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Planta Med 2014; 80(07): 583-589
DOI: 10.1055/s-0034-1368353
DOI: 10.1055/s-0034-1368353
Natural Product Chemistry
Original Papers
Anti-inflammatory Terpenes from Flowers of Inula japonica
Further Information
Publication History
received 16 October 2013
revised 21 January 2014
accepted 10 March 2014
Publication Date:
07 April 2014 (online)
Abstract
Five new terpenes (1–5) and ten known compounds (6–15) were isolated from Inula japonica, and their structures were identified by spectroscopic analysis. Compounds 3 and 14 showed positive inhibitory effects on nitric oxide production. Furthermore, compound 14 suppressed both leukotriene C4 synthesis and degranulation in c-kit ligand-induced bone marrow-derived mast cells.
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References
- 1 Liu S, Liu H, Yan W, Zhang L, Bai N, Ho CT. Studies on 1-O-acetylbritannilactone and its derivative, (2-O-butyloxime-3-phenyl)-propionyl-1-O-acetylbritannilactone ester. Bioorg Med Chem Lett 2004; 14: 1101-1104
- 2 Kobayashi T, Song QH, Hong T, Kitamura H, Cyong JC. Preventative effects of the flowers of Inula britannica on autoimmune diabetes in C57BL/KsJ mice induced by multiple low doses of streptozotocin. Phytother Res 2002; 16: 377-382
- 3 Shan JJ, Yang M, Ren JW. Anti-diabetic and hypolipidemic effects of aqueous-extract from the flower of Inula japonica in alloxan-induced diabetic mice. Biol Pharm Bull 2006; 29: 455-459
- 4 Song QH, Kobayashi T, Iijima K, Hong T, Cyong JC. Hepatoprotective effects of Inula britannica on hepatic injury in mice. Phytother Res 2000; 14: 180-186
- 5 Wang CM, Jia ZJ, Zheng RL. The effect of 17 sesquiterpenes on cell viability and telomerase activity in the human ovarian cancer cell line HO-8910. Planta Med 2007; 73: 180-184
- 6 Zheng MS. An experimental study of the anti-HSV-II action of 500 herbal drugs. J Tradit Chin Med 1989; 9: 113-116
- 7 Choi JH, Park YN, Li Y, Jin MH, Lee J, Lee Y, Son JK, Chang HW, Lee E. Flowers of Inula japonica attenuate inflammatory responses. Immune Netw 2010; 10: 145-152
- 8 Lu Y, Li Y, Jin M, Yang JH, Li X, Chao GH, Park HH, Park YN, Son JK, Lee E, Chang HW. Inula japonica extract inhibits mast cell-mediated allergic reaction and mast cell activation. J Ethnopharmacol 2012; 143: 151-157
- 9 Park YN, Lee YJ, Choi JH, Jin M, Yang JH, Li Y, Lee J, Li X, Kim KJ, Son JK, Chang HW, Kim JY, Lee E. Alleviation of OVA-induced airway inflammation by flowers of Inula japonica in a murine model of asthma. Biosci Biotechnol Biochem 2011; 75: 871-876
- 10 Lundberg IE. The role of cytokines, chemokines, and adhesion molecules in the pathogenesis of idiopathic inflammatory myopathies. Curr Rheumatol Rep 2000; 2: 216-224
- 11 Dawicki W, Marshall JS. New and emerging roles for mast cells in host defence. Curr Opin Immunol 2007; 19: 31-38
- 12 Boyce JA. The role of mast cells in asthma. Prostaglandins Leukot Essent Fatty Acids 2003; 69: 195-205
- 13 Laskin DL, Pendino KJ. Macrophages and inflammatory mediators in tissue injury. Annu Rev Pharmacol Toxicol 1995; 35: 655-677
- 14 Yang C, Wang CM, Jia ZJ. Sesquiterpenes and other constituents from the aerial parts of Inula japonica . Planta Med 2003; 69: 662-666
- 15 Herz W, Sumi Y, Sudarsanam V, Raulais D. Constituents of Iva species. IX. Ivangulin, a novel seco-eudesmanolide from Iva angustifolia . J Org Chem 1967; 32: 3658-3662
