Via dei Vestini 31, 66100 Chieti, Italy; simone.carradori@ 123456unich.it (S.C.); m.locatelli@ 123456unich.it (M.L.)
                [6 ]Department of Management, Sapienza University of Rome, via del Castro Laurenziano 9, 00161 Rome, Italy; giuliana.vinci@ 123456uniroma1.it (G.V.); mattia.rapa@ 123456uniroma1.it (M.R.); salvatore.ciano@ 123456uniroma1.it (S.C.)
                [7 ]Department of Experimental Medicine, Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy; annamaria.giusti@ 123456uniroma1.it
                [8 ]Center for Life Nano Science@Sapienza, Italian Institute of Technology, Viale Regina Elena 291, 00161 Rome, Italy; francesca.ghirga@ 123456iit.it
                Author notes
                [* ]Correspondence: anatoly.sobolev@ 123456cnr.it (A.P.S.); luisa.mannina@ 123456uniroma1.it (L.M.); Tel.: +39-06-9067-2385 (A.P.S.); +39-064-991-3735 (L.M.)
                [†]

                To whom this paper is dedicated, passed away on 20 September 2019.

                Author information
                https://orcid.org/0000-0003-4817-7318
                https://orcid.org/0000-0001-8709-7666
                https://orcid.org/0000-0001-5035-0971
                https://orcid.org/0000-0002-7467-1689
                https://orcid.org/0000-0003-3049-6644
                https://orcid.org/0000-0001-8655-524X
                https://orcid.org/0000-0002-4954-7635
                https://orcid.org/0000-0002-8698-9440
                https://orcid.org/0000-0002-0840-825X
                https://orcid.org/0000-0003-3025-1831
                https://orcid.org/0000-0002-9023-012X
                https://orcid.org/0000-0002-5694-3732
                https://orcid.org/0000-0001-8707-4333
                https://orcid.org/0000-0001-8659-5890
                Article
                molecules-25-01908
                10.3390/molecules25081908
                7221798
                32326129
                648bb493-c6a9-41d7-b2ef-89b682948b31
                © 2020 by the authors.

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                : 28 March 2020
                : 15 April 2020
                Categories
                Article

                cannabis sativa l.,monoecious cultivars,inflorescences,cannabinoids,metabolic profile,multimethodological analysis

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