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This work is licensed under a Creative Commons Attribution 4.0 International License.
Anti-Oxidative and Anti-Inflammatory Effects of Phenolic Compounds from the Stems of Quercus acuta Thunberg
Corresponding Author(s) : M.W. Lee
Asian Journal of Chemistry,
Vol. 26 No. 15 (2014): Vol 26 Issue 15
Abstract
Two flavan 3-ols i.e., (+)-catechin (1), (-)-epicatechin (2)], three flavanonols i.e., [taxifolin (3), taxifolin 3-O-b-D-glucopyranoside (4) and taxifolin 4'-O-b-D-glucopyranoside (5), one proanthocyanidin i.e., procyanidin B-3 (6) and one i.e., neolignan (+)-lyoniresinol 3a-O-b-D-xylopyranoside (7) have been isolated from the stems of Quercus acuta Thunberg (QAS) by anti-oxidative activity-guided isolation. Although these compounds have been reported previously. To our best of knowledge, this is the first study to report their isolation from Q. acuta Thunberg. Anti-oxidative activity was measured using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and superoxide dismutase (SOD)-like superoxide anion (generated by xanthine oxidase/hypoxanthine) scavenging assays. Anti-inflammatory activity was assessed by quantifying the nitric oxide in the supernatant of lipopolysaccharide (LPS)-stimulated mouse Raw 264.7 macrophage cells.
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- Y.N. Lee, Flora of Korea. Seoul, Republic of Korea: Kyo-Hak Publishing (1996).
- K.S. Ko, E.S. Jeon, Ferns, Fern-Allies and Seed-Bearing Plants of Korea, Il-Jin-Sa Publishing, Seoul, Republic of Korea (2003).
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- G.I. Nonaka and I. Nishioka, Chem. Pharm. Bull. (Tokyo), 30, 4268 (1982); doi:10.1248/cpb.30.4268.
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- T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.
- B. Epe, D. Ballmaier, I. Roussyn, K. Brivida and H. Sied, Nucleic Acids Res., 24, 4105 (1996); doi:10.1093/nar/24.21.4105.
- S.Y. Park, S.S. Hong, X.H. Han, J.S. Ro and B.Y. Hwang, Nat. Prod. Sci., 11, 85 (2005).
- Y. Lu and L. Yeap Foo, Food Chem., 65, 1 (1999); doi:10.1016/S0308-8146(98)00245-3.
- Y. Sudjaroen, R. Haubner, G. Würtele, W.E. Hull, G. Erben, B. Spiegelhalder, S. Changbumrung, H. Bartsch and R.W. Owen, Food Chem. Toxicol., 43, 1673 (2005); doi:10.1016/j.fct.2005.05.013.
- M. Watanabe, J. Agric. Food Chem., 46, 839 (1998); doi:10.1021/jf9707546.
- D.S. Yang, W.K. Whang and I.H. Kim, Arch. Pharm. Res., 19, 507 (1996); doi:10.1007/BF02986020.
- R. Zerback, M. Bokel, H. Geiger and D. Hess, Phytochemistry, 28, 897 (1989); doi:10.1016/0031-9422(89)80139-6.
- J.H. Lee, W.J. Jeon, E.S. Yoo, C.M. Kim and Y.S. Kwon, Nat. Prod. Sci., 11, 97 (2005).
- Z. Shen and O. Theander, Phytochemistry, 24, 155 (1985); doi:10.1016/S0031-9422(00)80826-2.
- S.E. Choi, K.H. Park, B.H. Han, M.S. Jeong, S.J. Seo, D.I. Lee, S.S. Joo and M.W. Lee, Phytother. Res., 25, 1301 (2011); doi:10.1002/ptr.3376.
- T. Fossen, A.T. Pedersen and O.M. Andersen, Phytochemistry, 47, 281 (1998); doi:10.1016/S0031-9422(97)00423-8.
- X. Xu, H. Xie, J. Hao, Y. Jiang and X. Wei, J. Agric. Food Chem., 59, 1205 (2011); doi:10.1021/jf104387y.
- M.W. Lee, T. Tanaka, G.I. Nonaka and D.R. Hahn, Arch. Pharm. Res., 15, 211 (1992); doi:10.1007/BF02974056.
- A. Benavides, P. Montoro, C. Bassarello, S. Piacente and C. Pizza, J. Pharm. Biomed. Anal., 40, 639 (2006); doi:10.1016/j.jpba.2005.10.004.
- J. Fan, X. Ding and W. Gu, Food Chem., 102, 168 (2007); doi:10.1016/j.foodchem.2006.05.049.
- E. Smite, H. Pan and L.N. Lundgren, Phytochemistry, 40, 341 (1995); doi:10.1016/0031-9422(95)00057-E.
- T. Kanchanapoom, R. Kasai and K. Yamasaki, Phytochemistry, 57, 1245 (2001); doi:10.1016/S0031-9422(01)00212-6.
- J. Han, X. Weng and K. Bi, Food Chem., 106, 2 (2008); doi:10.1016/j.foodchem.2007.01.031.
