| Canarium album(Lour.)Raeusch,also named Chinese olive,belongs to the family of Burseraceae Canarium.It is distributed mainly in south of China like Guangdong,Guangxi,Fujian,and Taiwan,as well as tropical Asia and subtropics zone.The ripe fruit of C.album is recorded in Chinese pharmacopeia 2015 edition to treat sore throat,cough,polydipsia,and poisoning of fish and crab,etc.The chemical compositions of C.album fruit vary in polyphenols,flavonoids,triterpenoids,and coumarins,etc.Its main pharmacological effects are reducing heat,detoxicating,soothing the sore throat,producing saliva,protecting liver,antimicrobial,and antioxidant.Recently our research group have also found its anti-HIV and anti-influenza A virus effects.In our anti-virus assays of the solvent extracts from C.album fruits,the chloroform extraction has good inhibitory effects on influenza A(H1N1)and HIV-1,with IC50 of 1.67±1.93 ?g/mL and 26.78±0.47 ?g/mL respectively,while the other two factions,petroleum ether extract and ethyl acetate extract can restrain HIV-1 to enter the target cells,with IC50 values of 3.97±0.38 ?g/mL and 6.80±0.10 ?g/mL respectively.It is promising to isolate and get pure compounds with strong activities of anti-influenza A and anti-HIV.This research aims to separate chemical components from chloroform and ethyl acetate extracts of C.album fruits,identify their structures and screen active compounds of anti-influenza virus A and anti-HIV.Further researches of anti-virus activites of those active compouds will provide theoretical and experimental basis for the development of new drugs of anti-influenza A and anti-HIV.It is also valuble of disclosing the material basis for efficacy of C.album fruit and exploring its new application.This research have separated and purified 17 compounds from 75%C2H5OH extraction of dry C.album fruits by means of column chromatography like silicon gel,MCI CHP20P,SephadexLH-20,ToyopearlHW-40S and ODS.Their structures were identified by physicochemical properties and modern spectroscopy methods(H-1 nuclear magnetic resonance,C-13 nuclear magnetic resonance,heteronuclear single quantum correlation,heteronuclear multiple bond correlation,nuclear overhauser effect,circular dichroism,mass spectrometry).The compounds were indentifyed as myo-inositol(1),(1'S,3'R,5'S,8'R)-dihydrophaseic acid-3'-O-?-D-glucopyranoside(2),3,4-dihydroxy benzoic acid(3),(1'R,3'S,5'R,8'R)-dihydrophacid-3'-O-?-D-glucopyranoside(4),3-O-galloyl quinic acid(5),ellagic acid(6),gallic acid(7),ethyl gallate(8),scopoletin(9),ellagic acid-4-O-?-D-glucopyranoside(10),ellagic acid-4-O-a-L-rhamnopyranoside(11),isocorilagin(12),urolithin M5(13),2-Furoic acid(14),methyl brevifolincarboxylate(15),digllic acid(16),brevifolin(17).Among all these compounds,3,5,6,7,8,9,10,11,12,13,15,16,and 17 were attribute to polyphenols,2 and 4 to sesquiterpenes,and 1 and 14 to other stuctures.Compounds 2 and 4 are two new compounds,while 3,11,13,14,15 and 16 are obtained from C.album fruit for the first time.The isolated compounds were screened for the activity of anti-influenza virus A(H1N1)by MTT methods.Results shows that isocorilagin(12)and methyl brevifolincarboxylate(15)have strong anti-influenza virus A(H1N1)activities within the concentration range of 0.78-50 ?g/mL and 0.78-100 ?g/mL,and IC50 values as 3.16±0.81 ?mol/L and 18.88 ±5.65 ?mol/L,respectively.The anti HIV-1 virus activity screening by luciferase reporter gene detection kit methods showes that compounds 12,13,15,16,11 have strong or moderate anti-HIV-1 activities with inhibition rates of 90.01%,85.48%,88.14%,65.35%and 56.47%,respectively at the concentration of 50?g/mL.Thses active compounds could be the lead compounds of anti-HIV and anti-influenza A.The determination of the active components contents,optimized methods of extraction and purification,further antiviral activity and mechanism research,and structural transformation for more effective and less toxic lead compounds from Chinese olive are worthy of performing and mining. |
PDF Full Text Request