2. Academic Validation
  3. A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol

A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol

  • Sci Rep. 2019 Dec 30;9(1):20335. doi: 10.1038/s41598-019-56785-1.
Cinzia Citti 1 2 3,  Pasquale Linciano 3,  Fabiana Russo 3,  Livio Luongo 4,  Monica Iannotta 4,  Sabatino Maione 4,  Aldo Laganà 2 5,  Anna Laura Capriotti 5,  Flavio Forni 3,  Maria Angela Vandelli 3,  Giuseppe Gigli 2,  Giuseppe Cannazza 6 7
Affiliations

Affiliations

  • 1 Mediteknology spin-off company of the National Council of Research (CNR), Via Arnesano, 73100, Lecce, Italy.
  • 2 Institute of Nanotechnology of the National Council of Research (CNR NANOTEC), Via Monteroni, 73100, Lecce, Italy.
  • 3 Department of Life Sciences, University of Modena and Reggio Emilia, Via Campi 103, 41125, Modena, Italy.
  • 4 Department of Experimental Medicine, Division of Pharmacology, Università della Campania "L. Vanvitelli", Via Santa Maria di Costantinopoli 16, 80138, Naples, Italy.
  • 5 Department of Chemistry, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185, Rome, Italy.
  • 6 Institute of Nanotechnology of the National Council of Research (CNR NANOTEC), Via Monteroni, 73100, Lecce, Italy. giuseppe.cannazza@unimore.it.
  • 7 Department of Life Sciences, University of Modena and Reggio Emilia, Via Campi 103, 41125, Modena, Italy. giuseppe.cannazza@unimore.it.
PMID: 31889124 DOI: 10.1038/s41598-019-56785-1
Abstract

(-)-Trans-Δ9-tetrahydrocannabinol (Δ9-THC) is the main compound responsible for the intoxicant activity of Cannabis sativa L. The length of the side alkyl chain influences the biological activity of this cannabinoid. In particular, synthetic analogues of Δ9-THC with a longer side chain have shown cannabimimetic properties far higher than Δ9-THC itself. In the attempt to define the phytocannabinoids profile that characterizes a medicinal cannabis variety, a new phytocannabinoid with the same structure of Δ9-THC but with a seven-term alkyl side chain was identified. The natural compound was isolated and fully characterized and its stereochemical configuration was assigned by match with the same compound obtained by a stereoselective synthesis. This new phytocannabinoid has been called (-)-trans-Δ9-tetrahydrocannabiphorol (Δ9-THCP). Along with Δ9-THCP, the corresponding cannabidiol (CBD) homolog with seven-term side alkyl chain (CBDP) was also isolated and unambiguously identified by match with its synthetic counterpart. The binding activity of Δ9-THCP against human CB1 receptor in vitro (Ki = 1.2 nM) resulted similar to that of CP55940 (Ki = 0.9 nM), a potent full CB1 agonist. In the cannabinoid tetrad pharmacological test, Δ9-THCP induced hypomotility, analgesia, catalepsy and decreased rectal temperature indicating a THC-like cannabimimetic activity. The presence of this new phytocannabinoid could account for the pharmacological properties of some cannabis varieties difficult to explain by the presence of the sole Δ9-THC.

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