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Archives of Pharmacal Research

, Volume 29, Issue 10, pp 849–858 | Cite as

Anti-inflammatory action of phenolic compounds fromGastrodia elata root

  • Ji Yun Lee
  • Young Woon Jang
  • Hyo Sook Kang
  • Hee Moon
  • Sang Soo Sim
  • Chang Jong KimEmail author
Articles Drug Design

Abstract

Previous screening of the pharmacological action ofGastrodia elata (GE) root (Orchidaceae) showed that methanol (MeOH) extracts have significant anti-inflammatory properties. The anti-inflammatory 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 outin 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 determinedin vitro. These phenolic compounds not only had anti-inflammatory and analgesic propertiesin 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.

Key words

Gastrodia elata Phenolic compounds Anti-inflammatory activity Anti-oxidant activity 

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References

  1. 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).PubMedCrossRefGoogle Scholar
  2. Beckman, J. S. and Crow, J. P., Pathological implications of nitric oxide, superoxide and peroxynitrite formation.Biochem. Soc. Trans., 21, 330–334 (1993).PubMedGoogle Scholar
  3. 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).Google Scholar
  4. 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).PubMedCrossRefGoogle Scholar
  5. Chen, Y., Wong, M., Rosen, R. T., and Ho, C. T., 2,2-Diphenyl-1-picrylhydrazyl radical-scavenging active components fromPolygonum multiflorum thunb.J. Agric. Food Chem., 47, 2226–2228 (1999).PubMedCrossRefGoogle Scholar
  6. 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).Google Scholar
  7. 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).PubMedCrossRefGoogle Scholar
  8. Ferrari, M., Fomasiero, M.C., and Isetta, A. M., MTT colorimetric assay for testing macrophage cytotoxic activityin vitro.J. Immunol. Methods, 131, 165–172 (1990).PubMedCrossRefGoogle Scholar
  9. Halliwell, B., and Chirico, S., Lipid peroxidation: its mechanism, measurement, and significance.Am. J. Clin. Nutr., 57, 715S-725S (1993).PubMedGoogle Scholar
  10. 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).PubMedCrossRefGoogle Scholar
  11. Junhua, H. and Guilian, W., Comparison studies on pharmacological properties of injection Gastrodia elata, gastrodin-free fration and gastrodin(chinese).Acta. Academiae Medicinae Sinicae, 11, 147–150 (1989).Google Scholar
  12. 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 fromBupleurum fruticescens.Planta Med., 64, 404–407 (1998).PubMedCrossRefGoogle Scholar
  13. Li, H. X., Ding, M. Y., and Yu, J. Y., Simultaneous determination ofp-hydroxybenzaldehyde,p-hydroxybenzyl alcohol, 4-(beta-D-glucopyranosyloxy)-benzyl alcohol, and sugars inGastrodia elata blume measured as their acetylated derivatives by GC-MS.J. Chromatogr. Sci., 39, 251–254 (2001).PubMedGoogle Scholar
  14. Lin, J. H., Liu, Y. C., Hau, J. P., and Wen, K. C., Parishins B and C from rhizomes ofGastrodia elata.Phytochemistry, 42, 549–551 (1996).CrossRefGoogle Scholar
  15. Liu, J. and Mori, A., Antioxidant and pro-oxidant activities ofp-hydroxybenzyl alcohol and vanillin: effects on free radicals, brain peroxidation and degradation of benzoate, deoxyribose, amino acids and DNA.Neuropharmacology, 32, 659–669 (1993).PubMedCrossRefGoogle Scholar
  16. Liu, J. and Mori, A., Antioxidant and free radical scavenging activities ofGastrodia elata Bl. andUncaria rhynchophylla (Miq.) Jacks.Neuropharmacology, 31, 1287–1298 (1992).PubMedCrossRefGoogle Scholar
  17. Noda, N., Kobayashi, Y., Miyahara, K., and Fukahori, S., 2,4-Bis(4-hydroxybenzyl)phenol fromGastrodia elata.Phytochemistry, 39, 1247–1248 (1995).CrossRefGoogle Scholar
  18. Ozaki, Y., Antiinflammatory effect ofCurcuma xanthorrhiza Roxb, and its active principles.Chem. Pharm. Bull., 38, 1045–1048 (1990).PubMedGoogle Scholar
  19. Raj, P. P., Pain mechanisms. In: Pain medicine: a comprehensive review, 1st ed. Mosby-Year Book, Inc., St. Louis, USA, pp. 12–24, 1996.Google Scholar
  20. 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).CrossRefGoogle Scholar
  21. Tang, W. and Eisenbrand, G., Chinese Drug of Plant Origin,Gastrodia elata Bl. Springer-Veriag, Berlin, Heidelberg., 545–548 (1992).Google Scholar
  22. Tanguchi, H., Yoshioka, I., Yamasaki, K., and Kim, I. H., Studies on the constituents ofGastrodia elata Blume.Chem. Pharm. Bull., 29, 55–62 (1981).Google Scholar
  23. 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).PubMedCrossRefGoogle Scholar
  24. Winter, C. A., Risley, E. A., and Nuss, G. W., Carrageen-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs.Pro. Soc. Exp. Biol. Med., 111, 544–547 (1962).Google Scholar
  25. Xiao, Y. Q., Li, L., You, X. L., Bian, B. L., Liang, X. M., and Wang, Y. Q., A new compound fromGastrodia elata Blume.J. Asian Nat. Prod. Res., 4, 73–79 (2002).PubMedCrossRefGoogle Scholar
  26. 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).CrossRefGoogle Scholar
  27. 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).PubMedCrossRefGoogle Scholar
  28. Yun-Choi, S. H., Pyo, M. K., and Park, K. M., Isolation of 4,4′-dihydroxybenzyl sulfoxide fromGasrtodia elata, Arch. Pharm. Res., 20, 91–92 (1997).PubMedCrossRefGoogle Scholar
  29. 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 ofGastrodia elata, Arch. Pharm. Res., 21, 357–360 (1998).PubMedCrossRefGoogle Scholar
  30. Zhou, J., Yang, Y. B., and Yang, T. R., The isolation identification of chemical constituents ofGastrodia elata Bl(chinese),Acta Chimica Sinica, 37, 183–189 (1979).Google Scholar

Copyright information

© The Pharmaceutical Society of Korea 2006

Authors and Affiliations

  • Ji Yun Lee
    • 1
  • Young Woon Jang
    • 1
  • Hyo Sook Kang
    • 1
  • Hee Moon
    • 1
  • Sang Soo Sim
    • 1
  • Chang Jong Kim
    • 1
    Email author
  1. 1.Division of Pathophysiology and Pharmacology, College of PharmacyChung-Ang UniversitySeoulKorea

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