Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Abstract

A lipid extract of Perna canaliculus (New Zealand green-lipped mussel) has reportedly displayed anti-inflammatory effects in animal models and in human controlled studies. However, the anti-inflammatory lipid components have not been investigated in detail due to the instability of the lipid extract, which has made the identification of the distinct active components a formidable task. Considering the instability of the active component, we carefully fractionated a lipid extract of Perna canaliculus (Lyprinol) and detected furan fatty acids (F-acids). These naturally but rarely detected fatty acids show potent radical-scavenging ability and are essential constituents of plants and algae. Based on these data, it has been proposed that F-acids could be potential antioxidants, which may contribute to the protective properties of fish and fish oil diets against chronic inflammatory diseases. However, to date, in vivo data to support the hypothesis have not been obtained, presumably due to the limited availability of F-acids. To confirm the in vivo anti-inflammatory effect of F-acids in comparison with that of eicosapentaenoic acid (EPA), we developed a semisynthetic preparation and examined its anti-inflammatory activity in a rat model of adjuvant-induced arthritis. Indeed, the F-acid ethyl ester exhibited more potent anti-inflammatory activity than that of the EPA ethyl ester. We report on the in vivo activity of F-acids, confirming that the lipid extract of the green-lipped mussel includes an unstable fatty acid that is more effective than EPA.

Synthesis and scavenging role of furan fatty acids

“…This result was somewhat surprising because the conditions used to produce 1 O 2 are known to be sufficient to increase σ E activity (19,20) so we expected to see accumulation of 19Fu-FA. 1 O 2 can directly oxidize furan moieties and produce fatty acyl radicals from unsaturated fatty acids so it has been proposed that Fu-FAs can act as a scavenger for this and other ROS (14,15,34,35). Thus, the failure to observe alterations of the fatty-acid content when wild-type cells were exposed to 1 O 2 could reflect the ability of 19Fu-FA to scavenge this ROS or products of its action on bilayer constituents.…”

Detailed Study of Furan Fatty Acids in Total Lipids and the Cholesteryl Ester Fraction of Fish Liver

“…Besides the saturated F-acids, homologues with double bonds in the carboxyalkyl chain and alkyl chain have also been described in food samples (Pacetti et al 2010;Ishii et al 1988a;Boselli et al 2000). F-acids are known to act as radical scavengers (Okada et al 1996;Wakimoto et al 2011;Okada et al 1990; Lemke et al 2014) and are thus considered as valuable, bioactive minor fatty acids in food (Spiteller 2005;Pacetti et al 2013b;Vetter and Wendlinger 2013). F-acids have frequently been reported in the lipids of fish (Glass et al 1974;Gunstone et al 1978;Wahl et al 1994;Pacetti et al 2010), plants (Hannemann et al 1989), in oils (Boselli et al 2000;Guth and Grosch 1991), and butter (Guth and Grosch 1992), with fish being the richest nutritional source (Wendlinger and Vetter 2014).…”

Mumiamicin: Structure and bioactivity of a new furan fatty acid from <i>Mumia</i> sp. YSP-2-79

“…They have displayed various biological activities, such as antioxidative (Teixeira et al, 2013) and anti-inflammatory (Wakimoto et al, 2011) prop-erties. To the best of our knowledge, mumiamicin (1) obtained from Mumia sp.…”