Abstract
Some C-benzylated flavonoids based on gericudranin A were synthesized and evaluated their cytotoxic activities for the elucidation of structure-activity relationship. 2,4,6-Trihydroxyacetophenone was converted to target molecules in 6∼7 steps via sequential protection, aldol condensation, cyclization, regioselective C-benzylation, and deprotection. The cellular growth inhibition of the synthetic C-benzylated flavonoids was investigated against sixteen human cancer cell lines. Among these compounds, 5b showed the most potent cytotoxicities against several cell lines, especially as potent as adriamycin against SNB19 cell lines with an IC50 value of 0.7 μM.
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Choi, Y. J., Shim, P. J., Ko, K. S., and Kim, H. D., Total synthesis of (±)-gericudranin A. Heterocycles, 43, 1223–1226, (1996).
Cole, J. R., Torrance, S. J., Wiedhopf, R. M., Arora, S. K., and Bates, R. B., Uvaretin, a new antitumor agent from Uvaria acuminata (Annonaceae). J. Org. Chem., 41, 1852–1855 (1976).
Harborne, J. B., The Flavonoids: Advance in Research since 1980, Chapman and Hall, London (1988).
Hufford, C. D. and Lasswell, Jr., W. L., Uvaretin and isouvaretin. Two novel cytotoxic C-benzylflavanones from Uvaria chamae L. J. Org. Chem., 41, 1297–1298 (1976).
Hufford, C. D., Lasswell, Jr., W. L., Hirotsu, K., and Clardy, J. Uvarinol: a novel cytotoxic tribenzylated flavanone from Uvaria chamae. J. Org. Chem., 44, 4709–4710 (1979).
Hufford, C. D. and Oguntimein, B. O., New dihydrochalcones and flavanones from Uvaria angolensis. J. Nat. Prod., 45,337–342 (1982).
Ichimaru, M., Nakatani, N., Takahashi, T., Nishiyama, Y., Moriyasu, M., Kato, A., Mathenge, S. G., Juma, F. D., and Nganga, J. N., Cytotoxic C-benzylated dihydrochalcones from Uvaria acuminate. Chem. Pharm. Bull., 52, 138–141 (2004).
Lee, I-K, Kim, C-J., Song, K-S., Kim, H-M., Yoo, I-D., Koshino, H., Esumi, Y., and Uramoto, M., Two benzylated dihydroflavonols from Cudrania tricuspidata. J. Nat. Prod., 58, 1614–1617 (1995).
Lee, I-K., Kim, C-J.; Song, K-S., Kim, H-M., Koshino, H., Uramoto, M., and Yoo, I-D., Cytotoxic benzyl dihydroflavonols from Cudrania tricuspidata. Phytochemistry, 41,213–216 (1996).
Nakatani, N., Ichimaru, M., Moriyasu, M., and Kato, A., Induction of apoptosis in human promyelocytic leukemia cell line HL-60 by C-benzylated dihydrochalcones, uvaretin, isouvaretin and diuvaretin. Biol. Pharm. Bull., 28, 83–86 (2005).
Skehan, P., Storeng, R., Scudiero, D., Monks, A., MaMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenny, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107–1112 (1990).
Wirasathien, L., Pengsuparp, T., Moriyasu, M., Kawanish, K., and Suttisri, R., Cytotoxic C-benzylated chalcone and other constituents of Ellipeiopsis cherrevensis. Arch. Pharm. Res., 29, 497–502 (2006).
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Choi, YJ., Kim, H.M. & Kim, HD. Synthesis and cytotoxic activities of C-benzylated flavonoids. Arch. Pharm. Res. 32, 59–63 (2009). https://doi.org/10.1007/s12272-009-1118-0
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DOI: https://doi.org/10.1007/s12272-009-1118-0