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Effects of Methyl Gallate on Arachidonic Acid Metabolizing Enzymes: Cyclooxygenase-2 and 5-Lipoxygenase in Mouse Bone Marrow-Derived Mast Cells  

Kim, Se-Jong (Research Institute of Natural Product Kyongbuk Provincial A. T. A)
Jin, Mei-Hua (College of Pharmacy, Yeungnam University)
Lee, Eun-Kyung (College of Pharmacy, Yeungnam University)
Moon, Tae-Chul (College of Pharmacy, Yeungnam University)
Quan, Zhe-Jiu (College of Pharmacy, Yeungnam University)
Yang, Ju-Hye (College of Pharmacy, Yeungnam University)
Son, Kun-Ho (Department of Food and Nutrition, Andong National University)
Kim, Kil-Ung (College of Agriculture and Life Science, Kyungpook National University)
Son, Jong-Kun (College of Pharmacy, Yeungnam University)
Chang, Hyeun-Wook (College of Pharmacy, Yeungnam University)
Publication Information
Archives of Pharmacal Research / v.29, no.10, 2006 , pp. 874-878 More about this Journal
Abstract
Methyl gallate (MG) is a medicinal herbal product that is isolated from Paeonia lactiflora that inhibits cyclooxygenase-2 (COX-2) dependent phases of prostaglandin $D_2\;(PGD_2)$ generation in bone marrow-derived mast cells (BMMC) in a concentration-dependent manner with an $IC_{50}$ values of $17.0\;{\mu}M$. This compound also found inhibited the COX-2-dependent conversion of the exogenous arachidonic acid to $PGD_2$ in a dose-dependent manner with an $IC_{50}$ values of $190\;{\mu}M$, using a COX enzyme assay kit. However, at concentrations up to $80\;{\mu}M$, MG did not inhibit COX-2 protein expression in BMMC, indicating that MG inhibits COX-2 activity directly. Furthermore, MG consistently inhibited the production of leukotriene $C_4\;(LTC_4)$ in a dose dependent manner, with an $IC_{50}$ value of $5.3\;{\mu}M$. These results demonstrate that MG has a dual cyclooxygenase-2/5-lipoxygenase inhibitory activity, which might provide the basis for novel anti-inflammatory drugs.
Keywords
Paeonia lactiflora; Methyl gallate; Inflammation; Cyclooxygenase-2,5-Lipoxygenase; Bone marrow-derived mast cells;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 11  (Related Records In Web of Science)
Times Cited By SCOPUS : 7
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1 Kim, H. C., Hanyak-Yakri-Hak, 1st edn. Jip-Moon Press: Seoul, 469-471 (2001)
2 Lee, S. C., Kwon, Y. S., Son, K. H., Kim, H. P., and Heo, M. Y., Antioxidative constituents from Paeonia lactiflora. Arch. Pharm. Res., 28, 775-783 (2005)   과학기술학회마을   DOI   ScienceOn
3 Lee, S. M., Li, M. L., Tse, Y. C., Leung, S. C., Lee, M. M., Tsui, S. K., Fung, K. P., Lee, C. Y., and Waye, M. M., Paeoniae Radix, a Chinese herbal extract, inhibit hepatoma cells growth by inducing apoptosis in a p53 independent pathway. Life Sci., 71, 2267–2277 (2002)   DOI   ScienceOn
4 Lim, M. Y., Park, Y. H., Son, D. J., Kim, M. K., and Lee, H. S., Antiplatelet activity of gallic acid and methyl gallate. Food Sci. Biot., 13, 806-809 (2004)
5 Murakami, M., Matsumoto, R., Austen, K. F., and Arm, J. P., Prostaglandin endoperoxide synthase-1 and -2 couple to different transmembrane stimuli to generate prostaglandin $D_2$ in mouse bone marrow-derived mast cells. J. Biol. Chem., 269, 22269-22275 (1994)
