Studies On Chemical Constituents Of Solanum Nigrum L.

Solanum nigrum L.is one of the Solanaceae species. Also known as Ye Putao, Tulipa eye grass, bitter herbs, bitter Kui. The whole plant of Solanum nigrum can be used as medicine herbs. They were distributed throughout the whole country. Modern pharmacology clarified that they can be used for anti-tumor, anti-inflammatory and anti-shock, anti-allergic, heat and toxic, expectorant cough, antibacterial, antihypert- ensive and other effects.In this paper, we study the chemical composition of leaves and fruit of Solanum nigrum .We discussed the extraction, separation and purification of them. Their biological anti-tumor activities have been also researched. Nine compounds were identified from Solanum nigrum L . The chemical structures of which has been elucidated by using IR, UV, MS, NMR and other spectroscopic analysis means.L1:26-O-β-D-glucopyranosyl-(25R)-5α-furost-22α-methoxyl-3β,26-triol- 3-O-β-D-glucopyranosy(1→2 )-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyran- osyl-(1→4)-β-D-galactopyranoside , L2:26-O-β-D-glucopyranosyl-(25R)-5α-furost-3β,22α,26-triol-3-O-β-D-glucopyranosy(1→2 )-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside ,L3: Solamargine , L5:{(25R)-5α-furost-3β,22α-diol-12-one-26-carboxylic acid-3-O-β-D-glucopyranosy(1→4 )-[O-β-D- glucopyranosyl -(1→2)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside},L6: quercetin-3-O-α-L-Rhaopyranosyl(1→6 )-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside L7:tigogenin3-O-β-D-glucopyranosyl-(1→2)-[β-D-xylo- yranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside, L5,L6,L7 is for the first time isolated from Solanum nigrum. There compounds is also isolated from the fruits. L8:β-sitsterol , L9:daucosterol , and L10: quercetin are discussed from Solanum nigrum. This experiment also tested the anti-tumor activities of the chemical biological components.Extraction,Separation and identification1.Extraction and isolationThe extraction of the fruits: The dried fruit 2.5Kg, 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h,1.0h,45min. The solution was concentrated and diluted wiyh water before . flew through the AB-8, we obtained extractions(200g).The extraction of the leaves: the dried leaves 3Kg , 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h,1.0h,45min. the solution was subjected the same manner as described as above, we obtained extractions (750g and 275g).The separation of total flavnoids : The dried leaves 3Kg , 80% ethanol extracted for three times, the amount of 80% ethanol were 21,18,15 L, the time were 1.5h, 1.0h, 45min, the solution was concentrated, adsorbed by AB-8 resin ,eluted by 0.1% NaOH first ,the solution was neutralized by 1%HCl to pH=7, then through the AB-8 resin again. After the components were eluted by ethanol ,concentrated and dried, we obtained extractions (350g).2 PurificationThe purification of the fruits: They were separated by silica gel column chromatography with solvent (Ⅰ-Ⅰ) as mobile phase , we obtained five parts ,the further purificayion to give L4 (270mg), L5 (120mg). Using thin layer chromatography silica gel plate (prepared board), we obtained L3 (15mg).The purification of the extracts from leaves: With sapration of silica gel column chromatography and elution (I-I), we obtained L1 (173mg). With ODS column chromatography we obtained L2 (530mg). H part with precipitation, filtration, repeatedly with methanol washing, we got L7(830mg).The purification of flavonoids Separated with eluentⅠ-Ⅷ, collected, detected, and obtained five parts . B part with ODS column chromatography, we obtained L6 (20mg). 3 IdentificationThrough MS, 1DNMR, 2DNMR spectral analysis and other literature we known compounds L1:26-O-β-D-glucopyranosyl-(25R)-5α-furost-22α-methoxyl-3β, 26-triol3-O-β-D-glucopyranosy(1→2 )-[O-β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)- O-β-D-galactopyranoside .L2:26-O-β-D-glucopyranosyl -(25R)-5α-furost-3β,22α,26-triol-3-O-β-D-glucopyranosy(1→2 )-[ O-β-D- xylo- pyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)- O-β-D-galactopyranoside. L3:Solamargine ,L5:{(25R)-5α-furost-3β,22α-diol-12-one-26-carboxylic acid-3-O-β-D-glucopyranosy(1→4 )-[O-β-D- glucopyranosyl -(1→2)]- O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside}L6:quercetin-3-O-α-L-Rhaopyranosyl(1→6 )-O-β-D-gluco- pyranosyl-(1→4)-O-β-D-glucopyranoside ,L7: (25R)-5α- spirost-3-O-β-D–xylo- pyranosyl-(1→3)- O-β-D-glucopyranosyl-(1→2)- O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside. It is the first time isolated from Solanum nigrum that L8,β-sitsterol , L9,daucosterol and L10,quercetin are discussed .The aglycone and alkaloid saponins in anti-tumor experimentsThis experiment also established the total saponins and total alkaloid of Solanum nigrum in anti-tumor activities. The results showed that they both can reduce liver cancer H22 and Lewis lung cancer cells viability in dose-dependent manner.In conclusion, all the results of the paper could provide science foundation of this medicine herb for the development and research in reason.