Artículos de revistas: "Linoleate"

1

Chen, Zhen-Yu, Chantale R. Menard y Stephen C. Cunnane. "Accumulation of polyunsaturates is decreased by weight-cycling: whole-body analysis in young, growing rats". British Journal of Nutrition 75, n.º 4 (abril de 1996): 583–91. http://dx.doi.org/10.1079/bjn19960161.

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Whole-body fatty acid analysis in rats has previously shown that 50–70% of dietary linoleate and α-linolenate is β-oxidized to CO2 and that this value increases with refeeding after a single episode of fasting. Our hypothesis was that repeated fasting-refeeding or weight-cycling would increase the β-oxidation of linoleate and α-linolenate thereby depleting their whole-body levels. In rats consuming 3% energy as linoleate and 0·15 % energy as α-linolenate during a 16 d balance period, 19% of the linoleate consumed accumulated in weight-cycled rats compared with 34% in the free-fed controls (P < 0.01). Similarly, 11% of the α-linolenate consumed accumulated in the weight-cycled rats compared with 22% in the controls (P < 0.01). Arachidonate and docosahexaenoate also accumulated to lower extents in the weight-cycled rats than in the controls. In contrast, whole-body accumulation of palmitate, stearate and oleate was not different between the weight-cycled group and the controls when measured as a proportion of intake or relative to weight gain. Thus, whole-body depletion of linoleate and α-linolenate did not occurper se but the partitioning of linoleate and α-linolenate was significantly altered by weight-cycling resulting in lower whole-body accumulation and higher apparent oxidation of all polyunsaturates especially linoleate and α-linolenate.

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2

Stymne, S. y A. K. Stobart. "Biosynthesis of γ-linolenic acid in cotyledons and microsomal preparations of the developing seeds of common borage (Borago officinalis)". Biochemical Journal 240, n.º 2 (1 de diciembre de 1986): 385–93. http://dx.doi.org/10.1042/bj2400385.

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The developing seeds of Borago officinalis (common borage) accumulate a triacylglycerol oil that is relatively rich in the uncommon fatty acid gamma-linolenate (octadec-6,9,12-trienoic acid). Incubation of developing, whole, cotyledons with [14C]oleate and [14C]linoleate showed that the gamma-linolenate was synthesized by the sequential desaturation of oleate—linoleate—gamma-linolenate. Microsomal membrane preparations from the developing cotyledons contained an active delta 6-desaturase enzyme that catalysed the conversion of linoleate into gamma-linolenate. Experiments were designed to manipulate the [14C]linoleate content of the microsomal phosphatidylcholine. The [14C]linoleoyl phosphatidylcholine labelled in situ was converted into gamma-linolenoyl phosphatidylcholine in the presence of NADH. The substrate for the delta 6-desaturase in borage was, therefore, the linoleate in the complex microsomal lipid phosphatidylcholine, rather than, as in animals, the acyl-CoA. This was further confirmed in experiments that compared the specific radioactivity of the gamma-linolenate, in acyl-CoA and phosphatidylcholine, that was synthesized when [14C]linoleoyl-CoA was incubated with microsomal membranes, NADH and non-radioactive gamma-linolenoyl-CoA. The delta 6-desaturase was positionally specific and only utilized the linoleate in position 2 of sn-phosphatidylcholine. Analysis of the positional distribution of fatty acids in the endogenous microsomal sn-phosphatidylcholine showed that, whereas position 1 contained substantial linoleate, only small amounts of gamma-linolenate were present. The results shed further light on the synthesis of C18 polyunsaturated fatty acids in plants and in particular its relationship to the regulation of the acyl quality of the triacylglycerols in oilseeds.

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3

Chen, Z. Y., C. R. Menard y S. C. Cunnane. "Moderate, selective depletion of linoleate and alpha-linolenate in weight-cycled rats". American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 268, n.º 2 (1 de febrero de 1995): R498—R505. http://dx.doi.org/10.1152/ajpregu.1995.268.2.r498.

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In rats, the response of adipose tissue composition to a single weight cycle (24-48 h of fasting followed by refeeding) is characterized by a decrease primarily in linoleate and alpha-linolenate, with little or no change in other fatty acids. We tested the hypothesis that during successive weight cycles caused by repeated fasting and refeeding, the depletion of linoleate and alpha-linolenate from whole body stores would be exacerbated despite their adequate availability during the refeeding period. Four complete weight cycles (24-h fasting followed by 72-h ad libitum refeeding) induced a significant quantitative decrease in total n-3 and n-6 polyunsaturates, particularly linoleate and alpha-linolenate, and a simultaneous increase in the accumulation of palmitate, palmitoleate, and oleate in carcass total lipids and in perirenal and epididymal adipose tissue. A significant positive relationship was observed between the increasing ratio of saturates+monounsaturates to n-3 + n-6 polyunsaturates in adipose tissue and the number of weight cycles (r = +0.96, P < 0.0001). The percentage of linoleate and alpha-linolenate in adipose tissue was inversely related to the number of weight cycles. We conclude that, despite providing adequate n-6 and n-3 polyunsaturates in the diet during the refeeding period, weight cycling in young growing rats causes a moderate, selective depletion of linoleate and alpha-linolenate from tissue stores.

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4

Cunnane, S. C. y J. Yang. "Zinc deficiency impairs whole body accumulation of polyunsaturates and increases the utilization of [1-14C]linoleate for de novo lipid synthesis in pregnant rats". Canadian Journal of Physiology and Pharmacology 73, n.º 9 (1 de septiembre de 1995): 1246–52. http://dx.doi.org/10.1139/y95-176.

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Zinc deficiency impairs the metabolism of polyunsaturates, but the degree to which its effects are independent of food intake are still in question. Identical amounts of a semiliquid control diet (26.4 mg zinc/kg) or moderately zinc deficient diet (3.2 mg zinc/kg) were tube fed to rats for 11 days during the second half of pregnancy to evaluate the specific effects of zinc deficiency on maternal utilization and fetal accumulation of polyunsaturates. The whole body fatty acid balance method was used to determine net accumulation of polyunsaturates and their whole-body disappearance. Incorporation of 14C from [1-14C]linoleate into maternal and fetal lipid classes was also studied on days 20–21. At term, zinc-deficient rats had significantly higher whole-body disappearance of linoleate and α-linolenate and lower accumulation of n−6 and n−3 long-chain polyunsaturates. Zinc-deficient rats had higher 14C activity in free cholesterol, saturates, and monounsaturates in several maternal organs but not in the fetuses. We conclude that during pregnancy, moderate zinc deficiency not affecting food intake or weight gain still alters whole-body metabolism of linoleate and α-linolenate towards increased β-oxidation and also increases the utilization of carbon from linoleate for de novo lipid synthesis.Key words: cholesterol, linoleate, α-linolenate, oxidation, polyunsaturates, pregnancy, zinc.

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5

Chen, Z. Y., M. M. Sea, K. Y. Kwan, Y. H. Leung y P. F. Leung. "Depletion of linoleate induced by weight cycling is independent of extent of calorie restriction". American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 272, n.º 1 (1 de enero de 1997): R43—R50. http://dx.doi.org/10.1152/ajpregu.1997.272.1.r43.

