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Natural product sciences v.10 no.6, 2004년, pp.315 - 320  

Inhibitory Effect of Benzofuran Compound on Cyclooxygenase

Min, Kyung-Rak    (College of Pharmacy & Research Center for Bioresource and Health, Chungbuk National University   ); Ahn, Ki-Young    (College of Pharmacy & Research Center for Bioresource and Health, Chungbuk National University   ); Chung, Eun-Yong    (College of Pharmacy & Research Center for Bioresource and Health, Chungbuk National University   ); Lee, Yong-Rok    (School of Chemical Engineering and Technology, Yeungnam University   ); Kim, Yeong-Shik    (Natural Products Research Institute, Seoul National University   ); Kim, Young-Soo    (College of Pharmacy & Research Center for Bioresource and Health, Chungbuk National University  );
  • 초록

    Alpha-viniferin was previously isolated as a cyclooxygenase (COX)-2 inhibitor from Carex humilis (Cyperaceae) and is an oligomeric stilbene compound with benzofuran (BF) moieties in its chemical structure. In the present study, a chemically synthetic BF compound, named as 3,3-dimethyl-2,3,4,6,7,8,9,10,11,12,13,14,15,16,17,18-hexadecahydro-1H-benzo[b] cyclopentadeca[d]furan-1-one, was discovered to inhibit bacterial lipo polysaccharide (LPS)-induced prostaglandin $E_2$ $(PGE_2)$ production in macrophages RAW 264.7. The BF compound exhibited a selectively preferred inhibitory effect on COX-2 activity over COX-1 activity. Furthermore, BF compound inhibited LPS-induced COX-2 expression at transcription level. As a down-regulatory mechanism of COX-2 expression shown by BF compound, suppression of nuclear factor $(NF)-{\kappa}B$ activation has been demonstrated. BF compound inhibited LPS-induced $NF-{\kappa}B$ transcriptional activity and nuclear translocation of $NF-{\kappa}B$ p65, in parallel, but did not affect LPS-induced degradation of inhibitory ${\kappa}B{\alpha}$ protein $(I{\kappa}B{\alpha})$ . Taken together, anti-inflammatory effect of BF compound on $PGE_2$ production was ascribed by its down-regulatory action on LPS-induced COX-2 synthesis in addition to inhibitory action on enzyme activity of COX-2.


  • 주제어

    Benzofuran compound .   Cyclooxygenase .   Nuclear $factor-{\kappa}B$ .   Macrophages.  

  • 참고문헌 (18)

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    1. 1989 "5-Lipoxygenase의 활성과 Leukotriene $B_4$ 생합성 억제물질" 약학회지 = Yakhak hoeji 33 (6): 319~323    
    2. 1990 "흰쥐의 다리종양에서 발현된 케이라스 암유전자" 한국생화학회지 23 (2): 185~189    
    3. 1991 "Pseudomonas putida의 Catechol 2,3-dioxygenase 유전자의 클로닝" Korean journal of microbiology = 미생물학회지 29 (3): 155~159    
    4. 1992 "Molecular Cloning and M13 Subcloning of Genes Encoding Catechol Dioxygenases" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea 15 (1): 48~51    
    5. 1992 "Cloning and Overexpression of Methylcatechol 2, 3-Dioxygenase Gene from Toluene-Degrading Pseudomonas putida mt-2(pWWO)" Archives of pharmacal research : a publication of the Pharmaceutical Society of Korea 15 (4): 360~364    
    6. 1995 "Inhibitory Effects of Herbal Medicines on Hyaluronidase Activity" 생약학회지 26 (3): 265~272    
    7. 1996 "Inhibitory Effects of Triterpenoids on Interleukin-8/CINC-1 Induction in LPS-Stimulated Rat Peritoneal Macrophages" Natural product sciences 2 (1): 48~55    
    8. 1996 "Inhibitory Effects of Herbal Extracts on Cyclooxygenase Activity of Prostaglandin $H_2$ Synthase from Sheep Seminal Vesicle" Natural product sciences 2 (1): 56~74    
    9. 1997 "Inhibitory Effects of Herbal Extracts on CINC-1 Induction in LPS-Stimulated Rat Kidney Epithelioid NRK-52E cells" Natural product sciences 3 (1): 59~70    
    10. 1997 "Inhibitory Effects of Herbal Extracts on Dopa Oxidase Activity of Tyrosinase" Natural product sciences 3 (2): 111~121    
  • 정은용 (12)

  • Lee, Yong-Rok (14)

  • Kim, Yeong-Shik (89)

  • Kim , Young-Soo (52)

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