Bioactive alkenylphenols from Piper obliquum.
Various parts of Piper obliquum Ruíz & Pavon yielded the new alkenylphenols obliquol A (1) and obliquol B (2), the new 4-chromanone 3 together with the known compounds 4 and 5. A synthesis of obliquol B (2) was developed in order to confirm its structure and to provide sufficient amounts for biological testing. Compounds 1 and 2 have antibacterial activity comparable to that of ampicillin, 2 in addition possesses potent anti-NF-kappaB activity by targeting early events in the TNFalpha-induced NF-kappaB inflammatory pathway, which may explain the effects reported for the traditional use of the plant.
Valdivia
Carola
C
Division of Organic Chemistry, Lund University, Box 124, Getingevagen 60, SE-221 00 Lund, Sweden.
Marquez
Nieves
N
Eriksson
John
J
Vilaseca
Antonio
A
Muñoz
Eduardo
E
Sterner
Olov
O
D000475:Alkenes / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000494:pharmacology; D002460:Cell Line; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors / Q000378:metabolism; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D031701:Piper / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors / Q000494:pharmacology
D000475:Alkenes; D000900:Anti-Bacterial Agents; D016328:NF-kappa B; D010636:Phenols; D014409:Tumor Necrosis Factor-alpha