Flavonoids and stilbenoids with COX-1 and COX-2 inhibitory activity from Dracaena loureiri.
Fom the stem wood of Dracaena loureiri, a new homoisoflavanone named loureiriol (1) and eight known flavonoid and stilbenoid derivatives, including 5,7-dihydroxy-3-(4-hydroxybenzyl)-4-chromanone (2), 4,4'-dihydroxy-2,6-dimethoxydihydrochalcone (3), 2,4'-dihydroxy-4,6-dimethoxydihydrochalcone (4), 4'-hydroxy-2,4,6-trimethoxydihydrochalcone (5), 4,6,4'-trihydroxy-2-methoxydihydrochalcone (6), 4,3',5'-trihydroxystilbene (7), 4,3'-dihydroxy-5'-methoxystilbene (8) and 4-hydroxy-3',5'-dimethoxystilbene (9) were isolated. These compounds were evaluated for their inhibitory activity against the enzymes cyclooxygenase-1 and cyclooxygenase-2. Potent but non-selective activity was found for the stilbenoids 7-9 (IC(50) 1.29 - 4.92 microM) whereas weak or no activity was observed for the flavonoids 1-6.
D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D031409:Dracaena; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D007529:Isoflavones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry; D011451:Prostaglandin-Endoperoxide Synthases; D013267:Stilbenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
D052246:Cyclooxygenase 2 Inhibitors; D016861:Cyclooxygenase Inhibitors; D004791:Enzyme Inhibitors; D005419:Flavonoids; D007527:Isoenzymes; D007529:Isoflavones; D010936:Plant Extracts; D013267:Stilbenes; C469381:loureiriol; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2; D011451:Prostaglandin-Endoperoxide Synthases