Facile dehydrobromination ofvic-dibromo fatty acids: A one-vessel bromination-dehydrobromination of oleic acid to stearolic acid

1984 ◽  
Vol 61 (6) ◽  
pp. 1090-1092 ◽  
Author(s):  
Leonard S. Silbert
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Stearolic Acid

Fatty Acid Data and Crop Surveys Indicate Sources of Red Sunflower Seed Weevil (Coleoptera: Curculionidae), Populations and Suggest Strategies for Management

2020 ◽  
Author(s):  
Jarrad R Prasifka ◽  
Beth Ferguson ◽  
James V Anderson
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Sunflower Seed ◽  
Cultural Practices ◽  
High Oleic ◽  
Fatty Acid Data ◽  
Smicronyx Fulvus ◽  
Combined Data ◽  
Fatty Acid Compositions

Abstract The red sunflower seed weevil, Smicronyx fulvus L., is a univoltine seed-feeding pest of cultivated sunflower, Helianthus annuus L. Artificial infestations of S. fulvus onto sunflowers with traditional (<25% oleic acid), mid-oleic (55–75%), or high oleic (>80%) fatty acid profiles were used to test if fatty acids could be used as natural markers to estimate the proportion of weevils developing on oilseed sunflowers rather than wild Helianthus spp. and confection (non-oil) types. Oleic acid (%) in S. fulvus confirmed the fatty acid compositions of mature larvae and weevil adults reflected their diets, making primary (oleic or linoleic) fatty acids feasible as natural markers for this crop-insect combination. Oleic acid in wild S. fulvus populations in North Dakota suggests at least 84 and 90% of adults originated from mid-oleic or high oleic sunflower hybrids in 2017 and 2018, respectively. Surveys in 2017 (n = 156 fields) and 2019 (n = 120 fields) extended information provided by S. fulvus fatty acid data; no significant spatial patterns of S. fulvus damage were detected in samples, damage to oilseed sunflowers was greater than confection (non-oil) types, and the majority of damage occurred in ≈10% of surveyed fields. Combined, data suggest a few unmanaged or mismanaged oilseed sunflower fields are responsible for producing most S. fulvus in an area. Improved management seems possible with a combination of grower education and expanded use of non-insecticidal tactics, including cultural practices and S. fulvus-resistant hybrids.

scholarly journals Ectopic overexpression of a type-II DGAT (CeDGAT2-2) derived from oil-rich tuber of Cyperus esculentus enhances accumulation of oil and oleic acid in tobacco leaves

2021 ◽  
Vol 14 (1) ◽  
Author(s):  
Yu Gao ◽  
Yan Sun ◽  
Huiling Gao ◽  
Ying Chen ◽  
Xiaoqing Wang ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Negative Impact ◽  
Value Added ◽  
Cyperus Esculentus ◽  
Wild Type ◽  
Tobacco Leaves ◽  
Vegetative Tissues ◽  
Oil Storage ◽  
Tag Biosynthesis

Abstract Background Engineering triacylglycerol (TAG) accumulation in vegetative tissues of non-food crops has become a promising way to meet our increasing demand for plant oils, especially the renewable production of biofuels. The most important target modified in this regard is diacylglycerol acyltransferase (DGAT) enzyme responsible for the final rate-limiting step in TAG biosynthesis. Cyperus esculentus is a unique plant largely accumulating oleic acid-enriched oil in its underground tubers. We speculated that DGAT derived from such oil-rich tubers could function more efficiently than that from oleaginous seeds in enhancing oil storage in vegetative tissues of tobacco, a high-yielding biomass crops. Results Three CeDGAT genes namely CeDGAT1, CeDGAT2-1 and CeDGAT2-2 were identified in C. esculentus by mining transcriptome of developing tubers. These CeDGATs were expressed in tissues tested, with CeDGAT1 highly in roots, CeDGAT2-1 abundantly in leaves, and CeDGAT2-2 predominantly in tubers. Notably, CeDGAT2-2 expression pattern was in accordance with oil dynamic accumulation during tuber development. Overexpression of CeDGAT2-2 functionally restored TAG biosynthesis in TAG-deficient yeast mutant H1246. Oleic acid level was significantly increased in CeDGAT2-2 transgenic yeast compared to the wild-type yeast and ScDGA1-expressed control under culture with and without feeding of exogenous fatty acids. Overexpressing CeDGAT2-2 in tobacco led to dramatic enhancements of leafy oil by 7.15- and 1.7-fold more compared to the wild-type control and plants expressing Arabidopsis seed-derived AtDGAT1. A substantial change in fatty acid composition was detected in leaves, with increase of oleic acid from 5.1% in the wild type to 31.33% in CeDGAT2-2-expressed tobacco and accompanied reduction of saturated fatty acids. Moreover, the elevated accumulation of oleic acid-enriched TAG in transgenic tobacco exhibited no significantly negative impact on other agronomic traits such as photosynthesis, growth rates and seed germination except for small decline of starch content. Conclusions The present data indicate that CeDGAT2-2 has a high enzyme activity to catalyze formation of TAG and a strong specificity for oleic acid-containing substrates, providing new insights into understanding oil biosynthesis mechanism in plant vegetative tissues. Overexpression of CeDGAT2-2 alone can significantly increase oleic acid-enriched oil accumulation in tobacco leaves without negative impact on other agronomy traits, showing CeDGAT2-2 as the desirable target gene in metabolic engineering to enrich oil and value-added lipids in high-biomass plants for commercial production of biofuel oils.

