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Furan Fatty Acid As an Anti-Inflammatory Component From Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus Toshiyuki Wakimotoa,1, Hikaru Kondob, Hirohiko Niia, Kaori Kimurab, Yoko Egamia, Yusuke Okab, Masae Yoshidab, Eri Kidab, Yiping Yeb, Saeko Akahoshib, Tomohiro Asakawab, Koichi Matsumurac, Hitoshi Ishidab, Haruo Nukayab, Kuniro Tsujib, Toshiyuki Kanb, and Ikuro Abea,1 aGraduate School of Pharmaceutical Sciences, University of Tokyo, Tokyo 113-0033, Japan; bSchool of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422-8526, Japan; and cGraduate School of Agricultural and Life Sciences, University of Tokyo, Tokyo 113-8657, Japan Edited by Jerrold Meinwald, Cornell University, Ithaca, NY, and approved September 13, 2011 (received for review June 30, 2011) A lipid extract of Perna canaliculus (New Zealand green-lipped mus- activity of degrading enzymes. The preparation process was sub- sel) has reportedly displayed anti-inflammatory effects in animal sequently improved, and a lipid-rich fraction (Lyprinol), a super- fl models and in human controlled studies. However, the anti-in am- critical fluid [CO2] extraction of the freeze-dried stabilized green- matory lipid components have not been investigated in detail due lipped mussel powder, was prepared. This extraction method to the instability of the lipid extract, which has made the identifi- avoids warming the biological material, and therefore prevents cation of the distinct active components a formidable task. Consid- activation of enzymes. The lipid-rich extract was found to contain ering the instability of the active component, we carefully fraction- five main lipid classes including sterol esters, triglycerides, free ated a lipid extract of Perna canaliculus (Lyprinol) and detected fatty acids, sterols, and polar lipids. A detailed analysis of the fatty furan fatty acids (F-acids). These naturally but rarely detected fatty acid composition revealed that omega-3 PUFAs, such as eicosa- acids show potent radical-scavenging ability and are essential con- pentaenoic acid (EPA; 20:5) and docosahexanoic acid (22:6), stituents of plants and algae. Based on these data, it has been pro- were the most abundant PUFAs among the 90 fatty acid com- posed that F-acids could be potential antioxidants, which may ponents in this extract (3, 4). Although omega-3 PUFAs are the contribute to the protective properties of fish and fish oil diets fl fl likely source of the anti-in ammatory activity of the green-lipped against chronic in ammatory diseases. However, to date, in vivo mussel, via the inhibition of both the 5-lipoxygenase and cyclo- data to support the hypothesis have not been obtained, presum- oxygenase arachidonate oxygenation pathways, Whitehouse and ably due to the limited availability of F-acids. To confirm the in vivo coworkers reported that the lipid-rich oil of the green-lipped anti-inflammatory effect of F-acids in comparison with that of eico- mussel showed potent anti-inflammatory activity in rat paw sapentaenoic acid (EPA), we developed a semisynthetic prepara- edema assays at a concentration two orders of magnitude lower tion and examined its anti-inflammatory activity in a rat model of than that of fish oil containing abundant EPA (9). More recently, adjuvant-induced arthritis. Indeed, the F-acid ethyl ester exhibited fi more potent anti-inflammatory activity than that of the EPA ethyl Howarth and coworkers also reported that the bene cial effect is ester. We report on the in vivo activity of F-acids, confirming that unlikely to be due to omega-3 fatty acid content (10). These data the lipid extract of the green-lipped mussel includes an unstable indicated the presence of another active component, in addition fi fatty acid that is more effective than EPA. to the omega-3 PUFAs commonly found in sh oils. Based on these reports, we hypothesized that other unstable fatty acids fi natural product | tetraalkyl-subsituted furan ring remained to be identi ed as the active components in the lipid extract. he green-lipped mussel Perna canaliculus is native to the New Results and Discussion Zealand coast and is a dietary staple of the indigenous Maori T We fractionated the lipid extract of the green-lipped mussel and culture. It is distinguished from other bivalve species by the used a rat model of adjuvant-induced arthritis to identify the presence of a bright green stripe around the posterior ventral active components. After separation into each lipid class by silica margin of the shell and its distinctive green lip, which is visible on gel chromatography, anti-inflammatory activities were usually the inside of the shell. The anti-inflammatory effects of the green- lipped mussel have been studied since the observation of the found in the cholesterol ester and free fatty acid fractions. Be- lower incidence of arthritis in coastal Maoris compared with its cause the common components for these fractions are appar- prevalence in European or inland Maori