Browse > Article
http://dx.doi.org/10.4062/biomolther.2010.18.3.321

Anti-Inflammatory Activity of Constituents Isolated from Ulmus davidiana var. japonica  

Zheng, Ming Shan (College of Pharmacy, Yeungnam University)
Yang, Ju-Hye (College of Pharmacy, Yeungnam University)
Li, Ying (College of Pharmacy, Yeungnam University)
Li, Xian (College of Pharmacy, Yeungnam University)
Chang, Hyeun-Wook (College of Pharmacy, Yeungnam University)
Son, Jong-Keun (College of Pharmacy, Yeungnam University)
Publication Information
Biomolecules & Therapeutics / v.18, no.3, 2010 , pp. 321-328 More about this Journal
Abstract
Twenty six compounds (1-26) were isolated from the root barks of Ulmus davidiana var. japonica. The anti-inflammatory activity of the isolated compounds were evaluated agai nst the generation of inflammatory chemical mediators in bone marrow-derived mast cells. Among them, compounds 10, 11, 13, 15 and 19 inhibited not only cyclooxygenase-2 dependent prostaglandin $D_2$ generation but also 5-lipoxygenase dependent leukotrien $C_4$ generation in a concentration-dependent manner. In addition, compounds 11, 12, 13, 15 and 19 also inhibited $\beta$-hexosaminidase release, a marker of mast cell degranulation reaction, from bone marrow-derived mast cell. These results suggest that the anti-inflammatory activity of U. davidiana might in part occur by both the inhibition of eicosanoid generations and the degranulation reaction of mast cells.
Keywords
Ulmus davidiana var. japonica; Bone marrow-derived mast cells; Cyclooxygenase-2, 5-Lipoxygenase; $\beta$-hexosaminidase; Anti-inflammatory activity;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 2
연도 인용수 순위
1 Yoshinari, K., Sashida, Y. and Shimomura, H. (1989). Two new lignan xylosides from the barks of Prunus ssiori and Prunus padus. Chem. Pharm. Bull. 37, 3301-3303.   DOI
2 Yumiko, K., Toshihiro, A., Ken, Y., Michio, T. and Toshitake, T. (1995). Structures of five hydroxylated sterols from the seeds of Trichosanthes kirilowii Maxim. Chem. Pharm. Bull. 43, 1813-1817.   DOI
3 Zhang, C. Z., Xu, X. Z. and Li, C. (1996). Fructosides from Cynomorium songaricum. Phytochemistry. 41, 975-976.   DOI
4 Sang, S., Kikuzaki, H., Lapsley, K., Rosen, R. T., Nakatani, N. and Ho, C. T. (2002). Sphingolipid and other constituents from almond nuts (Prunus amygdalus Batsch). J. Agric. Food Chem. 50, 4709-4712.   DOI
5 Seebacher, W., Simic, N., Weis, R., Saf, R. and Kunert, O. (2003). Complete assignments of $^1H$ and $^{13}C$ NMR resonances of oleanolic acid, 18-oleanolic acid, ursolic acid and their 11-oxo derivatives. Magn. Res. Chem. 41, 636-638.   DOI
6 Siddiqui, A. A., Wani, S. M., Rajesh, R. and Alagarsamy, V. (2006). Phytochemical and pharmacological investigation of Hibiscus rosasinensis Linn. Indian J. Pharm. Sci. 68, 588-593.   DOI
7 Smite, E., Pan, H. and Lundgren, L. N. (1995). Lignan glycosides from inner bark of Betula pendula. Phytochemistry 40, 341-343.   DOI
8 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. (2005). 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.   DOI
9 Song, I. K., Kim, K. S., Suh, S. J., Kim, M. S., Kwon, D. Y., Kim, S. L. and Kim, C. H. (2007). Anti-inflammatory effect of Ulmus davidiana Planch on collagen-induced inflammation in rats. Environ. Toxicol. Pharmacol. 23, 102-110.   DOI
10 Suh, S. J., Yun, W. S., Kim, K. S., Jin, U. H., Kim, J. K., Kim, M. S., Kwon, D. Y. and Kim, C. H. (2007). Stimulative effect of Ulmus davidiana Planch (Ulmaceae) on osteoblastic MC3T3-E1 cells. J. Ethnopharmacol. 109, 480-485.   DOI
11 Theoharides, T. C., Kempuraj, D., Tagen, M., Conti, P. and Kalogeromitros, D. (2007) Differential release of mast cell mediators and the pathogenesis of inflammation. Immunol. Rev. 217, 65-78.   DOI
12 Moon, Y. H. and Rim, G. R. (1995). Studies on the constituents of Ulmus parvifolia. Korean J. Pharmacognosy. 26, 1-7.
13 Murakami, M., Matsumoto, R., Austen, K. F. and Arm, J. P. (1994). Prostaglandin endoperoxide synthase-1 and -2 couple to different transmembrane stimuli to generate prostaglandin D2 in mouse bone marrow-derived mast cells. J. Biol. Chem. 269, 22269-22275.
