Study On The Chemical Constituents Of Baiying And Its Anti-tumor Activity

The medical plant Solanum lyratum Thunb.belong to the family of Solanaceace which widely distributed in south areas of Changjiang River.The whole plant of Solanum lyratum has long been use as traditional Chinese folk medicine to treat malarias,jaundices,edemas,gonorrheas,rheumatoid arthritis,cholecystitis.It was also used as an anti-tumor medicine in some folk remedy.Based on a re-view of the chemical constituents and pharmacological activities of Solarium lyratum in this paper,the tubers of S.lyratum were extracted with water to give ethanolic extract,which was subjected to column chromatography on D101 macroporous resin,silica gel,ODS-C18 silica gel,LH20,and preparative HPLC,and led to 86 compounds.Based on physical and chemical properties,MS,NMR data and the information reported in the literature,the structures of80 compounds were elucidated as:5,7,3',5'-tetrahydroxy-3,4'-dimethoxy-6'-prenyl flavonoid(1),5,7-dihydroxy,6-isopentenyl-2',4'-dimethoxydihydroflavone(2),3-methoxyquercetin(3),2,4,6-trihydroxy-2',6'-dimethoxy-5-isopentenylchalcone(4),5,7-dihydroxy-8-methoxylated flavones(5),7-(2,3-epoxy-3-methyl-3-butyloxy)-6-methoxycoumarin(6),5-hydroxy-4',7-dimethoxy-6,8-dimethylflavone(7),quercetin-3-O-?-D-glucoside(8),chlorophyllin ?(9),(R)-2-amino-5-(1H-indol-3-yl)-4-oxopentanoic acid(10),Diosgenin-O-a-L-rhamnopyranosyl-(1?2)-?-D-glucuronide uronic acid(11),25R-Spirost-4-ene-3,12-dione(12),6,7-bis-2',3'-(2,2-dimethyldihydropyrano)-5,4'-dihydroxy-3-methoxyflavone(13),wightianin(14),formononetin(15),genistein(16),3'-Hydroxy daidzein(17),syringin(18),diosgenin 3-O-?-D-glucopyranosiduronicacidmethylester(19),diosgenin 3-O-a-L-rhamnopyranosy l-(1?2)-?-D-glucopyranosiduronicacid(20),diosgenin3-O-?-L-rhamnopyranosy 1-(1?2)-?-D-glucuroniduronicacidmethylester(21),daidzein(22),periplogenin(23),protocatechuic acid(24),p-Hydroxy phenethylalcohol(25),(+)-(R)-5,5-dimethyl-4-(2,6-dimethylbenzyl)(26),p-Hydroxybenzoic acid(27),25(R)-4,6-Spirostadien-3-one(28),25(R)-spirost-4-en-3-one(29),20-hydroxy diosgenone(30),(25R)-3,20-dihydroxy-spirosterol-5-ene(31),7-ketodiosgenin(32),agigenin(33),diosgenin3-O-?-D-glucopyranosiduronicacid(34),3-hydroxy-11-urs-en-28,13-olide-11,12-dehydroumiolieacid lactone(35),grasshopper ketone(36),septemlobins G(37),septemlobins H(38),(+)-isolariciresinol(39),f-Amyrin acetate(40),(1'S,2R,5S,10R)-2-(1',2'-dihydroxy-1'-methylethyl)-6,10-dimethylspiro[4,5]dec-6-en-8-one(41),(+)-matairesinol(42),neoechinulin A(43),Leptolepisol D(44),(-)-secoisolariciresinol(45),N-trans-feruloyltyramine(46),aviculin(47),(H+)-pinoresinol(48),zhebeiresinol(49),N-Docosanoyl tyrumine(50),hiscopoletin(51),paeoveitol C(52),blumenol C(53),(+)-Lyoniresinol(54),hibiscuwanin B(55),trans-N-feruloyl-3-O-methyldopamine(56),ciwujiatone(57),(-)-(7,S,8S,8'R)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one(58),ent-isolariciresinol(59),cinncassin D(62),(-)-Syringaresinol(63),(+)-medioresinol(64),(-)-epipinoresinol(65),hecogenin(66),tigogenin(67),diosgenin(68),dibutyl phthalate(69),(+)-lariciresinol(70),ursolic acid(71),? 5(6)-22-isospirostene-2,3-diol(72),gitogenin(73),3?,6a,6?-trihydroxy-5a-pregnane-20 S-carboxylic acid(22,16)-lactone(74),(24S)-3-?-0-(2-acetamido-2-deoxy-p-D-gluco-pyranosyl)-ergosta-5-ene(75),(3?,25S)-spirost-5-en-3-yl-O-?-D-glucopyranosyl-(1?3)-O-?--D-glucopyranosyl-(1?4)-?-D-galactopyranoside(80),diosgenin 3?-O-?-D-xylopyranosyl-(1? 3)-?-D-glucopyranosyl-(1?4)-[?-L-rhamnopyranosyl-(1?2)]-?-D-glucopyranoside(81),gitogenin 3-O-?-D-glucopyranosyl(1?4)-?-D-galactopyranoside(82),diosgenin 3-O-?-D-glucopyranosyl(1?4)-?-D-galactopyranoside(83),pipelol A(84),2-phenylethyl-(6-I-?-L-arabinofuranosyl)-O-?-D-glucopyranoside(85),eugenyl O-?-apiofuranosyl(1"?6')-O-?-glucopyranoside(86).Among them,7 compounds(1,4,30,31,37,38,85)are new compounds,whlie49(2,3,6,10,13,14,18-21,23,26-28,32,35,39-45,47-49,52,54,55,57-65,70,72-75,80-86)separated from Solarium lyratum for the first time.The antiproliferative activities of some compounds against human cervix epithelial cell line HELA,human gastric carcinoma cell line BGC823and human lung cancer cell line A549 were evaluated by MTT.The results showed that most of the active compounds are derived from low-polar solvent extraction sites and compounds 4,11 and 12 have exhibited antiproliferative activity in that three toumor cell lines.Cell cycle analysis of BGC823 cells was investigated by using FACS afer PI staining.The results showd that compounds 11 and 12led to a marked accumulation in G1/S phase afer drug treatment.lt suggested that the growth inhibitory effect of compounds 11 and 12 were the result of arrest in G1/S phase and apoptosis,which is associated with Solanum lyratum extract have widely anti-tumor activity.