Archives of Pharmacal Research

, Volume 30, Issue 2, pp 161–166 | Cite as

Antioxidant flavone glycosides from the leaves ofSasa borealis

  • Hae-Suk Park
  • Ju Hee Lim
  • Hyun Jung Kim
  • Hyun Jin Choi
  • Ik-Soo Lee
Article Drug design

Abstract

Sasa borealis (Poaceae) is a perennial medicinal plant which is a major source of bamboo leaves in Korea. Then-BuOH extract ofS. borealis leaves exhibited significant antioxidant activity against the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and a cytoprotective effect against oxidative damage in HepG2 cells. Bioactivity-guided fractionation by column chromatography led to the isolation of two antioxidative flavonoid C-glycoside derivatives, isoorientin (2) and isoorientin 2”-O-α-i_-rhamnoside (4) along with tricin 7-0-β-D-glucopyranoside (1) and apigenin 6-C-β-D-xylopyranosyl-8-C-β-D-glucopyranoside (3). Their structures were identified on the basis of chemical and spectroscopic methods. The radical scavenging activity and cytoprotective effect against oxidative damage of all the isolated compounds were also evaluated. Isoorientin (2) and isoorientin 2-O-α-L-rhamnoside (4) showed potent free radical scavenging activity with 1C50 values of 9.5 and 34.5 μM, respectively, and strong cytoprotective effects againstt-BOOH-induced oxidative damage in HepG2 cells, at very low concentrations of 1.1 μM isoorientin and 0.8 μM isoorientin 2-O-α-L-rhamnoside. This is the first report of the isolation and antioxidant activity of compounds 2 and 4 from S.borealis.