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Recent epidemiological studies have suggested that weight cycling induced by repeated dieting over time may increase the risk of cardiovascular disease. It is speculated that the increased mortality from coronary heart disease for people with a history of excessive weight cycling could be attributed to change in lipid metabolism. Previous studies have demonstrated that repeated cycling of 100% food restriction followed by ad libitum refeeding caused a depletion of linoleate and alpha-linolenate in rats. The objective of the present study was to test the hypothesis that the weight cycling-induced reduction in linoleate and alpha-linolenate is independent of extent of calorie restriction. Two consecutive weight cycles in three experiments were induced by 100% calorie restriction, 60% calorie restriction, and 36% calorie restriction, respectively, followed by ad libitum refeeding. As the consequence of the two weight cycles, linoleate and linolenate were decreased, whereas myristate, palmitate, and palmitoleate were proportionally increased in carcass and adipose tissue lipids. The results of all three experiments showed a preferential depletion of linoleate and alpha-linolenate without changes in final body weight, total body fat, and adipose tissue pads in the weight-cycled rats. In addition, the triacylglycerol species profile in the adipose tissue of weight-cycled rats was significantly remodeled, with a proportional depletion of linoleate-enriched triacylglycerol species (LLL, LLO, and LLP, where L, O, and P are linoleic, oleic, and palmitic acid, respectively) and a proportional accumulation of palmitate-enriched triacylglycerol species (OPPo, PPPo, and PPP, where Po is palmitoleic acid). We conclude that weight cycling changes the ratio of polyunsaturated fatty acids to saturated fatty acids and remodels the adipose tissue triacylglycerol species profile in rats.

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6

Cunnane, Stephen C. "The conditional nature of the dietary need for polyunsaturates: a proposal to reclassify ‘essential fatty acids’ as ‘conditionally-indispensable’ or ‘conditionally-dispensable’ fatty acids". British Journal of Nutrition 84, n.º 6 (diciembre de 2000): 803–12. http://dx.doi.org/10.1017/s0007114500002415.

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The term essential fatty acid no longer clearly identifies the fatty acids it was originally used to describe. It would be more informative if the concept of essentiality shifted away from the symptoms arising from the lack of de novo synthesis of linoleate or α-linolenate and towards the adequacy of the capacity for synthesis and conservation of both the parent and the derived long-chain polyunsaturates. For instance, despite the existence of the pathway for synthesis of docosahexaenoate from α-linolenate, the former would be more correctly classified as ‘conditionally indispensable’ because the capacity of the pathway appears insufficient during early development, although it may be sufficient later in life in healthy individuals. Similarly, despite the inability to synthesize linoleate de novo, abundant linoleate stores and its relatively slow turnover in healthy adults probably makes linoleate ‘conditionally dispensable’ for long periods. There are two other anomalies with the terms essential and non-essential fatty acids: (1) under several different experimental circumstances, the C-skeleton of essential fatty acids is avidly used in the synthesis of non-essential fatty acids; (2) to function normally, the brain is required to endogenously synthesize several non-essential fatty acids. As with essential amino acids, which have been reclassified as indispensable or conditionally indispensable, such a change in terminology should lead to an improved understanding of the function and metabolism of polyunsaturates in particular, and long-chain fatty acids in general.

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7

Griffiths, G., A. K. Stobart y S. Stymne. "Δ 6- and Δ12-desaturase activities and phosphatidic acid formation in microsomal preparations from the developing cotyledons of common borage (Borago officinalis)". Biochemical Journal 252, n.º 3 (15 de junio de 1988): 641–47. http://dx.doi.org/10.1042/bj2520641.

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Microsomal membrane preparations from the maturing cotyledons of common borage (Borago officinalis) exhibit delta 12- and delta 6-desaturase activities, which resulted in the synthesis of linoleate and gamma-linolenate respectively. The desaturase enzymes utilized the complex lipid substrate phosphatidylcholine. The activity of these enzymes was sufficiently high to allow the monitoring of the mass changes in the endogenous oleate, linoleate and gamma-linolenate in the microsomal phosphatidylcholine in the presence of NADH (i.e. under desaturating conditions). The results illustrate that the delta 12-desaturase uses the oleate substrate at both the sn-1 and -2 positions of sn-phosphatidylcholine, whereas the delta 6-desaturase is almost totally restricted to the linoleate at position 2 of the complex lipid. Estimate of the acyl-substrate pool size at position 2 of sn-phosphatidylcholine for both desaturases indicated that some 50% of the oleate and linoleate was available to the enzymes. The microsomes (microsomal fractions) had a somewhat impaired Kennedy [(1961) Fed. Proc. Fed. Am. Soc. Exp. Biol. 20, 934-940] pathway for the formation of triacylglycerols when compared with other oil-rich plant species that have been studied [Stymne & Stobart (1987) The Biochemistry of Plants: a Comprehensive Treatise (Stumpf, P.K., ed.), vol. 10, chapter 8, pp. 175-214, Academic Press, New York]. In the presence of sn-glycerol 3-phosphate and acyl-CoA, large quantities of phosphatidic acid accumulated in the membranes. Acyl-selectivity studies on the glycerol-acylating enzymes showed that gamma-linolenate could be acylated to both the sn-1 and sn-2 positions of sn-glycerol 3-phosphate. However, stereochemical analysis of the acyl components of the sn-triacylglycerol obtained from mature seeds indicated that, whereas no gamma-linolenate was present at the sn-1 position, it accounted for over 50% of the fatty acids at position sn-3. The results indicate that the diacylglycerol acyltransferase (EC 2.3.1.20) may show a strong selectivity for gamma-linolenoyl-CoA and hence result in the efficient removal of this fatty acid from the acyl-CoA pool in vivo, leaving negligible substrate for utilization by the sn-glycerol 3-phosphate acyltransferase (EC 2.3.1.15).

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8

Awl, R. A., E. N. Frankel y D. Weisleder. "Synthesis and characterization of triacylglycerols containing linoleate and linolenate". Lipids 24, n.º 10 (octubre de 1989): 866–72. http://dx.doi.org/10.1007/bf02535761.

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9

Awl, R. A., E. N. Frankel y D. Weisleder. "Synthesis and characterization of triacylglycerols containing linoleate and linolenate". Lipids 25, n.º 1 (enero de 1990): 72. http://dx.doi.org/10.1007/bf02562432.

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10

Thompson, Alison L., Megan Y. C. Lim-Fraser, Edward W. Kraegen y Gregory J. Cooney. "Effects of individual fatty acids on glucose uptake and glycogen synthesis in soleus muscle in vitro". American Journal of Physiology-Endocrinology and Metabolism 279, n.º 3 (1 de septiembre de 2000): E577—E584. http://dx.doi.org/10.1152/ajpendo.2000.279.3.e577.

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Soleus muscle strips from Wistar rats were preincubated with palmitate in vitro before the determination of insulin-mediated glucose metabolism in fatty acid-free medium. Palmitate decreased insulin-stimulated glycogen synthesis to 51% of control in a time- (0–6 h) and concentration-dependent (0–2 mM) manner. Basal and insulin-stimulated glucose transport/phosphorylation also decreased with time, but the decrease occurred after the effect on glycogen synthesis. Preincubation with 1 mM palmitate, oleate, linoleate, or linolenate for 4 h impaired glycogen synthesis stimulated with a submaximal physiological insulin concentration (300 μU/ml) to 50–60% of the control response, and this reduction was associated with impaired insulin-stimulated phosphorylation of protein kinase B (PKB). Preincubation with different fatty acids (all 1 mM for 4 h) had varying effects on insulin-stimulated glucose transport/phosphorylation, which was decreased by oleate and linoleate, whereas palmitate and linolenate had little effect. Across groups, the rates of glucose transport/phosphorylation correlated with the intramuscular long-chain acyl-CoA content. The similar effects of individual fatty acids on glycogen synthesis but different effects on insulin-stimulated glucose transport/phosphorylation provide evidence that lipids may interact with these two pathways via different mechanisms.

