DOI QR코드

DOI QR Code

Ailanthoidol Derivatives and their Anti-inflammatory Effects

  • Lee, Na-Li (Department of Chemistry and Institute of Natural Medicine, Hallym University) ;
  • Lee, Jae-Jun (Department of Chemistry and Institute of Natural Medicine, Hallym University) ;
  • Kim, Jin-Kyung (Department of Biomedical Science, College of Natural Science, Catholic University of Daegu) ;
  • Jun, Jong-Gab (Department of Chemistry and Institute of Natural Medicine, Hallym University)
  • Received : 2012.01.20
  • Accepted : 2012.03.07
  • Published : 2012.06.20

Abstract

Ailanthoidol showed a strong $anti$-inflammatory effect in a previous result. Ailanthoidol derivatives were prepared for the $anti$-inflammatory test using Sonogashira coupling, iodine induced cyclization and Wittig reaction. $Anti$-inflammatory effects of the prepared ailanthoidol derivatives were examined in lipopolysaccharide (LPS)-stimulated RAW 264-7 macrophages. The results showed that some ailanthoidol derivatives inhibited significantly the production of inflammatory mediator nitric oxide.

Keywords

References

  1. Sheen, W.-S.; Tsai, I.-L.; Teng, C.-M.; Chen, I.-S. Phytochemistry 1994, 36, 213.
  2. Navarro, E.; Alanso, S. J.; Trujillo, J.; Jorge, E.; Perez, C. J. Nat. Prod. 2001, 64, 134. https://doi.org/10.1021/np9904861
  3. Ikeda, R.; Nagao, T.; Okabe, H.; Nakano, Y.; Matsunaga, H.; Katano, M.; Mori, M. Chem. Pharm. Bull. 1998, 46, 871. https://doi.org/10.1248/cpb.46.871
  4. Day, S. H.; Chiu, N. Y.; Tsao, L. T.; Wang, J. P.; Lin, C. N. J. Nat. Prod. 2000, 63, 1560. https://doi.org/10.1021/np000191j
  5. Craigo, J.; Callahan, M.; Huang, R. C. C.; DeLucia, A. L. Antiviral. Res. 2000, 47, 19. https://doi.org/10.1016/S0166-3542(00)00089-9
  6. Zacchino, S.; Rodriguez, G.; Pezzenati, G.; Orellana, G.; Enriz, R.; Gonzalez, S. M. J. Nat. Prod. 1997, 60, 659. https://doi.org/10.1021/np9605504
  7. Gordaliza, M.; Castro, M.; del Corral, J. M.; Lopez-Vazquez, M.; Feliciano, A. S.; Faircloth, G. T. Bioorg. Med. Chem. Lett. 1997, 7, 2781. https://doi.org/10.1016/S0960-894X(97)10072-5
  8. Chen, C. C.; Hsin, W. C.; Ko, F. N.; Huang, Y. L.; Ou, J. C.; Teng, C. M. J. Nat. Prod. 1996, 59, 1149. https://doi.org/10.1021/np960443+
  9. Silva, D. H. S.; Pereira, F. C.; Zanoni, M. V. B.; Yoshida, M. Phytochemistry 2001, 57, 437. https://doi.org/10.1016/S0031-9422(00)00477-5
  10. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183. https://doi.org/10.1039/np9951200183
  11. Brader, G.; Greger, H.; Bacher, M.; Kalchhauser, H.; Hofer, O.; Vajrodaya, S. J. Nat. Prod. 1998, 61, 1482. https://doi.org/10.1021/np9801965
  12. Hwang, J. W.; Choi, D. H.; Jeon J.-H.; Kim, J.-K.; Jun, J.-G. Bull. Korean Chem. Soc. 2010, 31, 965. https://doi.org/10.5012/bkcs.2010.31.04.965
  13. Bang, H. B.; Han S. Y.; Choi, D. H.; Hwang, J. W.; Jun, J.-G. Arkivoc 2009, (ii), 112.
  14. Vernooy, J. H.; Dentener, M. A.; Suylen, R. J. van.; Buurman, W. A.; Wouters, E. F. Am. J. Respir Cell Mol. Biol. 2002, 26, 152. https://doi.org/10.1165/ajrcmb.26.1.4652
  15. Sakagami, T.; Vella, J.; Dixon, M. F.; Rourke, J.; Radcliff, F.; Sutton, P.; Shimoyama, T.; Beagley, K.; Lee, A. Infect. Immun. 1997, 65, 3310.
  16. Kwon, K. H.; Murakami, A.; Hayashi, R.; Ohigashi, H. Biochem. Biophys. Res. Commun. 2005, 337, 647. https://doi.org/10.1016/j.bbrc.2005.09.107

Cited by

  1. Pd-Catalyzed Tandem Chemoselective Synthesis of 2-Arylbenzofurans using Threefold Arylating Triarylbismuth Reagents vol.2013, pp.4, 2012, https://doi.org/10.1002/ejoc.201201314
  2. 2-(4-Hydroxyphenyl)-5-(3-Hydroxypropenyl)-7-Methoxybenzofuran, a Novel Ailanthoidol Derivative, Exerts Anti-Inflammatory Effect through Downregulation of Mitogen-Activated Protein Kinase in Lipopolysaccharide-Treated RAW 264.7 Cells vol.17, pp.3, 2013, https://doi.org/10.4196/kjpp.2013.17.3.217
  3. Expeditious Synthesis of Natural Benzofuran, Eupomatenoid-6 by Umpolung of α-Aminophosphonates vol.35, pp.12, 2012, https://doi.org/10.5012/bkcs.2014.35.12.3618
  4. Rapid Access to Benzofuran‐Based Natural Products through a Concise Synthetic Strategy vol.2016, pp.12, 2012, https://doi.org/10.1002/ejoc.201600154
  5. Benzofuran: A Key Heterocycle - Ring Closure And Beyond vol.17, pp.3, 2012, https://doi.org/10.2174/1570193x16666190710122912