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http://dx.doi.org/10.20307/nps.2020.26.1.90

Chemical Constituents from the Aerial Parts of Artemisia capillaris Thunb. and Their Anti-allergic and Anti-inflammatory Effects  

Nguyen, Thi Thu (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University)
Vu, Thi Oanh (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University)
Cao, Thao Quyen (College of Pharmacy, Drug Research and Development Center, Daegu Catholic University)
Min, Byung Sun (College of Pharmacy, Drug Research and Development Center, Daegu Catholic University)
Kim, Jeong Ah (College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University)
Publication Information
Natural Product Sciences / v.26, no.1, 2020 , pp. 90-96 More about this Journal
Abstract
Artemisia capillaris Thunb. (Compositae) is a traditional medicinal plant with various pharmacological activities. To elucidate new anti-allergic and anti-inflammatory constituents, the aerial parts of A. capillaries were investigated to afford a new compound, (6E,8E)-6-methylundeca-6,8-diene-2,5,10-trione (17) together with 19 known compounds (1 - 16, 18 - 20). The structures of these compounds were determined by extensive spectroscopic analyses including 1D, 2D NMR, HREIMS, and optical rotation [α]D. The absolute configuration of compound 2 was determined to be S form for the first time. All isolates (1 - 20) were tested their inhibitory effects on interleukin 2 (IL-2) expression in T cells and NO production in lipopolysaccharide (LPS)-stimulated RAW246.7. Among them, compounds 10, 11, 19, and 20 reduced IL-2 expression in a dose-dependent manner. In addition, compound 10 also inhibited NO production with an IC50 value of 37.3 ± 0.4 μM.
Keywords
Artemisia capillaris Thunb.; (6E,8E)-6-methylundeca-6,8-diene-2,5,10-trione; anti-allergic; anti-inflammatory; IL-2; NO inhibition;
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1 Furue, M.; Terao, H.; Rikihisa, W.; Urabe, K.; Kinukawa, N.; Nose, Y.; Koga, T. Br. J. Dermatol. 2003, 148, 128-133.   DOI
2 Zedler, S.; Faist, E. Curr. Opin. Crit. Care 2006, 12, 595-601.   DOI
3 Tabas, I.; Glass, C. K. Science 2013, 339, 166-172.   DOI
4 Moncada, S.; Palmer, R. M.; Higgs, E. Phramacol. Rev. 1991, 43, 109-142.
5 Evans, C. H. Agents Actions Suppl. 1995, 47, 107-116.
6 Puripattanavong, J.; Tewtrakul, S. Songklanakarin J. Sci. Technol. 2015, 37, 37-41.
7 Justiz Vaillant, A. A.; Zito, P. M. Immediate Hypersensitivity Reactions; StatPearls Publishing: USA, 2019.
8 Blaser, K. T Cell Regulation in Allergy, Asthma and Atopic Skin Diseases; Karger Medical and Scientific Publishers: USA, 2008, p 158.
9 Abdel-Gadir, A.; Massoud, A. H.; Chatila, T. A. F1000Res. 2018, 7, 38.   DOI
10 Bonnet, B.; Vigneron, J.; Levacher, B.; Vazquez, T.; Pitoiset, F.; Brimaud, F.; Churlaud, G.; Klatzmann, D.; Bellier, B. J. Immunol. 2016, 197, 188-198.   DOI
11 Yang, X. O.; Nurieva, R.; Martinez, G. J.; Kang, H. S.; Chung, Y.; Pappu, B. P.; Shah, B.; Chang, S. H.; Schluns, K. S.; Watowich, S. S.; Feng, X. H.; Jetten, A. M.; Dong, C. Immunity 2008, 29, 44-56.   DOI