6 Murakami, M., Austen, K. F., and Arm, J. P., The immediate phase of c-kit ligand stimulation of mouse bone marrow-derived mast cells elicits rapid leukotriene C4 generation through posttranslational activation of cytosolic phospholipase A2 and 5-lipoxygenase. J. Exp. Med., 182, 197-206 (1995)   DOI   ScienceOn
7 Murakami, M., Kambe, T., Shimbara, S., and Kudo, I., Functional coupling between various phospholipase A2s and cyclooxygenases in immediate and delayed prostanoid biosynthetic pathways. J. Biol. Chem., 274, 3103-3115 (1999)   DOI   ScienceOn
8 Murakami, M. and Kudo, I., Diversity and regulatory functions of mammalian secretory phospholipase A2s. Adv. Immunol., 77, 163-194 (2001)   DOI
9 Son, J. K., Son, M. J., Lee, E. K., Moon, T. C., Son, K. H., Kim, C. H., Kim, H. P., Kang, S. S., and Chang, H. W., Ginkgetin, a biflavone from Ginko biloba leaves, inhibits cyclooxygenases- 2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. Biol. Pharm. Bull., 28, 2181-2184 (2005)   DOI   ScienceOn
10 Westenburg, H, E., Lee, K. J., Lee, S. K., Fong, H. H., van Breemen, R. B., Pezzuto, J. M., and Kinghorn, A. D., Activityguided isolation of antioxidative constituents of Cotinus coggygria. J. Nat. Prod., 63, 1696-1698 (2000)   DOI   ScienceOn
11 Whang, W. K., Park, H. S., Ham, I. H., Oh, M., Namkoong, H. Kim, H. K., Hwang, D. W., Hur, S. Y., Kim, T. E., Park, Y. G.., Kim, J. R., and Kim, J. W., Methyl gallate and chemicals structurally related to methyl gallate protect human umbilical vein endothelial cells from oxidative stress. Exp. Mol. Med., 37, 343-352 (2005)   DOI   ScienceOn
12 Yamaguchi, M., Sayama, K., Yano, K., Lantz, C. S., Noben- Trauth, N., Ra ,C., Costa, J. J., and Galli, S. J., IgE enhances Fc epsilon receptor I expression and IgE-dependent release of histamine and lipid mediators from human umbilical cord blood-derived mast cells: synergistic effect of IL-4 and IgE on human mast cell Fc epsilon receptor I expression and mediator release. J. Immunol., 162, 5455-5465 (1999)
13 Vane, J. R., Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat .New Biol., 231, 232-235 (1971)   DOI
14 Cho, E. J., Yokozawa, T., Kim, H. Y., Shibahara, N., and Park, J. C., Rosa rugosa attenuates diabetic oxidative stress in rats with streptozotocin-induced diabetes. Am .J. Chin. Med., 32, 487-496 (2004)   DOI   ScienceOn
15 Moon, T. C., Murakami, M., Kudo, I., Son, K. H., Kim, H. P., Kang, S. S., and Chang, H. W., A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa. Inflamm. Res., 48, 621-625 (1999)   DOI
16 Piper, P. J., Leukotrienes: possible mediators in bronchial asthma. Eur. J. Respir. Dis., Suppl. 129, 45-64 (1983)
17 Kim, H. J., Chang, E. J., Bae, SJ, Shim, S. H., Park, H. D., Rhee, C. H., Park, J. H., and Choi, S. W., Cytotoxic and antimutagenic stilbenes from seeds of Paeonia lactiflora. Arch. Pharm. Res., 25, 293-299 (2002)   DOI   ScienceOn
18 O'Banion, M. K., Winn, V. D., and Young, D. A., cDNA cloning and functional activity of a glucocorticoid-regulated inflammatory cyclooxygenase. Proc. Natl. Acad. Sci., U.S.A., 89, 4888-4892 (1992)
19 Sohi, K. K., Mittal, N., Hundal, M. K., and Khanduja, K. L., Gallic acid, an antioxidant, exhibits antiapoptotic potential in normal human lymphocytes: A Bcl-2 independent mechanism. J. Nutr. Sci. Vitaminol., 49, 221-227 (2003)   DOI   ScienceOn
20 Stevens, R. L. and Austen, K. F., Recent advances in the cellular and molecular biology of mast cells. Immunol. Today, 10, 381-386 (1989)   DOI   ScienceOn
