Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme.
Milled Piper methysticum roots were extracted sequentially with hot water and methanol. Cyclooxygenase (COX) enzyme inhibitory assay directed purification of the methanol extract yielded bornyl esters of 3,4-methylenedioxy cinnamic acid (1) and cinnamic acid (2), pinostrobin (3), flavokawain B (4), and 5,7-dimethoxyflavanone (5). The structures of compounds 1-5 were accomplished by spectral experiments. The aqueous extract contained previously reported kava lactones, as confirmed by TLC analysis. Compounds 3 and 5 were isolated for the first time from kava kava roots. Compound 4 showed the highest COX-I inhibitory activity at 100 microg/mL. All the compounds tested gave good COX-I and moderate COX-II enzyme inhibitory activities at 100 microg/mL. This is the first report of COX-I and -II inhibitory activities for compounds 1-5.
Wu
Di
D
Bioactive Natural Products and Phytoceuticals, Department of Horticulture and National Food Safety and Toxicology Center, and Department of Biochemistry, Michigan State University, East Lansing, Michigan 48824, USA.
Nair
Muraleedharan G
MG
DeWitt
David L
DL
D002934:Cinnamates / Q000302:isolation & purification / Q000494:pharmacology; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D044950:Flavanones; D005419:Flavonoids / Q000302:isolation & purification / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D007527:Isoenzymes / Q000037:antagonists & inhibitors; D020901:Kava / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D018517:Plant Roots / Q000737:chemistry*; D011451:Prostaglandin-Endoperoxide Synthases
D002934:Cinnamates; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D044950:Flavanones; D005419:Flavonoids; D007527:Isoenzymes; C452039:flavokawain B; C029010:cinnamic acid; C060298:5,7-dimethoxyflavone; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases; C411294:pinostrobin