- 16 Qin JJ, Jin HZ, Zhu JX, Fu JJ, Zeng Q, Cheng XR, Zhu Y, Shan L, Zhang SD, Pan YX, Zhang WD. New sesquiterpenes from Inula japonica Thunb. with their inhibitory activities against LPS-induced NO production in RAW264.7 macrophages. Tetrahedron 2010; 66: 9379-9388
- 17 Kuai YH, Bi ZM, Li P, Zhang YH. A novel kaurane diterpenoid from the bark of Annona glabra Linn. Chem Ind Forest Prod 2006; 26: 13-15
- 18 Gong HQ, Wu QX, Liu LL, Yang JL, Wang R, Shi YP. Sesquiterpenoids from the Aerial Parts of Inula japonica . Helvetica Chimica Acta 2011; 94: 1269-1276
- 19 Bing-Nan Z, Nai-Sheng B, Long-Ze L, Cordell GA. Sesquiterpene lactones from Inula britannica . Phytochemistry 1993; 34: 249-252
- 20 Wu YC, Hung YC, Chang FR, Cosentino M, Wang HK, Lee KH. Identification of ent-16beta,17-dihydroxykauran-19-oic acid as an anti-HIV principle and isolation of the new diterpenoids annosquamosins A and B from Annona squamosa . J Nat Prod 1996; 59: 635-637
- 21 Henderson jr. WR. The role of leukotrienes in inflammation. Ann Intern Med 1994; 121: 684-697
- 22 Whan Han J, Gon Lee B, Kee Kim Y, Woo Yoon J, Kyoung Jin H, Hong S, Young Lee H, Ro Lee K, Woo Lee H. Ergolide, sesquiterpene lactone from Inula britannica, inhibits inducible nitric oxide synthase and cyclo-oxygenase-2 expression in RAW 264.7 macrophages through the inactivation of NF-kappaB. Br J Pharmacol 2001; 133: 503-512
- 23 Han M, Wen JK, Zheng B, Zhang DQ. Acetylbritannilatone suppresses NO and PGE2 synthesis in RAW 264.7 macrophages through the inhibition of iNOS and COX-2 gene expression. Life Sci 2004; 75: 675-684
- 24 Lee J, Tae N, Lee JJ, Kim T, Lee JH. Eupatolide inhibits lipopolysaccharide-induced COX-2 and iNOS expression in RAW264.7 cells by inducing proteasomal degradation of TRAF6. Eur J Pharmacol 2010; 636: 173-180
- 25 Nam KW, Oh GT, Seo EK, Kim KH, Koo U, Lee SJ, Mar W. Nuclear factor kappaB-mediated down-regulation of adhesion molecules: possible mechanism for inhibitory activity of bigelovin against inflammatory monocytes adhesion to endothelial cells. J Ethnopharmacol 2009; 123: 250-256
- 26 Song YJ, Lee DY, Kim SN, Lee KR, Lee HW, Han JW, Kang DW, Lee HY, Kim YK. Apoptotic potential of sesquiterpene lactone ergolide through the inhibition of NF-kappaB signaling pathway. J Pharm Pharmacol 2005; 57: 1591-1597
- 27 Lee J, Hwangbo C, Lee JJ, Seo J, Lee JH. The sesquiterpene lactone eupatolide sensitizes breast cancer cells to TRAIL through down-regulation of c-FLIP expression. Oncol Rep 2010; 23: 229-237
- 28 Khan AL, Hussain J, Hamayun M, Gilani SA, Ahmad S, Rehman G, Kim YH, Kang SM, Lee IJ. Secondary metabolites from Inula britannica L. and their biological activities. Molecules 2010; 15: 1562-1577
- 29 Liu B, Han M, Sun RH, Wang JJ, Liu YP, Wen JK. Acetylbritannilactone induces G1 arrest and apoptosis in vascular smooth muscle cells. Int J Cardiol 2011; 149: 30-38
- 30 Zhao JP, Pawar RS, Ali Z, Khan IA. Phytochemical investigation of Turnera diffusa . J Nat Prod 2007; 70: 289-292
- 31 Murakami M, Kambe T, Shimbara S, Kudo I. Functional coupling between various phospholipase A2s and cyclooxygenases in immediate and delayed prostanoid biosynthetic pathways. J Biol Chem 1999; 274: 3103-3115
- 32 Murakami M, Matsumoto R, Austen KF, Arm JP. 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 1994; 269: 22269-22275