U>-Unsaturated fatty acids

Tor TAG shorthand description P = palmitic acid S = stearic acid O = oleic acid L = linoleic acid U = unsaturated fatty acid. 

S, saturated fatty acids and U, unsaturated fatty acids. TAG, triacylglycerol. 

In contrast to the composition of triacylglycerols found in beef fat (Table 3.13), lard contains fewer triacylglycerols of the type SSS and more of the types SUU, USU and UUU (S = saturated U = unsaturated fatty acid). As a consequence, lard melts at lower temperatures and over a range of temperatures rather than sharply at a single temperature, and its shelf life is not particularly long. In comparison with beef, pig depot fat... 

S = Saturated fatty acid, U = unsaturated fatty acid. Fat contains mainiy iauric and myristic acids. ... 

Phthalic anhydride, a polyol, and an unsaturated fatty acid are usually copolymerized to unsaturated polyesters for coating purposes. Many other combinations in variable ratios are possible for preparing these resins. The 1998 U.S. production of polyesters was approximately 1.7 billion pounds. 

Figure 41-3. Diagrammatic representation of a phospholipid or other membrane lipid. The polar head group is hydrophilic, and the hydrocarbon tails are hydrophobic or lipophilic. The fatty acids in the tails are saturated (S) or unsaturated (U) the former are usually attached to carbon 1 of glycerol and the latter to carbon 2. Note the kink in the tail of the unsaturated fatty acid (U), which is important in conferring increased membrane fluidity.

Jacobs, P.A., Maes, P., Paulussen, S.J., Tielen, M., Van Steenkiste, D.F.E., and Van Looveren, L.K. (2001) Elimination of trans-unsaturated fatty acid compounds by selective adsorption with zeolites. U.S. Patent 6,229,032. 

Warensjo, E., Riserus, U., Gustafsson, I. B., Mohsen, R., Cederholm, T., and Vessby, B. (2008). Effects of saturated and unsaturated fatty acids on estimated desaturase activities during a controlled dietary intervention. Nutr. Metab. Cardiovasc. Dis. 18, 683-690. 

A few years ago, we began a research program to develop methods of analysis which would involve the use of FAB and a high performance tandem mass spectrometer. The tandem instrument was the first triple sector mass spectrometer to be designed and built by a commercial instrument company (Kratos of Manchester, U.K.). The first mass spectrometer of the combination is a double focussing Kratos MS-50 which is coupled to a low resolution electrostatic analyzer, which serves as the second mass spectrometer U). This FAB MS-MS combination has been used to verify the structures of an unknown cyclic peptide (2), a new amino acid modified by diphtheria toxin (3), and an ornithine-containing lipid (4). A number of methods have also been worked out which rely on this instrumentation. They Include the structural determination of cyclic peptides (5), nucleosides and nucleotides (6), and unsaturated fatty acids (7) and the analysis of mixtures of both anionic (8) and cationic surfactants (9). 

The spectroscopic and synthetic investigations suggested that these two compounds A and B were novel unsaturated methylketones determined as 5Z, Z,11Z)- and (5 E,8jZ,llZ)-5,8, ll-tetradecatrien-2-one, respectively (10). They are stereoisomers to each other, compound A having the same partial structure and configuration as that of a u-3 fatty acid. 

Triacylglycerols are named in various ways. For example, unsaturated fatty acids sometimes are indicated as U and the saturated as S. If glycerol is completely esterified with stearic acid, the resulting monoacid TAG may be designated as SSS, or, more descriptively as StStSt, tristearin, tristearoylglycerol, or glycerol tristearate. 

Ballou LR, and Oreung WY. (1985). Inhibition of human platelet phospholipase A2 activity by unsaturated fatty acids. Proc. Natl. Acad. Sci. U.S.A. 82,371-375. 

The mixed-acid TAG containing saturated fatty acids at the sn-1 and sn-3 glycerol carbon positions and unsaturated fatty acids at the sn-2 position, namely the St-U-St TAG, chain-chain interactions among the saturated and unsaturated fatty acid moieties, or within every saturated or unsaturated moieties, play critical roles in their complicated polymorphic transformations. Precise observation was recently... 

Riserus, U., Basu, S., Jovinge, S., Fredrikson, G.N., Aralov, J., and Vessby, B. 2002. Supplementation with conjugated linoleic acid causes isomer-dependent oxidative stress and elevated C-reactive protein A potential link to fatty acid-induced insulin resistance. Circulation 106, 1925-1929. Rossetti, R.G., Seiler, C.M., DeLuca, P., Laposata, M., and Zurier, R.B. 1997. Oral administration of unsaturated fatty acids Effects on human peripheral blood T lymphocyte proliferation. J. Leukoc. Biol 62, 438-443. 

The answer is e. (Murray, pp 230-267. Scrivei pp 2297-2326. Sack, pp 121-138. Wilson, pp 287-320.) In mammals, a variety of fatty acids are considered essential and cannot be synthesized. These include linoleate (C-I8 cis-A , A h and linolenate (C-I8 cis-A , A u A h Either these fatty acids or fatty acids for which they are precursors must be supplied in the diet as starting points lor synthesis of a variety ol other unsaturated fatty acids that lead to the synthesis of prostaglandins, thromboxanes, and leukotrienes. For example, arachidonate, a 20-carbon fatty acid with four... 