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11

KIKUGAWA, KIYOMI y KUNITAROU KOGI. "Oxidation products of linoleate and linolenate exposed to nitrogen dioxide." CHEMICAL & PHARMACEUTICAL BULLETIN 35, n.º 1 (1987): 344–49. http://dx.doi.org/10.1248/cpb.35.344.

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12

Hirano, Shinya, Kazuo Miyashita, Toru Ota, Masazumi Nishikawa, Kazuki Maruyama y Suguru Nakayama. "Aqueous Oxidation of Ethyl Linoleate, Ethyl Linolenate, and Ethyl Docosahexaenoate". Bioscience, Biotechnology, and Biochemistry 61, n.º 2 (enero de 1997): 281–85. http://dx.doi.org/10.1271/bbb.61.281.

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13

Graham, A., V. A. Zammit y D. N. Brindley. "Fatty acid specificity for the synthesis of triacylglycerol and phosphatidylcholine and for the secretion of very-low-density lipoproteins and lysophosphatidylcholine by cultures of rat hepatocytes". Biochemical Journal 249, n.º 3 (1 de febrero de 1988): 727–33. http://dx.doi.org/10.1042/bj2490727.

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1. The synthesis and secretion of glycerolipids by monolayer cultures of rat hepatocytes was measured by using radioactive choline, glycerol and fatty acids and by measuring the concentration of triacylglycerols in the cells. 2. The incorporation of glycerol into triacylglycerol and the accumulation of this lipid in hepatocytes showed little specificity for fatty acids, except for eicosapentaenoate, which stimulated least. Oleate was more effective at stimulating triacylglycerol secretion than were palmitate, stearate, arachidonate and eicosapentaenoate. 3. Linoleate, linolenate, arachidonate and eicosapentaenoate stimulated the incorporation of glycerol and choline into phosphatidylcholine that was secreted into the medium. By contrast, palmitate and stearate produced relatively high incorporations into the phosphatidylcholine that remained in the cells. 4. The incorporation of glycerol and choline into lysophosphatidylcholine in the medium was stimulated 2-3-fold by all of the unsaturated fatty acids tested, whereas palmitate and stearate failed to stimulate if the acids were added separately. When 1 mM-stearate was added with 1 mM-linoleate, the incorporation of linoleate into lysophosphatidylcholine was about 4 times higher than that of stearate. 5. It is proposed that the secretion of lysophosphatidylcholine by the liver could provide a transport system for choline and essential unsaturated fatty acids to other organs.

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14

Vicky Ocsandy, R. Marwita Sari Putri y Jumsurizal. "Characteristics of Paracaudina australis Fatty Acid from Karimun, Riau Islands". Marinade 2, n.º 01 (30 de abril de 2019): 53–58. http://dx.doi.org/10.31629/marinade.v2i01.1256.

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P. australis is one of the marine biota that has not been used optimally, especially in Karimun Regency, Riau Islands. One effort that can be done to increase the added value of Berunok is to conduct research on the characteristics of the proximate content of P. australis. The purpose of this study is to determine the comparison of the proximate composition of two species of P. australis from different sampling locations. Sampling was carried out at Pelawan Beach and Tanjung Melolo from Karimun regency waters, the Riau archipelago. Calculation results of Pelawan Beach Fatty Acid content, Laurat 0.271%, Mirristate 10.503%, Palmitate 16.336%, Stearate 3.985%, Oleat 5.059 Linoleate 30.619% Linolenic 14.522% While at Tanjung Melolo Laurat 0%, Miristat 8,353%, Palmitate 21,197%, Stearate 4.493%, Oleate 6.128%, Linoleate 31.989%, Linolenat 11.840%.

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15

Watkins, Bruce A. "Influences of biotin deficiency and dietary trans-fatty acids on tissue lipids in chickens". British Journal of Nutrition 61, n.º 1 (enero de 1989): 99–111. http://dx.doi.org/10.1079/bjn19890096.

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1. The combined effects of feeding hydrogenated fats and varying the levels of biotin and linoleate (18:2ω6) on polyunsaturated fatty acids were studied in the chicken.2. Biotin deficiency signs were not exacerbated by feeding hydrogenated fats or by diets low in linoleate for 21 d.3. Biotin deficiency resulted in proportionately higher levels of 18:2ω6 and γ-linolenate (18:3ω6) in liver triglycerides, and lower levels of dihomo-γ-linolenate (20:3ω6) in liver and heart phospholipids irrespective of the 18:2ω6 level in the diet.4. Biotin deficiency did not alter arachidonate (20:4ω6) levels in tissue lipids at 21 d.5. Feeding high levels of trans-18:1 isomers with adequate biotin led to reduced 20:3ω6 and 20:4ω6 levels in liver and heart phospholipids with compensatory increases in ω3 fatty acids.6. The trans-isomers of 18:1 were incorporated into several tissues of the chick. Incorporation was dependent on the levels fed. Very small amounts were incorporated into brain compared with other tissues when dietary trans-isomer levels were high, but were similar when dietary trans-isomer levels were low. The trans-18:1 isomers appear to be preferentially incorporated into phospholipids as opposed to triglycerides in heart and liver.

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16

GRECHKIN, Alexander N., Lucia S. MUKHTAROVA y Mats HAMBERG. "The lipoxygenase pathway in tulip (Tulipa gesneriana): detection of the ketol route". Biochemical Journal 352, n.º 2 (24 de noviembre de 2000): 501–9. http://dx.doi.org/10.1042/bj3520501.

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The in vitro metabolism of [1-14C]linoleate, [1-14C]linolenate and their 9(S)-hydroperoxides was studied in cell-free preparations from tulip (Tulipa gesneriana) bulbs, leaves and flowers. Linoleate and its 9-hydroperoxide were converted by bulb and leaf preparations into three ketols: (12Z)-9-hydroxy-10-oxo-12-octadecadienoic acid (α-ketol), (11E)-10-oxo-13-hydroxy-11-octadecadienoic acid (γ-ketol) and a novel compound, (12Z)-10-oxo-11-hydroxy-12-octadecadienoic acid (10,11-ketol), in the approximate molar proportions of 10:3:1. The corresponding 15,16-dehydro α- and γ-ketols were the main metabolites of [1-14C]linolenate and its 9-hydroperoxide. Thus bulbs and leaves possessed 9-lipoxygenase and allene oxide synthase activities. Incubations with flower preparations gave α-ketol hydro(pero)xides as predominant metabolites. Bulb and leaf preparations possessed a novel enzyme activity, γ-ketol reductase, which reduces γ-ketol to 10-oxo-13-hydroxyoctadecanoic acid (dihydro-γ-ketol) in the presence of NADH. Exogenous linolenate 13(S)-hydroperoxide was converted mostly into chiral (9S,13S)-12-oxo-10-phytodienoate (99.5% optical purity) by bulb preparations, while [1-14C]linolenate was a precursor for ketols only. Thus tulip bulbs possess abundant allene oxide cyclase activity, the substrate for which is linolenate 13(S)-hydroperoxide, even though 13(S)-lipoxygenase products were not detectable in the bulbs. The majority of the cyclase activity was found in the microsomes (105g pellet). Cyclase activity was not found in the other tissues examined, but only in the bulbs. The ketol route of the lipoxygenase pathway, mediated by 9-lipoxygenase and allene oxide synthase activities, has not been detected previously in the vegetative organs of any plant species.