people. The develop- ently fatty acids, we focused on the further analysis of the fatty acid components. This estimation agrees with Macrides and ment of a natural remedy for the management of arthritis that will ’ not only replace nonsteroidal anti-inflammatories (NSAIDs) as coworkers report that the free fatty acid fraction, and to a lesser the standard treatment for all types of arthritis but also treat the extent the triglyceride fraction, were the only lipid classes to condition successfully, without any known side effects, is being exhibit strong inhibition of COX isoforms (8). However, a pre- fi eagerly pursued (1). Therefore, numerous studies have been cise separation of the free fatty acid fraction is usually dif cult published on the lipid composition of the extract (2–4), its com- for minor fatty acids in the presence of an abundance of PUFAs. plex mode of action (5–8), activity in animal models (9, 10), and Moreover, further fractionation based on the guidance of the efficacy in controlling osteoarthritis (11, 12) and moderate asthma in patients (13). However, the active component from the mussel is a lipid rich in polyunsaturated fatty acids (PUFAs) and Author contributions: T.W., H.K., H.I., H. Nukaya, K.T., T.K., and I.A. designed research; PHARMACOLOGY T.W., H.K., H. Nii, K.K., Y.E., Y.O., M.Y., E.K., Y.Y., S.A., and T.A. performed research; T.W. is therefore prone to activation of degrading enzymes including and H. Nii contributed new reagents/analytic tools; T.W., H.K., and K.M. analyzed data; phospholipases and lipoxygenases (14, 15) after cell damage, and T.W. wrote the paper. unless it is stored and transported properly. In the case of severe The authors declare no conflict of interest. damage, this enzymatic reaction switches to a nonenzymatic one This article is a PNAS Direct Submission. producing radicals (16). A freeze-dried powdered preparation of 1To whom correspondence may be addressed. E-mail: [email protected] or whole mussel (i.e., without shell) was first tested orally in rats, [email protected]. fl and showed either modest or no anti-in ammatory activity (car- This article contains supporting information online at www.pnas.org/lookup/suppl/doi:10. rageenan paw edema in rats), probably due to the remaining 1073/pnas.1110577108/-/DCSupplemental. www.pnas.org/cgi/doi/10.1073/pnas.1110577108 PNAS | October 18, 2011 | vol. 108 | no. 42 | 17533–17537 Downloaded by guest on September 24, 2021 bioassay was a formidable task, due to the concomitant decom- parative TLC to separate the lipid classes would have allowed the position of the active compounds. F-acids to decompose before GC-MS analysis, even though over There is a large body of evidence demonstrating a role for re- 90 component fatty acids were detected. Therefore, we expected active oxygen species and oxidant stress in the pathogenesis of that the F-acids might still be detected. chronic inflammation such as rheumatoid arthritis (17–19). The However, the separation of F-acids from other fatty acids is high susceptibility of the cellular membrane to oxidation triggers usually difficult and requires special workup procedures. F-acids, lipid peroxidation and concomitant radical chain reactions, especially those with two β-methyl substituents, are quite suscep- resulting in severe progression of symptoms (20). To suppress lipid tible to the peroxy radicals produced during lipid peroxidation, and peroxidation, there are many lipophilic antioxidants, such as are no longer detectable after homogenization in aqueous media. vitamins A and E, astaxanthin as a natural product, and probucol Thus, F-acids were found only occasionally, when a tissue rich in F- as an antioxidant drugs (21). On the other hand, if an antioxidative acids was homogenized in organic solvents. Additionally, to cir- fatty acid can be embedded into the lipid component, then its cumvent the autoxidation of the tetraalkyl-substituted furan ring antioxidative effect would be more promising. Spiteller hypothe- on the surface of silica gel (30, 39), careful manipulations are re- sized that furan fatty acids (F-acids), which were first isolated from quired, especially in the case of lower quantities from natural the northern pike in 1974 (22), are such naturally occurring anti- sources. Previous reports used the method of Folch et al. (40) or oxidative fatty acids that ameliorate the oxidative risk of the cel- Bligh and Dyer (41) to extract total lipids, which were further lular membrane (23, 24). Even though F-acid concentration is separated by silica gel into cholesteryl ester, triglycerides, and usually low, these fatty acids are widely distributed in plants and phospholipid fractions (25–35). These esters were transesterified aquatic organisms (25–36). The unique structural feature of F- with a methanolic sodium methoxide solution to form fatty acid acids is the tetraalkyl-substituted furan ring, which is a rarely ob- methyl esters and then were investigated by GC-MS.
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