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Eicosapentaenoic acid derivatives

Table 3. M- and C-NMR data for the eicosapentaenoic acid derivatives (E-1 and E-2) isolated from alkali-treated EPA prepared by treatment with 70 i 5% humidity at 40 2 C for 6 months according to the methods of ICH stability testing. Table 3. M- and C-NMR data for the eicosapentaenoic acid derivatives (E-1 and E-2) isolated from alkali-treated EPA prepared by treatment with 70 i 5% humidity at 40 2 C for 6 months according to the methods of ICH stability testing.
Willumsen, N., Vaagenes, H., Holmsen, H. Beige, R.K. 19%) Biochim. Biophys. Acta-, 1369, 193-203 On the effect of 2-deuterium- and 2-methyl-eicosapentaenoic acid derivatives on triglycerides, peroxisomal P-oxidation and platelet aggregation in rats. [Pg.226]

Eicosapentaenoic acid derived isoprostanes Synthesis and discovery of two major isoprostanes... [Pg.37]

Fig. 2. (a) The basis for prostaglandin nomenclature, where the letters A—F and J define principal families (b) defines the side chains for PG derived from dihomo-y-linolenic acid (c) PG2 derived from arachidonic acid and (d), PG derived from eicosapentaenoic acid. [Pg.151]

Hybridalactone, a novel marine derived eicosanoid from Laurencia hybrida, appears to be biosynthesized by a unique pathway from eicosapentaenoic acid. The synthesis of hybridalactone was carried out enantiospecifically from (+)-bicyclo[3.2.0]hept-4-ene-l-one so as to provide proof of stereochemistry (Ref. 4). [Pg.307]

There are three groups of eicosanoids that are synthesized from C20 eicosanoic acids derived from the essential fatty acids linoleate and a-linolenate, or directly from dietary arachidonate and eicosapentaenoate (Figure 23-5). Arachidonate, usually derived from the 2 position of phospholipids in the plasma membrane by the action of phospholipase Aj (Figure 24-6)—but also from the diet—is the substrate for the synthesis of the PG2, 1X2 series (prostanoids) by the cyclooxygenase pathway, or the LT4 and LX4 series by the lipoxygenase pathway, with the two pathways competing for the arachidonate substrate (Figure 23-5). [Pg.192]

Figure 9.5 Prostaglandins (PG) and leukotrienes (LT) derived from arachidonic (n - 6) and eicosapentaenoic acid... Figure 9.5 Prostaglandins (PG) and leukotrienes (LT) derived from arachidonic (n - 6) and eicosapentaenoic acid...
EPA Eicosapentaenoic acid EpDIF Epithelial-derived inhibitory factor also known as epithelium/derived relaxant fector EPO Eosinophil peroxidase EPOR Erythropoietin receptor EPR Effector cell protease EPX Eosinophil protein X ER Endoplasmic reticulum ERCP Endoscopic retrograde cholangiopancreatography E-selectin Endothelial selectin formerly known as endothelial leucocyte adhesion molecule-1 (ELAM-1)... [Pg.282]

Colquhoun and Schumacher [98] have shown that y-linolcnic acid and eicosapentaenoic acid, which inhibit Walker tumor growth in vivo, decreased proliferation and apoptotic index in these cells. Development of apoptosis was characterized by the enhancement of the formation of reactive oxygen species and products of lipid peroxidation and was accompanied by a decrease in the activities of mitochondrial complexes I, III, and IV, and the release of cytochrome c and caspase 3-like activation of DNA fragmentation. Earlier, a similar apoptotic mechanism of antitumor activity has been shown for the flavonoid quercetin [99], Kamp et al. [100] suggested that the asbestos-induced apoptosis in alveolar epithelial cells was mediated by iron-derived oxygen species, although authors did not hypothesize about the nature of these species (hydroxyl radicals, hydrogen peroxide, or iron complexes ). [Pg.756]

