Disease relevance of AI3-36443

• Palmitoleic acid in erythrocytes from carriers of Duchenne muscular dystrophy [1].
• Our results indicate that three nonessential fatty acids--stearic acid, palmitoleic acid, and omega 9 eicosatrienoic acid, and one essential fatty acid--dihomogammalinolenic acid, are independent correlates of blood pressure among middle-aged American men at high risk of coronary heart disease [2].
• Plasma palmitoleic acid content and obesity in children [3].
• On the other hand, application of unsaturated fatty acids, oleic acid, and palmitoleic acid induced scaly skin, abnormal keratinization, and epidermal hyperplasia [4].
• Potentiometric studies demonstrate that the heme iron reduction potential becomes progressively more positive as the proportion of high-spin heme iron increases (potential for low-spin BioI = -330 +/- 1 mV; for BioI as purified from E. coli (mixed-spin) = 228 +/- 2 mV; for palmitoleic acid-bound BioI = -199 +/- 2 mV) [5].

Psychiatry related information on AI3-36443

• The results show that palmitoleic acid is strongly associated with alcohol consumption and blood pressure and that its association with blood pressure is absent in nondrinkers [6].

High impact information on AI3-36443

• Erythrocyte membranes from heterozygous carriers of Duchenne muscular dystrophy exhibit a diminished amount of palmitoleic acid when compared to membranes from normal subjects [7].
• In contrast, unsaturated fatty acids such as palmitoleic acid (16:1), oleic acid (18:1), linoleic acid (18:2), linolenic acid (18:3), arachidonic acid (20:4), all of which were detected in the particulate fraction, or longer chained unsaturated fatty acids inhibited PLA2 activity by 50% at approximately equal to 5 X 10(-7) M [8].
• Evidence for cytochrome f involvement in eggplant cell death induced by palmitoleic acid [9].
• Additionally, palmitic acid but not palmitoleic acid decreased the expression of the mitochondrial adenine nucleotide translocator and induced release of cytochrome c from the mitochondria into the cytosol [10].
• In contrast, monounsaturated palmitoleic acid alone (0.5 mmol/l) or in combination with palmitic acid (0.25 or 0.5 mmol/l each) did not affect DNA fragmentation [10].

Chemical compound and disease context of AI3-36443

• Pseudomonas oleovorans contains an isomerase which catalyzes the cis-trans conversion of the abundant unsaturated membrane fatty acids 9-cis-hexadecenoic acid (palmitoleic acid) and 11-cis-octadecenoic acid (vaccenic acid) [11].
• In a prospective study, patients with arrhythmias (n = 106) had higher levels of long-chain saturated fatty acids (32.1 +/- 0.5% vs 30.7 +/- 0.4%, p less than 0.05) and of stearic acid (4.9 +/- 0.2% vs 4.4 +/- 0.1%, p less than 0.02) and a lower concentration of palmitoleic acid (7.3 +/- 0.3% vs 8.1 +/- 0.2%, p less than 0.005) [12].
• Alleviation of the cytotoxic activity induced by trans10, cis12-conjugated linoleic acid in rat hepatoma dRLh-84 cells by oleic or palmitoleic acid [13].
• Liver biotin and palmitoleic acid levels in the fatty liver and kidney syndrome of chickens [14].

Biological context of AI3-36443

• We have now found that this preparation catalyzes the epoxidation as well as the hydroxylation of palmitoleic acid and a variety of other monounsaturated fatty acids [15].
• BACKGROUND: Palmitoleic acid (16:1n-7) is a product of endogenous lipogenesis [3].
• However, the gap junction inhibitors carbenoxolone (100 microM) and palmitoleic acid (50 microM) did not affect vasorelaxation to anandamide [16].
• Increasing concentrations of palmitoleic acid from 10 to 100 microM increased hydrolysis of [3H]cAMP with maximal activation (60%) at 100 microM; higher concentrations were inhibitory [17].
• Thus, we wanted to investigate electrophysiology and anisotropy in aged vs. young rabbit heart, as well as the response to the gap junction uncoupler palmitoleic acid [18].

