A computational exploration into the structure, antioxidant capacity, toxicity and drug-like activity of the anthocyanidin "Petunidin"

Vijisha K Rajan; C Ragi; K Muraleedharan

doi:10.1016/j.heliyon.2019.e02115

A computational exploration into the structure, antioxidant capacity, toxicity and drug-like activity of the anthocyanidin "Petunidin"

Heliyon. 2019 Jul 20;5(7):e02115. doi: 10.1016/j.heliyon.2019.e02115. eCollection 2019 Jul.

Authors

Vijisha K Rajan¹, C Ragi¹, K Muraleedharan¹

Affiliation

¹ Department of Chemistry, University of Calicut, Malappuram, 673635, India.

Abstract

A computational investigation on the structure and antioxidant property of a natural food colorant Petunidin (PT) was performed under DFT/B3LYP/6-31+ G (d, p). PT has a drug score of +0.804 which indicates its drug-like nature. The antioxidant property of PT was well explained by HAT mechanism and it has been found that the electron releasing substituents decreases the BDE value. PT has lowest BDE value at C3 position and is confirmed by the lowest pKa value, high atomic charge and lowest bond order. PT easily donates the hydrogen atom and exists in the deprotonated form in blood as the pKa value at C3 is less than the pH value of blood. PT shows no violation to Lipinski's rule of 5 indicating its nature as an orally admissible drug. More over PT has considerable bioactivity against nuclear receptor ligand while it shows only moderate activity towards GPCR and ion channel modulator. Also it shows moderate activity as an enzyme inhibitor and protease inhibitor but shows considerable activity as a kinase inhibitor. PT is non toxic in nature and all these factors favor its use as a potential antioxidant and a drug.

Keywords: Antioxidant; Bond dissociation energy; Computational biology; Computational chemistry; Drug score; Food chemistry; Natural product chemistry; Petunidin; Pharmaceutical chemistry; Pharmaceutical science; Theoretical chemistry; Toxicity.