Dietary polyunsaturated fatty acids (PUFAs), especially the n-3 series that are found in marine fish oils, modulate a variety of normal and disease processes, and consequently affect human health. PUFAs are classified based on the position of double bonds in their lipid structure and include the n-3 and n-6 series. Dietary n-3 PUFAs include a-linolenic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA) whereas the most common n-6 PUFAs are linoleic acid, y-linolenic acid, and arachidonic acid (AA). AA is the primary precursor of eicosanoids, which includes the prostaglandins, leukotrienes, and thromboxanes. Collectively, these AA-derived mediators can exert profound effects on immune and inflammatory processes. Mammals can neither synthesize n-3 and n-6 PUFAs nor convert one variety to the other as they do not possess the appropriate enzymes. PUFAs are required for membrane formation and function... [Pg.192]

Lipids can be oxidized by some ROS such as hydroxyl ( OH). but not by H202, NO, or 02 - (Halliwell and Gutteridge 1999). However, both enzymatic and nonenzymatic cellular mechanisms can oxidize fatty acids. Challenging L. digitata sporophytes with lipopolysaccharides from various sources resulted in a rapid release of free fatty acids (FFAs) with a concomitant accumulation of oxidized derivatives of linolenic (08 2) and eicosapentaenoic acid (C20 5) (Kiipper et al. 2006). Other strong inducers of the oxidative burst, such as oligoguluronates, in Laminaria could induce neither the release of FFAs nor the oxylipin production. These results... [Pg.255]

The conversion of oleoyl-CoA to linoleoyl-CoA is accomplished by some insects118 but does not take place in most animals. As a result of this biosynthetic deficiency, polyunsaturated fatty acids such as linoleic, linolenic, and the C20 arachidonic acid are necessary in the diet (Box 21-B). One essential function of linoleic acid is to serve as a precursor of prostaglandins and related prostanoids (Section D). Dietary linoleate is converted to its Co A derivative and then by sequential A6 desaturation,119 elongation, and then A5 desaturation, to the 20 4 (A5 8 11 14) arachidonoyl-CoA (Fig. 21-2, lower right). These acids are referred to as 0)6 because of the position of the last double bond. Linolenic acid can be converted in an analogous fashion to the CoA derivative of the 20 5 (A5 8 11 14 17 co6) eicosapentaenoic acid (EPA). The 22 6 docasahexaenoic acid (DHA Fig. 21-2) is apparently formed by elongation of the 22 5 acyl-CoA to 24 5, desaturation, transfer to a peroxisome or mitochondrion, and p oxidation to shorten the chain.953... [Pg.1193]

Either native winterized or concentrated whole-body fish oils or fish liver oils have been utilized in most studies as dietary source of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). The physiological effects and possible health benefits of administered fish oils generally have been attributed to either EPA or DHA alone or to a synergistic effect between the two. As a result, there has been controversy over the contribution of individual fish oil constituents to particular pharmacological actions and the optimal dosages required for achieving established and/or suspected beneficial effects. The predominant marine triglyceride-derived m-3-fatty acids are all-cA-5,8,11,14,17-eicosapentaenoic acid (C20 5i3, EPA) and all-ci.v-4,7,10,13,16,19-docosa-hexaenoic acid (C22 6,3, DHA). [Pg.198]

Kragballe, K., P. Voorhees, C.R. Darley, and E.J. Goetzl, Leukotriene B5 derived from eicosapentaenoic acid does not stimulate DNA synthesis of cultured human keratinocytes but inhibits the stimulation induced by leukotriene B4. J. Invest. Dermatol., 1985, 84. [Pg.143]

The mammalian organism is unable to introduce double bonds at fatty acids, and this is probably why these families must be present in the diet. These fatty acids can be desaturated and elongated (see Chapter 19) to form derived essential fatty acids, dihomo-T-linoleic acid (20 3o>6), arachidonic acid (20 4ft)6), and eicosapentaenoic acid (20 5ft>3), the three direct precursor acids of PGs. Dihomo-r-linoleic acid, an intermediate in the biosynthesis of arachidonic acid from linoleic acid, is the precursor of PGs of the 1 series. Arachidonic acid and eicosapentaenoic acid are precursors of PGs of the 2 series and 3 series, respectively. [Pg.428]

