Mertensia (Boraginaceae) seeds are new sources of γ-linolenic acid and minor functional compounds.

In this work, seeds from selected Mertensia species were analyzed for γ-linolenic acid-rich oils and minor functional compounds. Fatty acids (FA) were analyzed by GC-FID; tocopherols, sterols, squalene, and phenolics compounds by HPLC-DAD, and the structures of the latter were confirmed by LC-MS. M. maritima spp. asiatica and M. sibirica showed the highest amounts of γ-linolenic acid (22.8 and 18.7%, respectively) and total FA (15.9 and 10.9 g/100 g seeds, respectively). M. sibirica had the greatest levels of sterols, phenolics and tocopherols (244.8, 243.9 and 66.3 mg/100 g, respectively), in which stigmasterol, rosmarinic acid and α-tocopherol (237.7, 180.1 and 53.6 mg/100 g, respectively) were the most abundant components. M. maritima spp. asiatica and M. arizonica showed the highest amounts of squalene (2.5 and 1.1 mg /100 g seeds). Mertensia species constitute a new source of GLA-rich oils, suitable to be marketed by the pharmaceutical and food industries.

Fish Oil and Primrose Oil Suppress the Progression of Alzheimer's Like Disease Induced by Aluminum in Rats.

The role of fish oil, primrose oil and their mixture in ameliorating the changes in Alzheimer's like model was evaluated in rats. Primrose oil and primrose/fish oil mixture fatty acids composition was assessed by gas chromatography. The rat experiment consisted of 5 groups; the first fed on balanced diet as control normal (CN); the other four groups treated with intraperitoneal aluminum lactate and consumed dyslipidemic diet; one group served as control Alzheimer's like disease (CA) while the other three groups (test groups) received daily oral dose from primrose oil, fish oil and primrose/fish oil mixture separately for 5 weeks. Results showed primrose oil and primrose/ fish oil mixture to contain gamma linolenic acid as 9.15 and 4.3% of total fatty acids, respectively. Eicosapentaenoic and docosahexaenoic were present as 10.9 and 6.5 %, respectively in the oil mixture. Dyslipidemia and increased erythrocyte sedimentation rate (ESR), plasma butyrylcholinesterase (BChE), brain malondialdehyde (MDA) and NO with decrease in plasma magnesium, brain catalase, reduced glutathione, body weight gain and brain weight were demonstrated in CA compared to CN. Brain histopathology and immuno-histochemistry showed neuronal degeneration and neurofibrillary tangles with elevated myeloperoxidase and nuclear factor-kappa B in CA compared to CN. The tested oils demonstrated neuro-protection reflected in the variable significant improvement of biochemical parameters, immuno-histochemistry and brain histopathology. Primrose/fish oil mixture was superior in reducing ESR, brain MDA, plasma activity of BChE and brain histopathological changes along with elevating plasma magnesium. Primrose/fish oil mixture and fish oil were more promising in improving plasma high density lipoprotein cholesterol (HDL-C) than primrose. Fish oil was the most efficient in improving plasma total cholesterol (T-C), low density lipoprotein cholesterol and T-C /HDL-C. Primrose/fish oil mixture and primrose oil were superior in elevating brain catalase compared to fish oil. Other parameters were equally improved by the different oil treatments. Primrose oil, fish oil and their mixture reduced the progression of Alzheimer's disease in rats with superiority to primrose/fish oil mixture.

Spirulina Lipids Alleviate Oxidative Stress and Inflammation in Mice Fed a High-Fat and High-Sucrose Diet.

