Skip to main content
Log in

A new anti-inflammatory triterpene saponin isolated from Anabasis setifera

  • Research Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

A bio-guided fractionation of Anabasis setifera Moq. (Chenopodiaceae) for anti-inflammatory activity was carried out using carrageenin rat paw edema model in rats. On the basis of percent edema inhibition after 3 h of carrageenin injection, n-butanol fraction showed promising activity through a significant (p < 0.05) decrease in paw volume by 85.6 % from control using indomethacin as reference standard. Moreover, the n-butanol fraction significantly (p < 0.05) decreased PGE2 and TNF-α in the exudates of rat paw edema. Chemical investigation of n-butanol fraction afforded α-amyrin 3-O-glucopyranoside (1), patuletin 7-O-glucopyranoside (2), myricitrin (3) and a new oleanane triterpene saponin derivative (4), sophradiol 3-O-α-l-1C4-rhamnopyranosyl-(1′′′→4′′)-O-β-d-4C1-galactopyranosyl (1′′→6′)-O-β-d-4C1-glucopyranoside. The structure of the new compound was determined by comprehensive analyses of their 1D and 2D NMR, mass spectral data and comparison with previously known analogs. Only compound 4 revealed a significant (p < 0.05) inhibition of cyclooxygenase 1 and 2 (COX) activities.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  • Ahmed, A.A., M. Spaller, and T.J. Mabry. 1992. Flavonoids of Pallenis spinosa (Asteraceae). Biochemical Systematics and Ecology 20: 785–786.

    Article  CAS  Google Scholar 

  • Ahn, K.S., J.H. Kim, S.R. Oh, B.S. Min, J. Kinjo, and H.K. Lee. 2002. Effects of oleanane-type triterpenoids from fabaceous plants on the expression of ICAM-1. Biological and Pharmaceutical Bulletin 25: 1105–1107.

    Article  PubMed  CAS  Google Scholar 

  • Alsofany, R.H. 1998. A study of saponin content of Anabasis setifera Moq growing in Egypt. Bulletin of the Faculty of Pharmacy (Cairo University) 36: 17–19.

    CAS  Google Scholar 

  • Camuesco, D., M. Comalada, M.E. Rodriguez-Cabezas, A. Nieto, M.D. Lorente, and A. Concha. 2004. The intestinal anti-inflammatory effect of quercitrin is associated with an inhibition in iNOS expression. British Journal of Pharmacology 143: 908–918.

    Article  PubMed  CAS  Google Scholar 

  • Gamble, J.R., J.M. Harlan, S.J. Klebanoff, and M.A. Vadas. 1985. Stimulation of the adherence of neutrophils to umbilical vein endothelium by human recombinant tumor necrosis factor. Proceedings of the National Academy of Sciences of the United States of America 82: 8667–8671.

    Article  PubMed  CAS  Google Scholar 

  • Gibbs, R.D. 1974. Chemotaxonomy of flowering plants, 1236–1238. London: McGill-Queen’s University.

    Google Scholar 

  • Harada, A., N. Sekido, T. Akahoshi, T. Wada, N. Mukaida, and K. Matsushima. 1994. Essential involvement of interleukin-8 (IL-8) in acute inflammation. Journal of Leukocyte Biology 56: 559–564.

    PubMed  CAS  Google Scholar 

  • Hegnauer, R. 1989. Chemotaxonomie Der Pflanzen. Berlin: Birkhauser.

    Google Scholar 

  • Holtman, M.H., M. Schuchmann, G. Zeller, P.R. Galle, and M.F. Neurath. 2002. The emerging distinct role of TNF-receptor 2 (p80) signaling in chronic inflammatory disorders. Archivum immunolgiae et therapiae experimentalis 50: 279–288.

    Google Scholar 

  • Hussein, F.T.K. 1985. Medicinal plants in Libya, 1st ed, 244. Libya: Arab Encyclopedia House.

    Google Scholar 

  • Jenny, M., M. Klieber, D. Zaknun, S. Schroecksnadel, K. Kurz, M. Ledochowski, H. Schennach, and D. Fuchs. 2011. In vitro testing for anti-inflammatory properties of compounds employing peripheral blood mononuclear cells freshly isolated from healthy donors. Inflammation Research 60: 127–135.

    Article  PubMed  CAS  Google Scholar 

  • Kulmacz, J.R., and W.E. Lands. 1983. Requirements for hydroperoxide by the cyclooxygenase and peroxidase activities of prostaglandin H synthase. Prostaglandins 25: 531–540.

    PubMed  CAS  Google Scholar 

  • Lipsky, L.P., S.B. Abramson, L. Crofford, R.N. Dubois, L.S. Simon, and L.B. van de Putte. 1998. The classification of cyclooxygenase inhibitors. Journal of Rheumatology 25: 2298–2303.

    PubMed  CAS  Google Scholar 

  • Mimaki, Y., M. Kuroda, A. Yokosuka, H. Harada, M. Fukushima, and Y. Sashida. 2003. Triterpenes and triterpene saponins from the stems of Akebia trifoliata. Chemical and Pharmaceutical Bulletin (Tokyo) 51: 960–965.

