Study On Chemical Modification Of 20?R?-Ginsenoside Rg₃ And Its Antitumor Activity

20?R?-ginsenoside Rg₃ is the micro bioactive ingredient of red ginseng?The processed products of fresh ginseng by steaming and drying?and has many pharmacological effects,including anti-cancer,anti-viral,anti-aging and anti-fatigue effects.However,The structural modification of 20?R?-ginsenoside Rg₃ are rarely studied.In this paper,20?R?-ginsenoside Rg₃ was modified to improve its lipid solubility and bioavailability.First of all,the discovery,preparation and physiological activity of 20?R?-ginsenoside Rg₃ were reviewed.Secondly,the research on the structural modification of ginsenoside was reviewed,which are mainly classified as protopanaxdiol-type?protopanaxtriol-type and ocotillol-type saponin.In this paper,based on previous research on the synthesis of ginsenoside fatty acid esters,20?R?-ginsenoside Rg₃ was prepared by Baeks method,The DFT-B3LYP methods with 6-31G basis set have been applied to optimization of 20?R?-ginsenoside Rg₃,the charges distribution was investigated,the molecular structure characteristics were discovered.Then,selectivity acylation molecules of Sophorose part 6'and 6''primary hydroxyl of 20?R?-ginsenoside Rg₃ by using TBTU/DIEA as condensation agent,provide three acylation products:20?R?-ginsenoside Rg₃-6',6''-palmitates?Rg₃-PA?,20?R?-ginsenoside Rg₃-6'-palmitate?Rg₃-PB?and 20?R?-ginsenoside Rg₃-6''-palmitate?Rg₃-PC?.The structures were confirmed by means of 2D-NMR,IR and MS.In this paper,20?R?-ginsenoside Rg₃ structural modification products were studied in vitro antitumor activity.Determined by MTT method is used to detect structural modifications product value-added inhibition of human pancreatic cancer cells,the results show that the structure of the modified product all have different degrees of human pancreatic cancer cell PANC-1 proliferation inhibition,manifests the high medicinal value and broad application prospects in tumor treament.