EFFECTS OF DIET ON THE COMPOSITION OF BODY FAT IN AGRIA AFFINIS (FALLÉN)

1965 ◽  
Vol 43 (2) ◽  
pp. 337-340 ◽  
Author(s):  
J. S. Barlow
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Body Fat ◽  
Acid Content ◽  
Palmitoleic Acid ◽  
The Body ◽  
Nutritional Adequacy

When larvae of the parasitic fly Agria affinis (Fallén) were reared on fatty acid free diets, the characteristically high palmitoleic acid content of the body fats was much increased. Oleic acid in the diet was effective in reducing this, but not so effective as a mixture of fatty acids. The body fats still contained unusually high proportions of palmitic, palmitoleic, and oleic acids even when a mixture of fatty acids was fed. These observations are related to earlier observations on the nutritional adequacy of various fatty acids.

scholarly journals Energy intake, gastrointestinal transit, and gut hormone release in response to oral triglycerides and fatty acids in men with and without severe obesity

2019 ◽  
Vol 316 (3) ◽  
pp. G332-G337 ◽  
Author(s):  
Carsten Dirksen ◽  
Jesper Graff ◽  
Stefan Fuglsang ◽  
Jens F. Rehfeld ◽  
Jens J. Holst ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Olive Oil ◽  
Energy Intake ◽  
Severe Obesity ◽  
Gastrointestinal Transit ◽  
Calorie Intake ◽  
Double Blind ◽  
Gut Hormone ◽  
Ad Libitum

Dietary fat, and particularly fatty acids (FAs) from hydrolyzed triglycerides (TGs), reduces appetite, whereas paradoxically, a high-fat diet leads to excess calorie intake. We therefore hypothesized that the appetite-regulating effects of FAs are perturbed in obesity. Ten men with severe obesity [median body mass index (BMI) of 51.0 kg/m2(range of 47.9–69.0)] and 10 men without obesity [BMI of 24.6 kg/m2(range of 21.7–26.8)] were recruited for a double-blind randomized crossover study. On two occasions, participants were given isocaloric (2,660 kJ) and isovolemic (80 ml) loads of either oleic acid (long-chain FA) or olive oil (TG) containing radiolabeled lipid and water markers. Postload scintigraphy, blood sampling, and assessment of appetite were performed for 10 h, after which an ad libitum meal was served. Compared with olive oil, oleic acid slowed gastric mean emptying time (GMET) for lipids ( P < 0.001), accelerated orocoecal transit time (OCTT; P = 0.005), increased postload cholecystokinin section ( P < 0.001), and suppressed ad libitum energy intake ( P = 0.028) in men with severe obesity, and similar effects were seen in the nonobese group (no group × lipid interactions). However, independent of lipid loads, GMET and OCTT were slower (GMETlipidP = 0.046; GMETwaterP = 0.003; OCTT P = 0.001), and basal and postload secretion of glucagon-like peptide-1 (GLP-1) was attenuated ( P = 0.045 and P = 0.048, respectively) in men with severe obesity compared with men without obesity. We conclude that the more potent appetite-regulating effects of oleic acid versus olive oil are unimpaired in men with severe obesity. However, regardless of lipid formulations, severe obesity is associated with slowed gastrointestinal transit and attenuated GLP-1 secretion.NEW & NOTEWORTHY Orally ingested fatty acids more efficiently reduce appetite and energy intake than triglycerides also in men with severe obesity. Men with severe obesity have delayed gastrointestinal transit and attenuated early gut hormone responses after an oral lipid load compared with men without obesity.

