Methanolysis of triterpenoid saponin from Ardisia gigantifolia stapf. and structure–activity relationship study against cancer cells
| Autor: | Li-Hua Mu, Dai-Hong Guo, Cui-li Huang, Ping Liu, Wen-Bin Zhou |
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| Rok vydání: | 2013 |
| Předmět: |
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Molecular Stereochemistry Clinical Biochemistry Molecular Conformation Saponin Pharmaceutical Science Antineoplastic Agents Biochemistry Ardisia Structure-Activity Relationship Cell Line Tumor Drug Discovery Humans Moiety Cytotoxic T cell Structure–activity relationship Nuclear Magnetic Resonance Biomolecular Molecular Biology IC50 Triterpenoid saponin chemistry.chemical_classification Molecular Structure Methanol Organic Chemistry Saponins Cell cycle Triterpenes chemistry Cancer cell Molecular Medicine Drug Screening Assays Antitumor |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 23:6073-6078 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2013.09.029 |
| Popis: | Thirteen 13,28-epoxy triterpenoid saponins were isolated from Ardisia gigantifolia stapf. and one potential anti-tumor saponin was methanolysised by H2SO4 to afford four new compounds. The seventeen compounds were evaluated for their anti-proliferative activity on A549, HCT-8 and Bel-7402 cells. The structure-activity relationship analysis indicated that the incorporation of =O group at C-16, L-rhamnose at R(5) and acetyl group at OH-6 of the D-glucose lead to a significant increase of the cytotoxic activity on A549 and HCT-8 but significant reduction of the cytotoxic activity on Bel-7402 cells. The synthesized saponins losing 13,28-epoxy and CHO at C-30, losed their cytotoxicities on A549 and HCT-8 cells, suggesting that the two moieties play an essential role for activity. 3β-O-α-L-rhamnopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-l-arabinopyranoside-16α-hydroxy-13,28-epoxy-oleanane (2) showed better inhibitory activity to Bel-7402 (IC50 0.86 μM) than that of 5-FU (IC50 8.30 μM), which indicate that five saccharide and methyl moiety at C-30 are important for anti-proliferative activity. The activities of saponins 15>14, 17>16, suggested that the configuration of 28,30-epoxy is preferable to be 30(R) rather than 30(S) on Bel-7402 cells. Further molecular mechanism studies of saponins 1 and 2 were carried out on the cell cycle distribution of Bel-7402 cells. |
| Databáze: | OpenAIRE |
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