Four undescribed, β-, α-chevicospiranol (1, 2), 4-prenylspirenone B (3), and, 6-prenylspirenone B (4), along with ten known spiroindans were discovered in Cannabis sativa. The structures were determined through 1D, 2D NMR, HRMS, and quantum mechanical calculations. Compounds 1 and 2 have an unprecedented fused system of 3-hydroxychavicol with β- and α-cannabispiranol core, respectively, while 3 and 4 are prenylated spiroindan congeners. Detailed NMR data assignments of isomeric pairs 2a – 2b, 3a – 3b, and 4a – 4b, corrected the misidentification of the previously reported spiroindane, prenylspirodinone (5). Besides, the crystal structures of 2a, 3a, and 5a were determined by SC-XRD experiments.
Phytochemical investigation of Cannabis sativa: Isolation and structure determination of spiroindans
Boccia, Eleonora;Lauro, Gianluigi;Bifulco, Giuseppe;
2025-01-01
Abstract
Four undescribed, β-, α-chevicospiranol (1, 2), 4-prenylspirenone B (3), and, 6-prenylspirenone B (4), along with ten known spiroindans were discovered in Cannabis sativa. The structures were determined through 1D, 2D NMR, HRMS, and quantum mechanical calculations. Compounds 1 and 2 have an unprecedented fused system of 3-hydroxychavicol with β- and α-cannabispiranol core, respectively, while 3 and 4 are prenylated spiroindan congeners. Detailed NMR data assignments of isomeric pairs 2a – 2b, 3a – 3b, and 4a – 4b, corrected the misidentification of the previously reported spiroindane, prenylspirodinone (5). Besides, the crystal structures of 2a, 3a, and 5a were determined by SC-XRD experiments.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
