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Anti-inflammatory Action of Phenolic Compounds from Gastrodia elata Root  

Lee, Ji-Yun (Division of Pathophysiology and Pharmacology, College of Pharmacy, Chung-Ang University)
Jang, Young-Woon (Division of Pathophysiology and Pharmacology, College of Pharmacy, Chung-Ang University)
Kang, Hyo-Sook (Division of Pathophysiology and Pharmacology, College of Pharmacy, Chung-Ang University)
Moon, Hee (Division of Pathophysiology and Pharmacology, College of Pharmacy, Chung-Ang University)
Sim, Sang-Soo (Division of Pathophysiology and Pharmacology, College of Pharmacy, Chung-Ang University)
Kim, Chang-Jong (Division of Pathophysiology and Pharmacology, College of Pharmacy, Chung-Ang University)
Publication Information
Archives of Pharmacal Research / v.29, no.10, 2006 , pp. 849-858 More about this Journal
Abstract
Previous screening of the pharmacological action of Gastrodia elata (GE) root (Orchidaceae) showed that methanol (MeOH) extracts have significant anti-inflammatory properties. The antiinflammatory agents of GE, however, remain unclear. In this experiment, MeOH extracts of GE were fractionated with organic solvents for the anti-inflammatory activity-guided separation of GE. Eight phenolic compounds from the ether (EtOEt) and ethyl acetate (EtOAc) fractions were isolated by column chromatography: 4-hydroxybenzaldehyde (I), 4-hydroxybenzyl alcohol (II), benzyl alcohol (III), bis-(4-hydroxyphenyl) methane (IV), 4(4'-hydroxybenzyloxy)benzyl-methylether (V), 4-hydroxy-3-methoxybenzyl alcohol (VI), 4-hydroxy-3-methoxybenzaldehyde (VII), and 4-hydroxy-3-methoxybenzoic acid (VIII). To investigate the anti-inflammatory and anti-oxidant activity of these compounds, their effects on carrageenan-induced paw edema, arachidonic acid (AA)-induced ear edema and analgesic activity in acetic acid (HAc)-induced writhing response were carried out in vivo; cyclooxygenase (COX) activity, reactive oxygen species (ROS) generation in rat basophilic leukemia (RBL 2H3) cells and 1,1-diphenyl-2-picryl-hydroazyl (DPPH) scavenging activity were determined in vitro. These phenolic compounds not only had anti-inflammatory and analgesic properties in vivo, but also inhibited COX activity and silica-induced ROS generation in a dose-dependent manner. Among these phenolic compounds, compound VII was the most potent anti-inflammatory and analgesic. Compound VII significantly inhibited silica-induced ROS generation and compound VI significantly increased DPPH radical scavenging activity. Compounds I, II and III significantly inhibited the activity of COX-I and II. These results indicate that phenolic compounds of GE are anti-inflammatory, which may be related to inhibition of COX activity and to anti-oxidant activity. Consideration of the structure-activity relationship of the phenolic derivatives from GE on the anti-inflammatory action revealed that both C-4 hydroxy and C-3 methoxy radicals of benzyl aldehyde play an important role in anti-inflammatory activities.
Keywords
Gastrodia elata; Phenolic compounds; Anti-inflammatory activity; Anti-oxidant activity;
Citations & Related Records

Times Cited By Web Of Science : 15  (Related Records In Web of Science)
Times Cited By SCOPUS : 9
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1 Lin, J. H., Liu, Y. C., Hau, J. P., and Wen, K. C., Parishins B and C from rhizomes of Gastrodia elata. Phytochemistry, 42, 549-551 (1996)   DOI   ScienceOn
2 Noda, N., Kobayashi, Y., Miyahara, K., and Fukahori, S., 2,4- Bis(4-hydroxybenzyl)phenol from Gastrodia elata. Phytochemistry, 39, 1247-1248 (1995)   DOI   ScienceOn
3 Tanguchi, H., Yoshioka, I., Yamasaki, K., and Kim, I. H., Studies on the constituents of Gastrodia elata Blume. Chem. Pharm. Bull., 29, 55-62 (1981)   DOI
4 Xiao, Y. Q., Li, L., You, X. L., Bian, B. L., Liang, X. M., and Wang, Y. T., A new compound from Gastrodia elata Blume. J. Asian Nat. Prod. Res., 4, 73-79 (2002)
5 Yun-Choi, S. H., Pyo, M. K., and Park, K. M., Isolation of 4,4'- dihydroxybenzyl sulfoxide from Gasrtodia elata, Arch. Pharm. Res., 20, 91-92 (1997)   DOI   ScienceOn
6 Chen, Y., Wong, M., Rosen, R. T., and Ho, C. T., 2,2-Diphenyl- 1-picrylhydrazyl radical-scavenging active components from Polygonum multiflorum thunb. J. Agric. Food Chem., 47, 2226-2228 (1999)   DOI   ScienceOn
7 Ozaki, Y., Antiinflammatory effect of Curcuma xanthorrhiza Roxb, and its active principles. Chem. Pharm. Bull., 38, 1045-1048 (1990)   DOI   ScienceOn
8 Junhua, H. and Guilian, W., Comparison studies on pharmacological properties of injection Gastrodia elata, gastrodinfree fration and gastrodin(chinese). Acta. Academiae Medicinae Sinicae, 11, 147-150 (1989)
