Studies On The Chemical Constituents And Biological Activities Of Helichrysum Arenarium (L.) And The Aerial Part Of Echinops Latifolius Tausch

In the dissertation,2 kinds of medicinal plants were studied.1.Helichrysum arenarium(L.) distributed mainly in Xinjiang Uygur Autonomous Region of China,Mongolia,Europe and Russia.It is a medicinal plant which has been long known in European traditional medicine as a cholagogue,choleretic, hepatoprotective and detoxifying agent.It also has antioxidant,and anti-bacterial activities on the basis of modern pharmacological reasearch,and previous phytochemical study on this plant revealed the presence of flavonoids and phenolic acids.From the ethanol extracts of the whole herbal of H.arenarium,41 compounds were isolated by means of solvent partition,repeated column chromatography on silica gel,polyamide,Sephadex LH-20,pre-HPLC,and recrystallization.On the basis of analysis of NMR,MS data,measurement of physico-chemical characters and chemical methods,their structures were identified as:apigenin(1), apigenin-7-O-β-D-glucopyranoside(2),kaempferol(3), kaempferol-3-O-β-D-glucopyranoside(4),kaempferol-7-O-β-D-glucopyranoside(5), kaempferol-7-O-α-L-rhamnoside(6),luteolin(7),luteolin-7-O-β-D-glucopyranoside(8), quercetin(9),quercitrin(10),rutin(11),naringenin(12),5-hydroxy-4’-methoxyisoflavone(13),5-hydroxy- 4’-methoxyisoflavone-7-O-β-D-glucopyranoside (14),6,8-dimethoxy-3,5,7-trihydroxy-flavone(15),3,5-dihydroxy-6,7, 8-trimethoxyflavone(16),5,6,4’-trihydroxyflavone-7-O-β-D-glucopyranoside(17),5, 4’-dihydroxy-6,7,3’,5’-tetramethoxyflavone(18),5,7,4’-trihydroxy-8-methoxyflavone (19),6,7-dimethoxy-4-hydroxy -1-naphthoic acid(20),caffeic acid(21),methyl caffeate (22),protocatechuic acid(23),p-hydroxybenzoic acid(24),arbutin(25),isovanillic acid (26),gallic acid(27),quininic acid(28),methyl quinic ester(29),caffeotannic acid(30), 1,3- O-dicaffeoylquinic acid(31), (Z)-5-hydroxy-7-methoxy-4-[3-methyl-4-(O-β-D-xylopyranosyl)but-2-enyl]isobenzofur an-l(3H)-one(32),5-hydroxy-7-O-β-D-glucopyranosyl-isobenzofuran-l(3H)-one(33), scopoletin(34),6-(4’-hydroxy-trans-styryl)-4-methoxy-2-pyrone(35),syllo-insitol(36), betulic acid(37),oleanolic acid(38),ursolic acid(39),β-sitosterol(40),daucosterol (41).Among them,compounds 20,and 32 were new compounds;compounds 6,13,14, 17,18,26,29,33,and 37 were firstly isolated from the Helichrysum genus.The extracts and some compounds from H.arenarium were tested for anti-bacterial, anti-tumor and anti-inflammatory activities.On the basis of references,a review was given on the structural modification of natural bioactive products.2.Echinops latifolius Tausch is a traditional Chinese medicine,which widely distributed in the northern part of China.The roots of E.latifolius have been used to clear heat,expel miasma and stimulate milk section for a long history.It has been recorded in Chinese Pharmacopoeia(1995 Edition) as one of the sources for Yuzhou Loulu.Recent researches indicated that Yuzhou Loulu had the effects of anti-tumor, anti-virus,anti-fungal,anti-inflammatory and hepatoprotective effects.By means of column chromatography,preparative thin-layer chromatography and Sephadex LH-20,14 compounds were isolated from the aerial part of E.latifolius.On the basis of physico-chemical properties and spectroscopic analysis,they were identified as:β-sitosterol(1),echinopsine(2),taraxerol acetate(3),daucosterol(4),α-terthienyl(5),5 -(but-3-en-1-ynyl)-2,2’-bithiophene(6),fredelin(7),cardopatine(8), isocardopatine(9),lupeol(10),5-acetyl-2,2’-bithiophene(11),ergosta-4,6,8(14),22 (E) -tetraen-3-one(12),succinic acid(13),5-hydroxymethylfuraldehyde(14).Among them,compounds 7 and 12 were isolated from the Echinops genus for the first time,the thiophene derivates were obtained from the aerial part of the plant for the first time also.The extracts of the aerial part of E.latifolius were bioassied for their cell cycle inhibitory and apoptosis inducing activities using K562 cells.The anti-tumor parts were found in the petroleum ester extract and the chloroform extract.By MTT and SRB methods,the cytotoxic activities of the thiophenes isolated were assayed in vitro.All the compounds showed significant phototoxic activities against tumor cell lines,dependent on the long wavelength ultraviolet(UVA).