Constituents in evening primrose oil with radical scavenging, cyclooxygenase, and neutrophil elastase inhibitory activities.
Cold-pressed, non-raffinated evening primrose oil was found to contain lipophilic radical scavengers. A highly enriched fraction of these compounds could be obtained from the oil by extraction with aqueous ethanol and subsequent liquid-liquid partitioning with petroleum. LC-DAD-MS analysis revealed that the fraction contained three aromatic compounds with identical UV and ESI-MS spectra. The compounds were isolated by RP-HPLC and their structures established by chemical and spectroscopic means as 3-O-trans-caffeoyl derivatives of betulinic, morolic, and oleanolic acid. The morolic acid derivative was a new compound. The three esters exhibited pronounced radical scavenging activity against the stable 2,2-diphenyl-1-picrylhydrazyl radical and were potent inhibitors of neutrophil elastase and cyclooxygenase-1 and -2 in vitro. Commercial samples of evening primrose oils contained only traces of these lipophilic antioxidants.
Hamburger
Matthias
M
Institute of Pharmacy, Friedrich-Schiller-University Jena, Semmelweisstrasse 10, Germany. b7hama@rz.uni-jena.de
Riese
Ulrike
U
Graf
Heidemarie
H
Melzig
Matthias F
MF
Ciesielski
Sylvia
S
Baumann
Dietmar
D
Dittmann
Kathrin
K
Wegner
Christian
C
D000975:Antioxidants / Q000032:analysis; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D016861:Cyclooxygenase Inhibitors / Q000032:analysis / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000032:analysis / Q000494:pharmacology*; D004952:Esters / Q000494:pharmacology; D005228:Fatty Acids, Essential / Q000737:chemistry* / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000032:analysis / Q000494:pharmacology*; D019272:Leukocyte Elastase / Q000037:antagonists & inhibitors*; D008041:Linoleic Acids; D013058:Mass Spectrometry / Q000379:methods; D031665:Oenothera biennis; D009828:Oleanolic Acid / Q000032:analysis; D053978:Pentacyclic Triterpenes; D010938:Plant Oils; D014315:Triterpenes / Q000737:chemistry; D017965:gamma-Linolenic Acid; D000094062:Betulinic Acid
D000975:Antioxidants; D016861:Cyclooxygenase Inhibitors; D004791:Enzyme Inhibitors; D004952:Esters; D005228:Fatty Acids, Essential; D016166:Free Radical Scavengers; D008041:Linoleic Acids; D053978:Pentacyclic Triterpenes; D010938:Plant Oils; D014315:Triterpenes; C459622:morolic acid; C028498:evening primrose oil; D009828:Oleanolic Acid; D017965:gamma-Linolenic Acid; D019272:Leukocyte Elastase; D000094062:Betulinic Acid