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      Factors Influencing the Eicosanoids Synthesis In Vivo

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          Abstract

          External factors activate a sequence of reactions involving the reception, transduction, and transmission of signals to effector cells. There are two main phases of the body's reaction to harmful factors: the first aims to neutralize the harmful factor, while in the second the inflammatory process is reduced in size and resolved. Secondary messengers such as eicosanoids are active in both phases. The discovery of lipoxins and epi-lipoxins demonstrated that not all arachidonic acid (AA) derivatives have proinflammatory activity. It was also revealed that metabolites of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) such as resolvins, protectins, and maresins also take part in the resolution of inflammation. Knowledge of the above properties has stimulated several clinical trials on the influence of EPA and DHA supplementation on various diseases. However, the equivocal results of those trials prevent the formulation of guidelines on EPA and DHA supplementation. Prescription drugs are among the substances with the strongest influence on the profile and quantity of the synthesized eicosanoids. The lack of knowledge about their influence on the conversion of EPA and DHA into eicosanoids may lead to erroneous conclusions from clinical trials.

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          Omega-3 fatty acids in health and disease and in growth and development.

          A. P. Simopoulos (1991)
          Several sources of information suggest that man evolved on a diet with a ratio of omega 6 to omega 3 fatty acids of approximately 1 whereas today this ratio is approximately 10:1 to 20-25:1, indicating that Western diets are deficient in omega 3 fatty acids compared with the diet on which humans evolved and their genetic patterns were established. Omega-3 fatty acids increase bleeding time; decrease platelet aggregation, blood viscosity, and fibrinogen; and increase erythrocyte deformability, thus decreasing the tendency to thrombus formation. In no clinical trial, including coronary artery graft surgery, has there been any evidence of increased blood loss due to ingestion of omega 3 fatty acids. Many studies show that the effects of omega 3 fatty acids on serum lipids depend on the type of patient and whether the amount of saturated fatty acids in the diet is held constant. In patients with hyperlipidemia, omega 3 fatty acids decrease low-density-lipoprotein (LDL) cholesterol if the saturated fatty acid content is decreased, otherwise there is a slight increase, but at high doses (32 g) they lower LDL cholesterol; furthermore, they consistently lower serum triglycerides in normal subjects and in patients with hypertriglyceridemia whereas the effect on high-density lipoprotein (HDL) varies from no effect to slight increases. The discrepancies between animal and human studies most likely are due to differences between animal and human metabolism. In clinical trials eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) in the form of fish oils along with antirheumatic drugs improve joint pain in patients with rheumatoid arthritis; have a beneficial effect in patients with ulcerative colitis; and in combination with drugs, improve the skin lesions, lower the hyperlipidemia from etretinates, and decrease the toxicity of cyclosporin in patients with psoriasis. In various animal models omega 3 fatty acids decrease the number and size of tumors and increase the time elapsed before appearance of tumors. Studies with nonhuman primates and human newborns indicate that DHA is essential for the normal functional development of the retina and brain, particularly in premature infants. Because omega 3 fatty acids are essential in growth and development throughout the life cycle, they should be included in the diets of all humans. Omega-3 and omega 6 fatty acids are not interconvertible in the human body and are important components of practically all cell membranes. Whereas cellular proteins are genetically determined, the polyunsaturated fatty acid (PUFA) composition of cell membranes is to a great extent dependent on the dietary intake.(ABSTRACT TRUNCATED AT 400 WORDS)
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            Myeloid-derived suppressor cell heterogeneity and subset definition.

