Cannabinoid Ester Constituents from High Potency Cannabis Sativa L.

Twelve new cannabinoid esters, together with three known cannabinoid acids and Δ⁹-THC, were isolated from a high potency variety of Cannabis sativa L [1,2]. The structures were determined by extensive spectral analysis to be: β-fenchyl-Δ ⁹-THCA ester (1), α-fenchyl-Δ ⁹-THCA ester (2), bornyl-Δ ⁹-THCA ester (3), epi-bornyl-Δ ⁹-THCA ester (4), α-terpenyl-Δ ⁹-THCA ester (5), 4-terpenyl-Δ ⁹-THCA ester (6), α-cadinyl-Δ ⁹-THCA ester (7), γ-eudesmyl-Δ ⁹-THCA ester (8), inseparable mixture of two sesquiterpenyl-Δ ⁹-THCA esters (9), α-cadinyl-CBGA ester (10), γ-eudesmyl-CBGA ester (11), 4-terpenyl-CBNA ester (12), Δ ⁹-tetrahydrocannabinol (Δ⁹-THC), Δ ⁹-tetrahydrocannabinolic acid A (Δ⁹-THCA), cannabinolic acid A (CBNA) and cannabigerolic acid (CBGA). CB-1 receptor assays [3–6] indicated that these esters, as well as the parent Δ⁹-THCA, are not active compared to Δ⁹-THC. Acknowledgements: This work is supported by the National Institute on Drug Abuse (contract # N01DA-5-7746) and by the Center of Research Excellence in Natural Products Neuroscience, The University of Mississippi (contract # 1P20RR021929-01). We are grateful to Dr. Bharathi Avula for assistance with the HR-ESI-MS, and to Dr. Melissa Jacob and Ms. Marsha Wright for conducting the antimicrobial testing. References: [1] ElSohly MA, et al. (2000) Journal of Forensic Science 45: 24–30. [2] ElSohly MA, Slade D (2005) Life Sciences 78: 539–548. [3] Devane WA, (1988) Molecular Pharmacology 34: 605–613. [4] Munro S, et al. (1993) Nature 365: 61–65. [5] Barth F (2005) Annual Reports in Medicinal Chemistry 40: 103–118. [6] Ashton JC, Giass M (2007) Current Neuropharmacology 5: 73–80.