Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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First Total Synthesis of Highly Anti-Inflammatory Active Licochalcone D Through Water-Accelerated [3,3]-Sigmatropic Rearrangement

  • Kim, Si-Jun (Department of Chemistry and Institute of Natural Medicine, Hallym University) ;
  • Jun, Jong-Gab (Department of Chemistry and Institute of Natural Medicine, Hallym University)
  • Received : 2012.09.14
  • Accepted : 2012.10.04
  • Published : 2013.01.20
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Abstract

Licochalcones, derived from the dried roots of Glycyrrhiza inflata, have been reported to show various biological activities including antitumor, antiparasitic, antileishmanial, antioxidative, superoxide scavenging, antibacterial, and PTP1B activity. Licochalcone D has an allyl group on ring A instead of ring B, however, most other natural licochalcones possess the group on ring B. Total synthesis of licochalcone D has not been reported even possessing the strongest anti-inflammatory activity. Therefore, the first total synthesis of licochalcone D has been developed by using water-accelerated [3,3]-sigmatropic rearrangement method.

Keywords

References

  1. Wang, Z. Y.; Nixon, D. W. Nutr. Cancer 2001, 39, 1. https://doi.org/10.1207/S15327914nc391_1
  2. Asl, M. N.; Hosseinzadeh, H. Phytother. Res. 2008, 22, 709. https://doi.org/10.1002/ptr.2362
  3. Shibata, S. Stem Cells 1994, 12, 44. https://doi.org/10.1002/stem.5530120109
  4. Liu, X. L.; Xu, Y. J.; Go, M. L. Eur. J. Med. Chem. 2008, 43, 1681. https://doi.org/10.1016/j.ejmech.2007.10.007
  5. Liu, M.; Wilarirat, P.; Go, M.-L. J. Med. Chem. 2001, 44, 4443. https://doi.org/10.1021/jm0101747
  6. Nagai, H.; He, J.-X.; Tani, T.; Akao, T. J. Pharm. Pharmacol. 2007, 59, 1421. https://doi.org/10.1211/jpp.59.10.0013
  7. Cho, Y.-C.; Lee, S. H.; Yoon, G.; Kim, H.-S.; Na, J. Y.; Choi, H. J.; Cho, C.-W.; Cheon, S. H.; Kang, B. Y. Int. Immunopharmacol. 2010, 10, 1119. https://doi.org/10.1016/j.intimp.2010.06.015
  8. Yoon, G.; Oak, M.-H.; Lee, J.-O.; Cheon, S. H. Bull. Korean Chem. Soc. 2010, 31, 1085. https://doi.org/10.5012/bkcs.2010.31.04.1085
  9. Funakoshi-Tago, M.; Tago, K.; Nishizawa, C.; Tkahashi, K.; Mashino, T.; Iwata, S.; Inoue, H.; Sonda, Y.; Kasahara, T. Biochem. Pharmacol. 2008, 6, 1681.
  10. Park, J.-H.; Lim, H. J.; Lee, K.-S.; Lee, S.; Kwak, H.-J. Biol. Pharm. Bull. 2008, 31, 1996. https://doi.org/10.1248/bpb.31.1996
  11. Sato, T.; Inoue, H.; Shibata, S. J. Pharm. Pharmacol. 2005, 57, 1661. https://doi.org/10.1211/jpp.57.12.0017
  12. Yoon, G.; Lee, W.; Kim, S. N.; Cheon, S. H. Bioorg. Med. Chem. Lett. 2009, 19, 5155. https://doi.org/10.1016/j.bmcl.2009.07.054
  13. Tanifuji, S.; Aizu-Yokota, E.; Funakoshi-Tago, M.; Sonoda, Y.; Inoue, H.; Kasahara, T. Int. Immunopharmacol. 2010, 10, 769. https://doi.org/10.1016/j.intimp.2010.04.007
  14. Furusawa, J.; Funakoshi-Tago, M.; Mashino, T.; Tago, K.; Inoue, H.; Sonoda, Y.; Kasahara, T. Int. Immunopharmacol. 2009, 9, 499. https://doi.org/10.1016/j.intimp.2009.01.031
  15. Xie, Q. W.; Kashiwabara, Y.; Nathan, C. J. Biol. Chem. 1994, 269, 4705.
  16. Kajiyama, K.; Demizu, S.; Hiraga, Y.; Kinoshita, K.; Koyama, K.; Takahashi, K.; Tamura, Y.; Okada, K.; Kinoshita, T. Phytochemistry 1992, 31, 3229. https://doi.org/10.1016/0031-9422(92)83481-D
  17. Jeon, J.-H.; Kim, M. R.; Jun, J.-G. Synthesis 2011, 370.
  18. Jeon, J.-H.; Kim, M. R.; Kwon, E. M.; Lee, N. R.; Jun, J.-G. Bull. Korean. Chem. Soc. 2011, 32, 1059. https://doi.org/10.5012/bkcs.2011.32.3.1059

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