Chalcones isolated from Angelica keiskei and their inhibition of IL-6 production in TNF-α-stimulated MG-63 cell

Abstract

Six chalcone compounds, 2′,4′,4-trihydroxy-3′-[2-hydroxy-7-methyl-3-methylene-6-octaenyl]chalcone (1), 2′,4′,4-trihydroxy-3′-geranylchalcone (2), 2′,4′,4-trihydroxy-3′-[6-hydroxy-3,7-dimethyl-2,7-octadienyl]chalcone (3), 2′,4-dihydroxy-4′-methoxy-3′-[2-hydroperoxy-3-methyl-3-butenyl]chalcone (4), 2′,4-dihydroxy-4′-methoxy-3′-geranylchalcone (5), and 2′,4-dihydroxy-4′-methoxy-3′-[3-methyl-3-butenyl]chalcone (6) were isolated from the leaves of Angelica keiskei K (Umbelliferae). The structure of each isolated compound was determined using spectroscopic methods. Among the isolates, compounds 13 appeared to have potent inhibitory activity of IL-6 production in TNF-α-stimulated MG-63 cell, while compounds 46 did not. The distinct structural difference between compounds 13 and 46 was the presence of C-4′ hydroxyl group in the chalcone moiety. Our results imply that the inhibitory activity of IL-6 production in TNF-α-stimulated MG-63 cell may be affected by the presence of C-4′ hydroxyl group in the chalcone moiety.

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

References

  1. Akihisa, T., Tokuda, H., Ukiya, M., Iizuka, M., Schneider, S., Ogasawara, K., Mukainaka, T., Iwatsuki, K., Suzuki, T., and Nishino, H., Chalcones, coumarins, and flavanones from the exudate of Angelica keiskei and their chemopreventive effects. Cancer Lett., 201, 133–137 (2003).

    PubMed  Article  CAS  Google Scholar 

  2. Akihisa, T., Tokuda, H., Hasegawa, D., Ukiya, M., Kimura, Y., Enjo, F., Suzuki, T., and Nishino, H., Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects. J. Nat. Prod., 69, 38–42 (2006).

    PubMed  Article  CAS  Google Scholar 

  3. Aoki, N., Muko, M., Ohta, E., and Ohta, S., C-geranylated chalcones from the stems of Angelica keiskei with superoxide-scavenging activity. J. Nat. Prod., 71, 1308–1310 (2008).

    PubMed  Article  CAS  Google Scholar 

  4. Baba, K., Najata, K., Taniguchi, M., Kido, T., and Kozawa, M., Chalcones from Angelica keikei. Phytochemistry, 29, 3907–3910 (1990).

    Article  CAS  Google Scholar 

  5. Enoki, T., Ohnogi, H., Nagamine, K., Kudo, Y., Sugiyama, K., Tanabe, M., Kobayashi, E., Sagawa, H., and Kato, I., Antidiabetic activities of chalcones isolated from a Japanese Herb, Angelica keiskei. J. Agric. Food Chem., 55, 6013–6017 (2007).

    PubMed  Article  CAS  Google Scholar 

  6. Hirano, T., Yasukawa, K., Harada, H., Taga, T., Watanabe, Y., Matsuda, T., Kashiwamura, S., Nakajima, K., Koyama, K., Iwamatsu, A., Tsunsawa, S., Sakiyama, F., Matsui, H., Takahara, Y., Taniguchi, T., and Kishimoto, T., Complementary DNA for a novel human interleukin (BSF-2) that induced lymphocytes to produce immunoglobulin. Nature, 324, 73–76 (1986).

    PubMed  Article  CAS  Google Scholar 

  7. Hirano, T., Akira, S., Taga, T., and Kishimoto, T., Biological and clinical aspects of interleukin 6. Immunol. Today, 11, 443–449 (1990).

    PubMed  Article  CAS  Google Scholar 

  8. Jayasinghe, L., Balasooriya, B. A. I. S., Padmini, W. C., Hara, N., and Fujimoto, Y., Geranyl chalcone derivatives with antifungal and radical scavenging properties from the leaves of Arctocarpus nobilis. Phytochemistry, 65, 1287–1290 (2004).

    PubMed  Article  CAS  Google Scholar 

  9. Kim, B. H., Chung, E. Y., Ryu, J.-C., Jung, S.-H., Min, K. R., and Kim, Y., Anti-inflammatory mode of isoflavone glycosides sophoricoside by inhibition of interleukin-6 and cyclooxygenase-2 in inflammatory response. Arch. Pharm. Res., 26, 306–311 (2003).

    PubMed  Article  CAS  Google Scholar 

  10. Kimura, Y., Taniguchi, M., and Baba, K., Antitumor and antimetastatic activities of 4-hydroxyderricin isolated from Angelica keiskei roots. Planta Med., 70, 211–219 (2004).

