Novel anti-inflammatory omega-3 PUFAs from the New Zealand green-lipped mussel, Perna canaliculus.
The present study has identified in the marine mollusc, Perna canaliculus, an homologous series of novel omega 3 polyunsaturated fatty acids (omega-3 PUFA) with significant anti-inflammatory (AI) activity. The free fatty acid (FFA) class was isolated from a supercritical-CO2 lipid extract of the tartaric acid-stabilised freeze-dried mussel powder by normal phase chromatography, followed by reversed-phase high performance liquid chromatography (RP-HPLC). The RP-HPLC involved separation based on carbon numbers, followed by argentation-HPLC (Ag-HPLC) of the methyl esters based on degree of unsaturation. Identification of the FFA components was performed using gas chromatography (GC) with flame ionisation detection, and individual structures were assigned by GC-mass spectroscopy (GC-MS). Inhibition of leukotriene production by stimulated human neutrophils was used as an in vitro screening method to test the AI activity of the purified PUFAs. A structurally related family of omega-3 PUFAs was identified in the most bioactive fractions, which included C18:4, C19:4, C20:4, and C21:5 PUFA. The C20:4 was the predominant PUFA in the extract, and was a structural isomer of arachidonic acid (AA). The novel compounds may be biologically significant as AI agents, as a result of their in vitro inhibition of lipoxygenase products of the AA pathway.
Treschow
A P
AP
Natural Products Research Group, School of Medical Sciences, RMIT University, Bundoora, Victoria, 3083, Australia.
Hodges
L D
LD
Wright
P F A
PF
Wynne
P M
PM
Kalafatis
N
N
Macrides
T A
TA
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000032:analysis / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid; D015525:Fatty Acids, Omega-3 / Q000032:analysis / Q000302:isolation & purification*; D015289:Leukotrienes / Q000032:analysis / Q000737:chemistry; D008954:Models, Biological; D049883:Perna / Q000737:chemistry*; D014020:Tissue Extracts / Q000737:chemistry
D000893:Anti-Inflammatory Agents; D015525:Fatty Acids, Omega-3; D015289:Leukotrienes; D014020:Tissue Extracts