Formation of modulated phases and domain rigidification in fatty acid-containing lipid membranes

2017 ◽  
Vol 19 (20) ◽  
pp. 13252-13263 ◽  
Author(s):  
Naofumi Shimokawa ◽  
Rieko Mukai ◽  
Mariko Nagata ◽  
Masahiro Takagi
Keyword(s):  
Oleic Acid ◽  
Fatty Acid ◽  
Palmitic Acid ◽  
Elaidic Acid ◽  
Lipid Membranes ◽  
Phytanic Acid ◽  
Domain Boundary ◽  
Line Tension ◽  
Modulated Phases ◽  
Liquid Ordered

A liquid-ordered domain is transformed into a solid-ordered domain by the addition of palmitic acid or elaidic acid. Oleic acid and phytanic acid reduce the line tension at the liquid domain boundary and consequently modulated phases appear.

P–227 Fatty acid regulation of Nrf2/Keap1 pathway during mouse preimplantation embryo development

2021 ◽  
Vol 36 (Supplement_1) ◽  
Author(s):  
G Dionne ◽  
A J Watson ◽  
D H Betts ◽  
B A Rafea
Keyword(s):  
Oleic Acid ◽  
Fatty Acid ◽  
Palmitic Acid ◽  
Embryo Development ◽  
Embryo Culture ◽  
Preimplantation Embryo ◽  
Culture Media ◽  
Control Group ◽  
Blastocyst Development ◽  
Preimplantation Embryo Development

Abstract Study question Our objective is determining whether supplementing embryo culture media with palmitic acid and/or oleic acid impacts Nrf2/Keap1 antioxidant response pathways during preimplantation mouse embryo development. Summary answer Supplementation of embryo culture media with palmitic acid increases cellular Nrf2 levels per embryo after 48-hour culture, while oleic acid reverses this effect. What is known already Obese women experience higher incidence of infertility than women with healthy BMIs. The obese reproductive tract environment supporting preimplantation embryo development is likely to include enhanced free fatty acid (FFA) levels and increased accumulation of reactive oxygen species. Exposure to palmitic acid (PA) in vitro significantly impairs mouse embryo development while increasing ER stress mRNAs. Oleic acid (OA) reverses these effects. To further define effects of FFA exposure, we are characterizing the influence of FFAs on the Nrf2–Keap1 pathway and its downstream antioxidant defense systems. We hypothesize that PA treatment induces Nrf2-Keap1 activity, while OA treatment alleviates pathway activity. Study design, size, duration Female CD–1 mice (4–6 weeks) were super-ovulated via intraperitoneal injections of PMSG, followed 48 hours later by hCG. Female mice were mated with male CD–1 mice (6–8 months) overnight. Females were euthanized using CO2 and two-cell embryos were collected by flushing oviducts. Two-cell embryos were placed into KSOMaa-based treatment groups: 1) BSA (control); 2) 100µM PA; 3) 100µM OA; 4) 100µM PA+OA, and cultured for 48 hours (37 °C; 5% O2, 5% CO2, 90% N2). Participants/materials, setting, methods After 48-hour embryo culture, developmental stages of all mouse embryos were recorded. Immunofluorescence analysis of Nrf2 and Keap1 localization was performed for embryo treatments (BSA, 100µM PA, 100µM OA & 100µM PA+OA) using rabbit polyclonal anti-Nrf2 antibody, with Rhodamine-Phalloidin and DAPI staining. Embryos were imaged using confocal microscopy and Nrf2-positive cells were counted using ImageJ. Nrf2 and Keap1 mRNA abundances were assessed after culture in each treatment condition using RT-qPCR and the delta-delta Ct method. Main results and the role of chance Inclusion of 100µM PA in embryo culture significantly decreased blastocyst development frequency from 70.06±16.38% in the BSA (control) group to 11.61±8.19% in the PA-treated group (p < 0.0001). Embryo culture with 100µM OA and 100µM PA+OA co-treatment did not significantly impair blastocyst development (OA: 61.59±8.07%, p = 0.4053; PA+OA: 63.53±7.63%, p = 0.6204). Embryo culture with PA treatment significantly increased the mean percentage of Nrf2-positive cells to 56.83±30.49% compared with 21.22±15.63% in the control group (p < 0.0001). Conversely, 100µM OA and 100µM PA+OA treatments did not significantly affect Nrf2-positive cell frequencies compared with the control group (OA: 33.28±21.83%, p = 0.1825; PA+OA: 34.84±12.66%, p = 0.0691). Immunofluorescence results show that treating embryos with 100µM PA for 48 hours results in increased levels of cellular Nrf2, while combining 100µM PA with 100µM OA reversed these effects. Preliminary qPCR analysis showed no significant differences in Nrf2 or Keap1 relative transcript abundance between any embryo treatment groups. Nrf2 and Keap1 mRNA levels were both higher after embryo culture with 100µM OA than all other culture groups (p = 0.6268; p = 0.3201). Notably, Keap1 relative transcript levels dropped to undetectable levels after culture with 100µM PA, which suggests an increase in Nrf2 activation.Limitations, reasons for caution: While immunofluorescence localization of Nrf2/Keap1 provides insight into how the proteins behave during preimplantation embryo development, confocal images cannot determine protein-protein interactions or activity levels. Similarly, transcript information from RT-qPCR analysis only provides information about Nrf2 and Keap1 at the transcript level. Nrf2 activity will be assessed via downstream targets. Wider implications of the findings: The Nrf2–Keap1 pathway coordinates numerous cellular defence mechanisms, and is implicated in various diseases, including cancer. Establishing an impact of free fatty acid exposure on Nrf2–Keap1 during preimplantation embryo development will provide valuable information regarding the effects of maternal obesity on outcomes for embryos produced from these patients. Trial registration number Not applicable