9 Li, H. X., Ding, M. Y., and Yu, J. Y., Simultaneous determination of p-hydroxybenzaldehyde, p-hydroxybenzyl alcohol, 4- (beta-D-glucopyranosyloxy)-benzyl alcohol, and sugars in Gastrodia elata blume measured as their acetylated derivatives by GC-MS. J. Chromatogr. Sci., 39, 251-254 (2001)   DOI   ScienceOn
10 Bentley, G. A., Newton, S. H., and Star, J., Studies on the antinociceptive action of a-agonist drugs. Brit. J. Pharmacol., 79, 125-134 (1983)   DOI   ScienceOn
11 Tang, W. and Eisenbrand, G., Chinese Drug of Plant Origin, Gastrodia elata Bl. Springer-Veriag, Berlin, Heidelberg., 545- 548 (1992)
12 Zhou, J., Yang, Y. B., and Yang, T. R., The isolation identification of chemical constituents of Gastrodia elata Bl(chinese), Acta Chimica Sinica, 37, 183-189 (1979)
13 Carlson, R. P., O'Neill-Davis, L., Chang, J., and Lewis, A. J., Modulation of mouse ear edema by cyclooxygenase and lipoxygenase inhibitors and other pharmacologic agents. Agents Actions, 17, 197-204 (1985)   DOI
14 Winter, C. A., Risley, E. A., and Nuss, G. W., Carrageeninduced edema in hind paw of the rat as an assay for antiinflammatory drugs. Pro. Soc. Exp. Biol. Med., 111, 544-547 (1962)
15 Young, J. M., Spires, D. A., Bedord, C. J., Wagner, B., Ballaron, S. J., and De Young, L. M., The mouse ear inflammatory response to topical arachidonic acid. J. Invest. Dermatol., 82, 367-371 (1989)   DOI   ScienceOn
16 Hayashi, J., Sekine, T., Deguchi, S., Lin, Q., Horie, S., Tsuchiya, S., Yano, S., Watanabe, K., and Ikegami, F., Phenolic compounds from Gastrodia rhizome and relaxant effects of related compounds on isolated smooth muscle preparation. Phytochemistry, 59, 513-519 (2002)   DOI   ScienceOn
17 Liu, J. and Mori, A., Antioxidant and free radical scavenging activities of Gastrodia elata Bl. and Uncaria rhynchophylla (Miq.) Jacks. Neuropharmacology, 31, 1287-1298 (1992)   DOI   ScienceOn
18 Yamazaki, R., Aijama, R., Matsuzaki, T., Hahimoto, S., and Ykkokura, T., Anti-inflammatory effect of YPE-01, a novel diarylheptanoid derivative, on dermal inflammation in mice. Inflamm. Res., 47, 182-186 (1998)   DOI   ScienceOn
19 Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Roda. A., Guardigli, M., Traniello, S., and Spisani, S., N-Benzyl-2-chloroindole-3-carboxylic acids as potential anti-inflammatory agents. Synthesis and screening for the effects on human neutrophil functions and on COX1/ COX2 activity. Eur. J. Med. Chem., 39, 785-791 (2004)   DOI   ScienceOn
20 Raj, P. P., Pain mechanisms. In: Pain medicine: a comprehensive review, 1st ed. Mosby-Year Book, Inc., St. Louis, USA, pp.12-24, 1996
21 Ferrari, M., Fornasiero, M.C., and Isetta, A. M., MTT colorimetric assay for testing macrophage cytotoxic activity in vitro. J. Immunol. Methods, 131, 165-172 (1990)   DOI   ScienceOn
22 Halliwell, B. and Chirico, S., Lipid peroxidation: its mechanism, measurement, and significance. Am. J. Clin. Nutr., 57, 715S- 725S (1993)   DOI
23 Yun-Choi, S. H. and Pyo, M. K., Isolation of 3-O-(4'-hydroxybenzyl)- beta-sitosterol and 4-[4'-(4''-hydrobenzyloxy)benzyloxy] benzyl methyl ether from fresh tubers of Gastrodia elata, Arch. Pharm. Res., 21, 357-360 (1998)   DOI   ScienceOn
24 Trenam, C. W., Blake, D. R., and Morris, C. J., Skin inflammation: reactive oxygen species and the role of iron. J. Invest. Dermatol., 99, 675-682 (1992)   DOI   ScienceOn
25 Beckman, J. S. and Crow, J. P., Pathological implications of nitric oxide, superoxide and peroxynitrite formation. Biochem. Soc. Trans., 21, 330-334 (1993)   DOI
26 Just, M. J., Recio, M. C., Giner, R. M., Cullar, M. J., Manez, S., Bilia, A. R., and Rios, J. L., Anti-inflammatory activity of unusual Lupane saponins from Bupleurum fruticescens. Planta Med., 64, 404-407 (1998)   DOI   ScienceOn
27 Crummey, A., Harper, G. P., Boyle, E. A., and Mangan, F. R., Inhibition of arachidonic acid-induced ear oedema as a model for assessing topical anti-inflammatory compounds. Agents Actions, 20, 69-76 (1987)   DOI
28 Shen, H. M., Shi, C. Y., Shen, Y., and Ong, C. N., Detection of elevated reactive oxygen species level in cultured rat hepatocytes treated with aflatoxin B1. Free Radical Biol. Med., 21, 139-146 (1996)   DOI   ScienceOn
29 Coller, H. O., Dinneen, L. C., Johnson, C. A., and Schneider, C., The abdominal constriction response and its suppression by analgesic drugs in the mouse. Br. J. Pharmacol. Chemother., 32, 295-310 (1968)   DOI   ScienceOn
30 Liu, J. and Mori, A., Antioxidant and pro-oxidant activities of phydroxybenzyl alcohol and vanillin: effects on free radicals, brain peroxidation and degradation of benzoate, deoxyribose, amino acids and DNA. Neuropharmacology, 32, 659-669 (1993)   DOI   ScienceOn