Premium
Aryl Ketones from Acronychia pedunculata with Cyclooxygenase‐2 Inhibitory Effects
Author(s) -
Pathmasiri Wimal,
ElSeedi Hesham R.,
Han Xiao,
Janson JanChrister,
Huss Ulrika,
Bohlin Lars
Publication year - 2005
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200590026
Subject(s) - chemistry , cyclooxygenase , ic50 , stereochemistry , ketone , aryl , bioassay , inhibitory postsynaptic potential , dept , fractionation , heteronuclear single quantum coherence spectroscopy , two dimensional nuclear magnetic resonance spectroscopy , in vitro , enzyme , biochemistry , organic chemistry , alkyl , neuroscience , biology , genetics
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 CH 2 Cl 2 extract of the bark of Acronychia pedunculata by a bioassay‐guided fractionation procedure. Compound 2 inhibited COX‐2 with an IC 50 value of 142.0±2.15 μ M , compared to the COX‐2 inhibitory reference compound NS‐398 with an IC 50 value of 11.3±1.12 μ M . Compound 1 inhibited COX‐2‐catalyzed PG biosynthesis with 68% at a concentration of 500 μ M . The structures were determined by UV, IR, and 1D‐ and 2D‐NMR, including TOCSY, HSQC‐DEPT, and HMBC, and MS investigations.