Chemical constituents of Plectranthus amboinicus and the synthetic analogs possessing anti-inflammatory activity

  • Bioorg Med Chem. 2014 Mar 1;22(5):1766-72. doi: 10.1016/j.bmc.2014.01.009.
Yuan-Siao Chen  1 ,  Hui-Ming Yu  2 ,  Jiun-Jie Shie  2 ,  Ting-Jen Rachel Cheng  2 ,  Chung-Yi Wu  3 ,  Jim-Min Fang  4 ,  Chi-Huey Wong  5
Affiliations
  • 1. Graduate Institute of Life Science, National Defense Medical Center, Taipei 114, Taiwan; The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
  • 2. The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
  • 3. The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan. Electronic address: [email protected].
  • 4. Graduate Institute of Life Science, National Defense Medical Center, Taipei 114, Taiwan; Department of Chemistry, National Taiwan University, Taipei 106, Taiwan. Electronic address: [email protected].
  • 5. Graduate Institute of Life Science, National Defense Medical Center, Taipei 114, Taiwan; The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan. Electronic address: [email protected].
PMID: 24491635 DOI: 10.1016/j.bmc.2014.01.009
Abstract

This study demonstrates that compounds 1-4 from an extract of Plectranthus amboinicus inhibit the binding of AP-1 to its consensus DNA sequence. Thymoquinone (5) was further identified as a nonpolar ingredient from the hexane extract of P. amboinicus to suppress the expression of lipopolysaccharide-induced tumor necrosis factor-alpha (TNF-α). We then synthesized 2-alkylidenyl-4-cyclopentene-1,3-diones as the designed biomimetics of thymoquinone, and found that compounds 8a, 8b and 8d were more potent TNF-α inhibitors.

Keywords
2-Alkylidenyl-4-cyclopentene-1,3-diones; Anti-inflammation; Plectranthus amboinicus; Rosmarinic acid; Thymoquinone.