Advertisement

Archives of Pharmacal Research

, Volume 34, Issue 3, pp 437–442 | Cite as

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

  • Ji Eun Shin
  • Eun Jin Choi
  • Qinglong Jin
  • Hong-Guang Jin
  • Eun-Rhan WooEmail author
Research Articles Drug Discovery and Development

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.

Key words

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

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle Scholar
  4. Baba, K., Najata, K., Taniguchi, M., Kido, T., and Kozawa, M., Chalcones from Angelica keikei. Phytochemistry, 29, 3907–3910 (1990).CrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle Scholar
  7. Hirano, T., Akira, S., Taga, T., and Kishimoto, T., Biological and clinical aspects of interleukin 6. Immunol. Today, 11, 443–449 (1990).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedGoogle 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).PubMedCrossRefGoogle 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).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).PubMedGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle Scholar
  18. Nakata, K., Taniguchi, M., and Baba, K., Three chalcones from Angelica keiskei. Nat. Med., 53, 329–332 (1999).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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle 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).PubMedCrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea and Springer Netherlands 2011

Authors and Affiliations

  • Ji Eun Shin
    • 1
  • Eun Jin Choi
    • 1
  • Qinglong Jin
    • 1
  • Hong-Guang Jin
    • 1
  • Eun-Rhan Woo
    • 1
    Email author
  1. 1.College of PharmacyChosun UniversityGwangjuKorea

Personalised recommendations