In Silico Pharmacological Prediction of Capitavine, Buchenavianine and Related Flavonoid Alkaloids

Flavonoid alkaloids represent an interesting subgroup of the alkaloid family.Several plants containing flavonoid alkaloids are used in folk medicine for the treatment of various diseases.The interesting biological properties of flavonoid alkaloids make them attractive candidates for lead compounds in drug discovery.Capitavine, or 5,7-dihydroxy-6-(1-methylpiperidin-2-yl)flavone, and related compounds, belong to piperidine-flavonoid alkaloids, possessing a piperidine ring connected to the C6-position of flavonoid skeleton, while buchenavianine is C8 piperidine-bonded analog.Capitavine derivatives were isolated mainly from Buchenavia capitata, while buchenavianine derivatives are present mainly in B. macrophylla.It was found that the chloroform extract of the leaves of B. capitata showed anti-HIV activity.The biological activity of capitavine and buchenavianine derivatives needs to be investigated in terms of their pharmacokinetic properties and toxicity, which are important factors in finding potential drug candidates.The present in silico study using SwissADME, Osiris, and Molinspiration software shows that studied capitavine-derived flavonoid alkaloids exhibit considerable bioactivity for the GPCR ligand (0.12 to 0.20), as enzyme inhibitors (0.17 to 0.22) and as nuclear receptor ligands (0.07 to 0.28).All compounds exhibit good gastrointestinal absorption and low risks of being irritants, tumorigenic, or having a reproductive effect.The risk of mutagenicity was calculated for two compounds related to buchenavianine, and at this point the role of 5-methoxy group appears to be crucial for the low risk of mutagenicity.