High-fat and high-sucrose diet (HFHSD)-induced obesity leads to oxidative stress and chronic inflammatory status. However, little is known about the beneficial effects of total lipids extracted from Spirulina. Hence, in the present study, Spirulina lipids were extracted with chloroform/methanol (SLC) or ethanol (SLE) and then their effects on oxidative stress and inflammation in the mice fed a HFHSD were investigated. The results show that the major lipid classes and fatty acid profiles of SLC and SLE were almost similar, but the gamma-linolenic acid (GLA) and carotenoid contents in SLE was a little higher than that in SLC. Dietary 4% SLC or SLE for 12 weeks effectively decreased the hepatic lipid hydroperoxide levels as well as increased the activities and mRNA levels of antioxidant enzymes in the mice fed a HFHSD. In addition, supplementation with SLC and SLE also markedly decreased the levels of serum pro-inflammatory cytokines and the mRNA expression of pro-inflammatory cytokines in the liver and epididymal white adipose tissue of mice fed a HFHSD, and the effects of SLC and SLE were comparable. These findings confirm for the first time that dietary Spirulina lipids could alleviate HFHSD-induced oxidative stress and inflammation.

Ribes taxa: A promising source of γ-linolenic acid-rich functional oils.

Fifty Ribes species and R. nigrum-based cultivars from eight Ribes sections were surveyed for γ-linolenic acid (GLA, 18:3, n-6)- and stearidonic acid (SDA, 18:4, n-3)-rich oils. R. pallidiflorum, R. glabellum and R. pubescens seed oils contain noticeable GLA amounts: 13.3, 11.8, and 11.9% of total fatty acids (FA), respectively. However, the highest GLA contents were found in the seed oils of several blackcurrant cultivars, highlining Ribes 'Myuryucheene' with 20.2% GLA of total FA. Principal Component Analysis showed that similarities in FA profiles allow grouping species as botanical criteria for Ribes sections do. The main GLA-taxa detected in this study correspond to blackcurrant cultivars, all of them native to Siberia. Considering that such cultivars are notable fruit-producers, its cultivation in Siberia besides producing fruits in very difficult agronomic areas, could produce a valuable by-product, i.e. the seeds, which will add economic value to agricultural systems if devoted to GLA-rich oils extraction.

Fatty Acid, Triacylglycerol and Unsaponifiable Matters Profiles and Physicochemical Properties of Chinese Evening Primrose Oil.

This work focused on physicochemical property assaying, fatty acid composition, triacylglycerol (TAG) profiles, and unsaponifiable matters composition of the Chinese evening primrose oil. The cold press oil possessed very low acid value and peroxide value, and relatively high iodine value. Fatty acid composition results indicated that this oil was especially high in linoleic acid and linolenic acid. Characterization of TAG composition was achieved by a two-dimensional HPLC coupling of nonaqueous reverse-phase and silver ion HPLC with atmospheric pressure chemical ionization MS method. There was a total of 38 TAGs including 27 regioisomers which had been determined. Unsaponifiable matters composition results revealed that this oil possessed a number of phytosterols, in which ß-sitosterol and stigmasterol were most predominant.

Polycyclic aromatic hydrocarbons content and fatty acids profile in coconut, safflower, evening primrose and linseed oils.

This study aimed at evaluating the polycyclic aromatic hydrocarbons (PAHs) contamination of commercial vegetable oils and examined the identity through the fatty acids profiles. Coconut, safflower, evening primrose, and linseed oils marketed in São Paulo (Brazil) were investigated totaling 69 samples. Four PAHs, benzo[a]anthracene (BaA), chrysene (Chr), benzo[b]fluoranthene (BbF), and benzo[a]pyrene (BaP), were detected in 96% of the samples at individual levels ranging from not detected to 14.99 µg kg-1. Chrysene was the abundant hydrocarbon found among all types of oils, with the highest median values. The results of the fatty acid profiles revealed that 43% showed different profiles according to the ones on their labels, with a higher incidence of adulteration of evening primrose oils. The maximum tolerable limits by European Regulation No. 835/2011 were exceeded for BaP in 12%, and for total 4 PAHs in 28%, with a greater contribution of adulterated samples.

Influence of gestational diabetes mellitus on fatty acid concentrations in human colostrum.

