Alicja Urbaniak
University of Arkansas for Medical Sciences, USA
Title: Novel resveratrol triesters demonstrate activity in diverse biological systems
Biography
Biography: Alicja Urbaniak
Abstract
Resveratrol (3, 5, 4`-trihydroxy-trans-stilbene, tRV) is a polyphenol found in numerous plant species, e. g. grapes, berries, peanuts, that exhibits many beneficial properties namely antioxidant, anti-inflammatory and cytostatic. However, its wide application is limited due to its rapid metabolism and low solubility. Our laboratory synthesized 16 derivatives of tRV by conjugation with other bioactive compounds such as hydroxycinnamic acids. Rigorous structure identification was carried out, and the crystal structure of selected compounds was determined. In this work, tRV esters were tested for biological activity. Specifically, radical scavenging effect, elastase, collagenase and the inhibitory activity of tyrosynase and cholinesterases were investigated in vitro studies. Interestingly, resveratryl tri-p- and tri-m-coumatare were the best inhibitors of both cholinesterases. We have also checked the ability of resveratrol esters to bind to and activate CB1 and CB2 cannabinoid receptors. Preliminary data indicates that several of tRV esters also bind to CB1 and CB2 with low affinity (µmol range) but comparable to tRV. Based on these observations, we hypothesiezed that CB1 and CB2 receptors may play an important role in the molecular mechanism of action for tRV esters. Minor modifications to the basic tRV structure resulted in marked alterations in the affinity of various analogs for CBRs; this indicates that tRV could be used as a scaffold for the design of highly selective and efficacious CB1R and CB2R ligands. It is expected that the conjugation of tRV with other bioactive compounds may lead to synergistic biological effects and, consequently, higher activity as compared to the unbound, individual components.