Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants

Author(s)

Borges, Rosivaldo S. ^[1] ; Batista, Jr., Joao ^[1] ; Viana, Rommel B. ^[2] ; Baetas, Ana C. ^[1] ; Orestes, Ednilsom ^[2] ; Andrade, Marcieni A. ^[1] ; Honorio, Kathia M. ^[3] ; da Silva, Alberico B. F. ^[2]

Affiliation

^[1] Fed Univ Para, Inst Hlth Sci, BR-66075110 Belem, PA - Brazil

^[2] Univ Sao Paulo, Inst Chem Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil

^[3] Univ Sao Paulo, Sch Arts Sci & Humanities, BR-03828000 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: Molecules; v. 18, n. 10, p. 12663-12674, OCT 2013.
• Web of Science Citations: 11

Abstract

An antioxidant mechanism of tetrahydrocannabinol (THC) and cannabidiol (CBD) were compared with a simplified model of alpha-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. (AU)

• FAPESP's process: 12/19175-2 - Characterization of metal complexes with medicinal applications: a spectroscopy and a quantum chemical investigation
• Grantee: Rommel Bezerra Viana
• Support Opportunities: Scholarships in Brazil - Post-Doctoral