Skip to main content
SpringerLink
Log in

Concise synthesis of licochalcone C and its regioisomer, licochalcone H

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

Abstract

Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcus luteus. Since pharmacological activity studies of licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20 % overall yield, respectively.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1

Similar content being viewed by others

References

  • Dao, T.T., P.H. Nguyen, H.S. Lee, E. Kim, J. Park, S.I. Lim, and W.K. Oh. 2011. Chalcones as novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza inflata. Bioorganic & Medicinal Chemistry Letters 21: 294–298.

    Article  CAS  Google Scholar 

  • Franceschelli, S., M. Pesce, I. Vinciguerra, A. Ferrone, G. Riccioni, A. Patruno, A. Grilli, M. Felaco, and L. Speranza. 2011. Licocalchone-C extracted from Glycyrrhiza glabra inhibits lipopolysaccharide-interferon-gamma inflammation by improving antioxidant conditions and regulating inducible nitric oxide synthase expression. Molecules 16: 5720–5734.

    Article  PubMed  CAS  Google Scholar 

  • Haraguchi, H., H. Ishikawa, K. Mizutani, Y. Tamura, and T. Kinoshita. 1998a. Antioxidative and superoxide scavenging activities of retrochalcones in Glycyrrhiza inflata. Bioorganic & Medicinal Chemistry 6: 339–347.

    Article  CAS  Google Scholar 

  • Haraguchi, H., K. Tanimoto, Y. Tamura, K. Mizutani, and T. Kinoshita. 1998b. Mode of antibacterial action of retrochalcones from Glycyrrhiza inflata. Phytochemistry 48: 125–129.

    Article  PubMed  CAS  Google Scholar 

  • Kajiyama, K., S. Demizu, Y. Hiraga, K. Kinoshita, K. Koyama, K. Takahashi, Y. Tamura, K. Okada, and T. Kinoshita. 1992. Two prenylated retrochalcones from Glycyrrhiza inflata. Phytochemistry 31: 3229–3232.

    Article  CAS  Google Scholar 

  • Kromann, H., M. Larsen, T. Boesen, K. Schønning, and S.F. Nielsen. 2004. Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A. European Journal of Medicinal Chemistry 39: 993–1000.

    Article  PubMed  CAS  Google Scholar 

  • Na, Y., J.H. Cha, H.G. Yoon, and Y. Kwon. 2009. A concise synthesis of licochalcone E and its regio-isomer, licochalcone F. Chemical & Pharmaceutical Bulletin 57: 607–609.

    Article  CAS  Google Scholar 

  • Nandy, J.P., B. Rakic, B.V.N.B. Sarma, N. Babu, M. Lefrance, G.D. Enright, D.M. Leek, K. Daniel, L.A. Sabourin, and P. Arya. 2008. Benzofuran-derived cyclic β-amino acid Scaffold for building a diverse set of flavonoid-like probes and the discovery of a cell motility inhibitor. Organic Letters 10: 1143–1146.

    Article  PubMed  CAS  Google Scholar 

  • Nielsen, S.F., M. Chen, T.G. Theander, A. Kharazmi, and S. Brøgger Christensen. 1995a. Synthesis of antiparasitic licorice chalcones. Bioorganic & Medicinal Chemistry Letters 5: 449–452.

    Article  Google Scholar 

  • Nielsen, S.F., M. Chen, T.G. Theander, A. Kharazmi, and S. Brøgger Christensen. 1995b. Synthesis of antiparasitic licorice chalcones. Bioorganic & Medicinal Chemistry Letters 5: 449–452.

    Article  Google Scholar 

  • Nomura, T., and T. Fukai. 1998. Phenolic constituents of licorice (Glycyrrhiza species). Fortschritte der Chemie organischer Naturstoffe. Progress in the chemistry of organic natural products. Progres dans la chimie des substances organiques naturelles 73: 1–158.

    CAS  Google Scholar 

  • Park, E.J., H.R. Park, J.S. Lee, and J. Kim. 1998a. Licochalcone A: An inducer of cell differentiation and cytotoxic agent from Pogostemon cablin. Planta Medica 64: 464–466.

    Article  PubMed  CAS  Google Scholar 

  • Park, E.J., H.R. Park, J.S. Lee, and J.W. Kim. 1998b. Licochalcone A: An inducer of cell differentiation and cytotoxic agent from Pogostemon cablin. Planta Medica 64: 464–466.

    Article  PubMed  CAS  Google Scholar 

  • Saitoh, T., and S. Shibata. 1975. New type chalcones from licorice root. Tetrahedron Letters 16: 4461–4462.

    Article  Google Scholar 

  • Yoon, G., Y.D. Jung, and S.H. Cheon. 2005. Cytotoxic allyl retrochalcone from the roots of Glycyrrhiza inflata. Chemical & Pharmaceutical Bulletin 53: 694–695.

    Article  CAS  Google Scholar 

  • Yoon, G., B.Y. Kang, and S.H. Cheon. 2007. Topoisomerase I inhibition and cytotoxicity of licochalcones A and E from Glycyrrhiza inflata. Archives of Pharmacal Research 30: 313–316.

    Article  PubMed  CAS  Google Scholar 

  • Yoon, G., W. Lee, S.N. Kim, and S.H. Cheon. 2009. Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B. Bioorganic & Medicinal Chemistry Letters 19: 5155–5157.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by Basic Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grant No. 2012R1A1A2006613). We also thank the Korea Basic Science Institute (KBSI), Gwangju branch, for performing the NMR and analytical experiments.

Author information

Authors and Affiliations

  1. College of Pharmacy and Research Institute of Drug Development, Chonnam National University, Gwangju, 500-757, Korea

    Zengtao Wang, Yongkai Cao, Suresh Paudel & Seung Hoon Cheon

  2. College of Pharmacy, Mokpo National University, 1666 Youngsan-ro, Cheonggye-myeon, Muan-gun, Jeonnam, Korea

    Goo Yoon

Authors
  1. Zengtao Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yongkai Cao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Suresh Paudel
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Goo Yoon
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Seung Hoon Cheon
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Seung Hoon Cheon.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wang, Z., Cao, Y., Paudel, S. et al. Concise synthesis of licochalcone C and its regioisomer, licochalcone H. Arch. Pharm. Res. 36, 1432–1436 (2013). https://doi.org/10.1007/s12272-013-0222-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-013-0222-3

Keywords

Search

Navigation