scholarly journals High rates of [1-14C]acetate incorporation into the lipid of isolated spinach chloroplasts

1976 ◽  
Vol 158 (3) ◽  
pp. 593-601 ◽  
Author(s):  
P G Roughan ◽  
C R Slack ◽  
R Holland
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Palmitic Acid ◽  
Free Fatty Acids ◽  
Acid Synthesis ◽  
Polar Lipids ◽  
Acetate Incorporation ◽  
Spinach Chloroplasts ◽  
Triton X

Spinach chloroplasts, isolated by techniques yielding preparations with high O2- evolving activity, showed rates of light-dependent acetate incorporation into lipids 3-4 fold higher than any previously reported. Incorporation rates as high as 500 nmol of acetate/h per mg of chlorophyll were measured in buffered sorbitol solutions containing only NaHCO3 and [1-14C]acetate, and as high as 800 nmol/h per mg of chlorophyll when 0.13 mM-Triton X-100 was also included in the reaction media. The fatty acids synthesized were predominantly oleic (70-80% of the total fatty acid radioactivity) and palmitic (20-25%) with only minor amounts (1-5%) of linoleic acid. Linolenic acid synthesis was not detected in the system in vitro. Free fatty acids accounted for 70-90% of the radioactivity incorporated and the remainder was shared fairly evenly between 1,2-diacylglycerols and polar lipids. Oleic acid constituted 80-90% of the free fatty acids synthesized, but the diacylglycerols and polar lipids contained slightly more palmitic acid than oleic acid. Triton X-100 stimulated the synthesis of diacylglycerols 3-6 fold, but stimulated free fatty acid synthesis only 1-1.5-fold. Added glycerol 1-phosphate stimulated both the synthesis of diacylglycerols and palmitic acid relative to oleic acid, but did not increase acetate incorporation into total chloroplast lipids. CoA and ATP, when added separately, stimulated acetate incorporation into chloroplast lipids to variable extents and had no effect on the types of lipid synthesized, but when added together resulted in 34% of the incorporated acetate appearing in long-chain acyl-CoA. Pyruvate was a much less effective precursor of chloroplast fatty acids than was acetate.

scholarly journals Composition of Oil from the Seeds of Cassia Sophera Linn.

1970 ◽  
Vol 42 (1) ◽  
pp. 75-78 ◽  
Author(s):  
M Mostafa ◽  
Momtaz Ahmed ◽  
Ismet Ara Jahan ◽  
Jasim Uddin Choudhury
Keyword(s):  
Oleic Acid ◽  
Linoleic Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Elaidic Acid ◽  
Lauric Acid ◽  
Arachidic Acid

The oil obtained from the seeds of Cassia sophera Linn was analyzed by GC-MS and a total of 42 compounds have been identified. The major constituents are palmitic acid (22.82 %), linoleic acid (8.32 %), elaidic acid (19.16 %), stearic acid (9.86 %), 5-isopropyl -6-methyl-3-heptyne-2,5-diol (6.44 %), undecyl lauric acid (6.61 %), oleic acid (2.1 %), arachidic acid (3.57 %) and 3α, 7β-dihyodxy -5β, 6β-epoxycholestane (5.9 %). Bangladesh J. Sci. Ind. Res. 42(1), 75-78, 2007

The Trans-Fatty Acid, Elaidic Acid, Inhibits Macrophage Fatty Acid Catabolism and Stimulates Expression of Inflammatory Mediators

