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The American Journal of Clinical... Jul 2014α-Linolenic acid (ALA) is an n-3 (ω-3) fatty acid found mostly in plant foods such as flaxseed, walnuts, and vegetable oils, including canola and soybean oils. Most of...
α-Linolenic acid (ALA) is an n-3 (ω-3) fatty acid found mostly in plant foods such as flaxseed, walnuts, and vegetable oils, including canola and soybean oils. Most of the health benefits observed for n-3 fatty acids have been attributed to the marine-derived long-chain n-3 fatty acids eicosapentaenoic acid (EPA) and docosahexaenoic acid, because of the strength of evidence from both epidemiologic studies and randomized controlled trials. Furthermore, the observed cardioprotective and other health effects of ALA have been credited to its precursor role in converting to EPA in the body. The promotion of fatty fish consumption for its documented health benefits may not be practical for those who are concerned with the unsustainability of marine sources or who avoid eating fish for a variety of reasons. ALA-rich plant sources are more abundant and may serve as a suitable alternate. It is therefore worthwhile to consider the evidence for the health benefits of ALA. The purpose of this review is to present the evidence from recent studies on the association between ALA and cardiovascular disease, type 2 diabetes, and fracture risk. The potential mechanisms that explain these associations will also be briefly discussed.
Topics: Cardiovascular Diseases; Diabetes Mellitus, Type 2; Diet; Dietary Fats; Fractures, Bone; Health; Humans; Plant Oils; alpha-Linolenic Acid
PubMed: 24898228
DOI: 10.3945/ajcn.113.071514 -
Food Chemistry Dec 2017An α-linolenic acid (ALA)-rich triacylglycerol (TAG) was synthesized from an ALA-rich fatty acid (FA) from perilla oil and glycerol, using a newly prepared immobilized...
An α-linolenic acid (ALA)-rich triacylglycerol (TAG) was synthesized from an ALA-rich fatty acid (FA) from perilla oil and glycerol, using a newly prepared immobilized lipase under vacuum. The ALA-rich FA (purity >90wt%) used as the substrate was prepared by urea complexation from perilla oil FAs. Liquid Lipozyme TL 100L lipase from Thermomyces lanuginosus was used for immobilization. Nine different hydrophilic and hydrophobic carriers for immobilization were tested, and Duolite A568, which is a hydrophilic resin, was selected as the best carrier. This immobilized lipase was used to synthesize TAG by direct esterification under vacuum. The parameters investigated were temperature, enzyme loading, and vacuum level. The optimum reaction conditions were a temperature of 60°C, an enzyme loading of 15% (based on the total weight of the substrate), and a vacuum of 0.7kPa, respectively. The maximum conversion to TAG of ca. 88wt% was obtained in 12h under the optimum conditions.
Topics: Ascomycota; Enzymes, Immobilized; Esterification; Lipase; Triglycerides; alpha-Linolenic Acid
PubMed: 28764049
DOI: 10.1016/j.foodchem.2017.05.161 -
Lipids Mar 2009In this study, we assessed the ability of six strains of bifidobacteria (previously shown by us to possess the ability to convert linoleic acid to c9, t11-conjugated...
In this study, we assessed the ability of six strains of bifidobacteria (previously shown by us to possess the ability to convert linoleic acid to c9, t11-conjugated linoleic acid (CLA) to grow in the presence of alpha-linolenic acid and to generate conjugated isomers of the fatty acid substrate during fermentation for 42 h. The six strains of bifidobacteria were grown in modified MRS (mMRS) containing alpha-linolenic acid for 42 h at 37 degrees C, after which the fatty acid composition of the growth medium was assessed by gas liquid chromatography (GLC). Indeed, following fermentation of one of the strains, namely Bifidobacterium breve NCIMB 702258, in the presence of 0.41 mg/ml alpha-linolenic acid, 79.1% was converted to the conjugated isomer, C18:3 c9, t11, c15 conjugated alpha-linolenic acid (CALA). To examine the inhibitory effect of the fermented oils produced, SW480 colon cancer cells were cultured in the presence of the extracted fermented oil (10-50 microg/ml) for 5 days. The data indicate an inhibitory effect on cell growth (p
alpha-linolenic acid (p Topics: Bifidobacterium; Biotransformation; Cell Division; Cell Line, Tumor; Colonic Neoplasms; Humans; Intestines; alpha-Linolenic Acid
PubMed: 19048324
DOI: 10.1007/s11745-008-3269-z -
Journal of Chromatography. A Jan 2020α-Linolenic acid (ALA) and its most important positional isomer γ-linolenic acid (GLA), are essential fatty acids (vitamin F). Therefore, ALA- and GLA-rich edible oils...
