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Planta Med 2020; 86(05): 338-347
DOI: 10.1055/a-1110-1045
Natural Product Chemistry and Analytical Studies
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

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

Josep Basas-Jaumandreu
Department of Mining, Industrial and ICT, Escola Politècnica Superior dʼEnginyeria de Manresa (EPSEM), Universitat Politècnica de Catalunya (UPC-BarcelonaTech), Manresa, Catalonia, Spain
,
F. Xavier C. de las Heras
Department of Mining, Industrial and ICT, Escola Politècnica Superior dʼEnginyeria de Manresa (EPSEM), Universitat Politècnica de Catalunya (UPC-BarcelonaTech), Manresa, Catalonia, Spain
› Author Affiliations
Further Information

Publication History

received 14 August 2019
revised 30 December 2019

accepted 26 January 2020

Publication Date:
13 February 2020 (online)

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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.

Key words

Cannabinoids - Cannabis sativa - Cannabaceae - phytochemical analysis - GC-MS

Supporting Information

 

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