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17

Huynh, S., H. Oulhaj, J. Bocquet y A. Nouvelot. "Metabolic utilization of linoleate and α-linolenate in cultured Sertoli cells". Comparative Biochemistry and Physiology Part B: Comparative Biochemistry 99, n.º 2 (enero de 1991): 265–70. http://dx.doi.org/10.1016/0305-0491(91)90039-g.

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18

Miyashita, K., E. N. Frankel, W. E. Neff y R. A. Awl. "Autoxidation of polyunsaturated triacylglycerols. III. Synthetic triacylglycerols containing linoleate and linolenate". Lipids 25, n.º 1 (enero de 1990): 48–53. http://dx.doi.org/10.1007/bf02562427.

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19

Belza, K., M. J. Anderson, M. A. Ryan y S. C. Cunnane. "Carbon recycling from linoleate during severe dietary linoleate deficiency". Lipids 34, S1 (enero de 1999): S129—S130. http://dx.doi.org/10.1007/bf02562260.

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20

Gomez-Muñoz, A., P. Hales y D. N. Brindley. "Unsaturated fatty acids activate glycogen phosphorylase in cultured rat hepatocytes". Biochemical Journal 276, n.º 1 (15 de mayo de 1991): 209–15. http://dx.doi.org/10.1042/bj2760209.

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Oleate, linoleate, linolenate, arachidonate and eicosapentaenoate, but not myristate, palmitate and stearate, stimulated glycogen phosphorylase activity by 2-8-fold when added to cultured rat hepatocytes. Addition of BSA or Ca2- to the incubation medium decreased the stimulating effects of the unsaturated fatty acids. The combination of oleate or linolenate, with corticosterone, testosterone or estradiol produced synergistic stimulations of phosphorylase activity. The stimulation of glycogen phosphorylase activity by linolenate was inhibited by staurosporine or sphingosine. Staurosporine (80 nM) alone also decreased basal phosphorylase activities by about 60%. The results show that unsaturated fatty acids can be used as model agonists to stimulate phosphorylase activity by a mechanism that probably involves protein kinase C. On the basis of the fatty acid: BSA ratios used, this stimulation should only occur in vivo at high fatty acid concentrations when accompanied by hypoalbuminaemia.

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21

Grechkin, A. N., L. S. Mukhtarova y M. Hamberg. "Lipoxygenase pathway in tulip: biosynthesis of ketols". Biochemical Society Transactions 28, n.º 6 (1 de diciembre de 2000): 851–53. http://dx.doi.org/10.1042/bst0280851.

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The metabolism in vitro of [1-14C]linoleate, [1-14C]linolenate and their 9(S)-hydroperoxides in tulip (Tulipa gesneriana) was found to be under the control of 9-lipoxygenase and allene oxide synthase, and directed towards α-ketol, γ-ketol and the novel compound (12Z)-10-oxo-11-hydroxy- 12-octadecadienoic acid (10,11-ketol). Potent activity of allene oxide cyclase (in bulbs) and a new enzyme, γ-ketol reductase (in bulbs and leaves), was detected. Metabolism in flowers is directed predominantly towards α-ketol hydroperoxide.

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22

Zrnzevic, Ivana, Ivana Zlatanovic, Jelena Lazarevic, Olga Jovanovic y Gordana Stojanovic. "GC-MS analysis of Ramalina capitata (Ach.) Nyl. extract". Facta universitatis - series: Physics, Chemistry and Technology 13, n.º 2 (2015): 91–97. http://dx.doi.org/10.2298/fupct1502091z.

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This is the first report on the GC-MS profile of the ether-soluble fraction (ESF) of the methanol extract of the lichen Ramalina capitata (Ach.) Nyl. (Ramalinaceae). The profile was dominated by orcinol (22.9 %) and its monomethyl ether (30.9 %), which accounted for more than a half of the GC-MS analyzable fraction of ESF. Significantly lower amounts of structurally related sparassol (5.8%) and atraric acid (0.9 %) were also detected. Additionally, ESF contained methyl linoleate, methyl linolenate and methyl palmitate (17.3 %, 7.3 % and 5.0 %, respectively).

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23

Mortley, Desmond G., Jun-Hyun Oh, Damicca S. Johnson, Conrad K. Bonsi y Walter A. Hill. "Influence of Harvest Intervals on Growth Responses and Fatty Acid Content of Purslane (Portulaca oleracea)". HortScience 47, n.º 3 (marzo de 2012): 437–39. http://dx.doi.org/10.21273/hortsci.47.3.437.

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A greenhouse study was conducted to evaluate the influence of harvest intervals on biomass yield and omega fatty acids of ‘Golden purslane’ (Portulaca oleracea). Nutrients were supplied as a modified full-strength Hoagland solution two to three times weekly. Plants were harvested sequentially at 20, 40, and 60 days after transplanting (DAT) corresponding to 42, 63, and 84 days after sowing. Fatty acids were determined using a gas chromatography–mass spectrometry. Harvest intervals significantly influenced foliage fresh and dry weight, leaf number and plant height, and root length and fresh weight and were greatest at 60 DAT. Fatty acid analysis verified the presence of myristate, palmitate, linoleate, and linolenate at 20 DAT and in all three harvests, whereas stearate and oleate were detected only in the last two harvests (40 and 60 DAT). Linoleate, palminate, and linolenate were the most abundant fatty acids in purslane with levels in excess of 300 mg·kg−1. Those for myristate, stearate, and oleate were in excess of 200 mg·kg−1. The ratio of omega-6/omega-3 ranged from 0.44 for Harvest 1 to 1.1 for Harvest 3, whereas ratios for harvest intervals two and three were equal to or greater than the recommended daily human requirement. Results showed qualitative and quantitative differences of harvest intervals of purslane, suggesting that an optimal ratio of omega-6 to omega-3 fatty acids can be achieved ≈20 DAT.

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24

Nieman, David C., R. Andrew Shanely, Beibei Luo, Mary Pat Meaney, Dustin A. Dew y Kirk L. Pappan. "Metabolomics approach to assessing plasma 13- and 9-hydroxy-octadecadienoic acid and linoleic acid metabolite responses to 75-km cycling". American Journal of Physiology-Regulatory, Integrative and Comparative Physiology 307, n.º 1 (1 de julio de 2014): R68—R74. http://dx.doi.org/10.1152/ajpregu.00092.2014.

