Flavonoids Isolated From Vitex grandifolia, an Underutilized Vegetable, Exert Monoamine A & B Inhibitory and Anti-inflammatory Effects and Their Structure-activity Relationship

Objectives: Vitex grandifolia belongs to family Lamiaceae; it consists of flowering plants and it is also called the mint family. The Yoruba people of southwest Nigeria called it "Oriri" or "Efo oriri". This plant is classified as an underutilized vegetable and little is known about its phytochemistry or its biological evaluations.

Materials and methods: Methanol extracts of the dried leaves and stem of the plant were subjected to fractionation and isolation using vacuum layer and column chromatography methods. The structures of the compounds were elucidated using spectroscopic techniques including IR, 1D-, and 2D-NMR and by comparison with the data reported in the literature. They were evaluated in vitro for the inhibition of monoamine recombinant human MAO-A and -B and anti-inflammatory activities.

Results: Three known flavonoids were isolated from the methanolic extract of the leaves of V. grandifolia for the first time to the best of our knowledge, i.e. isoorientin (1), orientin (2), and isovitexin (3). Most of the isolated compounds showed selective inhibition of monoamine oxidase B, inhibition of MAO-B by isoorientin (1) and orientin (2) were 9-fold more potent (IC₅₀ (μg/mL) of 11.08 and 11.04) compared to the inhibition of MAO-A (IC₅₀ (μg/mL) of ˃100), while clorgyline and deprenyl were used as positive standards. The isolated flavonoids displayed good activity against the NF-ﭏb assay with IC₅₀ (μg/mL) of 8.9, 12, and 18. This study establishes a link between the structure and the biological activities on the basis of the different patterns of substitution, particularly the C2=C3 double bond and the position of glucose moiety.

Conclusion: This study is the first to establish the phytochemistry of the polar part of V. grandifolia and the anti-inflammatory and neuroprotective role of these isolated compounds.

Keywords: MAO-A and B; Vitex grandifolia; lupeol; neurodegenerative; underutilized vegetable.