title: Understanding the molecular aspects of tetrahydrocannabinol and cannabidiol as antioxidants.
abstract: An antioxidant mechanism of tetrahydrocannabinol (THC) and cannabidiol (CBD) were compared with a simplified model of α-tocopherol, butylhydroxytoluene and hydroxytoluene in order to understand the antioxidant nature of THC and CBD molecules using DFT. The following electronic properties were evaluated: frontier orbitals nature, ionization potential, O-H bond dissociation energy (BDEOH), stabilization energy, and spin density distribution. An important factor that shows an influence in the antioxidant property of THC is the electron abstraction at the phenol position. Our data indicate that the decrease of the HOMO values and the highest ionization potential values are related to phenol, ether, and alkyl moieties. On the other hand, BDEOH in molecules with the cyclohexenyl group at ortho position of phenol are formed from lower energies than the molecules with an ether group at the meta position. In the light of our results, the properties calculated here predict that THC has a sightly higher antioxidant potential than CBD.
authors.affiliation: Institute of Health Sciences, Federal University of Pará, Belém 66075-110, PA, Brazil. rosborg@ufpa.br.
authors.forename: Rosivaldo S
authors.initials: RS
authors.lastname: Borges
authors.forename: João
authors.initials: J
authors.lastname: Batista
authors.forename: Rommel B
authors.initials: RB
authors.lastname: Viana
authors.forename: Ana C
authors.initials: AC
authors.lastname: Baetas
authors.forename: Ednilsom
authors.initials: E
authors.lastname: Orestes
authors.forename: Marcieni A
authors.initials: MA
authors.lastname: Andrade
authors.forename: Káthia M
authors.initials: KM
authors.lastname: Honório
authors.forename: Albérico B F
authors.initials: AB
authors.lastname: da Silva
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D002185:Cannabidiol / Q000737:chemistry*; D003198:Computer Simulation; D013759:Dronabinol / Q000737:chemistry*; D004563:Electrochemistry; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory
chemical_list: D000975:Antioxidants; D002185:Cannabidiol; D013759:Dronabinol