McCloy U, Cunnane SC, Pencharz PB. Metabolism of C unsaturated fatty acids by healthy women. FASEB, 2000, in press. 

Galliard and Matthew (5) have reported the biogenesis of C15, C14, C13 and C12-saturated fatty aldehydes from palmitic acid in cucumber fruits. However, that of the unsaturated Cn-aldehydes such as (Z, Z, Z)-8,11,14-heptadecatrienal, (Z, Z)-8, 11-heptadecadienal and (Z)-8-heptadecenal had not been studied so far. Thus, the enzymatic formation of the long-chain aldehydes from unsaturated fatty acids in a green seaweed, U. pertusa, was explored. 

Enzymatic Formation of Long-Chain Fatty Aldehydes in a Green Seaweed U. pertusa. In preliminary experiments, they were found to increase during incubations of unsaturated fatty acids with homogenates of U. pertusa fronds. The acetone powder preparations from the homogenates were shown to retain this activity (20). Thus, enzyme solutions solubilized from the acetone powders with 0.1% Triton X-100 were used as a source of the enzyme activity. The products, (Z)-8-heptadecenal, (Z, Z)-8, 11-heptadecadienal and (Z, Z, Z)-8, 11, 14-heptadecatrienal and pentadecanal, were identified by GC and GC-MS analysis using authentic specimens... 

Long chain fatty aldehydes such as (Z)-8-heptadecenal, (Z, Z)-8, 11-heptadeca-dienal and (Z, Z, Z)-8,11,14-heptadecatrienal have been identified as major volatile compounds in the Ulvaceae essential oils (4). They have been shown to be produced enzymatically from unsaturated fatty acids in the field fronds of U. pertusa collected from the sea (20,29). Thus, it remained to establish unequivocally that the enzymatic activity does not derive from the attached bacteria or other epiphytes. 

Schematic structure of the calmodulin (CaM)-activated plasma membrane Ca -ATPase of erythrocytes. Some molecular characteristics are = 138,000 transport rate (30°C), 20-70 Ca " ions per protein molecule per second KMlCa " ) = 0.5 /u,M (cytoplasmic side in high-affinity form) Ca /ATP ratio, 1( ) activated not only by CaM but also by acidic phospholipids and unsaturated fatty acids. Figure kindly provided by R. Moser and E. Carafoli.

Ou, J., Tu, H., Shan, B., Luk, A., DeBose-Boyd, R.A., Bashmakov, Y, Goldstein, J.L., Brown, M.S. 2001. Unsaturated fatty acids inhibit transcription of the sterol regulatory element-binding protein-lc (SREBP-lc) gene by antagonizing ligand-dependent activation of the LXR. Proc. Natl. Acad. Sci. U.S.A. 98 6027-6032. 

The United States currently produces over 3.1 billion bushels of soybeans per year (The American Soybean Association, 2007). In 2006, over one-third (1.1 billion bushels) of the crop was exported, while the remainder was sold on the domestic market. Of the edible soybean products in the U.S. market, the consumption of soybean oil (SBO) is greatest U.S. production of SBO has surpassed 20 billion pounds per year (The American Soybean Association, 2007). SBO is the major edible oil in the United States and represented 75% of the total edible oils and fats consumed in 2006. The predominant dietary sources of SBO are salad and cooking oil (48%) and baking and frying fats (34%). SBO has a unique fatty acid profile it is comprised predomi-nandy of unsaturated fatty acids including monounsaturated fatty acids (MU FA) and polyunsaturated fatty acids (PUFA), of which the predominant PUFA is linoleic acid (LA), and to a much lesser extent, a-linolenic acid (ALA). 

Metzger, J.O., and U. Linker, Synthesis of Linear and Branched Perfluoroalkylated Carboxylic Acids by Radical Addition of PerfluoroaUcyl Iodides to Unsaturated Fatty Acids, Liebigs Ann. Chem., 209-216 (1992). 

Nylon 9 or poly(co-pelargonamide) is produced in Russia together with nylon 7, poly(ami-noenanthic acid) as described above. In the U.S., Kohlhase, Pryde, and Cowan developed a route to nylon 9 via ozonolysis of unsaturated fatty acids like those that can be obtained from soybean oil. The glycerol fatty acid esters of oleic, linoleic, and linolenic acids are transesterified with methanol to form methyl esters. The esters are then cleaved via ozonolysis to yield methylazelaldehyde and byproducts that are removed. The purified product is reacted with ammonia and then reduced over Raney nickel to yield a methyl ester of the amino acid ... 

Collomb, M., Sieber, R., Biitikofer, U. (2004). CLA isomers in milk fat from cows fed diets with high levels of unsaturated fatty acids. Lipids, 39, 355-364. 

Kratz, M., Cullen, P. and Wahrburg, U. The impact of dietary mono- and poly-unsaturated fatty acids on risk factors for atherosclerosis in humans. Eur. J. Lipid Sci. Technol. 104, 300-311 (2002). 

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