title: Novel compounds from Piper methysticum Forst (Kava Kava) roots and their effect on cyclooxygenase enzyme.
abstract: 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.
authors.affiliation: 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.
authors.forename: Di
authors.initials: D
authors.lastname: Wu
authors.forename: Muraleedharan G
authors.initials: MG
authors.lastname: Nair
authors.forename: David L
authors.initials: DL
authors.lastname: DeWitt
mesh_terms: 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
chemical_list: 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