Studies On The Chemical Constituents And Their Bioactivities Of Dianthus Superbus And The Flowers Of Tussilago Farfara

‘Qumai’,the dry aerial parts of the plant Dianthus Superbus L.(family Caryophyllaceae),has long been used as a common traditional Chinese medicine in China.It is widely distributed in the north temperate zone and mostly grows in Asia and Europe.It has the functions of clearing heat,diuresis,breaking extravasated blood and dredging meridians.In clinical tirals,it is often used for the treatment of urinary system disorders,nephropathy and menstruation regulation.‘Kuandonghua’ is the dry flower buds of Tussilago fargesii of family Compositae,which is mainly distributed in temperate regions of Asia and Europe.It has the functions of moistening the lung,relieving cough and resolving phlegm.It is mostly used to treat asthma,chronic bronchitis and other diseases in modern clinical trials.In order to further explore the active ingredients of traditional medicinal plants and exploit and utilize the medicinal resources better,the chemical constituents and biological activities of the ethanol extracts of the aforementioned two herbs were studied systematicallyin the current work.All the compounds were separated by silica gel Sephadex LH-20 and ODS column chromatography,as well as semi-preparative high performance liquid chromatography.The structures of the these compounds were identified by various spectroscopic and chemical methods,including two alkaloid glycosides,fifteen benzopyran derivatives,nine sesquiterpenes,six fatty acids,three benzofuran derivatives,two small molecule phenolic compounds,six lignans and their glycosides,one triterpenoid and one phenolic glycoside.Seven of them are unreported compounds and 11 are new natural products.Sixteen compounds were isolated and identified from Dianthus superbus.Among them,nine compounds were isolated from the ethyl acetate partition,including six fatty acid derivatives(1–6),one triterpenoid(7)and two lignans(15–16).Seven compounds were obtained from n-butanol parition,including four lignans(8–11),one phenolic glycoside(12)and two alkaloid glycosides(13–14).Among them,13–14 are new compounds.The known compounds are(9E,11 E,15Z)-13-hydroxyoctadeca-9,11,15-trienoic acid(1),(E,E)-13-hydroxyoctadeca-9,11-dienoic acid(2),(E,E)-9-hydroxyoctadeca-10,12-dienoic acid(3),glycerol 1-9’,12’-octadecadienoate(4),(Z,Z,Z)-9,12,15-octadecatrienoic acid methyl ester(5),methyl linoleate(6),villosagenin Ⅰ(7),syringaresinol-β-D-glucoside(8),β-Dglucopyranoside,4-[2,3-dihydro-3-(hydroxymethyl)-7-methoxy-5-[(1E)-3-methoxy-1-propen-1-yl]-2-benzofuranyl]-2-methoxyphenyl(9),(7R,8S)-syringylglycerol 8-O-4’-sinapyl ether4-O-β-D-glucopyranoside(10),(7S,8R)-syringylglycerol 8-O-4’-sinapyl ether4-O-β-D-glucopyranoside(11),1-O-(3-hydroxy-4-methoxybenzoyl)-β-D-glucopyranose(12),(–)-dehydrodiconiferyl alcohol(15),and(–)-simulanol(16).Twenty-six compounds,including 15 benzopyrone derivatives(17–30,32),nine sesquiterpenes(36,38–45),three benzofuran derivatives(33–34,37)and two small molecule phenolic compounds(31 and 35),were isolated and identified from the ethyl acetate partition of the flower buds of Tussilago farfara.Among them,17–18,20,and 23–30 are new natural prouducts,and 40–44 are undescribed compounds.The known compounds are(S)-1-(4-hydroxy-2,2-dimethylchroman-6-yl)ethanone(19),(S)-6-(1-hydroxyethyl)-2,2-dimethylchroman-4-one(21),(R)-6-(1-hydroxyethyl)-2,2-dimethylchroman-4-one(22),ethyl caffeate(31),6-hydroxy-2,2-dimethylchroman-4-one(32),hydroxytremetone(33),1-[2,3-dihydro-3,6-dihydroxy-2-(1-methylethenyl)-5-benzofuranyl](34),4-methyl-2-hydroxyphenol(35),1β,6α-dihydroxy-4(15)-eudesmane(36),2,5-diacetyl-6-hydroxybenzofuran(37),eudesma-4,11-diene-1β,15-diol(38),lα,5β-guai-10(14)-ene-4β,6β-diol(39),and(4R,6E)-2,8-bisangeloyloxy-4-hydroxybisabola-2,6,10-trien-1-one(45).The protective effects of compounds 13 and 14 on nerve cell SH-SY5 Y induced by Aβwere tested.It was found that compounds 13 and 14 had weak protective effects on nerve cell SH-SY5Y.