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Bioactive oxidized linoleic acid metabolites (OXLAMs) include 13- and 9-hydroxy-octadecadienoic acid (13-HODE + 9-HODE) and have been linked to oxidative stress, inflammation, and numerous pathological and physiological states. The purpose of this study was to measure changes in plasma 13-HODE + 9-HODE following a 75-km cycling bout and identify potential linkages to linoleate metabolism and established biomarkers of oxidative stress (F2-isoprostanes) and inflammation (cytokines) using a metabolomics approach. Trained male cyclists ( N = 19, age 38.0 ± 1.6 yr, wattsmax 304 ± 10.5) engaged in a 75-km cycling time trial on their own bicycles using electromagnetically braked cycling ergometers (2.71 ± 0.07 h). Blood samples were collected preexercise, immediately post-, 1.5 h post-, and 21 h postexercise, and analyzed for plasma cytokines (IL-6, IL-8, IL-10, tumor necrosis factor-α, monocyte chemoattractant protein-1, granulocyte colony-stimulating factor), F2-isoprostanes, and shifts in metabolites using global metabolomics procedures with gas chromatography mass spectrometry (GC-MS) and liquid chromatography mass spectrometry (LC-MS). 13-HODE + 9-HODE increased 3.1-fold and 1.7-fold immediately post- and 1.5 h postexercise (both P < 0.001) and returned to preexercise levels by 21-h postexercise. Post-75-km cycling plasma levels of 13-HODE + 9-HODE were not significantly correlated with increases in plasma cytokines but were positively correlated with postexercise F2-isoprostanes ( r = 0.75, P < 0.001), linoleate ( r = 0.54, P = 0.016), arachidate ( r = 0.77, P < 0.001), 12,13-dihydroxy-9Z-octadecenoate (12,13-DiHOME) ( r = 0.60, P = 0.006), dihomo-linolenate ( r = 0.57, P = 0.011), and adrenate ( r = 0.56, P = 0.013). These findings indicate that prolonged and intensive exercise caused a transient, 3.1-fold increase in the stable linoleic acid oxidation product 13-HODE + 9-HODE and was related to increases in F2-isoprostanes, linoleate, and fatty acids in the linoleate conversion pathway. These data support the use of 13-HODE + 9-HODE as an oxidative stress biomarker in acute exercise investigations.

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25

Guesnet, P., S. M. Lallemand, J. M. Alessandri, M. Jouin y S. C. Cunnane. "α-Linolenate reduces the dietary requirement for linoleate in the growing rat". Prostaglandins, Leukotrienes and Essential Fatty Acids 85, n.º 6 (diciembre de 2011): 353–60. http://dx.doi.org/10.1016/j.plefa.2011.08.003.

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26

Cunnane, Stephen C., Mary Ann Ryan, Kerr S. Craig, Steven Brookes, Berthold Koletzko, Hans Demmelmair, Janet Singer y David J. Kyle. "Synthesis of linoleate and α-linolenate by chain elongation in the rat". Lipids 30, n.º 8 (agosto de 1995): 781–83. http://dx.doi.org/10.1007/bf02537807.

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27

Hoptroff, Michael J., Simon V. Avery y Simon Thomas. "Influence of altered plasma membrane fatty acid composition on cesium transport characteristics and toxicity inSaccharomyces cerevisiae". Canadian Journal of Microbiology 43, n.º 10 (1 de octubre de 1997): 954–62. http://dx.doi.org/10.1139/m97-137.

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The influence of altered plasma membrane fatty acid composition on cesium uptake and toxicity was investigated in Saccharomyces cerevisiae. Detailed kinetic studies revealed that both the Vmaxand Kmvalues for Cs+transport increased (by approximately twofold in the latter case) when S. cerevisiae was grown in medium supplemented with the polyunsaturated fatty acid linoleate. In addition, Cs+uptake by linoleate-enriched cells was considerably less sensitive to the competitive effects of other monovalent cations (K+, Rb+, and NH4+) than that by unsupplemented cells. Stimulation of Cs+uptake in the presence of certain K+and Rb+concentrations was only evident in linoleate-enriched S. cerevisiae. At 100 mM CsCl, the initial rate of Cs+uptake was greater in linoleate-supplemented cells than in unsupplemented cells and this was reflected in a more rapid displacement of cellular K+. However, little difference in net Cs+accumulation between linoleate-supplemented and unsupplemented cells was evident during prolonged incubation in buffer or during growth. Thus, Cs+toxicity was similar in linoleate-supplemented and unsupplemented cells. The results were consistent with the Cs+(K+) transport mechanism adopting an altered conformational state in linoleate-enriched S. cerevisiae.Key words: monovalent cation transport, plasma membrane fatty acid composition, lipid–protein interactions, metal–microbe interactions, cation competition.

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28

Koshiishi, Ichiro, Kazunori Tsuchida, Tokuko Takajo y Makiko Komatsu. "Radical scavenger can scavenge lipid allyl radicals complexed with lipoxygenase at lower oxygen content". Biochemical Journal 395, n.º 2 (28 de marzo de 2006): 303–9. http://dx.doi.org/10.1042/bj20051595.

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Lipoxygenases have been proposed to be a possible factor that is responsible for the pathology of certain diseases, including ischaemic injury. In the peroxidation process of linoleic acid by lipoxygenase, the E,Z-linoleate allyl radical–lipoxygenase complex seems to be generated as an intermediate. In the present study, we evaluated whether E,Z-linoleate allyl radicals on the enzyme are scavenged by radical scavengers. Linoleic acid, the content of which was greater than the dissolved oxygen content, was treated with soya bean lipoxygenase-1 (ferric form) in the presence of radical scavenger, CmP (3-carbamoyl-2,2,5,5-tetramethylpyrrolidine-N-oxyl). The reaction rate between oxygen and lipid allyl radical is comparatively faster than that between CmP and lipid allyl radical. Therefore a reaction between linoleate allyl radical and CmP was not observed while the dioxygenation of linoleic acid was ongoing. After the dissolved oxygen was depleted, CmP stoichiometrically trapped linoleate-allyl radicals. Accompanied by this one-electron redox reaction, the resulting ferrous lipoxygenase was re-oxidized to the ferric form by hydroperoxylinoleate. Through the adduct assay via LC (liquid chromatography)–MS/MS (tandem MS), four E,Z-linoleate allyl radical–CmP adducts corresponding to regio- and diastereo-isomers were detected in the linoleate/lipoxygenase system, whereas E,E-linoleate allyl radical–CmP adducts were not detected at all. If E,Z-linoleate allyl radical is liberated from the enzyme, the E/Z-isomer has to reach equilibrium with the thermodynamically favoured E/E-isomer. These data suggested that the E,Z-linoleate allyl radicals were not liberated from the active site of lipoxygenase before being trapped by CmP. Consequently, we concluded that the lipid allyl radicals complexed with lipoxygenase could be scavenged by radical scavengers at lower oxygen content.

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29

Vlahov, Giovanna. "13C Nuclear Magnetic Resonance Spectroscopic Detection of the Adulteration of Extra Virgin Olive Oils Extracted from Different Cultivars with Cold-Pressed Hazelnut Oil". Journal of AOAC INTERNATIONAL 92, n.º 6 (1 de noviembre de 2009): 1747–54. http://dx.doi.org/10.1093/jaoac/92.6.1747.

