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Chinese Medicine Solanum Nigrum Anticancer Constituents

Posted on:2007-08-09Degree:DoctorType:Dissertation
Country:ChinaCandidate:X L ZhouFull Text:PDF
GTID:1114360185489179Subject:Medicinal chemistry
Abstract/Summary:PDF Full Text Request
The total saponins extract from Solarium nigrum L. exhibited inhibitory activity on S180, and the anti-tumor effect demonstrated a positive effect relationship on the basis of amount.In our systematical study on the chemical constituents of Solarium nigrum L., 43 compounds were obtained from the ethanolic extract of the whole herb of this plant through various chromatographic techniques. Their structures were elucidated on the basis of physic-chemical property, spectroscopic analysis and chemical correlation (acidic hydrolysis, Mosher method). The 43 compounds from Solarium nigrum are solasonine (1),β1-solasonine (2),β2-solasonine (3), solamargine (4),β2-solamargine (5), solanigroside P (6)*, solanigroside Q (7)*, (3β, 12β, 22α, 25R)-3, 12-dihydroxy-spirosol-5-en-27-oic acid (8), hypoglaucin H (9), dumoside (10), degalactotigonin (11), tigogenin 3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (12), nigrumnin I (13), solanigroside C(14)*, solanigroside D (15)*, solanigroside E (16)*, solanigroside F (17)*, solanigroside G(18)*, solanigroside H (19)*, uttroside B (20), uttroside A (21), (22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furost-Δ5-3β26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (22), (22α, 25β)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-Δ5-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-C)-β-D-galac-topyranoside (23), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-methoxy-furostan-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (24), (5α, 22α, 25R)-26-O-(β-D-glucopyranosyl)-22-hydroxy-furost-3β, 26-diol-3-O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (25), solanigroside I (26)*, solanigroside J (27)*, solanigroside K (28)*, solanigroside L (29)*, solanigroside M (30)*, solanigroside N (31)*, solanigroside O (32)*, solanigroside R (33)*, solanigroside S (34)*, solanigroside T (35)*, 5α-pregn-16-en-3β-ol-20-one lycotetraoside (36), solanigroside A (37)*, solanigroside B (38)*, (5α, 20S)-3β,16β-dihydroxy pregn-22-carboxylic acid (22, 16)-lactone-3-(O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside (39), solanigroside U (40)*, solanigroside V (41)*, solanigroside W (42)*, solanigroside X (43)*. These compounds are comprised of 1 sapogenin and 42 saponins, including 8 steroidal alkaloids and 35 other steroidal saponins. Compounds 6, 7, 14-19, 26-35, 37, 38, 40-43 are new compounds. Compounds 9, 10, 22-25, 36, 39 were isolated for the first time from the solanum genus, and compounds 2, 3 were isolated from this plant for the first time. Compounds 28-35 and 42 are steroidal glycosides with new sapogenin.Simultaneously, the fingerprint chromatomap of the total saponins extract from Solanum nigrum has been established using HPLC-ELSD. Above 85%of the peak areas in the chromatography have been identified by comparing with 11 compounds (4, 12, 13, 15, 17, 20, 25, 30, 31, 36) separated from the plant. The contents of two main steroidal saponins (11, 20) in the total glycosidic extract have been determined.MTT method was used to test the cytotoxic activity of 40 compounds against four human tumor cell lines. Alkaloidal steroidal saponins (1, 3 and 4), spirostane saponin (11) and pregane saponins (36 and 38) showed cytotoxic activity. On the basis of results of cytotoxic activity assay, the structure-activity relationship for the compounds with similar aglycone structures from Solanum nigrum was discussed.On the basis of chemical and bioactive studies in this academic dissertation, it was confirmed that the plant Solanum nigrum possess anti-tumor activities, and illustrated that the steroidal saponins from Solanum nigrum are responsible for its antitumor activity as a folk medicine.
Keywords/Search Tags:Solanum nigrum, steroidal saponins, alkaloidal steroidal saponins, fingerprint chromatomap, contents determination, cytotoxic activity, MTT method, structure-activity relationship
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