Chemical constituents of Plectranthus amboinicus and the synthetic analogs possessing anti-inflammatory activity.
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.
Graduate Institute of Life Science, National Defense Medical Center, Taipei 114, Taiwan; The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
Yuan-Siao
YS
Chen
The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
Hui-Ming
HM
Yu
The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
Jiun-Jie
JJ
Shie
The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan.
Ting-Jen Rachel
TJ
Cheng
The Genomics Research Center, Academia Sinica, Taipei 115, Taiwan. Electronic address: cyiwu@gate.sinica.edu.tw.
Chung-Yi
CY
Wu
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.
Jim-Min
JM
Fang
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.
Chi-Huey
CH
Wong
D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D006801:Humans; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry*; D010938:Plant Oils / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014409:Tumor Necrosis Factor-alpha / Q000378:metabolism*
D000893:Anti-Inflammatory Agents; D010936:Plant Extracts; D010938:Plant Oils; D014409:Tumor Necrosis Factor-alpha
2-Alkylidenyl-4-cyclopentene-1,3-diones; Anti-inflammation; Plectranthus amboinicus; Rosmarinic acid; Thymoquinone