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Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants
Institute of Health Sciences, Federal University of Pará, Belém 66075-110, PA, Brazil
Institute of Chemistry of São Carlos, University of São Paulo, São Carlos 13560-970, SP, Brazil
School of Arts, Sciences and Humanities, University of São Paulo, São Carlos 03828-000, SP, Brazil
* Author to whom correspondence should be addressed.
Received: 4 October 2013; in revised form: 4 October 2013 / Accepted: 10 October 2013 / Published: 14 October 2013
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.
Keywords: SAR; antioxidant; DFT; cannabinoids; CBD; electronic; THC
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MDPI and ACS Style
Borges, R.S.; Batista Jr., J.; Viana, R.B.; Baetas, A.C.; Orestes, E.; Andrade, M.A.; Honório, K.M.; da Silva, A.B.F. Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants. Molecules 2013, 18, 12663-12674.
Borges RS, Batista Jr. J, Viana RB, Baetas AC, Orestes E, Andrade MA, Honório KM, da Silva ABF. Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants. Molecules. 2013; 18(10):12663-12674.
Borges, Rosivaldo S.; Batista Jr., João; Viana, Rommel B.; Baetas, Ana C.; Orestes, Ednilsom; Andrade, Marcieni A.; Honório, Káthia M.; da Silva, Albérico B.F. 2013. "Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants." Molecules 18, no. 10: 12663-12674.