Studies On Chemical Constituents And Pharmacological Activities Of The Plant Of Artemisia Frigida

Artemisia frigida,also named xiaobaihao and “A gi” in traditional Mongolia medicines,is semishrub belongs to the Artemisia L.genus of Compositae family.It has the special fragrant smell of Artemisia,and mainly distributed in Inner Mongolia province of China.It also distributes in Jilin,Hebei,Liaoning,Qinghai,Shanxi,Xinjiang,Gansu,Ningxia,and Mongolia,Siberia and North America.It mainly grows in the grassland and desert zone.Artemisia frigida tastes bitter,and is used for a variety of bleeding,joint swelling,renal heat,irregular menstruation and sore carbuncle.The few existing literatures only showed that the main constituent of this plant are sesquiterpenes,flavonoids and coumarins.In order to effectively develop the medicinal value of Artemisia frigida,we studied the constituents of dichloromethane and ethyl acetate extractions of Artemisia frigida.And we identified the structures of the isolated compounds and screened their activities.Objective: The study of the chemical constituents of Artemisia frigida was carried out by methods of column chromatography,thin layer chromatography,perparative high performance liquid chromatography and perparative TLC chromatography.Effective methods to obtain pure compounds were established.All structures of the isolated compounds were elucidated by spectra of UV,MS,1H-NMR,13C-NMR,1H-1H COSY,HSQC,HMBC,NOESY,etc.Some of the compounds were screened for their activities.Methods: The air-dried plant of Artemisia frigida(about 14 kg)were crushed and extracted with 95% ethanol by reflux for three times,and got ethanol extract 2079.6 g.The residue was scattered with water,and extracted with petroleum ether(60~90℃),dichloromethane,and ethyl acetate,respectively.After concentration,we got three parts of extracts with the weights of 449.2 g,87.6 g,and 132.4 g.The extracts of dichloromethane and ethyl acetate were isolated and purified by methods of reversed phase silica gel column chromatography,polyamide column chromatography,Sephadex LH-20,preparative thin layer chromatography and preparative high-performance liquid chromatography.The structures of compounds were elucidated according the spectra of UV,MS,1H-NMR,13C-NMR,1H-1H COSY,HSQC,HMBC and NOESY,etc.The biological activities of compounds were evaluated.Results: There were twenty-six compounds were isolated from the plant of Artemisia frigida,including thirteen flavonoids,ten sesquiterpenoids,one coumarin,one acetopheone,and one benzoic acid.The results of identification as followings:pectolinarigenin(1),jaceosidin(2),chrysoeriol(3),tricin(4),3-oxo germacra-1(10),11(13)-dien-6α,12-olide(5),achillin(6),1,10β-epoxyach illin(7),scoparone(8),4-hydroxyacetophenone(9),chrysosplentin(10),ja ceidin(11),11α,13-dihydroyomogin(12),chrysanthemin A(13),eupatili n(14),eupatrin(15),artemorin(16),6-methoxytricin(17),hanphyllin(18),cirsimaritin(19),ridentin(20),desacetylmatricarin(21),subchrysine(22),luteolin(23),caffeic acid(24),agastachoside(25),tilianin(26).Among these compounds,jaceosidin(2)and eupatrin(15)exhibited weak activity of PPARγ(Peroxisome proliferator activated receptor γ).Pectolinarigenin(1)and chrysoeriol(3)had inhibitory effect on PTP1B(Protein Tyrosine Phosphatase-1B).Conclusions: Twenty-six compounds were isolated and identified from the dichloromethane and ethyl acetateextracts of the plant of Artemisia frigida.Compounds firstly isolated from this genus are 3-oxogermacra-1(10),11(13)-dien-6α,12-olide(5),1,10β-epoxyachillin(7),jaceidin(11),hanphyllin(18),agastachoside(25)and tilianin(26).Compounds firstly isolated from this plant are chrysosplentin(10),11α,13-dihydroyomogin(12),chrysanthemin A(13),artemorin(16),6-methoxytricin(17)and subchrysine(22).Compounds jaceosidin(2)and eupatrin(15)exhibited weak activity of PPARγ.Compounds pectolinarigenin(1)and chrysoeriol(3)had inhibitory effect on PTP1B.