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Biological Activity of Resveratrol‐Hydroxycinnamic Acid Ester Conjugates
Author(s) -
Urbaniak Alicja Joanna,
Kacprzak Karol,
Senol Fatma Sezer,
Orhan Ilkay Erdogan,
RadominskaPandya Anna
Publication year - 2017
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.31.1_supplement.666.8
Subject(s) - chemistry , ferulic acid , resveratrol , bioavailability , coumaric acid , antioxidant , biological activity , conjugate , polyphenol , in vitro , biochemistry , pharmacology , medicine , mathematical analysis , mathematics
Resveratrol (3,5,4′‐trihydroxy‐ trans ‐stilbene, t RV) is one of the most biologically active polyphenols of natural origin. It exhibits many beneficial properties namely antioxidant, anti‐inflammatory, cancer preventing, and cardio‐protective. Despite that, the wide application of t RV, is limited by its poor water solubility, low stability, and consequently, weak bioavailability when administered orally. To overcome this deficiency, our group has developed novel resveratrol‐based derivatives by conjugation with other bioactive compounds such as hydroxycinnamic acid derivatives ( p ‐, m ‐coumaric, ferulic and sinapinic). It is anticipated that conjugation of tRV will result in derivatives with lowered metabolism, higher stability, and altered molecular targets. The developed synthetic method is a four step procedure and leads to the high‐yield production of compounds with high purity. In this work, t RV esters and their unconjugated counterparts were tested in vitro for their biological activity. Experiments were carried out to check their potency to inhibit cholinoesterases, tyrozynaze, elastaze, and collagenase; moreover, their ability as antioxidants and metal chelators were investigated. Resveratryl tri‐ p ‐coumarate, resveratryl tri‐ m ‐coumarate, and resveratryl triferulate express significant inhibitory activity towards butyrylcholinesterase, IC 50 = 29.57 ± 3.33 μg/ml, IC 50 =32.40±1.29 μg/ml, IC 50 =36.89 ± 1.05 μg/ml respectively. These values were similar to the IC 50 values of reference compound galanthamine HBr. Inhibitory activity towards acetylcholinesterase were slightly lower. t RV conjugates with p ‐coumaric and ferulic acid were the most potent in elastase inhibition assay; however, the tyrosynase inhibition study showed more of an effect by resveratryl tri‐ p ‐coumarate and resveratryl trisinapinate. The unconjugated t RV exhibited the strongest collagenase inhibiting property. t RV ester with sinapinic acid exhibited the highest metal chelating activity. Unconjugated t RV, sinapinic, and ferulic acids exhibited the highest antioxidant activity in both 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and Ferric‐Reducing Antioxidant Power (FRAP) assays. The properties of free radical scavengers were diminished with the conjugated compounds; however, synthetic esters of those compounds may still be considered as good free radical scavengers. Support or Funding Information [NIH/NIDA DA039143 to ARP, Kosciuszko Foundation's Exchange Program to the US to AU]