Cw-polyenoic acids are present at low concentrations in milk fat, because of the biohydrogenation reactions that take place in the rumen. These acids are comprised almost exclusively of linoleic acid (9c, 12c-18 2), about 1.2 to 1.7% and a-linolenic acid (9c, 12c, 15c-18 3), about 0.9 to 1.2% (Table 1.2). These two fatty acids are essential fatty acids they cannot be synthesised within the body and must be supplied by the diet. In recent times, the usage of the term essential has been extended to include derivatives of these fatty acids, which are not synthesised in significant quantities (e.g., eicosapentaenoic acid, 20 5 and docosahexaenoic acid, 22 6). The proportion of a-linolenic acid appears to be affected by the cow s diet the concentration is higher in milk from pasture-fed cows than in milk from barn-fed cows (Hebeisen et al., 1993 Wolff et al., 1995). In the case of linoleic... [Pg.6]

Arita M, Yoshida M, Hong S, Tjonahen E, GUckman JN, Peta-sis NA, Blumberg RS, Serhan CN. Resolvin El, an endogenous Upid mediator derived from omega-3 eicosapentaenoic acid, protects against 2,4,6-trinitrobenzene sulfonic acid-induced colitis. Proc.Natl.Acad.Sci.U.S.A. 2005 102 7671-676. [Pg.874]

The essential dietary fatty acids include linolenic acid (LA, C18 2 co6) and alpha-linolenic acid (LN, C18 3 oo3). Mammals are missing a fatty acid desaturase capable of introducing a double bond between C9 and the methylene end of the fatty acid. Hence, to synthesize essential HUFAs, LA and LN are both required in the diet (Fig. lb). LA is the precursor to arachi-donic acid (AA, C20 4 006) and derivative eicosanoids, whereas LN is the precursor to eicosapentaenoic acid (EPA, C20 5 oo3), docosahexaenoic acid (DHA,C22 6 oo3), and oo3-derived... [Pg.884]

Antitumor and antimetastatic actions of eicosapentaenoic acid (EPA) ethylester and its new EPA derivatives [17,18/... [Pg.45]

The four groups of eicosanoids are derived, respectively, from a 20-carbon fatty acid with three, four, or five double bonds 8,11,14-eicosatrienoic acid (dihomo-y-linolenic acid), 5,8,11,14-eicosatetraenoic acid (arachi-donic acid), and 5,8,11,14,17-eicosapentaenoic acid (Figure 18-17). In humans, the most abundant precursor is arachidonic acid. Secretion of eicosanoids in response... [Pg.389]

The aromas associated widi very fi esh fish are usually mild, delicate and fi esh (53,54), and generally described as green (hexanal), melon-like ((E,Z)-3,6-nonadienal), iodine-like (bromophenols). Fresh fish and seafood aromas are due to volatile carbonyls and derive fi om lipoxygenase catalyzed oxidation of polyunsaturated fatty acids. The oxidation of Eicosapentaenoic acid (C20 5) leads to C5 to C9 alcohols, aldehydes, ketones and hydrocarbons. The formation of methyl mercaptan, dimethyl sulfide and dimethyl disulfide in fi esh fish at the time of harvest has been reported by Shiomi et al. (55). Although these compounds are usually associated with fish deterioration, they contribute to the fi esh aroma ch cter at low concentrations. For instance, dimethyl sulfide is... [Pg.15]

If sufficient scientific evidence is not available to calculate an Estimated Average Requirement, a reference intake called an Adequate Intake (Al) is used instead of a Recommended Dietary Allowance. The Al is a value based on experimentally derived intake levels or approximations of observed mean nutrient intakes by a group (or groups) of healthy people. The Al for children and adults is expected to meet or exceed the amount needed to maintain a defined nutritional state or criterion of adequacy in essentially all members of a specific healthy population LA = linoleic acid LNA = n-linolenic acid DHA = docosahexaenoic acid EPA = eicosapentaenoic acid TRANS-EA = trans fatty acids SAT = saturated fatty acids MONOs = monounsaturated fatty acids. [Pg.21]


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See also in sourсe #XX -- [ Pg.47 ]

See also in sourсe #XX -- [ Pg.47 ]




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