Blood ◽  
2012 ◽  
Vol 120 (21) ◽  
pp. 3277-3277
Author(s):  
Lisa J Robinson ◽  
Janelle Zacherl ◽  
Harry C Blair ◽  
Stephanie J Mihalik
Keyword(s):  
Gene Expression ◽  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Stearic Acid ◽  
Inflammatory Mediators ◽  
Elaidic Acid ◽  
Trans Fatty Acids ◽  
Trans Fat ◽  
Fatty Acid Catabolism

Abstract Abstract 3277 In recent decades, addition to the diet of synthetically hydrogenated vegetable oils has markedly increased human consumption of trans fatty acids. Epidemiological studies have linked this change in diet to current high rates of atherosclerotic cardiovascular disease. Despite recognition of this important connection, the basic mechanisms by which trans fatty acids contribute to the pathogenesis of atherosclerosis are still not well understood. In the present studies we examined the effects of trans fatty acids on macrophage functions and their possible role in the pathogenesis of atherosclerosis. Human macrophages, derived from peripheral blood mononuclear cells, were treated with the trans fat elaidic acid (C18:Δ9–10 trans), the corresponding cis fatty acid oleic acid (C18:Δ9–10 cis), or the saturated fatty acid stearic acid (C18:0). We examined changes in macrophage fat metabolism using GC/MS to measure cell fatty acid content and intermediates, and MS/MS to identify acylcarnitine derivatives, and assayed fatty acid oxidation using fatty acids radiolabeled at the [1–14C] position and the double bond at the [C9-C103H] position. After 44 hours treatment with 100 micromolar elaidic acid, macrophages showed an accumulation of multiple unsaturated fatty acid intermediates, both long-chain and short-chain, by GC/MS analysis, that were not observed in cultures containing either oleic or stearic acid. Using acylcarnitine analysis, we observed an increase in C12 and C18 intermediates in the macrophages exposed to trans fat (either as fatty acids or partially hydrogenated soy oil) compared to controls. These results suggest a block in acyl-CoA removal one group proximate to the trans bond. Beta-oxidation assays using carbon-1 radiolabeled oleic and elaidic acids revealed enhanced entry of the trans-fat into the catabolic cycle compared to the entry of the natural cis-fatty acid. Using carbon 9–10 radiolabeled oleic acid to study oleic acid catabolism, we discovered that in the presence of the trans fat, oxidation of the cis fat was diminished. Thus, in addition to the block in the catabolism of the trans fat itself, the degradation of the cis monounsaturated fatty acids are also impaired in the presence of the trans fat. We then examined the effects of inhibited fatty acid catabolism on macrophage function by examining changes in gene expression. Initial results from Affymetrix gene expression profiling, were confirmed using quantitative real time PCR. These studies revealed that exposure to trans fatty acid, compared to cis fatty acids, markedly upregulated macrophage expression of interleukin 1 beta, an inflammatory cytokine previously implicated in the pathogenesis of atherosclerosis. Also increased was expression of heparin-binding epidermal growth factor, previously implicated as a stimulus for vascular smooth muscle proliferation in atherosclerosis. The results overall suggest that the deleterious effects of trans fats may be linked to impaired macrophage fatty acid catabolism, contributing to lipid accumulation in the atheroma, and also to increased macrophage production of inflammatory mediators. Disclosures: No relevant conflicts of interest to declare.

scholarly journals Metabolic fate of oleic acid, palmitic acid and stearic acid in cultured hamster hepatocytes

1996 ◽  
Vol 316 (3) ◽  
pp. 847-852 ◽  
Author(s):  
Jennifer S. BRUCE ◽  
Andrew M. SALTER
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Ketone Bodies ◽  
Plasma Cholesterol ◽  
Saturated Fatty Acids ◽  
Metabolic Fate ◽  
Cellular Phospholipid

Unlike other saturated fatty acids, dietary stearic acid does not appear to raise plasma cholesterol. The reason for this remains to be established, although it appears that it must be related to inherent differences in the metabolism of the fatty acid. In the present study, we have looked at the metabolism of palmitic acid and stearic acid, in comparison with oleic acid, by cultured hamster hepatocytes. Stearic acid was taken up more slowly and was poorly incorporated into both cellular and secreted triacylglycerol. Despite this, stearic acid stimulated the synthesis and secretion of triacylglycerol to the same extent as the other fatty acids. Incorporation into cellular phospholipid was lower for oleic acid than for palmitic acid and stearic acid. Desaturation of stearic acid, to monounsaturated fatty acid, was found to be greater than that of palmitic acid. Oleic acid produced from stearic acid was incorporated into both triacylglycerol and phospholipid, representing 13% and 6% respectively of the total after a 4 h incubation. Significant proportions of all of the fatty acids were oxidized, primarily to form ketone bodies, but by 8 h more oleic acid had been oxidized compared with palmitic acid and stearic acid.