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Abstract 13C NMR spectroscopy was applied to detect the adulteration of olive oils with hazelnut oil. Considering that the linolenate chain and the squalene hydrocarbon were absent in hazelnut oil, unlike olive oil, a 13C NMR spectroscopy method was developed to measure in addition to the triglyceride normal chains (i.e., saturated, oleate, and linoleate chains), the resonances of the linolenate chain and of squalene hydrocarbon. Acyl chain and squalene resonances highly discriminated olive oil samples by cultivars. Nevertheless, the hazelnut oil percentage factor prevailed over the cultivar factor, thus correctly classifying 86 of the authentic and adulterated olive oil samples according to the hazelnut oil percentages. In particular, 85.7, 73.7, and 100.0 of the authentic olive oil samples, and the samples adulterated with 5 and 20 of hazelnut oil, were correctly classified through cross-validation.

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30

Hattori, Takefumi, Akira Ohta, Masayuki Itaya y Mikio Shimada. "The ability of ectomycorrhizal fungi to utilize fatty acids and a lipid as a carbon source for mycelial growth". Canadian Journal of Botany 81, n.º 12 (1 de diciembre de 2003): 1285–92. http://dx.doi.org/10.1139/b03-111.

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We have investigated growth of ectomycorrhizal (ECM) fungi (i.e., 55 strains of 32 species in 15 genera) on saturated (palmitate), monounsaturated (oleate), diunsaturated (linoleate), triunsaturated (linolenate) fatty acids, and the triacylglyceride of oleate (triolein) lipid to elucidate an ability to utilize the fatty acids and lipid as a carbon source for growth. Relative utilization ratios (URs, %) based on mycelial growth on glucose suggest that ECM fungi belonging to the family Thelephoraceae have an ability to utilize palmitate. On the other hand, ECM fungi in the genus Laccaria can utilize at least either palmitate or oleate. Furthermore, Hygropharus russula grows on palmitate, oleate, and slightly on triolein. Lactarius chrysorrheus grows only on palmitate. These fatty-acid- and lipid-utilizing fungi may be promising as model fungi for further elucidation of the metabolic ability to utilize the fatty acids and lipid as a carbon source. On the contrary, the fungi in the genus Suillus were shown to scarcely utilize the fatty acids and lipid. Furthermore, most ECM fungi did not grow on either linoleate or linolenate.Key words: carbon source, ectomycorrhizal fungi, fatty acid, lipid, mycelial growth.

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31

Reid, J. C. W. y D. R. Husbands. "Oxidative metabolism of long-chain fatty acids in mitochondria from sheep and rat liver. Evidence that sheep conserve linoleate by limiting its oxidation". Biochemical Journal 225, n.º 1 (1 de enero de 1985): 233–37. http://dx.doi.org/10.1042/bj2250233.

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Mitochondria isolated from the livers of sheep and rats were shown to oxidize palmitate, oleate and linoleate in a tightly coupled manner, by monitoring the oxygen consumption associated with the degradation of these acids in the presence of 2mM-L-malate. Rat liver mitochondria oxidized linoleate and oleate at a rate 1.2-1.8 times that of palmitate. Sheep liver mitochondria had a specific activity for the oxidation of palmitate that was 50-80% of that of rats and a specific activity for the oxidation of oleate and linoleate that was 30-40% that of rats. This would indicate that sheep conserved linoleate by limiting its oxidation. Carnitine acyltransferase I (CAT I) actively esterified palmitoyl-CoA and linoleate to carnitine in both rat and sheep liver mitochondria, and in both cases the rate for linoleate was faster than for palmitate. The CAT I reaction in both rat and sheep liver was inhibited by micromolar amounts of malonyl-CoA. With 90 microM-palmitoyl-CoA as substrate, CAT I was inhibited by 50% with 2.5 microM-malonyl-CoA in rats, and in sheep, 50% inhibition was found with all malonyl-CoA concentrations tested (1-5 microM). With 90 microM-linoleate as substrate for CAT I, a much larger difference in response to malonyl-CoA was seen, the rat enzyme being 50% inhibited at 22 microM-malonyl-CoA, whereas sheep liver CAT I was 91% and 98% inhibited at 1 microM- and 5 microM-malonyl-CoA respectively. We propose that malonyl-CoA may act as an important regulator of beta-oxidation in sheep, discriminating against the use of linoleate as an energy-yielding substrate.

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32

del Hoyo, N., J. A. Pulido, M. T. Carretero y M. A. Pérez-Albarsanz. "Comparison of linoleate, palmitate and acetate metabolism in rat ventral prostate". Bioscience Reports 10, n.º 1 (1 de febrero de 1990): 105–12. http://dx.doi.org/10.1007/bf01116858.

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Rat ventral prostate incorporated (1-14C)acetate, (1-14C)palmitate and (1-14C)linoleate into different phospholipids in a time-dependent process. The rate of incorporation into total phospholipids was higher with linoleate (10.0 nmol/g) than with either palmitate (5.8 nmol/g) or acetate (4.7 nmol/g). Predominant labelling with all the radioactive substrates assayed was found in choline glycerophospholipids (PC). The radioactive profiles for linoleate in the other ventral prostate phospholipids differed from those obtained with palmitate and acetate. Specifically linoleate was incorporated into inositol glycerophospholipids plus lysoethanolamine glycerophospholipids (PI+LPE) and not into sphingomyelin (SM), while palmitate and acetate incorporated into SM but not into PI+LPE. Acetate showed the highest oxidation to CO2 whereas no differences were observed in the radioactivity incorporated into CO2 from a saturated (palmitate) or an essential unsaturated fatty acid (linoleate). These studies also show zinc-dependence by the acetate to CO2 oxidation.

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33

Mukherjee, Supratim, Sumit Sen Santara, Shantanabha Das, Moumita Bose, Jayasree Roy y Subrata Adak. "NAD(P)H Cytochrome b5 Oxidoreductase Deficiency in Leishmania major Results in Impaired Linoleate Synthesis Followed by Increased Oxidative Stress and Cell Death". Journal of Biological Chemistry 287, n.º 42 (25 de agosto de 2012): 34992–5003. http://dx.doi.org/10.1074/jbc.m112.389338.

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NAD(P)H cytochrome b5 oxidoreductase (Ncb5or), comprising cytochrome b5 and cytochrome b5 reductase domains, is widely distributed in eukaryotic organisms. Although Ncb5or plays a crucial role in lipid metabolism of mice, so far no Ncb5or gene has been reported in the unicellular parasitic protozoa Leishmania species. We have cloned, expressed, and characterized Ncb5or gene from Leishmania major. Steady state catalysis and spectral studies show that NADH can quickly reduce the ferric state of the enzyme to the ferrous state and is able to donate an electron(s) to external acceptors. To elucidate its exact physiological role in Leishmania, we attempted to create NAD(P)H cytochrome b5 oxidoreductase from L. major (LmNcb5or) knock-out mutants by targeted gene replacement technique. A free fatty acid profile in knock-out (KO) cells reveals marked deficiency in linoleate and linolenate when compared with wild type (WT) or overexpressing cells. KO culture has a higher percentage of dead cells compared with both WT and overexpressing cells. Increased O2 uptake, uncoupling and ATP synthesis, and loss of mitochondrial membrane potential are evident in KO cells. Flow cytometric analysis reveals the presence of a higher concentration of intracellular H2O2, indicative of increased oxidative stress in parasites lacking LmNcb5or. Cell death is significantly reduced when the KO cells are pretreated with BSA bound linoleate. Real time PCR studies demonstrate a higher Δ12 desaturase, superoxide dismutase, and glyceraldehyde 3-phosphate dehydrogenase (GAPDH) mRNA with a concomitant fall in Δ9 desaturase mRNA expression in LmNcb5or null cell line. Together these findings suggest that decreased linoleate synthesis, and increased oxidative stress and apoptosis are the major consequences of LmNcb5or deficiency in Leishmania.

