Browse > Article
http://dx.doi.org/10.5012/bkcs.2006.27.8.1149

Synthesis of Lysophosphatidylcholine Analogues Using D-Mannitol as a Chiral Template and Their Biological Activity for Sepsis  

Heo, Hye Jin (Department of Chemistry, Institute of Natural Medicine, Infectious Disease Medical Research Center, Hallym University)
Jung, Jun-Sub (Department of Pharmacology, Institute of Natural Medicine, Infectious Disease Medical Research Center, Hallym University)
Lee, Jung Ho (Department of Chemistry, Institute of Natural Medicine, Infectious Disease Medical Research Center, Hallym University)
Han, Su Young (Department of Chemistry, Institute of Natural Medicine, Infectious Disease Medical Research Center, Hallym University)
Bang, Hyun Bae (Department of Chemistry, Institute of Natural Medicine, Infectious Disease Medical Research Center, Hallym University)
Song, Dong-Keun (Department of Pharmacology, Institute of Natural Medicine, Infectious Disease Medical Research Center, Hallym University)
Jun, Jong-Gab (Department of Chemistry, Institute of Natural Medicine, Infectious Disease Medical Research Center, Hallym University)
Publication Information
Bulletin of the Korean Chemical Society / v.27, no.8, 2006 , pp. 1149-1153 More about this Journal
Abstract
LPC analogues including natural and unnatural LPC, 3-L-2-PC, acetylated LPC and ethylene glycol derivative are prepared from D-mannitol using in convenient procedures by only changing the synthetic sequences, and their protective activities against cecal ligation and puncture (CLP)-induced severe sepsis are compared. The chirality at C2 position in LPC is found to be required as (S)-configuration for sepsis inhibition, comparing from the protection activity between LPC 6 and unnatural LPC 8. The hydroxyl functionality is also very important and required at C2 or C3 position as shown in the protection activities of ethylene glycol analogue 11 and 3-L-2-PC 9.
Keywords
Lysophosphatidylcholine (LPC); Sepsis; D-Mannitol; Phosphocholine;
Citations & Related Records

Times Cited By Web Of Science : 0  (Related Records In Web of Science)
Times Cited By SCOPUS : 0
연도 인용수 순위
  • Reference
1 Hoyert, D. L.; Kochanek, K. D.; Murphy, S. L. Natl. Vital Stat. Rep. 1999, 47, 1-104
2 Hotchkiss, R. S.; Karl, I. E. N. Engl. J. Med. 2003, 348, 138-150   DOI   ScienceOn
3 Yan, J.-J.; Jung, J.-S.; Lee, J.-E.; Lee, J.; Huh, S.-O.; Kim, H.-S.; Jung, K. C.; Cho, J.-Y.; Nam, J.-S.; Suh, H.-W.; Kim, Y.-H.; Song, D.-K. Nat. Med. 2004, 10, 161-167   DOI   ScienceOn
4 Drobnik, W. et al. J. Lipid Res. 2003, 44, 754-761   DOI   ScienceOn
5 Kim, Y.-A.; Park, M.-S.; Kim, Y. H.; Han, S.-Y. Tetrahedron 2003, 59, 2921-2928   DOI   ScienceOn
6 Burgos, C. E.; Ayer, D. E.; Johnson, R. A. J. Org. Chem. 1987, 52, 4973-4977   DOI
7 Byun, H.-S.; Sadlofsky, J. A.; Bittman, R. J. Org. Chem. 1998, 63, 2560-2563   DOI   ScienceOn
8 Deroo, P. W.; Rosenthal, A. F.; Isaacson, Y. A.; Vargas, L. A.; Bittman, R. Chem. Phys. Lipids 1976, 16, 60-70   DOI   ScienceOn
9 Baldwin, J. J.; Raab, A. W.; Mensler, K.; Arison, B. H.; McClure, D. E. J. Org. Chem. 1978, 43, 4876-4878   DOI
10 Maeng, Y. H.; Jun, J.-G. Bull. Korean Chem. Soc. 2004, 25, 143-146   DOI   ScienceOn