scholarly journals Quantitative Trait Loci and Candidate Genes Associated with Fatty Acid Content of Watermelon Seed

2014 ◽  
Vol 139 (4) ◽  
pp. 433-441 ◽  
Author(s):  
Geoffrey Meru ◽  
Cecilia McGregor
Keyword(s):  
Fatty Acids ◽  
Fatty Acid Composition ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Palmitic Acid ◽  
Acid Composition ◽  
Seed Oil ◽  
Unsaturated Fatty Acids ◽  
Watermelon Seed

Seed oil percentage (SOP) and fatty acid composition of watermelon (Citrullus lanatus) seeds are important traits in Africa, the Middle East, and Asia where the seeds provide a significant source of nutrition and income. Oil yield from watermelon seed exceeds 50% (w/w) and is high in unsaturated fatty acids, a profile comparable to that of sunflower (Helianthus annuus) and soybean (Glycine max) oil. As a result of novel non-food uses of plant-derived oils, there is an increasing need for more sources of vegetable oil. To improve the nutritive value of watermelon seed and position watermelon as a potential oil crop, it is critical to understand the genetic factors associated with SOP and fatty acid composition. Although the fatty acid composition of watermelon seed is well documented, the underlying genetic basis has not yet been studied. Therefore, the current study aimed to elucidate the quality of watermelon seed oil and identify genomic regions and candidate genes associated with fatty acid composition. Seed from an F2 population developed from a cross between an egusi type (PI 560023), known for its high SOP, and Strain II (PI 279261) was phenotyped for palmitic acid (16:0), stearic acid (18:0), oleic acid (18:1), and linoleic acid (18:2). Significant (P < 0.05) correlations were found between palmitic and oleic acid (0.24), palmitic and linoleic acid (–0.37), stearic and linoleic acid (–0.21), and oleic and linoleic acid (–0.92). A total of eight quantitative trait loci (QTL) were associated with fatty acid composition with a QTL for oleic and linoleic acid colocalizing on chromosome (Chr) 6. Eighty genes involved in fatty biosynthesis including those modulating the ratio of saturated and unsaturated fatty acids were identified from the functionally annotated genes on the watermelon draft genome. Several fatty acid biosynthesis genes were found within and in close proximity to the QTL identified in this study. A gene (Cla013264) homolog to fatty acid elongase (FAE) was found within the 1.5-likelihood-odds (LOD) interval of the QTL for palmitic acid (R2 = 7.6%) on Chr 2, whereas Cla008157, a homolog to omega-3-fatty acid desaturase and Cla008263, a homolog to FAE, were identified within the 1.5-LOD interval of the QTL for palmitic acid (R2 = 24.7%) on Chr 3. In addition, the QTL for palmitic acid on Chr 3 was located ≈0.60 Mbp from Cla002633, a gene homolog to fatty acyl- [acyl carrier protein (ACP)] thioesterase B. A gene (Cla009335) homolog to ACP was found within the flanking markers of the QTL for oleic acid (R2 = 17.9%) and linoleic acid (R2 = 21.5%) on Chr 6, whereas Cla010780, a gene homolog to acyl-ACP desaturase was located within the QTL for stearic acid (R2 = 10.2%) on Chr 7. On Chr 8, another gene (Cla013862) homolog to acyl-ACP desaturase was found within the 1.5-LOD interval of the QTL for oleic acid (R2 = 13.5%). The genes identified in this study are possible candidates for the development of functional markers for application in marker-assisted selection for fatty acid composition in watermelon seed. To the best of our knowledge, this is the first study that aimed to elucidate genetic control of the fatty acid composition of watermelon seed.

scholarly journals Fatty Acid Profiling and Chemometric Analyses for Zanthoxylum Pericarps from Different Geographic Origin and Genotype

Foods ◽  
2020 ◽  
Vol 9 (11) ◽  
pp. 1676
Author(s):  
Yao Ma ◽  
Jieyun Tian ◽  
Xiaona Wang ◽  
Chen Huang ◽  
Mingjing Tian ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Discriminant Analysis ◽  
Palmitic Acid ◽  
Soil Conditions ◽  
Potential Health ◽  
Geographical Variations ◽  
Fatty Acid Profiling