OBJECTIVE: The aim of this study was to examine differences in fatty acid concentrations in colostrum of women with and without gestational diabetes mellitus (GDM). The effect of GDM on fatty acid composition of colostrum is not fully understood, although rates of GDM are increasing globally. METHODS: A prospective case-control study was conducted of postpartum women with and without GDM. Gas chromatographic analysis was conducted to examine differences in colostral fatty acids of the colostrum samples of 29 women with and 34 without GDM. RESULTS: Analyses of the fatty acid composition revealed significantly higher concentrations of four essential ω-6 polyunsaturated fatty acids-γ-linolenic, eicosatrienoic, arachidonic, and docosatetraenoic-in the colostrum of GDM women compared with non-GDM women. Timing of collection influenced saturated medium chain fatty acid and monounsaturated fatty acid levels. CONCLUSIONS: Differences in concentrations of ω-6 fatty acids but not in dietary linoleic fatty acid or ω-3 fatty acids suggest that altered concentrations are attributed to changes in specific endogenous metabolic pathways. Implications of higher concentrations of ω-6 fatty acids in the colostrum of women with GDM have yet to be determined. Timing of colostrum collection is critical in determining colostral fatty acid and metabolite concentrations.

Potential oil yield, fatty acid composition, and oxidation stability of the hempseed oil from four Cannabis sativa L. cultivars.

The cultivation of four industrial hemp cultivars (Felina 32, Chamaeleon, Uso31, and Finola) was investigated for oil production in the north-east of Italy along two years. The oils of all cultivars resulted in rich amount of linoleic acid (ω-6) and α-linolenic acid (ω-3). Felina 32 and Chamaeleon oils exhibited the highest amount of linoleic acid (59%) and α-linolenic acid (18%). Finola and Uso31 oils resulted in the richest of γ-linolenic acid (5-6%). All hempseed oils presented high oxidation stability and an acceptable initial quality. It is suggested that these oils can be used to produce EFA dietary supplements high in ω-6 and ω-3 of vegetal origin.

Variations in Tunisian borage essential oil profiles and their antioxidant activities during flowering.

This study was conducted to examine the chemical composition and antioxidant activity of the essential oils (EOs) of Borago officinalis stem during its flowering stage. The EO composition was characterised by high proportions of E,E-decadienal, the main compound of monoterpene hydrocarbon class, with values varying from 47.08% to 55.28% in two Tunisian regions. The region of Korba exhibited the highest scavenging activity (2.05 mg/mL) by comparison with Beja region. In all tests, the fructification stage showed the best antioxidant activity of all flowering stages.

Dietary Spirulina (Arthrospira platensis) and Thyme (Thymus vulgaris) supplementation to growing rabbits: effects on raw and cooked meat quality, nutrient true retention and oxidative stability.

The study evaluated the effect of Spirulina and Thyme dietary supplementation on rabbit meat quality, nutrient true retention and protection against oxidative stress. Rabbits in the control group (C-C) received a non-supplemented pellet throughout the experiment (5-11weeks of age). In the other groups, the pellet contained 5% Spirulina (S), 3% Thyme (T), or both (ST) for either the entire (groups S-S, T-T, ST-ST) or only the final part of the growing period (8-11weeks: groups C-S, C-T, C-ST). Spirulina supplementation increased the γ-linolenic acid content of rabbit meat, whereas Thyme improved the oxidative stability of raw and freeze-dried meat.

Gamma-linolenic acid levels correlate with clinical efficacy of evening primrose oil in patients with atopic dermatitis.

