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http://dx.doi.org/10.5012/bkcs.2014.35.10.2945

Anti-inflammatory Triterpenes from Euonymus alatus Leaves and Twigs on Lipopolysaccharide-activated RAW264.7 Macrophage Cells  

Jeong, Eun Ju (Department of Agronomy & Medicinal Plant Resources and Institute of Fusion Biotechnology, Gyeongnam National University of Science and Technology)
Bae, Ji-Yeong (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University)
Rho, Jung-Rae (Department of Oceanography, Kunsan National University)
Kim, Young Choong (College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University)
Ahn, Mi-Jeong (College of Pharmacy and Research Institute of Pharmaceutical Sciences, Gyeongsang National University)
Sung, Sang Hyun (College of Pharmacy and Research Institute of Pharmaceutical Science, Seoul National University)
Publication Information
Abstract
As a part of ongoing phytochemical research on Euonymus alatus leaves and twigs, we have isolated one new reissantane-type triterpene (1), together with eight known triterpenes, isoarborinol (2), friedelin (3), abruslactone A (4), $3{\beta},22{\alpha}$-dihydroxyolean-12-en-29-oic acid (5), $3{\alpha},22{\alpha}$-dihydroxyolean-12-en-29-oic acid (6), $3{\alpha},22{\beta}$-dihydroxyolean-12-en-29-oic acid (7), $22{\alpha}$-hydroxy-3-oxoolean-12-en-29-oic acid (8), demethylregelin (9). The structure of 1 has been elucidated as 24,24-dimethyl-reissant-7(8),25-dien-$3{\alpha}$-ol, by extensive 1D and 2D spectroscopic methods including $^1H$-NMR, $^{13}C$-NMR, $^1H-^1H$ COSY, HSQC, HMBC and NOESY. Anti-inflammatory activities of the isolated compounds were determined as potential regulating excessive inflammatory responses in RAW264.7 macrophage cells. Particularly, abruslactone A (4) and demethylregelin (9) showed the most potent activity, which effectively reduced the expression of iNOS protein and subsequent nitric oxide production induced by lipopolysaccharide in RAW264.7 cells.
Keywords
Euonymus alatus; Triterpene; Inflammation; Nitric oxide; RAW264.7;
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1 Mosser, D. M.; Edwards, J. P. Nature Rev. Immunol. 2008, 8, 958.   DOI   ScienceOn
2 Akihisa, T.; Yamamoto, K.; Tamura, T.; Iida, T.; Nambara, T.; Cheng, F. C. Chem. Pharm. Bull. 1992, 40, 789.   DOI
3 De Fatima Silva, G. D.; Duarte, L. P.; Da Silva Paes, H. C.; De Sousa, J. R.; Nonato, M. C.; Portezani, P. J. J. Brazil. Chem. Soc. 1998, 9, 461.   DOI
4 Liu, C. M.; Wang, H. X.; Wei, S. L.; Gao, K. J. Nat. Prod. 2008, 71, 789.   DOI
5 Jeong, E. J.; Yang, H.; Kim, S. H.; Kang, S. Y.; Sung, S. H.; Kim, Y. C. Food Chem. Toxicol. 2011, 49, 1394.   DOI   ScienceOn
6 Jeong, E. J.; Cho, J. H.; Sung, S. H.; Kim, S. Y.; Kim, Y. C. Bioorg. Med. Chem. Lett. 2011, 15, 2283.
7 Adams, D. O.; Hamilton, T. A. Annu. Rev. Immuno. 1984, 2, 238.
8 Hinz, B.; Brune, K. J. Pharmacol. Exp. Ther. 2002, 300, 367.   DOI   ScienceOn
9 Molloy, R. G.; Mannick, J. A.; Rodrick, M. L. Brit. J. Surg. 1993, 80, 289.   DOI   ScienceOn
10 Klein, T. W. Nature Rev. Immunol. 2005, 5, 400.   DOI
11 Sun, Y.; Zhan, Y. C.; Pei, Y. H. J. Asian Nat. Prod. Res. 2007, 9, 321.   DOI
12 Nakano, K.; Oose, Y.; Takaishi, Y. Phytochemistry 1997, 46, 1179.   DOI
13 Nakagawa, H.; Takaishi, Y.; Fujimoto, Y.; Duque, C.; Garzon, C.; Sato, M. J. Nat. Prod. 2004, 67, 1919.   DOI
14 Kutney, J. P.; Hewitt, G. M.; Lee, G.; Piotrowska, K.; Roberts, M.; Rettig, S. Can. J. Chem. 1992, 70, 1455.   DOI
15 Takaishi, Y.; Wariishi, N.; Tateishi, H.; Kawazoe, K.; Nakano, K.; Ono, Y. Phytochemistry 1997, 45, 969.   DOI
16 Jiang, Z. H.; Tanaka, T.; Hirata, H.; Fukuoka, R.; Kouno, I. Tetrahedron 1997, 53, 16999.   DOI
17 Pal, R.; Kulshreshtha, D. K.; Rastogi, R. P. Phytochemistry 1975, 14, 2253.   DOI
18 Hui, W. H.; Luk, K.; Arthur, H. R.; Loo, S. N. J. Chem. Soc. 1971, 2826.
19 Mamta, M.; Yogendra, N.; Sushil, K. Phytochemistry 2000, 54, 835.   DOI   ScienceOn