Abstract
Structural modification of 5,7-dimethoxyflavone isolated from Kaempferia parviflora furnished two nitro and seven amino derivatives. Among these, six new (3, 5–6, 8–10) and three known (2, 4, 7) flavonoid derivatives were synthesized. All compounds were evaluated for cytotoxicity against KB cell line using colorimetric method. Compounds 6 and 8 exhibited strong cytotoxicity with IC50 values of 6.80 and 5.84 µg/mL, respectively.
Similar content being viewed by others
References
Brien, J. O., Wilson, I., Orton, T., and Pognan, F., Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur. J. Biochem., 267, 5421–5426 (2000).
Gao, H. and Kawabata, J., α-Glucosidaes inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as a-glucosidase inhibitors. Bioorg. Med. Chem., 13, 1661–1671 (2005).
Larget, R., Lockhart, B., Renard, P., and Largeron, M., A convenient extension of the Wessely-Moser rearrangement for the synthesis of substituted alkylaminoflavones as neuroprotective agent in vitro. Bioorg. Med. Chem. Lett., 10, 835–838 (2000).
Patanasethanont, D., Nagai, J., Yumoto, R., Murakami, T., Sutthanut, K., Sripanidkulchai, B., Yenjai, C., and Takano, M., Effects of Kaempferia parviflora extracts and their flavone constituents on P-glycoprotein function. J. Pharm. Sci., 96, 223–233 (2007).
Pengcharoen, O., Technology Chao Barn. Matichon Press, Bangkok, pp. 42–43 (2002).
Rujjanawate, C., Kanjanapothi, D., Amornlerdpison, D., and Pojanagaroon, S., Anti-gastric ulcer effect of Kaempferia parviflora. J. Ethnopharmacol., 102, 120–122 (2005).
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, 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).
Sookkongwaree, K., Geitmann, M., Roengsumran, S., Petsom, A., and Danielson, U. H., Inhibition of viral proteases by Zingiberaceae extracts and flavonoids isolated from Kaempferia parviflora. Pharmazie, 61, 717–721 (2006).
Sutthanut, K., Sripanidkulchai, B., Yenjai, C., and Jay, M., Simultaneous identification and quantitation of 11 flavonoid constituents in Kaempferia parviflora by gas chromatography. J. Chromatogr. A, 1143, 227–233 (2007).
Tsuji, P. A., Winn, R. N., and Walle, T., Accumulation and metabolism of the anticancer flavonoid 5,7-dimethoxyflavone compared to its unmethylated analog chrysin in the Atlantic killifish. Chem-Biol. Interact., 164, 85–92 (2006).
Wang, C. L., Li, H. Q., Meng, W. D., and Qing, F. L., Trifluoromethylation of flavonoids and anti-tumor activity of the trifluoromethylated flavonoid derivatives. Bioorg. Med. Chem. Lett., 15, 4456–4458 (2005).
Yenjai, C., Prasanphen, K., Daodee, S., Wongpanich, V., and Kittikoop, P., Bioactive flavonoids from Kaempferia parviflora. Fitoterapia, 75, 89–92 (2004).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Wanich, S., Yenjai, C. Amino and nitro derivatives of 5,7-dimethoxyflavone from Kaempferia parviflora and cytotoxicity against KB cell line. Arch. Pharm. Res. 32, 1185–1189 (2009). https://doi.org/10.1007/s12272-009-1901-y
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-009-1901-y