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34

Tso, P., M. D. Karlstad, B. R. Bistrian y S. J. DeMichele. "Intestinal digestion, absorption, and transport of structured triglycerides and cholesterol in rats". American Journal of Physiology-Gastrointestinal and Liver Physiology 268, n.º 4 (1 de abril de 1995): G568—G577. http://dx.doi.org/10.1152/ajpgi.1995.268.4.g568.

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We compared the intestinal absorption of trilinolein (1,2,3-tri-[1-14C]linoleyl-sn-glycerol) with two different structured triglycerides containing one linoleic acid (C18:2) and two octanoic acids (C8:0), 1,3-dioctanoyl-2-[1-14C]linoleyl-sn-glycerol (2-linoleate) and 1,2-di[1-14C]octanoyl-3-linoleyl-sn-glycerol (1,2-octanoate), respectively. Lymphatic radioactive lipid output of 2-linoleate resembled that of trilinolein rats but remained significantly lower during the lipid infusion. Radioactive lipid was recovered along the entire small intestinal lumen, with a significantly higher amount of [14C]lipid recovered in the lower small intestine and cecum in the 2-linoleate group. Delayed uptake of radioactive 2-linoleate was not due to poor digestion. In contrast, 1,2-octanoate was efficiently digested, and both the free fatty acid (FFA) and the monoacylglycerol (MG) containing octanoate were rapidly absorbed. Irrespective of its position on the triglyceride molecule, 14C-labeled octanoate was poorly transported into lymph. In addition, intestinal luminal and mucosal recovery of [14C]octanoate was significantly lower in the 1,2-octanoate group compared with [14C]linoleate recovery in the 2-linoleate or trilinolein groups. Total recovery of infused radioactive lipid was significantly less in the 1,2-octanoate group than in the 2-linoleate or trilinolein groups. Thus radioactive octanoate in the form of FFA or 2-MG was rapidly absorbed and transported via the portal vein. The infusion of either 2-linoleate or 1,2-octanoate did not affect the absorption and lymphatic transport of cholesterol compared with trilinolein. In summary, the type of the fatty acid on the structured triglyceride molecule affects its digestion, absorption, and lymphatic transport. Structured triglycerides containing octanoic acid in the 1- and 3-positions and linoleic acid in the 2-position may not be advantageous to use as a sole source of dietary lipid, but should be supplemented with long-chain triglycerides.

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35

XUE, H. Q., T. G. ISLEIB, G. A. PAYNE, W. F. NOVITZKY y G. OBRIAN. "Aflatoxin Production in Peanut Lines Selected To Represent a Range of Linoleic Acid Concentrations". Journal of Food Protection 68, n.º 1 (1 de enero de 2005): 126–32. http://dx.doi.org/10.4315/0362-028x-68.1.126.

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To determine whether concentrations of linoleate in peanut (Arachis hypogaea L.) seed oil could be used to predict an ability to support aflatoxin production, seeds of genotypes representing a range of linoleate content were inoculated with Aspergillus flavus Link ex Fries and assayed for aflatoxin content. Seeds were blanched and quartered, inoculated with conidia of A. flavus, placed on moistened filter paper in petri dishes, and incubated for 8 days at 28°C. Multiple regression analysis was used to account for the variation among lines with the use of fatty acid concentrations as independent variables. In test 1, linoleate accounted for 39 to 44% of the variation among lines for aflatoxin B1 and B2 and total aflatoxin (26 to 27% after log transformation). Oleate accounted for substantial additional variation (27 to 29%) among lines (20 to 23% after log transformation). Other fatty acids accounted for small fractions of among-line variation. In test 2, linoleate accounted for about 35 to 44% of the variation among entries across traits (29 to 37% for log-transformed data); arachidate accounted for 19 to 29% (27 to 33% after log transformation). Eicosenoate accounted for a small part of the total entry variation. In both experiments, residual variation among entries was significant. Low-linoleate lines consistently contained more aflatoxin, whereas normal- to high-linoleate lines contained variable amounts. Although fatty acid concentrations accounted for significant portions of genetic variation, it is not practical to use them as predictors for susceptibility to aflatoxin contamination, especially for lines in the normal range for oleate and linoleate.

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36

Frankel, E. N., W. E. Neff y R. D. Plattner. "Chemical lonization-mass spectrometry of secondary oxidation products from methyl linoleate and linolenate". Lipids 21, n.º 5 (mayo de 1986): 333–37. http://dx.doi.org/10.1007/bf02535696.

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37

Watanabe, Shiro y Harumi Okuyama. "Effect of dietary α-linolenate/linoleate balance on endotoxin-induced hepatitis in mice". Lipids 26, n.º 6 (junio de 1991): 467–71. http://dx.doi.org/10.1007/bf02536074.

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38

Matikainen, Jorma, Matti Laantera y Seppo Kaltia. "Determination of degree of oxidation of methyl linoleate and linolenate by weighing method". Journal of the American Oil Chemists' Society 80, n.º 6 (junio de 2003): 591–93. http://dx.doi.org/10.1007/s11746-003-0743-8.

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39

Hrelia, S., A. Bordoni, M. Celadon, E. Turchetto, P. L. Biagi y C. A. Rossi. "Age-related changes in linoleate and α-linolenate desaturation by rat liver microsomes". Biochemical and Biophysical Research Communications 163, n.º 1 (agosto de 1989): 348–55. http://dx.doi.org/10.1016/0006-291x(89)92142-6.

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40

Bearer, Cynthia F., Siemay Lee, Ann E. Salvator, Sonia Minnes, Alan Swick, Toyoko Yamashita y Lynn T. Singer. "Ethyl Linoleate in Meconium". Alcoholism: Clinical & Experimental Research 23, n.º 3 (marzo de 1999): 487. http://dx.doi.org/10.1097/00000374-199903000-00016.

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41

Hodson, Leanne, Siobhán E. McQuaid, Fredrik Karpe, Keith N. Frayn y Barbara A. Fielding. "Differences in partitioning of meal fatty acids into blood lipid fractions: a comparison of linoleate, oleate, and palmitate". American Journal of Physiology-Endocrinology and Metabolism 296, n.º 1 (enero de 2009): E64—E71. http://dx.doi.org/10.1152/ajpendo.90730.2008.

