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

The chemical constituents 1–5 of Plectranthus amboinicus and synthetic analogs 8a–d inhibit the binding of AP-1 to its consensus DNA sequence and suppress the expression of lipopolysaccharide-induced TNF-α. This study demonstrates that compounds 1–4 from an extract of Plectranthus amboinicus inhibit...

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Published in	Bioorganic & medicinal chemistry Vol. 22; no. 5; pp. 1766 - 1772
Main Authors	Chen, Yuan-Siao, Yu, Hui-Ming, Shie, Jiun-Jie, Cheng, Ting-Jen Rachel, Wu, Chung-Yi, Fang, Jim-Min, Wong, Chi-Huey
Format	Journal Article
Language	English
Published	OXFORD Elsevier Ltd 01.03.2014 Elsevier
Subjects	2-Alkylidenyl-4-cyclopentene-1,3-diones Anti-inflammation Anti-Inflammatory Agents - pharmacology Biochemistry & Molecular Biology Chemistry Chemistry, Medicinal Chemistry, Organic Humans Life Sciences & Biomedicine Pharmacology & Pharmacy Physical Sciences Plant Extracts - chemistry Plant Extracts - pharmacology Plant Leaves - chemistry Plant Oils - chemistry Plant Oils - isolation & purification Plant Oils - pharmacology Plectranthus Plectranthus amboinicus Rosmarinic acid Science & Technology Thymoquinone Tumor Necrosis Factor-alpha - metabolism Rosmarinic acid Plectranthus amboinicus Anti-inflammation 2-Alkylidenyl-4-cyclopentene-1,3-diones Thymoquinone RHEUMATOID-ARTHRITIS QUINONES BLACK CUMIN RAT MODELS IN-VIVO THYMOQUINONE VOLATILE OIL SALVIA-OFFICINALIS INHIBITORS EXPRESSION
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ISSN	0968-0896 1464-3391 1464-3391
DOI	10.1016/j.bmc.2014.01.009

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Summary:	The chemical constituents 1–5 of Plectranthus amboinicus and synthetic analogs 8a–d inhibit the binding of AP-1 to its consensus DNA sequence and suppress the expression of lipopolysaccharide-induced TNF-α. 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.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1
ISSN:	0968-0896 1464-3391 1464-3391
DOI:	10.1016/j.bmc.2014.01.009