            Elisa Peranzoni, Serena Zilio, Ilaria Marigo … (2010)
            Myeloid derived suppressor cells (MDSCs) are defined in mice on the basis of CD11b and Gr-1 marker expression and the functional ability to inhibit T lymphocyte activation. Nevertheless the term 'heterogeneous' remains the first, informal feature commonly attributed to this population. It is clear that CD11b(+)Gr-1(+) cells are part of a myeloid macropopulation, which comprises at least two subsets of polymorphonuclear and monocytic cells with different immunosuppressive properties. While recent literature shows substantial agreement on the immunoregulatory property of the monocytic MDSC subset, there is still contrasting evidence on the role of the granulocytic fraction. Moreover, this dichotomy holds true for human MDSCs. We attempt here to summarize conflicting findings in the field and provide some possible, unifying explanations. Copyright 2010 Elsevier Ltd. All rights reserved.
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              Resolvin D1 and its aspirin-triggered 17R epimer. Stereochemical assignments, anti-inflammatory properties, and enzymatic inactivation.

              Yee-Ping Sun, Sungwhan F. Oh, Jasim Uddin … (2007)
              We recently uncovered two new families of potent docosahexaenoic acid-derived mediators, termed D series resolvins (Rv; resolution phase interaction products) and protectins. Here, we assign the stereochemistry of the conjugated double bonds and chirality of alcohols present in resolvin D1 (RvD1) and its aspirin-triggered 17R epimer (AT-RvD1) with compounds prepared by total organic synthesis. In addition, docosahexaenoic acid was converted by a single lipoxygenase in a "one-pot" reaction to RvD1 in vitro. The synthetic compounds matched the physical and biological properties of those enzymatically generated. RvD1 proved to be 7S,8R,17S-trihydroxy-4Z,9E,11E,13Z,15E,19Z-docosahexaenoic acid, AT-RvD1 matched 7S,8R,17R-trihydroxy-4Z,9E,11E,13Z,15E,19Z-docosahexaenoic acid, and they both stopped transendothelial migration of human neutrophils (EC(50) approximately 30 nM). In murine peritonitis in vivo, RvD1 and AT-RvD1 proved equipotent (at nanogram dosages), limiting polymorphonuclear leukocyte infiltration in a dose-dependent fashion. RvD1 was converted by eicosanoid oxidoreductase to novel 8-oxo- and 17-oxo-RvD1 that gave dramatically reduced bioactivity, whereas enzymatic conversion of AT-RvD1 was sharply reduced. These results establish the complete stereochemistry and actions of RvD1 and AT-RvD1 as well as demonstrate the stereoselective basis for their enzymatic inactivation. RvD1 regulates human polymorphonuclear leukocyte transendothelial migration and is anti-inflammatory. When its carbon 17S alcohol is enzymatically converted to 17-oxo-RvD1, it is essentially inactive, whereas the 17R alcohol configuration in its aspirin-triggered form (AT-RvD1) resists rapid inactivation. These results may contribute to the beneficial actions of aspirin and omega-3 fish oils in humans.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Biomed Res Int
                Journal ID (iso-abbrev): Biomed Res Int
                Journal ID (publisher-id): BMRI
                Title: BioMed Research International
                Publisher: Hindawi Publishing Corporation
                ISSN (Print): 2314-6133
                ISSN (Electronic): 2314-6141
                Publication date (Print): 2015
                Publication date (Electronic): 11 March 2015
                Volume: 2015
                Electronic Location Identifier: 690692
                Affiliations
                1Department of Propaedeutic Oncology, Faculty of Health Sciences, Medical University of Gdańsk, Powstania Styczniowego 9b, 81-519 Gdynia, Poland
                2Department of Surgical Oncology, Gdynia Oncology Center, PCK's Maritime Hospital in Gdynia, Powstania Styczniowego 1, 81-519 Gdynia, Poland
                Author notes
                *Jarosław Szefel: jaszefel@ 123456mp.pl

                Academic Editor: Beverly Muhlhausler

                Author information
                http://orcid.org/0000-0002-2434-3599
                Article
                DOI: 10.1155/2015/690692
                PMC ID: 4377373
                PubMed ID: 25861641
                SO-VID: 3311d2ce-b89d-49e1-9bf2-d7c87929e76c
                Copyright © Copyright © 2015 Jarosław Szefel et al.
                License:

                This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

                History
                Date received : 19 November 2014
                Date accepted : 24 February 2015
                Categories
                Subject: Review Article

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