    Article  CAS  Google Scholar 

  • Mnich, S.J., A.W. Veenhuizen, J.B. Monahan, K.C. Sheehan, K.R. Lynch, P.C. Isakson, and J.P. Portanova. 1995. Characterization of a monoclonal antibody that neutralizes the activity of prostaglandin E2. The Journal of Immunology 155: 4437–4444.

    PubMed  CAS  Google Scholar 

  • Navarro, P., R.M. Giner, M.C. Recio, S. Manez, M. Cerda-Nicolas, and J.L. Rios. 2001. In vivo anti-inflammatory activity of saponins from Bupleurum rotundifolium. Life Sciences 68: 1199–1206.

    Article  PubMed  CAS  Google Scholar 

  • Ndom, J.C., Kouam, J.C. Vardamides, J.D. Wansi, A.W. Kamdem, J.T. Mbafor, and Z.T. Fomum. 2001. Constituents of Erythrina sigmoidea. The Bulletin of the Chemical Society of Ethiopia 15: 151–156.

    CAS  Google Scholar 

  • Neurauter, G., B. Wirleitner, A. Laich, H. Schennach, G. Weiss, and D. Fuchs. 2003. Atorvastatin suppresses interferon-gamma-induced neopterin formation and tryptophan degradation in human peripheral blood mononuclear cells and in monocytic cell lines. Clinical and Experimental Immunology 131: 264–267.

    Article  PubMed  CAS  Google Scholar 

  • Recio, M.C., R.M. Giner, S. Manez, and J.L. Rios. 1995. Structural requirements for the anti-inflammatory activity of natural triterpenoids. Planta Medica 61: 182–185.

    Article  PubMed  CAS  Google Scholar 

  • Safayhi, H., and E.R. Sailer. 1997. Anti-inflammatory actions of pentacyclic triterpenes. Planta Medica 63: 487–493.

    Article  PubMed  CAS  Google Scholar 

  • Seibert, K., Y. Zhang, K. Leahy, S. Hauser, J. Masferrer, W. Perkins, L. Lee, and P. Isakson. 1994. Pharmacological and biochemical demonstration of the role of cyclooxygenase 2 in inflammation and pain. Proceedings of the National Academy of Sciences United States of America 91: 12013–12017.

    Article  CAS  Google Scholar 

  • Shao, C.J., R. Kasai, J.D. Xu, and O. Tanaka. 1989. Saponins from Roots of Kalopanax septemlobus (THUNB.) KOIDZ., Ciqiu : structures of Kalopanax-saponins C, D, E and F. Chemical and Pharmaceutical Bulletin (Tokyo) 37: 311–314.

    Article  CAS  Google Scholar 

  • Shimizu, R., H. Shimabayashi, and M. Moriwaki. 2006. Enzymatic production of highly soluble myricitrin glycosides using beta-galactosidase. Bioscience, Biotechnology, and Biochemistry 70: 940–948.

    Article  PubMed  CAS  Google Scholar 

  • Suh, N., T. Honda, H.J. Finlay, A. Barchowsky, C. Williams, N.E. Benoit, Q.W. Xie, C. Nathan, G.W. Gribble, and M.B. Sporn. 1998. Novel triterpenoids suppress inducible nitric oxide synthase (iNOS) and inducible cyclooxygenase (COX-2) in mouse macrophages. Cancer Research 58: 717–723.

    PubMed  CAS  Google Scholar 

  • Tackholm, V. 1974. Student’s Flora of Egypt, 2nd ed, 102. Beirut: Cooperative printing company, Cairo University.

    Google Scholar 

  • Tunon, M., M.V. Garcia-Mediavilla, S. Sanchez-Campos, and J. Gonzalez-Gallego. 2009. Potential of flavonoids as anti-inflammatory agents: modulation of pro-inflammatory gene expression and signal transduction pathways. Current Drug Metabolism 10: 256–271.

    Article  PubMed  CAS  Google Scholar 

  • Vane, J.R. 1971. Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nature New Biology 231: 232–235.

    PubMed  CAS  Google Scholar 

  • Virella, G. 1998. Immunoserology, 4th ed, 259–281. New York: Marcel Dekker Inc.

    Google Scholar 

  • Winter, C.A., E.A. Risley, and G.W. Nuss. 1962. Carrageenin-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Proceedings of the Society for Experimental Biology and Medicine 111: 544–547.

    PubMed  CAS  Google Scholar 

  • Zhu, C.C., L. Gao, Z.X. Zhao, and C.Z. Lin. 2012. Triterpenes from Callicarpa integerrima. Acta Pharmacologica Sinica 47: 77–83.

    CAS  Google Scholar 

Download references

Acknowledgments

This research project was supported by a grant from the Research Centre of the Centre for Female Scientific and Medical Colleges, Deanship of Scientific Research, King Saud University, Saudi Arabia. The authors also are indebted and grateful to Prof. Dr. Olov Sterner and Dr. Karl-Erik Bergquist, faculty of science, Lund university, Sweden, for performing spectral data for all the isolated compounds.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mona A. Mohamed.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1139 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abdou, A.M., Abdallah, H.M., Mohamed, M.A. et al. A new anti-inflammatory triterpene saponin isolated from Anabasis setifera . Arch. Pharm. Res. 36, 715–722 (2013). https://doi.org/10.1007/s12272-013-0075-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-013-0075-9

Keywords

Navigation