| Cinnamic acid is an effective material component extracted from cinnamon bark of Traditional Chinese Medicine.The disturbance of free radical level balance in the body can cause many kinds of diseases.It was found that the activity of cinnamic acid could be further improved by derivatization modification.In this paper,methoxy-containing cinnamic acid was used as raw material to conduct structural derivatization modification,and a series ofcompoundscontainingpolyphenolichydroxylgroupswere synthesized.Through two different free radical scavenging methods,in vitro oxidative damage model verification and anti-tumor activity inhibition,their biological activity was studied.The effective results obtained are as follows:(1)Phenol hydroxyl synthesis of cinnamic acid derivatives were:this experiment with 3,4-dimethoxy cinnamic acid and 3,4,5,three oxygen radicals cinnamic acid as basic,the parent nucleus with acyl chloride reagent(oxalyl chloride)reaction,then respectively with amino phenol amino phenol,2-3-4-aminophenol in esterification reaction to obtain the new structure containing phenol hydroxyl 6compounds,respectively by thin layer chromatography(TLC),mass spectrometry(MS),~1H-NMR spectra and ~1C-NMR spectra analysis on the structure of the synthesized compounds were characterized to determine synthetic route is feasible,accurate structure.(2)Evaluation of antioxidant activity of phenolic hydroxyl cinnamic acid derivatives in vitro:in this study,the scavenging ability of synthesized derivatives was determined by two chemical methods:in vitro DPPH radical scavengingexperiment and ABTS radical scavenging experiment.The results showed that all kinds of derivatives had the ability of scavenging free radicals,but the scavenging ability of2R series cinnamic acid and 3R series cinnamic acid after structural modification was better than that of their respective active drugs,among which 2R-2 cinnamic acid,2R-1 cinnamic acid,3R-1 cinnamic acid and 3R-2 cinnamic acid were better.Thus,the antioxidant activity of derivatives was preliminarily evaluated,which laid a foundation for further research on antioxidant activity.(3)Phenol hydroxy cinnamic acid derivatives were red blood cells of AAPH induced oxidative stress protection:this experiment through synthetic derivatives by establishing AAPH oxidative damage red blood cells of rats model,the research on the oxidative damage erythrocyte hemolysis rate and the amount of time and the rate of oxidation of hemoglobin ralationship,investigate the antioxidant enzyme activity and the red blood cell oxidative damage model malondialdehyde(MDA)of dynamic impact.The results showed that derivative 2R series had antioxidant effect by increasing the activity of GSH-px and CAT in red blood cells,and derivative 2R-3 could significantly increase the activity of CAT in red blood cells compared with the original drug.Derivative3R series can increase the content of gsh-px,CAT activity and MDA in red blood cells,and play a protective role in oxidative damage.(4)Study on anti-tumor activity inhibition of phenolic hydroxyl cinnamic acid derivatives:in this study,MTT method was used to study the anti-tumor activity of cinnamic acid and its derivatives on breast cancer McF-7 in vitro,and to determine the effect of cinnamic acid and its derivatives on the activity inhibition of tumor cells.The results of MTT method showed that cinnamic acid series derivatives had anti-tumor activity on McF-7 cells and were superior to their respective prototypes,among which 2R-3 and 3R-3 had the strongest anti-tumor activity. |
