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Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L. |
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| Authors: | Alberto PaganiFernando Scala Giuseppina ChianeseGianpaolo Grassi Giovanni AppendinoOrazio Taglialatela-Scafati |
| Affiliation: | a Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Via Bovio 6, Università del Piemonte Orientale, 28100 Novara, Italy b Dipartimento di Chimica delle Sostanze Naturali, Università di Napoli ‘Federico II’, Via D. Montesano 49, 80131 Napoli, Italy c CRA-CIN, Viale G. Amendola 82, 45100 Rovigo, Italy |
| Abstract: | Apart from large amounts of cannabidiol, the known stilbenoids 1-4 and the oxylipins 7 and 8, a fibre cultivar of Cannabis sativa derived from the historical Carmagnola variety gave the novel spiranic stilbenoid isocannabispiradienone (5) and the biphenyl-type cannabinoid cannabioxepane (CBX, 6), a tetracyclic compound characterized by an unprecedented C-5/C-8′ oxygen bridge and devoid of cannabinoid activity. Structures were established by analysis of MS and NMR data, and the biogenetic derivation of the new compounds is discussed. |
| Keywords: | Cannabis sativa Cannabinoids Cannabioxepane Stilbenoids Structure elucidation |
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