Liquid chromatography separation of α- and γ-linolenic acid positional isomers with a stationary phase based on covalently immobilized cellulose tris(3,5-dichlorophenylcarbamate).
α-Linolenic acid (ALA) and its most important positional isomer γ-linolenic acid (GLA), are essential fatty acids (vitamin F). Therefore, ALA- and GLA-rich edible oils hold great potential in human and animal nutrition, as well as in nutraceutics and cosmetics. Quality control and nutritional validation of oil products is thus of increasing importance. In the present study, the cellulose tris(3,5-dichlorophenylcarbamate)-based chiral stationary phase was successfully used for separation of ALA and GLA, a major challenge in the liquid chromatography of these isomers. The chromatographic conditions were firstly optimized on a HPLC system with UV detection, and the use of a reversed-phase eluent system made up of aqueous 10 mM ammonium acetate/acetonitrile (40/60, v/v; pH6.0) with a 25 °C column temperature resulted optimal for the simultaneous discrimination of the two isomers at a 0.5 mL/min flow rate (α = 1.10; R = 1.21). The method was then optimized for LC-MS/MS implementation. The proposed innovative separation method holds a great potential for the quantification of ALA and GLA in food and biological matrices, thus opening the way to further investigations involving the two positional isomers.
Topics: Cellulose; Chromatography, High Pressure Liquid; Humans; Isomerism; Phenylcarbamates; Tandem Mass Spectrometry; Temperature; alpha-Linolenic Acid; gamma-Linolenic Acid
PubMed: 31445805
DOI: 10.1016/j.chroma.2019.460461 -
The American Journal of Clinical... Oct 2001Data on the relation between alpha-linolenic acid intake and coronary artery disease (CAD) are limited. Other dietary components appear to modify the reported relation...
BACKGROUND
Data on the relation between alpha-linolenic acid intake and coronary artery disease (CAD) are limited. Other dietary components appear to modify the reported relation between alpha-linolenic acid intake and CAD.
OBJECTIVE
We examined whether dietary alpha-linolenic acid intake was inversely associated with risk of CAD.
DESIGN
We prospectively studied 667 men aged 64-84 y from the Zutphen Elderly Study who were free of CAD at baseline. Dietary intake was assessed by using a cross-check dietary history method.
RESULTS
During the 10-y follow-up, we documented 98 cases of CAD. After adjustment for age, standard coronary risk factors, and intake of trans fatty acids and other nutrients, alpha-linolenic acid intake was not significantly associated with CAD risk. The relative risk of CAD for the highest compared with the lowest tertile of alpha-linolenic acid intake was 1.68 (95% CI: 0.86, 3.29). alpha-Linolenic acid intake from sources containing trans fatty acids was also nonsignificantly, yet positively, associated with CAD risk. alpha-Linolenic acid intake from foods that did not contain trans fatty acids was not associated with CAD risk, the relative risk of CAD for the highest compared with the lowest tertile was 1.15 (95% CI: 0.63, 2.11).
CONCLUSION
We did not observe a beneficial effect of dietary alpha-linolenic acid intake on the risk of 10-y CAD incidence. Investigating this hypothesis was complicated by the association between intakes of alpha-linolenic acid and trans fatty acids. Given the results of current prospective studies, a protective cardiac effect of alpha-linolenic acid is questionable.
Topics: Aged; Aged, 80 and over; Blood Pressure; Cholesterol; Coronary Disease; Diet; Dietary Fats; Humans; Incidence; Male; Netherlands; Risk Factors; alpha-Linolenic Acid
PubMed: 11566643
DOI: 10.1093/ajcn/74.4.457 -
Lipids Apr 2013Patients with cystic fibrosis (CF) exhibit characteristic polyunsaturated fatty acid abnormalities, including low linoleic acid and high arachidonic acid levels that are...
