Skip to main content
Log in

Flavonoid constituents in the leaves of Myrica rubra sieb. et zucc. with anti-inflammatory activity

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

Abstract

The leaves of Myrica rubra sieb. et zucc. have been used in oriental traditional medicine for the treatment of burns, skin diseases, and as an antidiarrheal in China, Japan, and Korea. Activity guided isolation of the leaves of M. rubra has led to the isolation of five flavonoid: myricetin (1), myricitrin (2), myricetin 3-O-(2″-O-galloyl)-α-L-rhamnopyranoside (3), myricetin 3-O-(2″-O-galloyl)-β-D-galactopyranoside (4), and quercetin 3-O-(2″-O-galloyl)-β-D-galactopyranoside (5). All isolates were evaluated for their antioxidant potency against the superoxide anion (O2 ), and compounds 35 showed potent scavenging activities with 50 % inhibition concentration (IC50) values compared to the positive control, allopurinol. Compounds 15 were evaluated as inhibitors of various macrophage functions involved in the inflammatory process. These five compounds significantly and dose dependently inhibited lipopolysaccharide (LPS)-stimulated nitric oxide (NO), pro-inflammatory cytokines, and the protein levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in LPS-stimulated RAW 264.7 macrophages. Our results suggest that galloyl flavonol glycosides (35) isolated from M. rubra might be beneficial for the treatment of inflammation‐related diseases.

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
Fig. 4

Similar content being viewed by others

References

  • Cheng, H.Y., T.C. Lin, K. Ishimaru, C.M. Yang, K.C. Wang, and C.C. Lin. 2003. In vitro antiviral activity of prodelphinidin B-2 3,3′-Di-O-gallate from Myrica rubra. Planta Medica 69: 953–956.

    Article  PubMed  CAS  Google Scholar 

  • Coussens, L.M., and Z. Werb. 2002. Inflammation and cancer. Nature 420: 860–867.

    Article  PubMed  CAS  Google Scholar 

  • D’Acquisto, F., M.J. May, and S. Ghosh. 2002. Inhibition of nuclear factor kappa B (NF-κB): an emerging theme in anti-inflammatory therapies. Molecular Interventions 2: 22–35.

    Article  PubMed  Google Scholar 

  • Dalgleish, A.G., and K.J. O’Byrne. 2002. Chronic immune activation and inflammation in the pathogenesis of AIDS and cancer. Advances in Cancer Research 84: 231–276.

    PubMed  CAS  Google Scholar 

  • Forstermann, U., H.H. Schmidt, J.S. Pollock, H. Sheng, J.A. Mitchell, T.D. Warner, M. Nakane, and F. Murad. 1991. Isoforms of nitric oxide synthase: characterization and purification from different cell types. Biochemical Pharmacology 42: 1849–1857.

    Article  PubMed  CAS  Google Scholar 

  • Hensley, K., K.A. Robinson, S.P. Gabbita, S. Salsman, and R.A. Floyd. 2000. Reactive oxygen species, cell signaling, and cell injury. Free Radical Biology and Medicine 28: 1456–1462.

    Article  PubMed  CAS  Google Scholar 

  • Inoue, T., Y. Aral, and M. Nagai. 1984. Diarylheptanoids in the bark of Myrica rubra sieb. et zucc. Yakugaku Zasshi 104: 37–41.

    PubMed  CAS  Google Scholar 

  • Kim, Y.I., S.H. Lee, and T.S. Cho. 1996. Isolation of anticancer agents from the leaves of Platycarya strobilacea S. et Z. Korean Journal of Pharmacognosy 27: 238–245.

    CAS  Google Scholar 

  • Kubes, P., and D.M. McCafferty. 2000. Nitric oxide and intestinal inflammation. American Journal of Medicine 109: 150–158.

    Article  PubMed  CAS  Google Scholar 

  • Lee, T.H., F. Qiu, G.R. Waller, and C.H. Chou. 2000. Three new flavonol galloyl glycosides from leaves of Acacia confusa. Journal of Natural Products 63: 710–712.

