Download PDF
Planta Med 2014; 80(07): 583-589
DOI: 10.1055/s-0034-1368353
Natural Product Chemistry
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Anti-inflammatory Terpenes from Flowers of Inula japonica

Sheng-An Tang
1   Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin, P. R. China
,
Hong Zhu
1   Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin, P. R. China
,
Nan Qin
2   Research Center of Basic Medical Sciences, Tianjin Medical University, Tianjin, P. R. China
,
Jing-Ya Zhou
1   Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin, P. R. China
,
Eunkyung Lee
3   Research and Development Division, Korean Promotion Institute for Traditional Medicine Industry, Gyeongsan, South Korea
,
De-Xin Kong
1   Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin, P. R. China
2   Research Center of Basic Medical Sciences, Tianjin Medical University, Tianjin, P. R. China
,
Mei-Hua Jin
1   Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin, P. R. China
,
Hong-Quan Duan
1   Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics, School of Pharmacy, Tianjin Medical University, Tianjin, P. R. China
2   Research Center of Basic Medical Sciences, Tianjin Medical University, Tianjin, P. R. China
› Author Affiliations
Further Information

Publication History

received 16 October 2013
revised 21 January 2014

accepted 10 March 2014

Publication Date:
07 April 2014 (online)

    Permissions and Reprints

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.

Key words

Inula japonica - Compositae - terpene - anti-inflammatory - NO - LTC4 - degranulation

Supporting Information

 

  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    Article in Thieme ConnectPubMedGoogle Scholar
  • 6 Zheng MS. An experimental study of the anti-HSV-II action of 500 herbal drugs. J Tradit Chin Med 1989; 9: 113-116
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 11 Dawicki W, Marshall JS. New and emerging roles for mast cells in host defence. Curr Opin Immunol 2007; 19: 31-38
    CrossrefPubMedGoogle Scholar
  • 12 Boyce JA. The role of mast cells in asthma. Prostaglandins Leukot Essent Fatty Acids 2003; 69: 195-205
    CrossrefPubMedGoogle Scholar
  • 13 Laskin DL, Pendino KJ. Macrophages and inflammatory mediators in tissue injury. Annu Rev Pharmacol Toxicol 1995; 35: 655-677
    CrossrefPubMedGoogle Scholar
  • 14 Yang C, Wang CM, Jia ZJ. Sesquiterpenes and other constituents from the aerial parts of Inula japonica . Planta Med 2003; 69: 662-666
    Article in Thieme ConnectPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 19 Bing-Nan Z, Nai-Sheng B, Long-Ze L, Cordell GA. Sesquiterpene lactones from Inula britannica . Phytochemistry 1993; 34: 249-252
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 21 Henderson jr. WR. The role of leukotrienes in inflammation. Ann Intern Med 1994; 121: 684-697
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 30 Zhao JP, Pawar RS, Ali Z, Khan IA. Phytochemical investigation of Turnera diffusa . J Nat Prod 2007; 70: 289-292
    CrossrefPubMedGoogle Scholar
  • 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
    CrossrefPubMedGoogle Scholar
  • 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
    PubMedGoogle Scholar