    PubMed  Article  CAS  Google Scholar 

  11. Kimura, Y., New anticancer agents: in vitro and in vivo evaluation of the antitumor and antimetastatic actions of various compounds isolated from medicinal plants. In Vivo, 19, 37–60 (2005).

    PubMed  CAS  Google Scholar 

  12. Kimura, Y., Sumiyoshi, M., and Baba, K., Anti-tumor actions of major component 3′-O-acetylhamaudol of Angelica japonica roots through dual actions, anti-angiogenesis and intestinal intraepithelial lymphocyte activation. Cancer Lett., 265, 84–97 (2008).

    PubMed  Article  CAS  Google Scholar 

  13. Kozawa, M., Morita, N., Baba, K., and Hata, K., The structure of xanthoangelol, a new chalcone from the roots of Angelica keiskei K. (Umbelliferae). Chem. Pharm. Bull., 25, 515–516 (1977).

    CAS  Google Scholar 

  14. Kozawa, M., Morita, N., Baba, K., and Hata, K., Chemical components of the roots of Angelica keiskei Koidzumi. II. The structure of the chalcone derivatives. Yakugaku Zasshi, 98, 210–214 (1978).

    PubMed  CAS  Google Scholar 

  15. Lee, H. J., Choi, T. W., Kim, H. J., Nam, D., Jung, S. H., Lee, E. H., Lee, H. J., Shin, E. M., Jang, H. J., Ahn, K. S., Shim, B. S., Choi, S. H., Kim, S. H., Sethi, G., and Ahn, K. S., Anti-Inflammatory activity of Angelica keiskei through suppression of mitogen-activated protein kinases and nuclear factor-kappa B activation pathways. J. Med. Food, 13, 691–699 (2010).

    PubMed  Article  CAS  Google Scholar 

  16. Liu, Q. H., Jeong, J.-E., Choi, E. J., Moon, Y. H., and Woo, E.-R., A new furofuran lignan from Geranium thunbergii. Arch. Pharm. Res., 29, 1109–1113 (2006).

    PubMed  Article  CAS  Google Scholar 

  17. Motani, K., Tabata, K., Kimura, Y., Okano, S., Shibata, Y., Abiko, Y., Nagai, H., Akihisa, T., and Suzuki, T., Proteomic analysis of apoptosis induced by xanthoangelol, a major constituent of Angelica keiskei, in neuroblastoma. Biol. Pharm. Bull., 31, 618–626 (2008).

    PubMed  Article  CAS  Google Scholar 

  18. Nakata, K., Taniguchi, M., and Baba, K., Three chalcones from Angelica keiskei. Nat. Med., 53, 329–332 (1999).

    CAS  Google Scholar 

  19. Nishimura, R., Tabata, K., Arakawa, M., Ito, Y., Kimura, Y., Akihisa, T., Nagai, H., Sakuma, A., Kohno, H., and Suzuki, T., Isobavachalcone, a chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma. Biol. Pharm. Bull., 30, 1878–1883 (2007).

    PubMed  Article  CAS  Google Scholar 

  20. Tabata, K., Motani, K., Takayanagi, N., Nishimura, R., Asami, S., Kimura, Y., Ukiya, M., Hasegawa, D., Akihisa, T., and Suzuki, T., Xanthoangelol, a major chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma and leukemia cells. Biol. Pharm. Bull., 28, 1404–1407 (2005).

    PubMed  Article  CAS  Google Scholar 

  21. Van Damme, J., Opdenakker, G., Simpson, R. J., Rubira, M. R., Cayphas, S., Vink, A., Billiau, A., and Van Snick. J., Identification of the human 26-kD protein, interferon beta 2(IFN-beta 2), as a B cell hybridoma/plasmacytoma growth factor induced in interleukin 1 and tumor necrosis factor. J. Exp. Med., 165, 914–919 (1987).

    PubMed  Article  Google Scholar 

  22. Webb, S. J., McPherson, J. R., Pahan, K., and Koka, S., Regulation of TNF-alpha-induced IL-6 production in MG-63 human osteoblast-like cells. J. Dent. Res., 81, 17–22 (2002).

    PubMed  Article  CAS  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to Eun-Rhan Woo.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Shin, J.E., Choi, E.J., Jin, Q. et al. Chalcones isolated from Angelica keiskei and their inhibition of IL-6 production in TNF-α-stimulated MG-63 cell. Arch. Pharm. Res. 34, 437–442 (2011). https://doi.org/10.1007/s12272-011-0311-0

Download citation

Key words

  • Angelica keiskei koidzumi
  • Umbelliferae
  • C-geranylated chalcone
  • IL-6 inhibitory activity