GC-MS Metabolite Profile and Identification of Unusual Homologous Cannabinoids in High Potency Cannabis sativa

Abstract

Phytochemical investigation of the lipids extracted from seeds of Cannabis sativa by GC-MS showed 43 cannabinoids, 16 of which are new. The extract is dominated by Δ⁹-tetrahydrocannabinolic acid (A) and its neutral derivative trans-Δ⁹-tetrahydrocannabinol-C₅ (THC) Cis and trans-Δ⁹-tetrahydrocannabinol-C₇ isomers with an ethyl-pentyl branched chain together with minor amounts of trans-Δ⁹-tetrahydrocannabinol with a methyl-pentyl C₆ branched side chain were identified as new natural compounds. Four cannabichromene isomers with a C₅ side chain are postulated to be derived from the double bond migration at the terminal isoprenyl unit. C₇ cannabichromene together with the neutral and acidic forms of cannabinol-C₇ were also detected. The mass spectrum of these homologues as trimethylsilyl (TMS) derivatives are presented, and the fragmentation patterns are discussed.