Study On Chemical Constituents And Antitumor Activity Of Solarium Lyratum Thunb

Solanum lyratum Thunb,dried whole herb of the plant S.lyratum Thunb,is a valuable traditional antipyretic herb in traditional Chinese medicine,firstly documented in a famous book 'Shennong Bencaojing'.It possesses the efficacies including clearing heat and detoxicating,dispelling the wind and removing dampness.It was often used in anti-cancer treatments clinically,such as lung cancer,liver cancer,cervical cancer.In addition,it can be used to treat malaria,jaundice,rheumatic arthritis and so on.Phytochemistry studies revealed that S.lyratum Thunb contains steroids(the major components),flavonoids,polyphenols,organic acids,sesquiterpenes,sterols,coumarins and etc.In our exploitation of antitumor active constituents from S.lyratum,a systemative phytochemistry studies were subjected to the 80% ethanol extract of S.lyratum.By combination of different kinds of modern chromatographies including open-column chromatography,preparative thin layer chromatography and preparative HPLC purification methods,twenty compounds were isolated and the structures of sixteen compounds among them were identified on the basis of physicochemical properties and spectroscopic data.Among them,there were six lignans,four amides,three flavonoids,two sesquiterpenoids,and one other type of compound.Their chemical structures were identified as(+)syringaresinol-O-?-D-glucopyranoside(SL-1),rutin(SL-2),quercetin3-O-?-D-glucofuranoside(SL-3),(1'R,2R,5S,10R)-2-(1',2'-dihydroxy-1'-methylethyl)-6,10-dimethylspiro [4,5] dec-6-en-8-one(SL-4),(7'R)-N-feruloyl normetanephrine(SL-5),(1R)-(3-ethylphenyl)ethane-1,2-diol(SL-6),(7S,8R,8'R)-5,5'-dimethoxylariciresinol(SL-7),(E)-3-(4-hydroxy-3-methoxyphenyl)-N-(2-(4-hydroxyphenyl)-2-methoxyethyl)acrylamide(SL-8),N-trans-feruloyloctopamine(SL-9),kaempferol 3-O-?-D-rutinoside(SL-10),(E)-N-(2-hydroxy-2-(4-hydroxyphenyl)ethyl)-3-(4-hydroxyphenyl)acrylamide(SL-11),(1'S,2R,5S,10R)-2-(1',2'-dihydroxy-1'-methylethyl)-6,10-dimethylspiro [4,5] dec-6-en-8-one(SL-12),alangilignoside B(SL-13),(+)-syringaresinol(SL-14),officinalioside(SL-15)and isolariciresinol-9-acetate(SL-16),respectively.To the best of our knowledge,compound SL-16 was a new lignan,and SL-11 was one new natural product.In addition,SL-13?SL-15 were isolated from the Solanum lyratum Thunb for the first time.Furthermore,the antiproliferative activities of SL-2?SL-15 against human liver cancer cell line Hep G2 were evaluated by MTT method.The results indicated that all compoudsshowed some inhibition activities at certain concentrations.Compound SL-8 at 100 ?mol/L exhibited the strongest antiproliferative activity in this test.An efficient approach for rapid characterization of the target compounds in SL n-butanol extract(SL-BU)was developed by UHPLC-ESI-QTOF-MS and NMR.As a result,total of 20 compounds were identified or tentatively characterized,including eleven steroid alkaloids,five amides,two sesquiterpenes,one lignan,and one flavonoid.By searching chemspider,pubchem and other databases,and comparing the retention time and mass spectrometry cleavage method of the reference substance previously obtained,we confirmed seven compounds among them.The result may contribute to the further quality control of S.lyratum Thunb.