References
Y.N. Lee, Flora of Korea. Seoul, Republic of Korea: Kyo-Hak Publishing (1996).
K.S. Ko, E.S. Jeon, Ferns, Fern-Allies and Seed-Bearing Plants of Korea, Il-Jin-Sa Publishing, Seoul, Republic of Korea (2003).
G. Nonaka, H. Nishimura and I. Nishioka, Chem. Pharm. Bull. (Tokyo), 30, 2061 (1982); doi:10.1248/cpb.30.2061.
G.I. Nonaka and I. Nishioka, Chem. Pharm. Bull. (Tokyo), 30, 4268 (1982); doi:10.1248/cpb.30.4268.
G. Nonaka, H. Nishimura, I. Nishioka, J. Chem. Soc., Perkin Trans. I, 159 (1985).
G. Nonaka, T. Sakai, T. Tanaka, K. Mihashi and I. Nishioka, Chem. Pharm. Bull. (Tokyo), 38, 2151 (1990); doi:10.1248/cpb.38.2151.
M. Serit, T. Okubo, R.H. Su, N. Hagiwara, M. Kim, T. Iwagawa, T. Yamamoto, Agric. Biol. Chem., 55, 19 (1991); doi:10.1271/bbb1961.55.19.
T. Hatano, R. Edamatsu, M. Hiramatsu, A. Mori, Y. Fujita and T. Yasuhara, Chem. Pharm. Bull. (Tokyo), 37, 2016 (1989); doi:10.1248/cpb.37.2016.
I. Parejo, F. Viladomat, J. Bastida, A. Rosas-Romero, N. Flerlage, J. Burillo and C. Codina, J. Agric. Food Chem., 50, 6882 (2002); doi:10.1021/jf020540a.
T. Mosmann, J. Immunol. Methods, 65, 55 (1983); doi:10.1016/0022-1759(83)90303-4.
B. Epe, D. Ballmaier, I. Roussyn, K. Brivida and H. Sied, Nucleic Acids Res., 24, 4105 (1996); doi:10.1093/nar/24.21.4105.
S.Y. Park, S.S. Hong, X.H. Han, J.S. Ro and B.Y. Hwang, Nat. Prod. Sci., 11, 85 (2005).
Y. Lu and L. Yeap Foo, Food Chem., 65, 1 (1999); doi:10.1016/S0308-8146(98)00245-3.
Y. Sudjaroen, R. Haubner, G. Würtele, W.E. Hull, G. Erben, B. Spiegelhalder, S. Changbumrung, H. Bartsch and R.W. Owen, Food Chem. Toxicol., 43, 1673 (2005); doi:10.1016/j.fct.2005.05.013.
M. Watanabe, J. Agric. Food Chem., 46, 839 (1998); doi:10.1021/jf9707546.
D.S. Yang, W.K. Whang and I.H. Kim, Arch. Pharm. Res., 19, 507 (1996); doi:10.1007/BF02986020.
R. Zerback, M. Bokel, H. Geiger and D. Hess, Phytochemistry, 28, 897 (1989); doi:10.1016/0031-9422(89)80139-6.
J.H. Lee, W.J. Jeon, E.S. Yoo, C.M. Kim and Y.S. Kwon, Nat. Prod. Sci., 11, 97 (2005).
Z. Shen and O. Theander, Phytochemistry, 24, 155 (1985); doi:10.1016/S0031-9422(00)80826-2.
S.E. Choi, K.H. Park, B.H. Han, M.S. Jeong, S.J. Seo, D.I. Lee, S.S. Joo and M.W. Lee, Phytother. Res., 25, 1301 (2011); doi:10.1002/ptr.3376.
T. Fossen, A.T. Pedersen and O.M. Andersen, Phytochemistry, 47, 281 (1998); doi:10.1016/S0031-9422(97)00423-8.
X. Xu, H. Xie, J. Hao, Y. Jiang and X. Wei, J. Agric. Food Chem., 59, 1205 (2011); doi:10.1021/jf104387y.
M.W. Lee, T. Tanaka, G.I. Nonaka and D.R. Hahn, Arch. Pharm. Res., 15, 211 (1992); doi:10.1007/BF02974056.
A. Benavides, P. Montoro, C. Bassarello, S. Piacente and C. Pizza, J. Pharm. Biomed. Anal., 40, 639 (2006); doi:10.1016/j.jpba.2005.10.004.
J. Fan, X. Ding and W. Gu, Food Chem., 102, 168 (2007); doi:10.1016/j.foodchem.2006.05.049.
E. Smite, H. Pan and L.N. Lundgren, Phytochemistry, 40, 341 (1995); doi:10.1016/0031-9422(95)00057-E.
T. Kanchanapoom, R. Kasai and K. Yamasaki, Phytochemistry, 57, 1245 (2001); doi:10.1016/S0031-9422(01)00212-6.
J. Han, X. Weng and K. Bi, Food Chem., 106, 2 (2008); doi:10.1016/j.foodchem.2007.01.031.