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.
Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L / A., Pagani; F., Scala; Chianese, Giuseppina; G., Grassi; G., Appendino; TAGLIALATELA SCAFATI, Orazio. - In: TETRAHEDRON. - ISSN 0040-4020. - 67:(2011), pp. 3369-3373. [10.1016/j.tet.2011.03.062]
Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.
CHIANESE, GIUSEPPINA;TAGLIALATELA SCAFATI, ORAZIO
2011
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
