Insights into biomimetic oxidized resveratrol metabolite mixtures

Resveratrol, a well-known natural polyphenol, has a plethora of pharmacological activities. It has low bioavailability and undergoes extensive metabolism; numerous reports are available on the bioactivities of glucuronidated and sulfated resveratrol conjugates [1]. Relatively little is known on its potentially bioactive oxidized metabolites. Resveratrol may directly scavenge free radicals in living systems, which can lead to the generation of a wide range of new metabolites with altered bioactivities [2]. Our studies aimed at evaluating some potential pharmacological implications of this phenomenon. Oxidation of resveratrol through various chemical reactions, including biomimetic approaches, resulted in several mixtures that exhibited greater bioactivities compared to the parent compound. Mixtures were tested for in vitro antioxidant activities (DPPH, ORAC), and inhibitory action on lipoxygenase, xanthine oxidase, acetylcholinesterase and angiotensin converting enzymes. Spectral analysis and metabolomic profiling against a library of resveratrol oligomers showed a diverse group of compounds including dimers, iodine-, methoxy- and benzofuran-substituted derivatives. Using a multi-step chromatographic isolation procedure, 20 compounds were obtained in pure form. Antioxidant and enzyme inhibitory studies show that iodine-substituted compounds and dimers exhibited greatest bioactivities. Additional studies to determine inhibition kinetics and molecular docking simulations are currently ongoing.

• References

• 1 Springer M, Moco S. Nutrients (2019), 11, 143
• 2 Hunyadi A. Med. Res. Rev. (2019) 1-29

Publication History

Article published online:
13 December 2021