Patients with cystic fibrosis (CF) exhibit characteristic polyunsaturated fatty acid abnormalities, including low linoleic acid and high arachidonic acid levels that are thought to contribute to the pathophysiology of this disease. Recent studies indicate that changes in fatty acid metabolism are responsible for these abnormalities. This study examines the role of fatty acid substrate concentrations in the development of these alterations in a cultured cell model of CF. By incubating cells with varying concentrations of exogenous fatty acids, it shows that increasing the concentration of substrates from the parallel n-3 and n-6 polyunsaturated fatty acid pathways (linoleic acid and alpha-linolenic acid, respectively) not only increases formation of the products in that pathway, but also reduces metabolism in the parallel pathway. In particular, we demonstrate that high levels of linoleic acid and low levels of alpha-linolenic acid are required to observe the typical fatty acid alterations of cystic fibrosis. These results shed light on the mechanisms of fatty acid metabolic abnormalities in cystic fibrosis. They also have implications for the nutritional therapy of CF, highlighting the importance of specific fatty acid content, and in understanding the anti-inflammatory effects of n-3 fatty acids.
Topics: Cell Line; Cystic Fibrosis; Fatty Acids; Fatty Acids, Omega-3; Humans; Lipid Metabolism; alpha-Linolenic Acid
PubMed: 23440519
DOI: 10.1007/s11745-013-3768-4 -
Journal of the Science of Food and... Sep 2020Medium- and long- chain triacylglycerols (MLCTs) are functional structural lipids that can provide the human body with essential fatty acids and a faster energy supply....
BACKGROUND
Medium- and long- chain triacylglycerols (MLCTs) are functional structural lipids that can provide the human body with essential fatty acids and a faster energy supply. This study aimed to prepare MLCTs rich in α-linolenic by enzymatic interesterification of perilla oil and medium-chain triacylglycerols (MCTs), catalyzed by Lipozyme RM IM, Lipozyme TL IM, Lipozyme 435, and Novozyme 435 respectively.
RESULTS
The effects of lipase loading, concentration of MCTs, reaction temperature, and reaction time on the yield of MLCTs were investigated. It was found that the reaction achieved more than a 70% yield of MLCTs in triacylglycerols under the conditions of 400 g kg MCTs and 60 g kg lipase loading after equilibrium. A novel two-stage deodorization was also applied to purify the interesterification products. The triacylglycerols reach over 97% purity in the products with significant removal (P < 0.05) of the free fatty acids, and the trans fatty acids were strictly controlled at below 1%. There was more than 40% α-linolenic in the purified products, with long-chain fatty acids mostly occupying the desired sn-2 position in acylglycerols, which are more active in hydrolysis.
CONCLUSION
A series of novel α-linolenic acid-rich medium- and long-chain triacylglycerols was prepared. Under appropriate reaction conditions, the yield of MLCTs in triacylglycerols was above 70%. A novel two-stage deodorization can be used to promote the elimination of free fatty acids and limit the generation of trans fatty acids. © 2020 Society of Chemical Industry.
Topics: Biocatalysis; Enzymes, Immobilized; Fatty Acids; Fungal Proteins; Lipase; Plant Oils; Triglycerides; alpha-Linolenic Acid
PubMed: 32419135
DOI: 10.1002/jsfa.10515 -
Molecular Nutrition & Food Research Jan 2022The proliferation and differentiation of intestinal stem cells (ISCs) are the basis of intestinal renewal and regeneration, and gut microbiota plays an important role in...
SCOPE
The proliferation and differentiation of intestinal stem cells (ISCs) are the basis of intestinal renewal and regeneration, and gut microbiota plays an important role in it. Dietary nutrition has the effect of regulating the activity of ISCs; however, the regulation effect of α-linolenic acid (ALA) has seldom been reported.
METHODS AND RESULTS
After intervening mice with different doses of ALA for 30 days, it is found that ALA (0.5 g kg ) promotes small intestinal and villus growth by activating the Wnt/β-catenin signaling pathway to stimulate the proliferation of ISCs. Furthermore, ALA administration increases the abundance of the Ruminococcaceae and Prevotellaceae, and promotes the production of short-chain fatty acids (SCFAs). Subsequent fecal transplantation and antibiotic experiments demonstrate that ALA on the proliferation of ISCs are gut microbiota dependent, among them, the functional microorganism may be derived from Ruminococcaceae. Administration of isobutyrate shows a similar effect to ALA in terms of promoting ISCs proliferation. Furthermore, ALA mitigates 5-fluorouracil-induced intestinal mucosal damage by promoting ISCs proliferation.
CONCLUSION
These results indicate that SCFAs produced by Ruminococcaceae mediate ALA promote ISCs proliferation by activating the Wnt/β-catenin signaling pathway, and suggest the possibility of ALA as a prebiotic agent for the prevention and treatment of intestinal mucositis.