Zanthoxylum plants, important aromatic plants, have attracted considerable attention in the food, pharmacological, and industrial fields because of their potential health benefits, and they are easily accessible because of the wild distribution in most parts of China. The chemical components vary with inter and intraspecific variations, ontogenic variations, and climate and soil conditions in compositions and contents. To classify the relationships between different Zanthoxylum species and to determine the key factors that influence geographical variations in the main components of the plant, the fatty acid composition and content of 72 pericarp samples from 12 cultivation regions were measured and evaluated. Four fatty acids, palmitic acid (21.33–125.03 mg/g), oleic acid (10.66–181.37 mg/g), linoleic acid (21.98–305.32 mg/g), and linolenic acid (0.06–218.84 mg/g), were the most common fatty acid components in the Zanthoxylum pericarps. Fatty acid profiling of Zanthoxylum pericarps was significantly affected by Zanthoxylum species and geographical variations. Stearic acid and oleic acid in pericarps were typical fatty acids that distinguished Zanthoxylum species based on the result of discriminant analysis (DA). Palmitic acid, palmitoleic acid, trans-13-oleic acid, and linoleic acid were important differential indicators in distinguishing given Zanthoxylum pericarps based on the result of orthogonal partial least squares discriminant analysis (OPLS-DA). In different Zanthoxylum species, the geographical influence on fatty acid variations was diverse. This study provides information on how to classify the Zanthoxylum species based on pericarp fatty acid compositions and determines the key fatty acids used to classify the Zanthoxylum species.

scholarly journals JENIS ASAM LEMAK MINYAK TEMPE BUSUK

Jurnal Kimia ◽  
2019 ◽  
Vol 13 (1) ◽  
pp. 82
Author(s):  
M. H. Rachmawati ◽  
H. Soetjipto ◽  
A. Ign A. Ign. Kristijanto
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Linoleic Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Food Product ◽  
Chemical Components ◽  
Purification Process ◽  
Before And After

Overripe tempe is a food product that used by peoples in Indonesia as a food seasoning. So far, overripe tempe received less attention than fresh tempe and research of overripe tempe is rarely done. The objective of the study is to identify the fatty acid compounds of the  fifth day fermentation overripe tempe oil before and after purification . The overripe tempe oil of fifth day fermentation was extracted with soxhletation method using n – hexane solvent, then it was purified. The various fatty acids  of overripe tempe oil were analyzed by GC – MS. The purification process was done by using H3PO4 0,2% and NaOH 0,1N. The result of the study showed that before purification the oil  was composed of eight compounds  are palmitic acid (13,33%),  linoleic acid (77,57%), stearic acid (6,15%), and the five chemical components, Dasycarpidan – 1 - methanol, acetate ,  oleic acid, 9 - Octadecenamide ,Cholestane - 3, 7, 12, 25 - tetrol, tetraacetate, (3?, 5?, 7?, 12?) and  6, 7 – Epoxypregn – 4 – ene -9, 11, 18- triol - 3, 20 - dione, 11, 18 – diacetate have percentage of areas less than 3%. After purification the oil  was composed of palmitic acid (12,38% ), linoleic acid (80,35 %), stearic acid (5,84%), and 17 – Octadecynoic acid (1,42 %) .

The digestion of fatty acids in the stomach and intestines of sheep given widely different rations

1970 ◽  
Vol 37 (1) ◽  
pp. 97-105 ◽  
Author(s):  
J. D. Sutton ◽  
J. E. Storry ◽  
J. W. G. Nicholson
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Stearic Acid ◽  
Palmitic Acid ◽  
Total Lipid ◽  
The Difference ◽  
Almost All

SummaryThe amounts of total lipid and fatty acids consumed, leaving the stomach and excreted in the faeces were examined in 4 sheep fitted with rumen and re-entrant duodenal cannulas. Diets of high (HM1) and low (CM1) roughage content were given at 0·9 times maintenance and the low-roughage diet was also given at 1·7 and 2·3 times maintenance. With all the rations more fatty acid left the abomasum than was consumed in the food, the difference being greater on ration CM1 than on ration HM1 and increasing irregularly with the amount of the low-roughage ration fed. Of the fatty acid entering the duodenum in the chyme, 72–89% was digested in the intestine. About 80% of the increase in fatty acids in the stomach was stearic acid and most of the remainder was palmitic acid. Almost all the polyunsaturated C18acids ingested in the food were hydrogenated in the stomach, and the amounts of oleic acid were also greatly reduced, although more oleic acid entered the duodenum in the chyme with ration CM1 than with ration HM1. The possible origins of the increase in fatty acids in the stomach are discussed.

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