Anatomical context of AI3-36443

• The respiratory rate of mitochondria was not decreased at lower levels of oleic or palmitoleic acid in lipids, although respiratory control was lower when the mole % of unsaturated fatty acid was lower [19].
• This wave spread through gap junctions since it was inhibited by the cell uncoupler palmitoleic acid [20].
• Palmitoleic acid is a minor monounsaturated fatty acid in the human diet and in blood plasma [21].
• Differences in indexes of insulin sensitivity lost significance after percent dietary intake of palmitic acid, palmitoleic acid, and skeletal muscle protein abundance of IRbeta were accounted for [22].
• In adipose tissue of obese patients only minor differences were found in palmitoleic acid, which was increased, and in the saturated fatty acids with 14, 16 and 18 carbon atoms which were decreased [23].

Associations of AI3-36443 with other chemical compounds

• Based on the lability of the bond in the presence of methanolic KOH or hydroxylamine (pH 8), we propose that [3H] palmitoleic acid is attached to proteins via a thioester linkage [24].
• The unsaturated fatty acid (UFA) composition of S. cerevisiae is relatively simple, consisting almost exclusively of the mono-UFAs palmitoleic acid (Delta(9)Z-C(16:1)) and oleic acid (Delta(9)Z-C(18:1)), with the former predominating [25].
• Arteriolar dilations to ACh were also inhibited by intraluminal administration of the Ca(2+)-activated K(+) (K(Ca)) channel blockers charybdotoxin plus apamin or by palmitoleic acid, an uncoupler of myoendothelial gap junctions without affecting changes in endothelial [Ca(2+)](i) [26].
• The CYP450 inhibitors 7-ethoxyresorufin and sulfaphenazole and the gap junction inhibitor palmitoleic acid, but not 18alpha-glycyrrhetinic acid, inhibited thapsigargin vasodilation in normotensive lungs [27].
• The subcutaneous adipose tissue of genetically obese mice (ob/ob) differs from that of lean littermates not only by virtue of its larger cells but also in its fatty acid composition; it contains a higher proportion of palmitoleic acid and a lower proportion of linoleic acid [28].

Gene context of AI3-36443

• Fatty acid analysis showed that the ratio of palmitoleic acid to oleic acid in the Sk-OLE1-expressing S. cerevisiae strain was lower than that of the S. cerevisiae strain expressing the Sc-OLE1 gene [29].
• We have previously shown that a desaturase gene, desat1, located in chromosome region 87 C could be involved in this process: the Desat1 enzyme preferentially leads to the synthesis of palmitoleic acid, a precursor of omega7 fatty acids and 7-unsaturated hydrocarbons [30].
• Palmitoleic acid inhibited the calmodulin-stimulated activity by 50% [31].
• Recently, we found that the MeOH extract of Penicillium oxalicum showed inhibitory activity towards DNA topoisomerase I. Subsequently, ergosterol peroxide, ergosterol, palmitoleic acid, and linoleic acid were isolated from the cultured mycelia of P. oxalicum [32].
• Thus, the extent to which the substrate-free form of P450 BM3 undergoes a conformational change upon binding of a typical fatty acid substrate, palmitoleic acid, has been the subject of recent active experimental effort [33].

Analytical, diagnostic and therapeutic context of AI3-36443

• The identity of the palmitoleic acid was established by C-18 reverse phase high performance thin layer chromatography and argentation thin layer chromatography analysis after the fatty acid was liberated from the proteins by either transesterification or saponification [24].
• The supplementation of the fat-free diet with linoelaidate produced no relevant changes in the fatty acid composition pattern of liver microsomes and did not modify the percentage of conversion of palmitic to palmitoleic acid [34].
• Exogenous treatment of the cells with palmitoleic acid (16:1, cis) induced a remarkable increase of membrane lipid fluidity resulting in easier passage of modified cells through capillary vessels, which was detected in an in vitro perfusion test of the lung [35].
• The on-column detection limit (signal-to-noise ratio of 3) with proposed HPLC separation and fluorescence detection is in the range of 19 (palmitic acid)--176 fmol (palmitoleic acid) [36].
• However, in the peritoneal fluids of the cancer patients the percentage amount of palmitoleic acid (16:1) was significantly higher than that in the control group [37].

References