INTRODUCTION: Atopic dermatitis (AD) has been related to a deficiency of delta-6-desaturase, an enzyme responsible for the conversion of linoleic acid to gamma-linolenic acid (GLA). Evening primrose oil (EPO) contains high amounts of GLA. Therefore, this study investigated whether EPO supplementation results in an increase in plasma GLA and its metabolite dihomo-gamma-linolenic acid (DGLA) correlating with clinical improvement of AD, assessed by the SCORing Atopic Dermatitis (SCORAD) index. METHODS: The open study included 21 patients with AD. EPO (4-6 g) was administered daily for 12 weeks. Before treatment, and 4 and 12 weeks after initiation of EPO supplementation, objective SCORAD was assessed and plasma concentrations of GLA and DGLA were determined by gas chromatography. RESULTS: A significant increase in plasma GLA and DGLA levels and a decrease in the objective SCORAD were observed 4 and 12 weeks after initiation of EPO treatment. In the per-protocol population (n = 14), a significant inverse correlation between the changes in plasma GLA levels and SCORAD was found (P = 0.008). CONCLUSION: The clinical disease activity under EPO treatment correlates with the individual increase in plasma GLA levels. Thus, the results of this pilot study indicate that an increase in plasma GLA might be used as predictive parameter for responsiveness of AD to EPO therapy.

Comparison of growth, serum biochemistries and n-6 fatty acid metabolism in rats fed diets supplemented with high-gamma-linolenic acid safflower oil or borage oil for 90 days.

Recently, steps have been taken to further developments toward increasing gamma-linolenic acid (GLA) concentration and lowering costs in plant seed oils using transgenic technology. Through identification and expression of a fungal delta-6 desaturase gene in the high linoleic acid safflower plant, the seeds from this genetic transformation produce oil with >40% GLA (high GLA safflower oil (HGSO)). The aim of the study was to compare the effects of feeding HGSO to a generally recognized as safe source of GLA, borage oil, in a 90 day safety study in rats. Weanling male and female Sprague-Dawley rats were fed a semi-synthetic, fat free, pelleted diet (AIN93G) supplemented with a 10% (wt/wt) oil blend containing HGSO or borage oil, with equivalent GLA levels. Results demonstrated that feeding diets containing HGSO or borage oil for 90 days had similar biologic effects with regard to growth characteristics, body composition, behavior, organ weight and histology, and parameters of hematology and serum biochemistries in both sexes. Metabolism of the primary n-6 fatty acids in plasma and organ phospholipids was similar, despite minor changes in females. We conclude that HGSO is biologically equivalent to borage oil and provides a safe alternative source of GLA in the diet.

Δ6-Desaturase from Mortierella alpina: cDNA cloning, expression, and phylogenetic analysis.

The open reading frame of the Δ(6)-desaturase gene was isolated from Mortierella alpina W15 and the gene was cloned into a pPIC3.5K vector. The vector was transformed into Pichia pastoris GS115 and expression was induced with methanol. The Δ(6)-desaturase expressed in P. pastoris GS115 catalyzed the conversion of linoleic acid to γ-linolenic acid but not the conversion of α-linolenic acid to octadecatetraenoic acid. The results indicate that the Δ(6)-desaturase gene from M. alpina W15 has substrate specificity in different organisms. Phylogenetic analysis revealed that Δ(6)-desaturase genes can be divided into four monophyletic groups. This work paves the way for further study of the functions of Δ(6)-desaturase in fatty acid metabolism and its three-dimensional structure.

Separation of γ-linolenic and other polyunsaturated fatty acids from Boraginaceae via supercritical CO2.

Essential fatty acids were extracted from Echium amoenum (Boraginaceae) seed oil via supercritical carbon dioxide and the results were compared with conventional Soxhlet method as the base case of 100% recovery. The response surface methodology was used to optimize the effective extraction parameters. The chemical composition of recovered oil was analyzed by polar and non-polar gas chromatograph-flame ionization detector columns. The experimental results indicated that echium seed contained 25 wt% oil and the maximum extraction oil recovery of 92% was obtained via supercritical CO(2) at optimal operating conditions (43°C, 280 bar, 1.5 mL/min, 25 min static time and 130 min dynamic time). At similar operating conditions, applying 2.5 and 5 mol% ethanol as a modifier enhanced the recovery to 96 and 112%, respectively. The results showed that supercritical fluid extraction is a viable technique for separation of constituents such as γ-linolenic acid (7-8%), palmitic acid (6-7%), stearic acid (3-4%), oleic acid (12-13%), linoleic acid (19-20%), α-linolenic acid (40-41%) and stearidonic acid (8-9%) from Boraginaceae.