Topics: Animals; Cell Proliferation; Fatty Acids, Volatile; Intestinal Mucosa; Intestines; Mice; Stem Cells; alpha-Linolenic Acid
PubMed: 34708542
DOI: 10.1002/mnfr.202100408 -
Nutrition (Burbank, Los Angeles County,... Feb 2019Alpha-linolenic acid (ALA) and quercetin are characteristic compounds in plant-based diets. Cardioprotective effects have been described for both substances, although a... (Randomized Controlled Trial)
Randomized Controlled Trial
Effect of alpha-linolenic acid in combination with the flavonol quercetin on markers of cardiovascular disease risk in healthy, non-obese adults: A randomized, double-blinded placebo-controlled crossover trial.
OBJECTIVES
Alpha-linolenic acid (ALA) and quercetin are characteristic compounds in plant-based diets. Cardioprotective effects have been described for both substances, although a possible benefit of combining ALA and quercetin has not, to our knowledge, been evaluated yet. The aim of this study was to investigate the potential independent and additive effects of ALA and quercetin on blood pressure (BP) and lipid and glucose metabolism, as well as on biomarkers of inflammation, oxidative stress, and antioxidant status in healthy, non-obese men and women. Another aim was to examine whether chronic supplementation of supranutritional doses of quercetin would result in an accumulation of plasma quercetin concentration over time.
METHODS
In a double-blinded, placebo-controlled crossover trial, healthy volunteers were randomized to receive 3.6 g/d ALA plus 190 mg/d quercetin or placebo for 8 wk. Data from 67 individuals (34 men, 33 women, mean age: 24.6 y) were assessed.
RESULTS
Plasma quercetin, tamarixetin, isorhamnetin, and kaempferol increased significantly from baseline to study end with ALA + quercetin but not with ALA + placebo. No significant effect on office systolic BP, mean 24 h ambulatory BP (ABP), or mean daytime ABP was seen in either study group. Both interventions significantly decreased total cholesterol, low-density lipoprotein cholesterol, non-high-density lipoprotein cholesterol, and apolipoprotein B to a similar extent. No effect on high-density lipoprotein cholesterol, apolipoprotein A1, glucose, uric acid, oxidized low-density lipoprotein, C-reactive protein, or lipid-adjusted retinol, α-tocopherol, or β-carotene was seen in either group.
CONCLUSION
Although dietary supplements of 3.6 g/d ALA over an 8-wk period improved lipid profiles in healthy adults, antioxidative and oxidative status, inflammation, and BP remained unchanged. No evidence was seen for an additive or synergistic effect of ALA plus quercetin on markers of cardiovascular disease risk.
Topics: Adult; Biomarkers; Cardiovascular Diseases; Cross-Over Studies; Dietary Supplements; Double-Blind Method; Female; Humans; Male; Quercetin; Risk Factors; Young Adult; alpha-Linolenic Acid
PubMed: 30278429
DOI: 10.1016/j.nut.2018.06.012 -
American Journal of Physiology.... Mar 2015Health concerns have led to recommendations to replace saturated fats with unsaturated fats. However, addition of unsaturated fatty acids may lead to changes in the way... (Clinical Trial)
Clinical Trial
Health concerns have led to recommendations to replace saturated fats with unsaturated fats. However, addition of unsaturated fatty acids may lead to changes in the way foods are perceived in the oral cavity. This study tested the taste sensitivity to and emulsion characteristics of oleic, linoleic, and α-linolenic acids. The hypothesis tested was that oral sensitivity to nonesterified fatty acids would increase with degree of unsaturation but that in vitro viscosities and particle sizes of these emulsions would not differ. Oral taste thresholds were obtained using the three-alternative, forced-choice, ascending method. Each participant was tested on each fat 7 times, for a total of 21 study visits, to account for learning effects. Viscosities were obtained for the blank solutions and all three emulsions. Results indicate lower oral thresholds to linoleic and α-linolenic than oleic acid. At higher shear rates, 5% oleic and linoleic acid were more viscous than other samples. More-dilute emulsions showed no significant differences in viscosity. Particle sizes of the emulsions increased very slightly with increasing unsaturation. Together, the emulsion characteristics and oral sensitivity data support a taste mechanism for nonesterified fatty acid detection.
Topics: Adolescent; Adult; Cross-Over Studies; Emulsions; Female; Humans; Linoleic Acid; Male; Middle Aged; Mouth Mucosa; Oleic Acid; Random Allocation; Sensory Thresholds; Taste; alpha-Linolenic Acid
PubMed: 25540234
DOI: 10.1152/ajpgi.00394.2014