14 Na, M. K., An, R. B., Lee, S. M., Min, B. S., Kim, Y. H., Bae, K. H. and Kang, S. S. (2002). Antioxidant compounds from the stem bark of Sorbus commixta. Nat. Prod. Sci. 8, 26-29.
15 Nahrstedt, A., Proksch, P. and Conn, E. E. (1987). (-)-Catechin, flavonol glycosides and flavones from Chamaebatia foliolosa. Phytochemistry. 26, 1546-1547.   DOI
16 Nawamaki, K. and Kuroyanagi, M. (1996). Sesquiterpenoids from Acorus calamus as germination inhibitors. Phytochemistry 43, 1175-1182.   DOI
17 Ono, E., Taniguchi, M., Mita, H., Fukutomi, Y., Higashi, N., Miyazaki, E., Kumamoto, T. and Akiyama, K. (2009) Increased production of cysteinyl leukotrienes and prostaglandin D2 during human anaphylaxis. Clin. Exp. Allergy 39, 72-80.   DOI
18 Pabst, A., Barron, D., Semon, E. and Schreier, P. (1992). Two diastereomeric 3-oxo-$\alpha$-ionol-$\beta$-glucosides from raspberry fruit. Phytochemistry 31, 1649-1652.   DOI
19 Rotondo, S., Dell'Elba, G., Krauze-Brzósko, K., Manarini, S., Martelli, N., Pecce, R., Evangelista, V. and Cerletti, C. (2002). Licofelone, a dual lipoxygenase-cyclooxygenase inhibitor, downregulates polymorphonuclear leukocyte and platelet function. Eur. J. Pharmacol. 453, 131-139.   DOI
20 Rouzer, C. A. and Marnett, L. J. (2009) Cyclooxygenases: structural and functional insights. J. Lipid Res. 50, 29-34.   DOI
21 Kohler, N., Wray, V. and Winterhalter, P. (2008). Preparative isolation of procyanidins from grap seed extracts by highspeed counter-current chromatography. J. Chromato. A. 1177, 114-125.   DOI
22 Lavaud, C., Massiot, G., Barrera, J. B., Moretti, C. and Le Men-Olivier, L. (1994). Triterpene saponins from Myrsine pellucida. Phytochemistry 37, 1671-1677.   DOI
23 Lee, M. K., Sung, S. H., Lee, H. S., Cho, J. H. and Kim, Y. C. (2001). Lignan and neolignan glycosides from Ulmus davidiana var. japonica. Arch. Pharm. Res. 24, 198-201.   DOI
24 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. (2004). Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin (anthricin) in mouse bone marrow-derived mast cells. Biol. Pharm. Bull. 27, 786-788.   DOI
25 Li, S., Chen, R. Y. and Yu, D. Q. (2007). Study on chemical constituents of Myricaria paniculata I. Zhongguo Zhong Yao Za Zhi. 32, 403-406.
26 Martel-Pelletier, J., Lajeunesse, D., Reboul, P., Pelletier, J. P. (2003) Therapeutic role of dual inhibitors of 5-LOX and COX, selective and non-selective non-steroidal anti-inflammatory drugs. Ann. Rheum. Dis. 62, 501-509.   DOI
27 Metcalfe, D. D., Peavy, R. D. and Gilfillan, A. M. (2009) Mechanisms of mast cell signaling in anaphylaxis. J. Allergy Clin. Immunol. 124, 639-646.   DOI
28 Mitchell, J. A. and Warner, T. D. (2006) COX isoforms in the cardiovascular system: understanding the activities of nonsteroidal anti-inflammatory drugs. Nat. Rev. Drug Discov. 5, 75-86.   DOI
29 Moon, T. C., Murakami, M., Kudo, I., Son, K. H., Kim, H. P. and Chang, H. W. (1999). A new class of COX-2 inhibitor, rutaecarpine from Evodia rutaecarpa. Inflamm. Res. 48, 621-625.   DOI
30 Jin, U. H., Lee, D. Y., Kim, D. S., Lee, I. S. and Kim, C. H. (2006). Induction of mitochondria-mediated apoptosis by methanol fraction of Ulmus davidiana Planch (Ulmaceae) in U87 glioblastoma cells. Environ. Toxicol. Pharmaco. 22, 136-141.   DOI
31 Jin, U. H., Suh, S. J., Park, S. D., Kim, K. S., Kwon, D. Y. and Kim, C. H. (2008). Inhibition of mouse osteoblast proliferation and prostaglandin E2 synthesis by Ulmus davidiana Planch (Ulmaceae). Food Chem. Toxicol. 46, 2135-2142.   DOI
