Abstract
Ten compounds, 1′,3′-propanediol,2′-amino-1′-(1,3-benzodioxol-5-yl) (1), artanomaloide (2), canin (3), eupatilin (4), quercetin-3-O-β-d-glucoside-7-O-α-l-rhamnoside (5), 1,3-di-O-caffeoylquinic acid (6), isoquercitrin (7), pinoresinol-4-O-β-d-glucoside (8), scopolin (9), and isofraxidin-7-O-β-d-glucopyranoside (10) were isolated from the aerial parts of A. selengensis. The structures of compounds (1–10) were identified based on 1D and 2D NMR, including 1H–1H COSY, HSQC, HMBC and NOESY spectroscopic analyses. Among them, compound 1 was isolated from this plant for the first time as a naturally occurring compound. The inhibitory activity of these isolated compounds against interleukin-6 (IL-6) production in TNF-α stimulated MG-63 cells was also examined.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ahn, D.K. 1998. Illustrated book of Korean medicinal herbs, 550. Seoul: Kyo-Hak Publishing.
An, R.-B., D.-H. Sohn, G.-S. Jeong, and Y.-C. Kim. 2008. In vitro hepatoprotective compounds from Suaeda glauca. Archives of Pharmacal Research 31: 594–597.
Cellitti, S.E., D.H. Jones, L. Lagpacan, X. Hao, Q. Zhang, H. Hu, S.M. Brittain, A. Brinker, J. Caldwell, B. Bursulaya, G. Spraggon, A. Brock, Y. Ryu, T. Uno, P.G. Schultz, and B.H. Geierstanger. 2008. In vivo incorporation of unnatural amino acids to probe structure, dynamics, and ligand binding in a large protein by nuclear magnetic resonance spectroscopy. Journal of American Chemical Society 130: 9268–9281.
Chung, S.-C., B.Y. Hwang, G.-J. Oh, S.-J. Kang, M.-J. Kim, W.-H. Choi, K.S. Lee, and J.S. Ro. 1999. Chemical components from the stem bark of Rhus javanica L. Korean Journal of Pharmacognosy 30: 295–300.
Duan, C.H., J.-N. Lee, C.-M. Lee, G.-T. Lee, and K.-K. Lee. 2009. Phytochemical constituents from Metasequoia glyptostroboids leaves. Natural Product Sciences 15: 12–16.
Hirano, T., K. Yasukawa, H. Harada, T. Taga, Y. Watanabe, T. Matsuda, S. Kashiwamura, K. Nakajima, K. Koyama, A. Iwamatsu, S. Tsunsawa, F. Sakiyama, H. Matsui, Y. Takahara, T. Taniguchi, and T. Kishimoto. 1986. Complementary DNA for a novel human interleukin (BSF-2) that induced lymphocytes to produce immunoglobulin. Nature 324: 73–76.
Heo, J.E., J.L. Jin, Y.Y. Lee, and H.S. Yun-Choi. 2005. Chemical constituents of the aerial parts of Chloranthus japonicas Sieb. Natural Product Sciences 11: 41–44.
Hirano, T., S. Akira, T. Taga, and T. Kishimoto. 1990. Biological and clinical aspects of interleukin 6. Immunology Today 11: 443–449.
Hu, J.-F., and X.-Z. Feng. 1999. New guaianolides from Artemisia selengensis. Journal of Asian Natural Product Report 1: 169–176.
Hu, H.-B., X.-D. Zheng, Y.-F. Jian, J.-X. Liu, and J.-H. Zhu. 2011. Constituents of the root of Anemone tomentosa. Archives of Pharmacal Research 34: 1097–1105.
Jang, W.Y., and K.R. Lee. 1993. A new endoperoxide from Artemisia selengensis. Korean Journal of Pharmacognosy 24: 107–110.
Jakupovic, J., Z.-L. Chen, and F. Bohlmann. 1987. Artanomaloide, a dimeric guaianolide and phenylalanine derivatives from Artemisia anola. Phytochemistry 26: 2777–2779.
Jiang, J., B.B. Zhang, and Z.X. Liao. 2010. A new dicaffeoyl quinic acid from Nannoglottis ravida. Chinese Chemical Letters 21: 203–205.
Kim, B.H., E.Y. Chung, J.-C. Ryu, S.-H. Jung, K.R. Min, and Y. Kim. 2003. Anti-inflammatory mode of isoflavone glycosides sophoricoside by inhibition of interleukin-6 and cyclooxygenase-2 in inflammatory response. Archives of Pharmacal Research 26: 306–311.
Kim, D.K., J.P. Lim, J.W. Kim, H.W. Park, and J.S. Eun. 2005. Antitumor and anti-inflammatory constituents from Celtis sinensis. Archives of Pharmacal Research 28: 39–43.
Kim, H.J., B.-G. Kim, and J.-H. Ahn. 2013. Regioselective synthesis of flavonoid bisglycosides using Escherichia coli harboring two glycosyltransferases. Applied Microbiology Biotechnology 97: 5275–5282.
Koo, K.A., J.H. Kwak, K.R. Lee, O.P. Zee, E.-R. Woo, H.K. Park, and H.J. Youn. 1994. Antitumor and immunomodulating activities of the polysaccharide fraction from Artemisia selengensis and Artemisia iwayomogi. Archives of Pharmacal Research 17: 371–374.
Lee, T.B. 1993. Illustrated flora of Korea, 759. Seoul: Hyang-Moon Publishing.
Lee, J.H., W.J. Jeon, E.S. Yoo, C.M. Kim, and Y.S. Kwon. 2005. The chemical constituents and their antioxidant activity of the stem of Rhododendron mucronulatum. Natural Product Sciences 11: 97–102.
Lee, Y.G., J.-Y. Cho, C.-M. Kim, S.-H. Lee, W.-S. Kim, T.-I. Jeon, K.-H. Park, and J.-H. Moon. 2013. Coumaroyl quinic acid derivatives and flavonoids from Immature Pear (Pyrus pyrifolia Nakai) fruit. Food Science Biotechnology 22: 803–810.
Li, D., X.H. Han, S.S. Hong, C. Lee, M.S. Lee, D. Lee, M.K. Lee, and B.Y. Hwang. 2010. Inhibitors of nitric oxide production from Artemisia princeps. Natural Product Sciences 16: 143–147.
Liu, Q.H., J.-E. Jeong, E.J. Choi, Y.H. Moon, and E.-R. Woo. 2006. A new furofuran lignan from Geranium thunbergii. Archives of Pharmacal Research 29: 1109–1113.
Shi, F., X. Jia, C. Zhao, and Y. Chen. 2010. Antioxidant activities of various extracts from Artemisia selengensis Turcz (LuHao). Molecules 15: 4934–4946.
Van Damme, J., G. Opdenakker, R.J. Simpson, M.R. Rubira, S. Cayphas, A. Vink, A. Billiau, and J. Van Snick. 1987. 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. Journal of Experimental Medicine 165: 914–919.
Wang, D.-M., W.-J. Pu, Y.-H. Wang, Y.-J. Zhang, and S.-S. Wang. 2012. A New isorhamnetin glycoside and other phenolic compounds from Callianthemum taipaicum. Molecules 17: 4595–4603.
Acknowledgments
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2012R1A1A3005531).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Kim, A.R., Ko, H.J., Chowdhury, M.A. et al. Chemical constituents on the aerial parts of Artemisia selengensis and their IL-6 inhibitory activity. Arch. Pharm. Res. 38, 1059–1065 (2015). https://doi.org/10.1007/s12272-014-0543-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-014-0543-x