Key words

Sasa borealis Bamboo leaves Antioxidative activity Cytoprotective effect Isoorientin lsoorientin-2-O-α-L-rhamnoside 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Agrawal, P. K. and Bansal, M. C, Flavonoid glycosides, In Agrawal, P. K. (Ed.). Carbon-13 NMR of Flavonoids, Elsevier, New York, pp. 293–312 (1989).Google Scholar
  2. Bae, K., The Medicinal Plants of Korea. Kyo-Hak Publishing Company, Seoul, pp. 565–567 (2000).Google Scholar
  3. Blois, M. S., Antioxidant determinations by the use of a stable free radical.Nature, 181,1199–1200 (1958).CrossRefGoogle Scholar
  4. Bors, W., Heller, W., Michel, C, and Saran, M., Flavonoids as antioxidants: determination of radical-scavenging efficiencies.Methods Enzymol., 186, 343–355 (1990).PubMedCrossRefGoogle Scholar
  5. Carr, A. and Frei, B., The role of natural antioxidants in preserving the biological activity of endothelium-derived nitric oxide.Free Radical Biol. Med., 28,1806–1814 (2000).CrossRefGoogle Scholar
  6. Choi, H. J., Lee, S. Y, Cho, Y, and Hwang, O., Inhibition of vesicular monoamine transporter enhances vulnerability of dopaminergic cells: relevance to Parkinson’s disease.Neurochem. Int., 46, 329–335 (2005).PubMedCrossRefGoogle Scholar
  7. Cimanga, K., De Bruyne, T., Lasure, A., Li, Q., Pieters, L., Claeys, M., Berghe, D. V, Vlietinck, A., Kambu, K., and Tona, L., Flavonoid O-glycosides from the leaves ofMorinda morindoides.Phytochemistry, 38,1301–1303 (1995).CrossRefGoogle Scholar
  8. Gao, Z., Huang, K., Yang, X., and Xu, H., Free radical scavenging and antioxidant activities of flavonoids extracted from the radix ofScutellaha baicalensis Georgi.Biochim. Biophys. Acta, 1472,643–650(1999).PubMedGoogle Scholar
  9. Hu, C, Zhang, Y, and Kitts, D. D., Evaluation of antioxidant and prooxidant activities of bambooPhyllostachys nigra vanhenonis leaf extract in vitro.J. Agric. Food Chem., 48, 3170–3176(2000).PubMedCrossRefGoogle Scholar
  10. Iwashina, T. and Ootani, S., Three flavonol allosides fromGlaucidium palmatum.Phytochemistry, 29,3639–3641 (1990).CrossRefGoogle Scholar
  11. Jeong, Y. H., Lee, J., Kwon, Y, and Seo, E.-K., Reverse-phase HPLC method for identification of diastereomeric constituents fromSasa borealis. Yakhak Hoeji, 50, 21–25 (2006).Google Scholar
  12. Jeong, Y. H., Nam, I.-W., Lee, N. Y, Seo, E.-K., and Kwon, Y, Isolation and Structural Identification of Minor Constituents fromSasa borealis, Nat. Prod, Sci., 11,170–173 (2005).Google Scholar
  13. Ju, Y, Sacalis, J. N., and Still, C. C, Bioactive flavonoids from Endophyte-infected blue grass(Poa ampla).J. Agric. Food Chem., 46, 3785–3788 (1998).CrossRefGoogle Scholar
  14. Kim, T.J., Korean Resources Plant. Vol. V. Seoul National University Press, Seoul, pp. 37–42 (1996).Google Scholar
  15. Kitts, D. D., Wijewickreme, A. N., and Hu, C, Antioxidant properties of a North American ginseng extract.Mol. Cell. Biochem., 203,1–10(2000).PubMedCrossRefGoogle Scholar
  16. Kumazawa, T., Minatogawa, T., Matsuba, S., Sato, S., and Onodera, J., An effective synthesis of isoorientin: the regio-selective synthesis of a 6-C-glucosylflavone.Carbohydr. Res., 329,507–513(2000).PubMedCrossRefGoogle Scholar
  17. Kweon, M. H., Hwang H. J., and Sung, H. C, Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo(Phyllostachys edulis).J. Agric. Food Chem., 49, 4646–4655(2001).PubMedCrossRefGoogle Scholar
  18. Mabry, T. J., Markham, K. R., and Thomas, M. B., The Systematic Identification of Flavonoids. Springer-Verlag, Berlin (1970).Google Scholar
  19. Namba, T., The Encyclopedia of Wakan-Yaku (Traditional Sino-Japanese Medicines) with Color Pictures, Vol. II. Hoikusha Publishing Company, Osaka, pp. 92–95 (1993).Google Scholar
  20. Okabe, S., Takeuchi, M., Takagi, K., and Shibata, M., Stimulatory effect of water extract of bamboo grass (Folin solution) on gastric acid secretion in Pylorus-ligated rats.Japanese J. Pharmacol., 25, 608–609 (1975).CrossRefGoogle Scholar
  21. Park, J.-C., Baek, N.-l., Chung, S.-K., Hur, J.-M., Lee, J.-H., Yu, Y.-B., and Choi, J.-W., Effect of hispidulin 7-O-neohesperidoside on lipid peroxidation in rat liver and NMR assignment.Kor. J. Pharmacogn., 28, 88–92 (1997).Google Scholar
  22. Peng, J., Fan, G., Hong, Z., Chai, Y, and Wu, Y, Preparative separation of isovitexin and isoorientin fromPatrinia villosa Juss by high-speed counter-current chromatography.J. Chromatogr. A, 1074,111–115 (2005).PubMedCrossRefGoogle Scholar
  23. Perry, G, Raina, A. K., Nunomura, A., Wataya, T, Sayre, L. M., and Smith, M. A., How important is oxidative damage? Lessons from Alzheimer’s disease.Free Radical Biol. Med., 28,831–834(2000).CrossRefGoogle Scholar
  24. Pietta, P.-G, Flavonoids as Antioxidants.J. Nat. Prod., 63, 1035–1042(2000).PubMedCrossRefGoogle Scholar
  25. Rush, G F., Gorski, J. R., Ripple, M. G, Sowinski, J., Bugelski, P., and Hewitt, W. R., Organic hydroperoxide-induced lipid peroxidation and cell death in isolated hepatocytes.Toxicol. Appl. Pharmacol., 78,473–483 (1985).PubMedCrossRefGoogle Scholar
  26. Shibata, M., Yamatake, M., Sakamoto, M., Kanamori, K., Takagi, K., and Okabe, S., Pharmacological studies on bamboo grass.Nippon Yakurigaku Zassi, 71, 481–485 (1975).Google Scholar
  27. Tanaka, N., Wada, H., Fuchino, H., Inoue, T., Yasuda, D., Kanda, S., Kiyokawa, C, Ashida, N., Suzuki, T, Yamazaki, K., and Hakamatsuka, T, Constituents of bamboos and bamboo grasses.Yakugaku Zasshi, 118, 332–337(1998).Google Scholar
  28. Ulubelen, A., Mabry, T J., Dellamonica, G, and Chopin, J., Flavonoids fromPassiflora palmeri.J. Nat. Prod., 47, 384–385 (1984).CrossRefGoogle Scholar
  29. Woo, S.-S., Jo, T. H., Kim, D. S., Sung, S.-Y, Do, S.-G, Lee, Y C, Nam, J. B., Ryu, J. H., Lee, K. W., Sung, H. S., Heo, Y M., Oh, M., Cho, J. N., Sung, S., Lee, J. Y, Kim, T. W., Song, J. S., Lee, S. H., and Kim, M. R., Composition comprising compounds isolated from bamboo extract and uses for treating and preventing inflammatory and blood circulation diseases. WO 2004098624 A1 (2004).Google Scholar
  30. Xie, C, Veitch, N. C, Houghton, P. J., and Simmonds, M. S., Flavone C-glycosides fromViola yedoensis Makino.Chem. Pharm. Bull., 51, 1204–1207 (2003).PubMedCrossRefGoogle Scholar
  31. Yook, C. S., Colored Medicinal Plants of Korea. Academy Book Publishing Company, Seoul, pp. 88–91 (1993).Google Scholar
  32. Yoon, K. D., Kim, C. Y, and Huh, H., The flavone glycosides ofSasa borealis.Kor. J. Pharmacogn., 31, 224–227 (2000).Google Scholar
  33. Zhang, Y, Bao, B., Lu, B., Ren, Y, Tie, X., and Zhang, Y, Determination of flavone C-glucosides in antioxidant of bamboo leaves (AOB) fortified foods by reversed-phase high-performance liquid chromatography with ultraviolet diode array detection.J. Chromatogr. A, 1065,177–185 (2005).PubMedCrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea 2007

Authors and Affiliations

  • Hae-Suk Park
    • 1
  • Ju Hee Lim
    • 1
  • Hyun Jung Kim
    • 1
  • Hyun Jin Choi
    • 1
  • Ik-Soo Lee
    • 1
  1. 1.College of Pharmacy and Research Institute of Drug DevelopmentChonnam National UniversityGwangjuKorea

Personalised recommendations