Flavonol Glycosides with Antioxidant Activity from the Aerial Parts of Epimedium koreanum Nakai

  • Kim, Eun-Sil (College of Natural Sciences, DukSung Women's University) ;
  • Kim, Mi-Kyung (College of Natural Sciences, DukSung Women's University) ;
  • Kang, Hyun-Kyu (College of Life Sciences and Biotechnology, Korea University) ;
  • Park, Young-In (College of Life Sciences and Biotechnology, Korea University) ;
  • Dong, Mi-Sook (College of Life Sciences and Biotechnology, Korea University) ;
  • Kim, Dong-Hyun (Bioanalysis and Biotransformation Research Center, Korea Institute of Science and Technology) ;
  • Chung, Ha-Sook (College of Natural Sciences, DukSung Women's University)
  • Published : 2008.12.31

Abstract

The aerial parts of Epimedium koreanum Nakai have been used to stimulate hormone secretion in treating impotence. Ten flavonol glycosides, 3,4,5-trihydroxy-8-prenylflavone 7-O-[${\beta}$-D-glucopyranosyl($1{\rightarrow}2$)-${\beta}$-D-glucopyranoside] (1), hyperoside (2), icarisid II (3), 2"-O-Rhamnosylicarisid II (4), epimedin A (5), epimedin B (6), epimedin C (7), icariin (8), hexandraside E (9), and epimedoside A (10) were isolated from the an ethylacetate soluble extracts of the aerial parts of Epimedium koreanum Nakai through activity-monitord fractionation and isolation method. The structures of compounds 1 - 10 were elucidated by high resolution fast atom bombardment mass spectrometry and two dimentional nuclear magnetic resonance spectroscopy analysis. Compounds 1 and 4 showed potent antioxidant activity, with $IC_{50}$ values of 19.7 and 11.5 ${\mu}g$/mL and 88.2 and 90.5 ${\mu}M$, respectively.

Keywords

References

  1. Chen, K.M., Ma, H.P., Ge, B.F., Liu, X.Y., Ma, L.P., Bai, M.H., and Wang, Y., Icariin enhances the osteogenic differentiation of bone marrow stromal cells but has no effects on the differentiation of newborn calvarial osteoblasts of rats. Pharmazie. 62, 785-789 (2007)
  2. Chung, H.S., Chang, L.C., Lee, S.K., Shamon, L.A., van Breeman, R.G., Mehta, R.G., Farnsworth, N.R.; Pezzuto, J.M., and Kinghorn, A.D., Flavonoid constituents of Chorizanthe diffusa with potential cancer chemopreventive activity. J. Agric. Food Chem. 47, 36-41 (1997) https://doi.org/10.1021/jf980784o
  3. Dou, J., Liu, Z., and Liu, S., Structure identification of a prenylflavonol glycoside from Epimedium koreanum by electrospray ionization tandem mass spectrometry. Anal. Sci. 22, 449-452 (1992) https://doi.org/10.2116/analsci.22.449
  4. Kuroda, M., Mimaki, Y., Sashida, Y., Umegaki, E., Yamazaki, M., Chiba, K., Mohri, T., Kitahara, M., Yasuda, A., Naoi, N., Xu, Z.W., and Li, M.R., Flavonol glycosides from Epimedium sagittatum and their neurite outgrowth activity on PC12h cells. Planta Med. 66, 575-577 (2000) https://doi.org/10.1055/s-2000-8611
  5. Fukai, T. and Nomura, T., Seven prenylated flavonol glycosides from two Epimedium species, Phytochem. 27, 259-266 (1988) https://doi.org/10.1016/0031-9422(88)80627-7
  6. Hyun, J.W. and Chung, H.S., Medicinal plants with cytotoxic and antioxidative activity. Govil, J.N. and Singh, V.K. (eds.), Recent progress in medicinal plants, vol. 12 (pp. 193-202). Texas: Studium Press, 2006
  7. Kang, S.S., Shin, K.H., Chung, S.G., and Cho, E.H., Flavonoids from Epimedium koreanum. Kor. J. Pharmacogn. 19, 93-96 (1988)
  8. Kumazawa, S., Ueda, R., Hamasaka, T., Fukumoto, S., Fujimoto, T., and Nakayama, T., Antioxidant prenylated flavonoids from Propolis collected in Okinawa. Japan. J. Agric. Food Chem. 55, 7722-7725 (2007) https://doi.org/10.1021/jf071187h
  9. Liang, H.R., Vuorela, P., Vuorela, H., and Hiltunen, R., Isolation and immunomodulatory effect of flavonol glycosides from Epimedium hunanense. Planta Med. 63, 316-319 (1997) https://doi.org/10.1055/s-2006-957690
  10. Li, W.K., Xiao, P.G., Tu, G.Z., and Zhang, R.Y., Flavonol glycosides from Epimedium koreanum. Phytochem. 38, 263-265 (1995) https://doi.org/10.1016/0031-9422(94)00522-U
  11. Li, W.K., Pan, J.Q., Lu, M.J., Xiao, P.G., and Zhang R.Y., Anhydroicaritin 3-O-rhamnosyl(1$\rightarrow$ 2)rhamnoside from epimedium koreanum and a reappraisal of other rhamnosyl(1$\rightarrow$ 2, 1$\rightarrow$ 3 and 1$\rightarrow$ 4)rhamnoside structures. Phytochem. 42, 213-216 (1996) https://doi.org/10.1016/0031-9422(95)00835-7
  12. Mizuno, M., SakakIbara, N., Hanioka, S., Iinuma, M., Tanaka, T., Liu, XS., and Shi, D-W., Flavonol glycosides from Epimedium sagittatum. Phytochem. 27, 3641-3643 (1988) https://doi.org/10.1016/0031-9422(88)80783-0
  13. Mizuno, M., Kanie, Y., Iinuma, M., Tanaka, T., and Lang, F.A., Two flavonol glycosides, hexandrasides C and D, from the underground parts of Vancouveria hexandra. Phytochem. 30, 2765-2768 (1991) https://doi.org/10.1016/0031-9422(91)85141-L
  14. Mizuno, M., Kanie, Y., Iinuma, M., Tanaka, T., and Lang, F.A., Two flavonol glycosides from Vancouveria hexandra. Phytochem. 31, 297- 299 (1992) https://doi.org/10.1016/0031-9422(91)83057-R
  15. Zhao, H.-Y., Fan, L., Zhou, L., Han, J., Wang, B.-R., Guo, D-A., 8-(3,3- Dimethylallyl)-Substituted Flavonoid Glycosides from the Aerial Parts of Epimedium koreanum. Helv. Chim. Acta 90, 2186-2195 (2007) https://doi.org/10.1002/hlca.200790226