    Article  PubMed  CAS  Google Scholar 

  • Lu, Y., and L.M. Wahl. 2005. Oxidative stress augments the production of matrix metalloproteinase-1, cyclooxygenase-2, and prostaglandin E2 through enhancement of NF-κB activity in lipopolysaccharide-activated human primary monocytes. The Journal of Immunology 175: 5423–5429.

    PubMed  CAS  Google Scholar 

  • Martínez-Cayuela, M. 1995. Oxygen free radicals and human disease. Biochimie 77: 147–161.

    Article  PubMed  Google Scholar 

  • Masuda, T., T. Someya, and A. Fujimoto. 2010. Phenolic inhibitors of chemical and enzymatic oxidation in the leaves of Myrica rubra. Bioscience, Biotechnology, and Biochemistry 74: 212–215.

    Article  PubMed  CAS  Google Scholar 

  • Matsuda, H., M. Higashino, W. Chen, H. Tosa, M. Iinuma, and M. Kubo. 1995. Studies of cuticle drugs from natural sources. III. Inhibitory effect of Myrica rubra on melanin biosynthesis. Biological &/and Pharmaceutical Bulletin 18: 1148–1150.

    Article  CAS  Google Scholar 

  • Matsuda, H., T. Morikawa, J. Tao, K. Ueda, and M. Yoshikawa. 2002. Bioactive constituents of Chinese natural medicines. VII.1 Inhibitors of degranulation in RBL-2H3 cells and absolute stereo structures of three new diarylheptanoid glycosides from the bark of Myrica rubra. Biological &/and Pharmaceutical Bulletin 50: 208–215.

    CAS  Google Scholar 

  • Nonaka, G., M. Muta, and I. Nishioka. 1983. Myricatin, a galloyl flavanonol sulfate and prodelphinidin gallates from Myrica rubra. Phytochemistry 22: 237–241.

    Article  CAS  Google Scholar 

  • Peri, K.G., P. Hardy, D.Y. Li, D.R. Varma, and S. Chemtob. 1995. Prostaglandin G/H synthase-2 is a major contributor of brain prostaglandins in the newborn. Journal of Biological Chemistry 270: 24615–24620.

    Article  PubMed  CAS  Google Scholar 

  • Sakurai, N., Y. Yaguchi, and T. Inoue. 1986. Triterpenoids from Myrica rubra. Phytochemistry 26: 217–219.

    Article  CAS  Google Scholar 

  • Smith, W.L., and R. Langenbach. 2001. Why there are two cyclooxygenase isozymes. The Journal of Clinical Investigation 107: 1491–1495.

    Article  PubMed  CAS  Google Scholar 

  • Surh, Y.J., and H.K. Na. 2008. NF-κB and Nrf2 as prime molecular targets for chemoprevention and cytoprotection with anti-inflammatory and antioxidant phytochemicals. Genes and Nutrition 2: 313–317.

    Article  PubMed  CAS  Google Scholar 

  • Thun, M.J., S.J. Henley, and T. Gansler. 2004. Inflammation and cancer: an epidemiological perspective. Novartis Foundation Symposium 256: 6–21.

    PubMed  Google Scholar 

  • Wang, S.J., Y. Tong, S. Lu, R. Yang, X. Liao, Y.F. Xu, and X. Li. 2010. Anti-inflammatory activity of myricetin isolated from Myrica rubra sieb. et zucc. Leaves. Planta Medica 76: 1492–1496.

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science, and Technology (2010-0022929).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Min Won Lee.

Additional information

Han Hyuk Kim and Dong Hee Kim contributed equally to this study.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kim, H.H., Kim, D.H., Kim, M.H. et al. Flavonoid constituents in the leaves of Myrica rubra sieb. et zucc. with anti-inflammatory activity. Arch. Pharm. Res. 36, 1533–1540 (2013). https://doi.org/10.1007/s12272-013-0147-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12272-013-0147-x

Keywords:

Navigation