scholarly journals Inhibition of steroid 5α-reductase by specific aliphatic unsaturated fatty acids

1992 ◽  
Vol 285 (2) ◽  
pp. 557-562 ◽  
Author(s):  
T Liang ◽  
S Liao
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Linoleic Acid ◽  
Linolenic Acid ◽  
Unsaturated Fatty Acids ◽  
Binding Assay ◽  
Reductase Activity ◽  
Undecylenic Acid ◽  
Gamma Linolenic Acid ◽  
Enzymic Assay

Human or rat microsomal 5 alpha-reductase activity, as measured by enzymic conversion of testosterone into 5 alpha-dihydrotestosterone or by binding of a competitive inhibitor, [3H]17 beta-NN-diethulcarbamoyl-4-methyl-4-aza-5 alpha-androstan-3-one ([3H]4-MA) to the reductase, is inhibited by low concentrations (less than 10 microM) of certain polyunsaturated fatty acids. The relative inhibitory potencies of unsaturated fatty acids are, in decreasing order: gamma-linolenic acid greater than cis-4,7,10,13,16,19-docosahexaenoic acid = cis-6,9,12,15-octatetraenoic acid = arachidonic acid = alpha-linolenic acid greater than linoleic acid greater than palmitoleic acid greater than oleic acid greater than myristoleic acid. Other unsaturated fatty acids such as undecylenic acid, erucic acid and nervonic acid, are inactive. The methyl esters and alcohol analogues of these compounds, glycerols, phospholipids, saturated fatty acids, retinoids and carotenes were inactive even at 0.2 mM. The results of the binding assay and the enzymic assay correlated well except for elaidic acid and linolelaidic acid, the trans isomers of oleic acid and linoleic acid respectively, which were much less active than their cis isomers in the binding assay but were as potent in the enzymic assay. gamma-Linolenic acid had no effect on the activities of two other rat liver microsomal enzymes: NADH:menadione reductase and glucuronosyl transferase. gamma-Linolenic acid, the most potent inhibitor tested, decreased the Vmax. and increased Km values of substrates, NADPH and testosterone, and promoted dissociation of [3H]4-MA from the microsomal reductase. gamma-Linolenic acid, but not the corresponding saturated fatty acid (stearic acid), inhibited the 5 alpha-reductase activity, but not the 17 beta-dehydrogenase activity, of human prostate cancer cells in culture. These results suggest that unsaturated fatty acids may play an important role in regulating androgen action in target cells.

scholarly journals CONTENT OF FATTY ACIDS IN CORN (ZEA MAYS L.) OIL FROM ECUADOR

2017 ◽  
Vol 10 (8) ◽  
pp. 150 ◽  
Author(s):  
Carrillo W ◽  
Carpio C ◽  
Morales D ◽  
Vilcacundo E ◽  
Álvarez M ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Zea Mays ◽  
Oleic Acid ◽  
Linoleic Acid ◽  
Corn Oil ◽  
Methyl Esters ◽  
Total Content ◽  
Pressing Method ◽  
A Value ◽  
Omega 6

  Objective: The aim of this work was to determine the fatty acids content in corn seeds oil (Zea mays) sample cultivated in Ecuador.Methods: Corn oil was obtained from corn oil seeds using the cold pressing method. Methyl esters fatty acids analysis were carried out using the gas chromatography (GC) method with a mass selective detector and using the database library NIST 14.L to identify the compounds present in the corn seed oil.Results: Methyl esters fatty acids were identified from corn (Z. mays) seeds using the GC mass spectrometer (GC-MS) analytical method. Fatty acids were analyzed as methyl esters on a capillary column DB-WAX 122-7062 with a good separation of palmitic acid, stearic acid, oleic acid, elaidic acid, linoleic acid, arachidic acid, and linolenic acid. The structure of methyl esters fatty acids was determined using the GS-MS method. Corn oil has a high content of linoleic acid (omega 6) with a value of 52.68% of the total content of fatty acids in corn oil and 29.70% of oleic acid (omega 9) of the total content of fatty acids in corn oil. The sample presented a value of 12.57% of palmitic acid.Conclusions: Corn oil shows a good content of fatty acids omega 6 and 9. The higher value was of omega 6 with 52.68% content. Corn oil has a good proportion of polyunsaturated of lipids (53.80%) and 14.86% of saturated lipids.

