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3 N 21:3 -Oxa Β Polyunsaturated Fatty Acid Inhibition of Neutrophil Leukotriene B4 Production by a Novel Synthetic N-3 Polyunsaturated Fatty Acid Analogue, β-Oxa 21:3 n-3 This information is current as of September 25, 2021. Brenton S. Robinson, Deborah A. Rathjen, Neil A. Trout, Christopher J. Easton and Antonio Ferrante J Immunol 2003; 171:4773-4779; ; doi: 10.4049/jimmunol.171.9.4773 http://www.jimmunol.org/content/171/9/4773 Downloaded from References This article cites 42 articles, 14 of which you can access for free at: http://www.jimmunol.org/content/171/9/4773.full#ref-list-1 http://www.jimmunol.org/ Why The JI? Submit online. • Rapid Reviews! 30 days* from submission to initial decision • No Triage! Every submission reviewed by practicing scientists • Fast Publication! 4 weeks from acceptance to publication by guest on September 25, 2021 *average Subscription Information about subscribing to The Journal of Immunology is online at: http://jimmunol.org/subscription Permissions Submit copyright permission requests at: http://www.aai.org/About/Publications/JI/copyright.html Email Alerts Receive free email-alerts when new articles cite this article. Sign up at: http://jimmunol.org/alerts The Journal of Immunology is published twice each month by The American Association of Immunologists, Inc., 1451 Rockville Pike, Suite 650, Rockville, MD 20852 Copyright © 2003 by The American Association of Immunologists All rights reserved. Print ISSN: 0022-1767 Online ISSN: 1550-6606. The Journal of Immunology Inhibition of Neutrophil Leukotriene B4 Production by a Novel Synthetic N-3 Polyunsaturated Fatty Acid Analogue, ␤-Oxa 21:3n-31 Brenton S. Robinson,* Deborah A. Rathjen,2*ʈ Neil A. Trout,*§ Christopher J. Easton,¶ and Antonio Ferrante3*†‡ We recently reported the synthesis and anti-inflammatory properties of a novel long chain polyunsaturated fatty acid (PUFA) with an oxygen atom in the ␤-position, ␤-oxa-21:3 n-3 (Z,Z,Z)-(octadeca-9,12,15-trienyloxy) acetic acid). Our data, from studies aimed at elucidating the mechanism of its action, show that pretreatment of human neutrophils with the ␤-oxa-PUFA substantially depresses the production of leukotriene B4 (LTB4) in response to calcium ionophore, A23187, comparable to standard leukotriene inhibitors such as zileuton and nordihydroguaiaretic acid. Interestingly, the n-6 equivalent, ␤-oxa 21:3 n-6, is also a strong Downloaded from inhibitor of LTB4 production. In contrast, naturally occurring PUFA only slightly reduce, for eicosapentaenoic (20:5n-3) and ␤ docosahexaenoic (22:6n-3) acids, or increase, for arachidonic acid (20:4n-6), the formation of LTB4. The parent -oxa-21:3n-3 molecule, rather than its derivatives (methyl ester, saturated, monohydroperoxy, or monohydroxy forms), is exclusively respon- ␤ 3 3 sible for attenuation of LTB4 formation. -Oxa-21:3n-3 inhibits the conversion of [ H]20:4n-6 to [ H]5-hydroxyeicosatetraenoic 3 acid and [ H]LTB4 by neutrophils in the presence of calcium ionophore and also suppresses the activity of purified 5-lipoxygenase, but not cyclooxygenase 1 and 2. ␤-Oxa-21:3n-3 is taken up by neutrophils and incorporated into phospholipids and neutral lipids. http://www.jimmunol.org/ In the presence of calcium ionophore, the leukocytes convert a marginal amount of ␤-oxa-21:3n-3 to a 16-monohydroxy-␤-oxa- 21:3n-3 derivative. After administration to rodents by gavage or i.p. injection, ␤-oxa-21:3n-3 is found to be incorporated into the lipids of various tissues. Thus, ␤-oxa-21:3n-3 has the potential to be used in the treatment of inflammatory diseases, which are mediated by products of the lipoxygenase pathway. The Journal of Immunology, 2003, 171: 4773–4779. olyunsaturated fatty acids (PUFA)4 are ubiquitous compo- idation (6). Apart from their important role as structural compo- nents of mammalian cell membranes, where they are gen- nents and as a source of energy, some of these fatty acids, in erally esterified in phospholipids and neutral lipids (1). In particular eicosatetraenoic acid (arachidonic acid, 20:4n-6) and ei- P by guest on September 25, 2021 addition to membranes, another PUFA-bearing domain in cells can cosapentaenoic acid (20:5n-3), act as precursors of physiologically be lipid bodies, which are lipid-rich cytoplasmic inclusions (2–4). active oxygenated metabolites, collectively termed eicosanoids. Most cellular PUFA are derived from the essential dietary fatty These include prostaglandins, thromboxanes, prostacyclins (cyclo- acids, octadecadienoic acid (linoleic acid, 18:2n-6) and octadeca- oxygenase products), hydroxylated fatty acids, leukotrienes, li- trienoic acid (␣-linoleic acid, 18:3n-3) by the process of chain poxins (lipoxygenase products), and epoxygenated fatty acids (ep- elongation and desaturation (5) and are mainly degraded by ␤-ox- oxygenase products) (7–11). When leukocytes such as neutrophils are challenged with certain agonists, the formation of leukotrienes is initiated by the release of *Department of Immunopathology, Women’s and Children’s Hospital, North Ad- 20:4n-6 from phospholipids by the activation of phospholipase A2. elaide, South Australia, Australia; and †Department of Pediatrics, University of Ad- elaide, South Australia, Australia; ‡School of Pharmaceutical, Molecular and Bio- The unesterified 20:4n-6 then undergoes 5-lipoxygenation to 5-hy- sciences, University of South Australia, Australia; §Department of Chemistry, droperoxyeicosatetraenoic acid (5-HPETE), which is further con- Flinders University of South Australia, Bedford Park, South Australia, Australia; verted to an unstable epoxide leukotriene A (LTA ). This inter- ¶Research School of Chemistry, Australian National University, Canberra, Australian 4 4 ʈ Capital Territory, Australia; and Peptech Ltd., North Ryde, New South Wales, Aus- mediate can be enzymatically hydrolyzed to LTB4. Alternatively, tralia LTA4 is transformed, by the addition of glutathione at C-6, into Received for publication April 4, 2003. Accepted for publication August 12, 2003. leukotriene C4 (LTC4). Stepwise enzymatic elimination of glu- The costs of publication of this article were defrayed in part by the payment of page tamic acid and glycine in the peptide side chain leads to formation charges. This article must therefore be hereby marked advertisement in accordance of LTD and LTE , respectively (9–11). The presumed asthma with 18 U.S.C. Section 1734 solely to indicate this fact. 4 4 mediator slow-reacting substance of anaphylaxis has now been 1 This work was supported by the National Health and Medical Research Council of Australia, the National Heart Foundation of Australia, and the Adelaide Women’s and identified as a biological activity composed of LTC4, LTD4, and Children’s Hospital Research Foundation. LTE4 (cysteinyl-leukotrienes), which are all potent bronchocon- 2 Current addresses: Bionomics Ltd., 31 Dalgleish Street, Thebarton, South Australia strictors (12–14). In addition, these leukotrienes have been impli- 5031, Australia. cated in hypoxic vasoconstriction and the pathophysiology of re- 3 Address correspondence and reprint requests to Prof. A. Ferrante, Department of Im- spiratory distress syndromes (15). The closely related compound, munopathology, Women’s and Children’s Hospital, 72 King William Road, North Ad- elaide, South Australia 5006, Australia. E-mail address: [email protected] LTB4, is a potent mediator of leukocyte-dependent inflammation 4 Abbreviations used in this paper: PUFA, polyunsaturated fatty acid(s); DPC, di- (16, 17) and hence is important for the inflammatory component of palmitoylphosphatidylcholine; GLC, gas-liquid chromatography; LTB4, leukotriene asthma and other pulmonary afflictions. B4; MS, mass spectrometry; 20:4n-6, eicosatetraenoic acid (arachidonic acid); 22: 6n-3, docosahexaenoic acid; 20:5n-3, eicosapentaenoic acid; NDGA, nordihydroguai- Our recent studies have shown that PUFA also have the ability aretic acid. to directly stimulate leukocytes (neutrophils and macrophages) to Copyright © 2003 by The American Association of Immunologists, Inc. 0022-1767/03/$02.00 ␤ 4774 INHIBITION OF NEUTROPHIL LTB4 PRODUCTION BY A -OXA PUFA release superoxide, degranulate, adhere, and display increased ex- HBSS by sonication (19). Controls contained micelles of DPC alone sim- pression of CR3 receptors (18–20). We have observed that the ilarly diluted. TLC and gas-liquid chromatography (GLC)-mass spectrom- modulation of biological activity induced by PUFA is related to etry (MS) indicated that the lipids were of high purity. Agonists and media were shown to be free of endotoxin contamination using the Limulus ame- their structure (21). These effects of naturally occurring PUFA on bocyte lysate assay. In the TLC analysis the oxa fatty acid is UV active, neutrophils are clearly proinflammatory and therefore would ex- such that when the TLC plate is sprayed with dichlorofluorescein and acerbate the asthmatic state. viewed under UV light, it quenches the fluorescence of the dichlorofluo- 20:5n-3 and docosahexaenoic acid (22:6n-3), which are prom- rescein to show up as a dark purple spot on a green background. inent in diets enriched with fish oil, competitively inhibit the con- Isolation of neutrophils version of 20:4n-6 to eicosanoids. With respect to leukotriene Human neutrophils were isolated from the peripheral blood of healthy vol- products of the 5-lipoxygenase pathway in leukocytes, LTB5, the unteers by the rapid single-step method described by Ferrante and Thong dihydroxy derivative of 20:5n-3 formed from LTA5, is a weak and (32) in which the blood was layered onto Ficoll-Hypaque
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