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There has been much interest in the health effects of dietary fat, but few studies have comprehensively compared the acute metabolic fate of specific fatty acids in vivo. We hypothesized that different classes of fatty acids would be variably partitioned in metabolic pathways and that this would become evident over 24 h. We traced the fate of fatty acids using equal amounts of [U-13C]linoleate, [U-13C]oleate, and [U-13C]palmitate given in a test breakfast meal in 12 healthy subjects. There was a tendency for differences in the concentrations of the tracers in plasma chylomicron-triacylglycerol (TG) (oleate > palmitate > linoleate). This pattern remained in plasma nonesterified fatty acid (NEFA) and very low-density lipoprotein (VLDL)-TG ( P ≤ 0.01 and P ≤ 0.02 for [U-13C]oleate vs. both [U-13C]palmitate and [U-13C]linoleate for NEFA and VLDL-TG, respectively). There was significantly more [U-13C]linoleate than the other two tracers in plasma cholesteryl ester and phospholipid (PL). Using the values for isotopic enrichment in the different lipid fractions compared with the test meal, we calculated the contribution of meal fatty acids to the respective fractions. At 24 h, 10% of plasma PL-linoleate originated from the breakfast test meal. This was significantly greater than for oleate and palmitate (both 3 ± 0.3%; P < 0.05). This pattern was also true for erythrocyte PL fatty acids. The marked rapid incorporation of linoleate from a single meal into blood PL fractions may have functional consequences such as maintenance of membrane fluidity and may explain why linoleate is a useful biomarker of dietary intake.

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42

Jiang, Jin y Afaf Kamal-Eldin. "Comparing Methylene Blue-Photosensitized Oxidation of Methyl-Conjugated Linoleate and Methyl Linoleate". Journal of Agricultural and Food Chemistry 46, n.º 3 (marzo de 1998): 923–27. http://dx.doi.org/10.1021/jf9704017.

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43

Matsuba, S., M. Itoh, T. John, H. Takeyama, N. Dohi, S. Watanabe y H. Okuyama. "Effect of dietary linoleate/α-linolenate balance on experimentally induced gastric injury in rats". Prostaglandins, Leukotrienes and Essential Fatty Acids 59, n.º 5 (noviembre de 1998): 317–23. http://dx.doi.org/10.1016/s0952-3278(98)90080-1.

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44

Frankel, E. N., E. Selke, W. E. Neff y K. Miyashita. "Autoxidation of polyunsaturated triacylglycerols. IV. Volatile decomposition products from triacylglycerols containing linoleate and linolenate". Lipids 27, n.º 6 (junio de 1992): 442–46. http://dx.doi.org/10.1007/bf02536386.

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45

Widiarti, Nuni, Wijianto Wijianto, Nanik Wijayati, Harjito Harjito, Samuel Budi Wardhana Kusuma, Didik Prasetyoko y Suprapto Suprapto. "CATALYTIC ACTIVITY OF CALCIUM OXIDE FROM FISHBONE WASTE IN WASTE COOKING OIL TRANSESTERIFICATION PROCESS". Jurnal Bahan Alam Terbarukan 6, n.º 2 (16 de octubre de 2017): 97–106. http://dx.doi.org/10.15294/jbat.v6i2.8335.

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Calcium oxide was obtained from waste fish bones that has been carried out systematically by decomposition at various temperatures that 800oC, 900oC and 1000oC for 4 hours. Calcium oxide from the decomposition process was characterized using XRD, FTIR, SEM EDX and SAA. The result of XRD Diffractogram showed that the crystallinity increased as the calcination temperature increased. The absorption bands in the FTIR spectra of calcium oxide from calcined waste fish bones shown at 355 cm-1 region indicated CaO vibration, which was reinforced by the emergence of a peak at 859 cm-1. Based on the analysis using SEM EDX, the calcined waste fish bones typically irregular particles and contained dominant calcium element. The low value of BET surface area and the total of pore volume were consistent with the adsorption measurement with SAA. The calcium oxide was applied for biodiesel synthesis from Waste cooking oil through transesterification reaction. The result of the optimization that the calcium oxide was decomposed from waste fish bones at 900oC. It exhibited best catalytic activity in the transesterification of waste cooking oil providing maximum biodiesel yield of 93% at 4% (w/v) of catalyst loading. The decomposition of biodiesel are determined by GC MS that produced methyl palmitate, methyl linoleate, methyl elaidate, methyl linoleolate, methyl stearate and methyl linolenate.

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46

Nand, Pratibha, Sushma Drabu y Rajinder K. Gupta. "Antimicrobial Investigation of Linum usitatissimum for the Treatment of Acne". Natural Product Communications 6, n.º 11 (noviembre de 2011): 1934578X1100601. http://dx.doi.org/10.1177/1934578x1100601133.

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Light petroleum, dichloromethane and methanolic extracts of Linum usitatissimum were investigated using GC/MS. The main components of three sequential extracts were methyl linolenate (11.9-33.9%) and methyl linoleate (3.4-9.1%). Components possessing antimicrobial activity against acne causing bacteria, namely α-linolenic acid (7.0 -7.1%), α-terpinene (1.7-3.1%), terpinen-4-ol (1.3-4.6%), 4-cymene (1.6-7.1%) and α-pinene (1.1%), were found in varying amounts. Antimicrobial screening indicated that the light petroleum extract was more active against aerobic and anaerobic test strains with a MIC value of 1.25 mg/mL and a MBC of 2.5 mg/mL against S. aureus and P. acnes. A MIC of 2.5 mg/mL was observed against S. epidermidis.

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47

Norman, Amos, Leslie R. Bennett, James F. Mead y Keisuke S. Iwamoto. "Antitumor activity of sodium Linoleate". Nutrition and Cancer 11, n.º 2 (enero de 1988): 107–15. http://dx.doi.org/10.1080/01635588809513977.

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48

Tiong, Sie Swan y H. I. Waterman. "Analysis of styrenated methyl linoleate". Journal of Applied Chemistry 6, n.º 5 (4 de mayo de 2007): 197–205. http://dx.doi.org/10.1002/jctb.5010060501.

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49

Du, Guodong, Aziz Tekin, Earl G. Hammond y L. Keith Wood. "Catalytic epoxidation of methyl linoleate". Journal of the American Oil Chemists' Society 81, n.º 5 (mayo de 2004): 477–80. http://dx.doi.org/10.1007/s11746-004-0926-3.

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50

Hasler, C. M., M. R. Bennink y J. E. Trosko. "Inhibition of gap junction-mediated intercellular communication by alpha-linolenate". American Journal of Physiology-Cell Physiology 261, n.º 1 (1 de julio de 1991): C161—C168. http://dx.doi.org/10.1152/ajpcell.1991.261.1.c161.

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The purpose of this investigation was to assess whether alterations in the fatty acid composition of rat liver epithelial (WB-F344) cell phospholipids would modulate gap junction-mediated intercellular communication (GJIC). WB-F344 cells were grown to confluency in culture medium supplemented with one of seven different fatty acids at a concentration of 50 microM for 48 h. Only alpha-linoleate (18:3 n-3) significantly inhibited GJIC. Saturated fatty acids (12:0, 16:0, and 18:0), a monounsaturated fatty acid (18:1 n-9), and n-6 polyunsaturated fatty acids (18:2 and 20:4) did not affect GJIC. The alpha-linolenate-induced inhibition of GJIC was not due to the activation of protein kinase C or intracellular hydroperoxide production, two lipid-dependent parameters previously shown to inhibit GJIC. In addition, alpha-linolenate did not alter membrane fluidity. Although the mechanism by which alpha-linolenate inhibits GJIC is unclear, changes in the fatty acid composition of cell phospholipids may be of critical importance. Subsequent to supplementation with alpha-linolenate, WB-F344 cell phospholipids had reduced 20:4 n-6 and elevated n-3 fatty acids. The results of this investigation emphasize the importance of current research into the influence of lipids on cell function and identify a new mechanism by which gap junctions can be modulated.

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