Cannabisol, a Novel Δ9-THC Dimer Possessing a Unique Methylene Bridge, Isolated from Cannabis sativa

F Zulfiqar; S Ross; D Slade; S Ahmed; MM Radwan; Z Ali; IA Khan; MA ElSohly

doi:10.1055/s-0032-1307535

Planta Medica, Table of Contents

Cannabisol, a Novel Δ9-THC Dimer Possessing a Unique Methylene Bridge, Isolated from Cannabis sativa

F Zulfiqar ¹, S Ross ¹^,², D Slade ¹, S Ahmed ³, MM Radwan ¹^,⁴, Z Ali ¹, IA Khan ¹^,², MA ElSohly ¹^,⁵

¹National Center for Natural Products Research
²Department of Pharmacognosy, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, United States
³Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia, Egypt
⁴Department of Pharmacognosy, Faculty of Pharmacy, Alexandrial University, Egypt
⁵Department of Pharmaceutics, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, United States

Abstract

Cannabis, the only genus in the plant family Cannabaceae, consists of only one highly variable species, Cannabis sativa L. More than 535 constituents have been isolated and/or identified from Cannabis sativa L., [1–3] with Δ⁹-THC being recognized as the main biologically active component [4]. Cannabisol (1), a unique dimer of Δ⁹-tetrahydrocannabinol (Δ⁹-THC) with a methylene bridge, was isolated from Cannabis sativa. This is the first example of a C-bridged dimeric cannabinoid. The structure of cannabisol (1) was unambiguously deduced by HRESIMS, GCMS and NMR spectroscopy. A plausible biogenesis of 1 will be presented.

Fig.1: Cannabisol (1)

Acknowledgement: The project was supported by Grant No. 5P20RR021929 from the National Center for Research Resources and grant # N01DA-05–7746 from NIDA. References: [1] ElSohly MA, Slade D (2005) Life Sci 78: 539–548. [2] Radwan M, ElSohly MA, et al. (2009)J Nat Prod 72(5): 906–911. [3] Pollastro F, Orazio T, et al. (2011)J Nat Prod 74(9): 2019–2022. [4] Williamson EM, Evans FJ (2000) Drugs 60: 1303–1314.