Isolation of linoleic and alpha-linolenic acids as COX-1 and -2 inhibitors in rose hip.
Rose hip has previously shown clinical efficacy in the treatment of osteoarthritis, and organic solvent extracts of rose hip have showed inhibition of cyclooxygenase-1 and -2. A petroleum ether extract of rose hip was fractioned by VLC on silica; on a C-18 column and by HPLC. Each step was COX-1/2 activity-guided. The bioassay-guided fractionation led to the isolation of linoleic acid (the IC50 for COX-1 was 85 microm and 0.6 microM for COX-2) and alpha-linolenic acid (the IC50 for COX-1 was 52 microM and 12 microM for COX-2). The COX-2/COX-1 ratio was 0.007 for linoleic acid and 0.2 for alpha-linolenic acid. Linoleic acid and alpha-linolenic acid contribute to the COX-1 and -2 inhibitory activity of rose hip.
Jäger
A K
AK
Department of Medicinal Chemistry, The Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark. ankj@farma.ku.dk
Petersen
K N
KN
Thomasen
G
G
Christensen
S Brøgger
SB
D002851:Chromatography, High Pressure Liquid; D052246:Cyclooxygenase 2 Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D019787:Linoleic Acid / Q000302:isolation & purification*; D010003:Osteoarthritis / Q000188:drug therapy; D008517:Phytotherapy; D010936:Plant Extracts / Q000302:isolation & purification* / Q000494:pharmacology; D027826:Rosa / Q000737:chemistry*; D014618:Vacuum; D017962:alpha-Linolenic Acid / Q000302:isolation & purification*
D052246:Cyclooxygenase 2 Inhibitors; D010936:Plant Extracts; D017962:alpha-Linolenic Acid; D019787:Linoleic Acid