12 Lu, C.; Li, Y.; Hu, S.; Cai, Y.; Yang, Z.; Peng, K. Biomed. Pharmacother. 2018, 106, 1169-1174.   DOI
13 Wu, T. S.; Tsang, Z. J.; Wu, P. L.; Lin, F. W.; Li, C. Y.; Teng, C. M.; Lee, K. H. Bioorg. Med. Chem. 2001, 9, 77-83.   DOI
14 Zhao, Y.; Geng, C. A.; Sun, C. L.; Ma, Y. B.; Huang, X. Y.; Cao, T. W.; He, K.; Wang, H.; Zhang, X. M.; Chen, J. J. Fitoterapia 2014, 95, 187-193.   DOI
15 Hong, J. H.; Lee, I. S. Biofactors 2009, 35, 380-388.   DOI
16 Geng, C. A.; Yang, T. H.; Huang, X. Y.; Yang, J.; Ma, Y. B.; Li, T. Z.; Zhang, X. M.; Chen, J. J. J. Ethnopharmacol. 2018, 224, 283-289.   DOI
17 Kim, Y. S.; Bahn, K. N.; Hah, C. K.; Gang, H. I.; Ha, Y. L. J. Food Sci. 2008, 73, T16-T20.   DOI
18 Camps, P.; Gonzalez, A.; Munoz-Torrero, D.; Simon, M.; Zuniga, A.; Martins, M. A.; Font-Bardia, M.; Solans, X. Tetrahedron 2000, 56, 8141-8151.   DOI
19 Lim, D. W.; Kim, Y. T.; Jang, Y. J.; Kim, Y. E.; Han, D. Molecules 2013, 18, 9241-9252.   DOI
20 Ding, H. Y.; Lin, H. C.; Teng, C. M.; Wu, Y. C. J. Chin. Chem. Soc. 2000, 47, 381-388.   DOI
21 Vijayan, N.; Bhagavannarayana, G.; Maurya, K. K.; Pal, S.; Datta, S. N.; Gopalakrishnan, R.; Ramasamy, P. Cryst. Res. Technol. 2007, 42, 195-200.   DOI
22 Neirinck, V.; Robert, D.; Nardin, R. Magn. Reson. Chem. 1993, 31, 815-822.   DOI
23 Morales-Rios, M. S.; Espineira, J.; Joseph-Nathan, P. Magn. Reson. Chem. 1987, 25, 377-395.   DOI
24 Jorgensen, M. R.; Olsen, C. A.; Mellor, I. R.; Usherwood, P. N.; Witt, M.; Franzyk, H.; Jaroszewski, J. W. J. Med. Chem. 2005, 48, 56-70.   DOI
25 Sankar, S. S.; Gilbert, R. D.; Fornes, R. E. Org. Magn. Reson. 1982, 19, 222-224.   DOI
26 Liu, Y. L.; Ho, D. K.; Cassady, J. M.; Cook, V. M.; Baird, W. M. J. Nat. Prod. 1992, 55, 357-363.   DOI
27 Lee, S.; Kim, K. S.; Shim, S. H.; Park, Y. M.; Kim, B. K. Arch. Pharm. Res. 2003, 26, 902-905.   DOI
28 Ali, M. S.; Jahangir, M.; Saleem, M. Nat. Prod. Res. 2003, 17, 1-4.   DOI
29 Park, Y.; Moon, B. H.; Lee, E.; Lee, Y.; Yoon, Y.; Ahn, J. H.; Lim, Y. Magn. Reson. Chem. 2007, 45, 674-679.   DOI
30 Gonzalez, A. G.; Estevez-Reyes, R.; Mato, C. J. Nat. Prod. 1989, 52, 1139-1142.   DOI
31 Wu, Y.; Su, J.; Guo, R. X.; Ren, T. K.; Zhang, M. L.; Dong, M.; Sauriol, F.; Shi, Q. W.; Gu, Y. C.; Huo, C. H. Chem. Nat. Compd. 2014, 50, 603-605.   DOI
32 Xie, L. H.; Akao, T.; Hamasaki, K.; Deyama, T.; Hattori, M. Chem. Pharm. Bull. 2003, 51, 508-515.   DOI
33 Brockmann Jr, H.; Knobloch, G. Chem. Ber. 1973, 106, 803-811.   DOI
34 Zhang, J.; Liang, Y.; Liao, X. J.; Deng. Z.; Xu. S. H. Nat. Prod. Res. 2014, 28, 150-155.   DOI
35 Kai, H.; Baba, M.; Okuyama, T. Chem. Pharm. Bull. 2007, 55, 133-136.   DOI
36 Bernart, M. W.; Cardellina, J. H.; Balaschak, M. S.; Alexander, M. R.; Shoemaker, R. H.; Boyd, M. R. J. Nat. Prod. 1996, 59, 748-753.   DOI
37 Nesterenko, V.; Putt, K. S.; Hergenrother, P. J. J. Am. Chem. Soc. 2003, 125, 14672-14673.   DOI
38 Khoo, B. Y.; Chua, S. L.; Balaram, P. Int. J. Mol. Sci. 2010, 11, 2188-2199.   DOI