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: cyiwu@gate.sinica.edu.tw.
4 Graduate Institute of Life Science, National Defense Medical Center, Taipei 114, Taiwan; Department of Chemistry, National Taiwan University, Taipei 106, Taiwan. Electronic address: jmfang@ntu.edu.tw.
5 Graduate Institute of Life Science, National Defense Medical Center, Taipei 114, Taiwan; The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan. Electronic address: chwong@gate.sinica.edu.tw.

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.

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