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.
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References
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).
Bae, K., The Medicinal Plants of Korea. Kyo-Hak Publishing Company, Seoul, pp. 565–567 (2000).
Blois, M. S., Antioxidant determinations by the use of a stable free radical.Nature, 181,1199–1200 (1958).
Bors, W., Heller, W., Michel, C, and Saran, M., Flavonoids as antioxidants: determination of radical-scavenging efficiencies.Methods Enzymol., 186, 343–355 (1990).
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).
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).
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).
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).
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).
Iwashina, T. and Ootani, S., Three flavonol allosides fromGlaucidium palmatum.Phytochemistry, 29,3639–3641 (1990).
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).
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).
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).
Kim, T.J., Korean Resources Plant. Vol. V. Seoul National University Press, Seoul, pp. 37–42 (1996).
Kitts, D. D., Wijewickreme, A. N., and Hu, C, Antioxidant properties of a North American ginseng extract.Mol. Cell. Biochem., 203,1–10(2000).
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).
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).
Mabry, T. J., Markham, K. R., and Thomas, M. B., The Systematic Identification of Flavonoids. Springer-Verlag, Berlin (1970).
Namba, T., The Encyclopedia of Wakan-Yaku (Traditional Sino-Japanese Medicines) with Color Pictures, Vol. II. Hoikusha Publishing Company, Osaka, pp. 92–95 (1993).
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).
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).
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).
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).
Pietta, P.-G, Flavonoids as Antioxidants.J. Nat. Prod., 63, 1035–1042(2000).
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).
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).
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).
Ulubelen, A., Mabry, T J., Dellamonica, G, and Chopin, J., Flavonoids fromPassiflora palmeri.J. Nat. Prod., 47, 384–385 (1984).
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).
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).
Yook, C. S., Colored Medicinal Plants of Korea. Academy Book Publishing Company, Seoul, pp. 88–91 (1993).
Yoon, K. D., Kim, C. Y, and Huh, H., The flavone glycosides ofSasa borealis.Kor. J. Pharmacogn., 31, 224–227 (2000).
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).
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Park, HS., Lim, J.H., Kim, H.J. et al. Antioxidant flavone glycosides from the leaves ofSasa borealis . Arch Pharm Res 30, 161–166 (2007). https://doi.org/10.1007/BF02977689
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DOI: https://doi.org/10.1007/BF02977689