Central composite design for the optimization of supercritical carbon dioxide fluid extraction of fatty acids from Borago officinalis L. flower.

UNLABELLED: In the present study, fatty acids and essential oils of the flower of borage (Borago officinalis L.) were obtained by supercritical carbon dioxide fluid extraction under different conditions. The extracts obtained were compared to oils of borage flower oil isolated by hydrodistillation. The obtained oils were analyzed by gas chromatography mass spectrometry. The compounds were identified according to their retention indices and mass spectra. The experimental parameters of supercritical fluid extraction (SFE) were optimized using a central composite design after a full factorial experimental design. Extraction yields based on SFE varied in the range of 0.02% to 1.96% (w/w), and the oil yield based on the hydrodistillation was 0.05% (v/w). The optimum conditions of SFE were obtained at a pressure of 350 atm, a temperature of 65 °C, a methanol modifier volume of 100 µL, and static and dynamic extraction time of 10 min. Main components of the extracts under optimum SFE conditions were palmitic acid, linoleic acid, γ-linolenic acid, and oleic acid. The results indicated that by using the suitable extraction conditions, SFE is more effective than the conventional hydrodistillation method in the extraction of fatty acids and the preservation of its quality. PRACTICAL APPLICATION: SFE is a good technique for the extraction of oils from plants. The extraction yields by SFE are more than the conventional method. SFE is used on a large scale for production of essential oils and pharmaceutical products from plants.

[Separation of gamma linolenic acid from evening primrose oil with urea inclusion--orthogonal experiment of optimizing technological parameters and observation of urea inclusion compound I].

OBJECTIVE: The influence on the urea inclusion compound under different conditions (allocated proportion, time of inclusion, temperature of inclusion) were studied through the orthogonal test, and theoretical reference of urea inclusion process for further optimization wound be offered. METHOD: The orthogonal experiment was adopted, and microscope was used to observe the shape, aperture size of the urea inclusion compound under different technological parameters, the GC was employed to inspect the purity of GLA. RESULT: The results indicated that the ratio of fatty acids and urea, inclusion of temperature, time of inclusion had great effect on urea inclusion compound. The three factors and its interactions significantly affected the purity of GLA. The results also showed that the best process was that the ratio of fatty acids and urea was 1 : 3, temperature of inclusion was--15 degrees C, time of inclusion was 24 h. CONCLUSION: Under the best condition, the purity of GLA reach up to 95.575 9%; and it is feasible to observe the shape and the amount of the urea inclusion compound to reflect and guide the urea inclusion technology.

Nutrition for the eye: different susceptibility of the retina and the lacrimal gland to dietary omega-6 and omega-3 polyunsaturated fatty acid incorporation.