21 Galato, D., Ckless, K., Susin, M. F., Giacomelli, C., Ribeiro-do- Valle, R. M., and Spinelli, A., Antioxidant capacity of phenolic and related compounds: correlation among electrochemical, visible spectroscopy methods and structure-antioxidant activity. Redox. Rep., 6, 243-250 (2001)   DOI   ScienceOn
22 Shoyma, Y., Yamada, Y., Nishioka, I., and Matsunaka, J., Depigmentation and inhibition of cell growth of B-16 melanoma cells by compounds isolated from Paeonia suffruticosa callus. Plant Cell Rep., 8, 711-713 (1990)   DOI   ScienceOn
23 Lin, H. C., Ding, H. Y., Ko, F. N., Teng, C. M., and Wu, Y. C., Aggregation inhibitory activity of minor acetophenones from paeonia species, Planta Medica, 65, 595–599 (1999)   DOI   ScienceOn
24 Dan, B. and Andrew, G., Chinese Herbal Medicine, 8th edn. Eastland Press: Seattle, 476–477 (1986)
25 Kane, C. J., Menna, J. H., Sung, C. C., and Yeh, Y. C., Methyl gallate, methyl-3, 4,5-trihydoxybenzoate, is a potent and highly specific inhibitor of herpes simplex virus in vitro. II. Antiviral activity of methyl gallate and its derivatives. Biosci. Rep., 8, 95-102 (1988)   DOI   ScienceOn
26 Yasuda, T., Kon, R., Nakazawa, T., and Ohsawa, K., Metabolism of paeonol in rats, J. Nat. Prod., 62, 1142–1144 (1999)   DOI   ScienceOn
27 Chou, T. C., Anti-inflammatory and analgesic effects of paeonol in carrageenan-evoked thermal hyperalgesia, Br. J. Pharmacol., 139, 1146-1152 (2003)   DOI   ScienceOn
28 Fiorucci, S., Meli, R., Bucci, M., and Cirino, G.., Dual inhibitors of cyclooxygenase and 5-lipoxygenase. A new avenue in anti-inflammatory therapy? Biochem. Pharmacol., 62, 1433- 1438 (2001)   DOI   ScienceOn
29 Bailey, A. E., Asplund, R. O., and Ali, M. S., Isolation of methyl gallate as the antitumor principle of Acer saccharinum. J. Nat. Prod., 49, 1149-1150 (1986)   DOI
30 Wu, H. K., and Sheu, S. J., Capillary electrophoretic determination of the constituents of paeonia radix. J. Chromatogr. A., 753, 139-146 (1996)   DOI   ScienceOn
31 Son, M. J., Moon, T. C., Lee, E. K., Son, K. H., Kim, H. P., Kang, S. S., Son, J. K., Lee, S. H., and Chang, H. W., Naturally occurring biflavonoid, ochanflavone, inhibits cyclooxygenases- 2 and 5-lipoxygenase in mouse bone marrow-derived mast cells. Arch. Pharm. Res., 29, 282-286 (2006)   과학기술학회마을   DOI   ScienceOn
32 Kato, K., Yamashita, S., Kitanaka, S., and Toyoshima, S., Effect of gallic acid derivatives on secretion of Th1 cytokines and Th2 cytokines from anti CD3-stimulated spleen cells. Yakugaku Zasshi, 121, 451-457 (2001)   DOI
33 Cho, E. J., Yokozawa, T., Rhyu, D. Y., Kim, S. C., Shibahara, N., and Park, J. C., Study on the inhibitory effects of Korean medicinal plants and their main compounds on the 1,1- diphenyl-2-picrylhydrazyl radical. Phytomedicine, 10, 544- 551 (2003)   DOI   ScienceOn
34 Lee, S. H., Son, M. J., JU, H. K., Lin, C. X., Moon, T. C., Choi, H. G., Son, J. K., and Chang, H. W., Dual inhibition of cyclooxygenases- 2 and 5-lipoxygenase by deoxypodophyllotoxin (anthricin) in mouse bone marrow-derived mast cells. Biol. Pharm. Bull., 27, 786-788 (2004)   DOI   ScienceOn
35 Whittle, B. J., Higgs, G. A., Eakins, K. E., and Vane, J. R., Selective inhibition of prostaglandin production in inflammatory exudates and gastric mucosa. Nature, 284, 271-273 (1980)   DOI   ScienceOn