Aryl ketones from Acronychia pedunculata with cyclooxygenase-2 inhibitory effects.
1-[2,4-Dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]ethanone (1), and a new aryl ketone, named acrovestenol (2), were isolated as cyclooxygenase-2 (COX-2) inhibitory principles from a CH2Cl2 extract of the bark of Acronychia pedunculata by a bioassay-guided fractionation procedure. Compound 2 inhibited COX-2 with an IC50 value of 142.0+/-2.15 microM, compared to the COX-2 inhibitory reference compound NS-398 with an IC50 value of 11.3+/-1.12 microM. Compound 1 inhibited COX-2-catalyzed PG biosynthesis with 68% at a concentration of 500 microM. The structures were determined by UV, IR, and 1D- and 2D-NMR, including TOCSY, HSQC-DEPT, and HMBC, and MS investigations.
Pathmasiri
Wimal
W
Division of Pharmacognosy, Department of Medicinal Chemistry, Biomedical Centre, Uppsala University, Box 574, SE-751 23 Uppsala.
el-Seedi
Hesham R
HR
Han
Xiao
X
Janson
Jan-Christer
JC
Huss
Ulrika
U
Bohlin
Lars
L
D000098:Acetophenones / Q000737:chemistry* / Q000494:pharmacology*; D052246:Cyclooxygenase 2 Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D007659:Ketones / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D027821:Rutaceae / Q000737:chemistry*
C516805:1-(2,4-dihydroxy-6-methoxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)ethanone; D000098:Acetophenones; D052246:Cyclooxygenase 2 Inhibitors; D007659:Ketones; C516806:acrovestenol