The purpose of this study was to compare the susceptibility of the retina and the exorbital lacrimal gland to dietary supplies of long-chain omega-3 (omega3) and omega-6 (omega6) polyunsaturated fatty acids (LC-PUFAs). Male Wistar rats were fed a 5% lipid diet containing: (1) 10% eicosapentaenoic acid (EPA) and 7% docosahexaenoic acid (DHA), or (2) 10% gamma-linolenic acid (GLA), or (3) 10% EPA, 7% DHA and 10% GLA or (4) a balanced diet deprived of EPA, DHA and GLA for 3 months. Lipids were extracted from plasma phospholipids, retina and exorbital lacrimal gland, and fatty acid composition was determined by gas chromatography. Dietary supplementation with EPA and DHA increased omega3 PUFA levels in plasma phospholipids as well as in the retina and the exorbital lacrimal gland. By contrast, GLA supplementation favored omega6 PUFA incorporation, and particularly the incorporation of the end-chain omega6 product, docosapentaenoic acid (DPA), into all tissues. Supplementation with EPA, DHA and GLA increased the levels of DHA, EPA and dihomo-GLA (dGLA), whereas arachidonic acid (AA) was unchanged and DPA decreased in the retina and the lacrimal gland. The ability of both tissues to incorporate PUFAs from blood was evaluated. The results showed that the retina was more selective than the lacrimal gland for EPA. In spite of the different susceptibility of the retina and the lacrimal gland to dietary PUFAs, these results suggest that the concomitant use of dietary omega3 and omega6 PUFAs may be useful in modulating inflammation in both tissues.

[Prepared evening primrose oil microspheres by spray drying].

OBJECTIVE: To explore the best technique parameters on preparing evening primrose oil microspheres by spray drying technique. METHOD: GC and internal standard method were used to determine the content of gamma-linolenic acid methyl esters, the technological parameters were investigated by orthogonal experimental design with the yield and entrapment rate as indexes. RESULT: The charging rate as 3 mL x min(-1), atomizing pressure as 100 kPa and the temperature of inlet as 105 degrees C were the best technique parameters. CONCLUSION: Evening primrose oil microspheres accorded with the expecting demand. The main influencing factor is the charging rate. Spray drying is reasonable and practical for preparing evening primrose oil microspheres.

Regioisomeric structure determination of alpha- and gamma-linolenoyldilinoleoylglycerol in blackcurrant seed oil by silver ion high-performance liquid chromatography and mass spectrometry.

Gamma-linolenic acid (Gla) and oils containing Gla have evident positive effects on a variety of disorders, and therefore, the structure of triacylglycerols (TAGs) containing Gla is of special interest. The regioisomeric structures of TAGs 18:3(n-3)/18:2/18:2 (Ala/L/L) and 18:3(n-6)/18:2/18:2 (Gla/L/L) in blackcurrant seed oil were determined by Ag-HPLC/APCI-MS and Ag-HPLC/ESI-MS/MS techniques. In the latter, silver ion adducts were prepared by adding silver nitrate to the postcolumn flow. A new Ag-HPLC solvent system containing nonchlorinated solvents for the separation of Gla- and Ala-containing TAGs is introduced. Ag-HPLC separation of Ala/L/L and Gla/L/L was sufficient and regioisomers sn-LnLL + sn-LLLn and sn-LLnL (Ln, linolenic acid) could be differentiated well with the MS methods used. No discrimination was made between the sn-1 and sn-3 positions. The results show that the methods used are suitable to discriminate and determine the regioisomeric structure of TAGs. The regioisomeric structure of TAG with the fatty acid combination Gla/L/L in blackcurrant seed oil was considered to be practically random (32.7-37.8% of sn-LGlaL). In the fatty acid combination Ala/L/L, the regioisomeric structure is nonrandom (7.3-12.1% of sn-LAlaL) with Ala preferentially in a primary position. It can be concluded that the positional distribution of Ala and Gla is different in Ln/L/L TAGs of blackcurrant seed oil.

High-performance liquid chromatography with nuclear magnetic resonance detection--A method for quantification of alpha- and gamma-linolenic acids in their mixtures with free fatty acids.

While many naturally occurring mixtures of free fatty acids are conveniently analyzed by hyphenated technique of LC-NMR, a complete separation of alpha- and gamma-linolenic acids for their quantitative determination appears impossible at least by the methods of reversed phase HPLC. However, they can be differentiated and quantified from 1H NMR spectra measured in the course of isocratic acetonitrile-chloroform (90:10, with C8 and C18 columns in series) LC-NMR analysis without the need for any derivatization.