TY - JOUR
T1 - Cannabioxepane, a novel tetracyclic cannabinoid from hemp, Cannabis sativa L.
AU - Pagani, Alberto
AU - Scala, Fernando
AU - Chianese, Giuseppina
AU - Grassi, Gianpaolo
AU - Appendino, Giovanni
AU - Taglialatela-Scafati, Orazio
PY - 2011/5/13
Y1 - 2011/5/13
N2 - 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.
AB - 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.
KW - Cannabinoids
KW - Cannabioxepane
KW - Cannabis sativa
KW - Stilbenoids
KW - Structure elucidation
UR - http://www.scopus.com/inward/record.url?scp=79955047924&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2011.03.062
DO - 10.1016/j.tet.2011.03.062
M3 - Article
SN - 0040-4020
VL - 67
SP - 3369
EP - 3373
JO - Tetrahedron
JF - Tetrahedron
IS - 19
ER -