Purification of natural metabolites from Radula complanata and towards the elucidation of perrottetinene’s biosynthetic route

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Date

2023-12

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University of New Brunswick

Abstract

The Bryophyte Radula complanata is a non-vascular plant and a unique source of medicinal metabolites. The plant is particularly rich in aromatic bibenzyls, which are likely generated to deal with environmental stressors, herbivory attacks, and plant pathogens. Particularly, the bibenzyl perrottetinene (isolated from related species R. marginata and R. perrottetii) is structurally similar to the well-known psychoactive cannabinoid tetrahydrocannabinol and is shown to have cannabinoid receptor agonism. In this study, two major bibenzyl compounds in R. complanata were purified and structurally elucidated by mass spectrometry and various Nuclear Magnetic Resonance (NMR) techniques. While perrottetinene biosynthesis remains elusive, several enzymes from R. complanata are biochemically characterized. The findings are the first steps towards the elucidation of the complete biosynthesis of perrottetinene and related bibenzyl cannabinoids.

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