scholarly journals Distinct effects of oleic acid and itstrans-isomer elaidic acid on the expression of myokines and adipokines in cell models

2011 ◽  
Vol 105 (8) ◽  
pp. 1226-1234 ◽  
Author(s):  
Nuria Granados ◽  
Jaume Amengual ◽  
Joan Ribot ◽  
Andreu Palou ◽  
M. Luisa Bonet
Keyword(s):  
Gene Expression ◽  
Fatty Acids ◽  
Oleic Acid ◽  
Insulin Sensitivity ◽  
Glucose Uptake ◽  
Elaidic Acid ◽  
C2c12 Myotubes ◽  
Cell Models ◽  
Monounsaturated Fat ◽  
Expression Levels

Trans-fatty acids (TFA) andcis-monounsaturated fat appear to exert detrimental and beneficial effects, respectively, on glucose metabolism and insulin sensitivity. Adipose tissue and skeletal muscle are a source of signalling proteins (adipokines and myokines), some of which have been related to the control of insulin sensitivity. Here, we investigated the possible differential effects of elaidic acid (EA;trans-9-18 : 1) – the major component in industrially produced TFA – and oleic acid (OA;cis-9-18 : 1) – itscis-isomer naturally present in food – on cellular glucose uptake and the expression of selected myokines and adipokines using cell models. Differentiated C2C12 myotubes and 3T3-L1 adipocytes were pretreated with the vehicle (control cells) or fatty acids for 24 h, after which basal and insulin-stimulated 2-deoxyglucose uptake and the expression of selected signalling proteins were measured. In C2C12 myotubes, pretreatment with OA, but not with EA, led to increased insulin-stimulated 2-deoxyglucose uptake and IL-6 expression levels, while pretreatment with EA, but not with OA, led to reduced IL-15 mRNA levels and increased TNF-α expression levels. In 3T3-L1 adipocytes, exposure to OA, but not to EA, resulted in reduced resistin gene expression and increased adiponectin gene expression. The results show evidence of distinct, direct effects of OA and EA on muscle glucose uptake and the expression of target myokines and adipokines, thus suggesting novel mechanisms by whichcis- andtrans-monounsaturated fat may differentially affect systemic functions.

scholarly journals Antioxidant and fatty acid profile of gabiroba seed (Campomanesisa Xanthocarpa Berg)

2012 ◽  
Vol 32 (2) ◽  
pp. 234-238 ◽  
Author(s):  
Marli da Silva Santos ◽  
Obdulio Gomes Miguel ◽  
Carmen Lúcia Oliveira Petkowicz ◽  
Lys Mary Bileski Cândido
Keyword(s):  
Fatty Acids ◽  
Oleic Acid ◽  
Fatty Acid ◽  
Fatty Acid Profile ◽  
Unsaturated Fatty Acids ◽  
Ethanol Extract ◽  
Solvent Polarity ◽  
Antioxidant Potential ◽  
Total Phenolic ◽  
Total Phenolic Compounds

This study aimed to evaluate the antioxidant potential and fatty acid profile of gabiroba (Campomanesia xanthocarpa Berg) seeds. In order to obtain the extract, the seeds were dried, crushed, and subjected to sequential extraction by maceration and percolation in a modified soxhlet extractor using solvent polarity gradient composed of hexane, chloroform, ethyl acetate, and alcohol, respectively. The extraction time was six hours. The ethanol extract showed the highest antioxidant potential, given by the EC50 value and the amount of total phenolic compounds. High amounts of unsaturated fatty acids were found in the oil studied, especially the oleic acid.

Sign in / Sign up

Export Citation Format

Share Document