Abstract
We have isolated a new prenylated chalcone from the roots of Sophora flavescens (Leguminosae). We determined that structure of this compound is 7,9,2’,4’-tetrahydroxy-8-isopentenyl-5-methoxychalcone (1) on the basis of spectroscopic analysis (1D and 2D NMR data). Compound 1 exhibited potent cytotoxicity against human acute promyelocytic (HL60), mouse lymphocytic (L1210) and human histiocytic (U937) leukemia cells.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Chung, M. Y., Rho, M. C., Ko, J. S., Ryu, S. Y., Jeune, K. H., Kim, K., Lee, H. S., and Kim, Y. K.,In vitro inhibition of diacylglycerol acyltransferase by prenylflavonoids fromSophora flavescens.Planta Med., 70, 258–260 (2004).
Ding, P. L., Hou, A. J., and Chen, D. F., Three new isoprenylated flavonoids from the roots ofSophora flavescens.J. Asian Nat. Prod. Res., 7, 237–243 (2005).
Ding, Y., Tian, R. H., Kinjo, J., Nohara, T., and Kitagawa, I., Three new oleanene glycosides fromSophora flavescens.Chem. Pharm. Bull., 40, 2990–2994 (1992).
Jung, B. S., and Shin, M. K., Encyclopedia of Illustrated Korean Natural drugs. Young Lim Sa, Seoul,.707–708 (1989).
Jung, H. J., Kang, S. S., Woo, J. J., and Choi, J. S., A new lavandulylated flavonoid with free radical and ONOO- scavenging activities fromSophora flavescens. Arch.Pharm. Res., 28, 1333–1336 (2005).
Kang, S. S., Kim, J. S., Son, K. H., Chang, H. W., and Kim, H. P., A new prenylated flavanone from the roots ofSophora flavescens.Fitoterapia, 71, 511–515 (2000a).
Kang, T. H., Jeong, S. J., Ko, W. G., Kim, N. Y., Lee, B. H., Inagaki, M., Miyamoto, T., Higuchi, R., and Kim, Y. C., Cytotoxic lavandulyl flavanones fromSophora flavescens.J. Nat. Prod., 63, 680–681 (2000b).
Kim, J. H., Ryu, Y. B., Kang, N. S., Lee, B. W., Heo, J. S., Jeong, I. Y., and Park, K. H., Glycosidase inhibitory flavonoids fromSophora flavescens.Biol. Pharm. Bull., 29, 302–305 (2006).
Kim, S. J, Son, K. H., Chang, H. W., Kang, S. S., and Kim, H. P., Tyrosinase inhibitory prenylated flavonoids fromSophora flavescens.Biol. Pharm. Bull., 26, 1348–1350 (2003).
Kuroyanagi, M., Arakawa, T., Hirayama, Y., and Hayashi, T., Antibacterial and antiandrogen flavonoids fromSophora flavescens.J. Nat. Prod., 62, 1595–1599 (1999).
Kyogoku, K., Hatayama, K., and Komatsu, M., Constituents of Chinese crude drug “Kushen” (the root ofSophora flavescens Ait.). Isolation of five new flavonoids and formononetin.Chem. Pharm. Bull., 21, 2733–2738 (1973).
Okuda, S., Murakoshi, I., Kamata, H., Kashida, Y., Haginiwa, J., and Tsuda, K., Studies on lupin alkaloids. I. The minor alkaloids of JapaneseSophora flavescens.Chem. Pharm. Bull., 13, 482–487 (1965).
Ryu S. Y., Lee H. S., Kim Y. K., and Kim S. H., Determination of isoprenyl and lavandulyl positions of flavonoids fromSophora flavescens by NMR experiment.Arch. Pharm. Res., 20, 491–495 (1997).
Shen, C. C., Lin, T. W., Huang, Y. L., Wan, S. T., Shien, B. J., and Chen, C. C., Phenolic constituents of the roots ofSophora flavescens.J. Nat. Prod., 69, 1237–1240 (2006).
Sohn, H. Y., Son, K. H., Kwon, C. S., Kwon, G. S., and Kang, S. S., Antimicrobial and cytotoxic activity of 18 prenylated flavonoids isolated from medicinal plants:Morus alba L.,Morus mongolica Schneider,Broussnetia papyrifera (L.) Vent,Sophora flavescens Ait andEchinosophora koreensis Nakai.Phytomedicine, 11, 666–672 (2004).
Son, J. K., Park, J. S., Kim, J. A., Kim, Y., Chung, S. R., and Lee, S. H., Prenylated flavonoids from the roots ofSophora flavescens with tyrosinase inhibitory activity.Planta Med., 69, 559–561 (2003).
Song, J. Z., Xu, H. X., Tian, S. J., and But, P. P., Determination of quinolizidine alkaloids in traditional Chinese herbal drugs by nonaqueous capillary electrophoresis.J. Chromatogr. A., 857, 303–311 (1999).
Sekine, T., Saito, K., Minami, R., Arai, N., Suzuki, H., Koike, Y., and Murakoshi, I., A new lupin alkaloid, (-)-leontalbinine N- oxide, inSophora flavescens vanangustifolia seeds and its synthesis by biomimetic transformation from (+)-matrine N- oxide.Yakugaku Zasshi, 113, 53–62 (1993).
Woo, E. R., Kwak, J. H., Kim, H. J., and Park, H., A new prenylated flavonol from the roots ofSophora flavescens.J. Nat. Prod., 61, 1552–1554 (1998).
Zhu, Y.-P., Chinese Materia Medica, Harwood Academic Publishers, Amsterdam,.149–155 (1998).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Lee, J.H., Baek, NI., Kim, SH. et al. A new cytotoxic prenylated chalcone fromsophora flavescens . Arch Pharm Res 30, 408–411 (2007). https://doi.org/10.1007/BF02980212
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02980212