32 Jippo, T., Kobayashi, Y., Sato, H., Hattori, A., Takeuchi, H., Sugimoto, K. and Shigekawa, M. (2009). Inhibitory effects of guarana seed extract on passive cutaneous anaphylaxis and mast cell degranulation. Biosci. Biotechnol. Biochem. 73, 2110-2112.   DOI
33 Jun, C. D., Pae, H. O., Kim, Y. C., Jeong, S. J., Yoo, J. C., Lee, E. J., Choi, B. M., Chae, S. W., Park, R. K. and Chung, H. T. (1998). Inhibition of nitric oxide synthesis by butanol fraction of the methanol extract of Ulmus davidiana in murine macrophages. J. Ethnopharmacol. 62, 129-135.   DOI
34 Kang, S. K., Kim, K. S., Byun, Y. S., Suh, S. J., Jin, U. H., Kim, K. H., Lee, I. S. and Kim, C. H. (2006). Effects of Ulmus davidiana Planch on mineralization, bone morphogenetic protein-2, alkaline phosphatase type I collagen, and collagenase-1 in bone cells. In Vitro Cell. Develop. Biol. Animal 42, 225-229.   DOI
35 Kim, H. J., Yeom, S. H., Kim, M. K., Shim, J. G., Lim, H. W. and Lee, M. W. (2004). Nitric oxide and prostaglandin E2 synthesis inhibitory activities of flavonoids from the barks of Ulmus macrocarpa. Nat. Prod. Sci. 10, 344-346.
36 Ishimaru, K., Nonaka, G. I. and Nishioka, I. (1987). Flavan-3-ol and procyanidin glycosides from Quercus miyagii. Phytochemistry. 26, 1167-1170.   DOI
37 Jin, M. H., Bae, K, H., Son, J. K. and Chang, H. W. (2009). Anti-inflammatory compounds from the leaves of Ailanthus altissima. Biomol. Therap. 17, 86-91.   DOI   ScienceOn
38 Aguirre, M. C., Delporte, C., Backhouse, N., Erazo, S., Letelier, M. E., Cassels, B. K., Silva, X., Alegria, S. and Negrete, R. (2006). Topical anti-inflammatory activity of 2alpha-hydroxy pentacyclic triterpene acids from the leaves of Ugni molinae. Bioorg. Med. Chem. 14, 5673- 5677.   DOI
39 Ali, M. S., Mahmud, S., Perveen, S., Ahmad, V. U. and Rizwani, G. H. (1999). Epimers from the leaves of Calophyllum inophyllum. Phytochemistry. 50, 1385-1389.   DOI
40 Boileau, C., Martel-Pelletier, J., Jouzeau, J. Y., Netter, P., Moldovan, F., Laufer, S., Tries, S. and Pelletier, J. P. (2002). Licofelone (ML-3000), a dual inhibitor of 5-lipoxygenase and cyclooxygenase, reduces the level of cartilage chondrocyte death in vivo in experimental dog osteoarthritis: inhibition of pro-apoptotic factors. J. Rheumatol. 29, 1446-1453.
41 Boileau, C., Martel-Pelletier, J., Jouzeau, J. Y., Netter, P., Moldovan, F., Laufer, S., Tries, S. and Pelletier, J. P. (2002). Licofelone (ML-3000), a dual inhibitor of 5-lipoxygenase and cyclooxygenase, reduces the level of cartilage chondrocyte death in vivo in experimental dog osteoarthritis: inhibition of pro-apoptotic factors. J. Rheumatol. 29, 1446-1453.
42 Foo, L. Y. and Karchesy, J. J. (1989). Polyphenolic glycosides from Douglas fir inner bark. Phytochemistry. 28, 1237-1240.   DOI
43 Gulliksson, M., Palmberg, L., Nilsson, G., Ahlstedt, S. and Kumlin, M. (2006). Release of prostaglandin D2 and leukotriene C4 in response to hyperosmolar stimulation of mast cells. Allergy. 61, 1473-1479.   DOI
44 Hisashi, K. and Haruo, O. (1989). Configurational studies on hydroxy groups at C-2, 3 and 23 or 24 of oleanene and ursene-type triterpenes by NMR spectroscopy. Phytochemistry. 28, 1703-1710.   DOI
45 Inoshiri, S., Sasaki, M., Kohda, H., Otsuka, H. and Yamasaki, K. (1987). Aromatic glycosides from Berchemia racemosa. Phytochemistry. 26, 2811-2814.   DOI
46 Umlauf, D., Zapp, J., Becker, H. and Adam, K. P. (2004). Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae). Phytochemistry. 65, 2463-2470.   DOI
47 Wang, D., Xia, M. and Cui, Z. (2006). New triterpenoids isolated from the root bark of Ulmus pumila L. Chem. Pharm. Bull. 54, 775-778.   DOI