Physicochemical characterization of oil, antioxidant potential, and phenolic profile of seeds isolated from Tunisian pomegranate (Punica granatum L.) cultivars.

Pomegranate (Punica granatum L.) seeds oils (PSO) from three Tunisian varieties namely Jebali, Testouri, and Gabsi were extracted by ultrasonic-assisted extraction and analyzed for their physicochemical properties, fatty acids (FA) profile, and sterol composition. PSO of Gabsi and Testouri showed the best quality indexes in terms of peroxide and acid values and the highest oxidative stability index was observed for PSO of Gabsi ecotype (2.534 hr). Polyphenol content of PSO of Gabsi ecotype (886.909 mg/kg) was roughly 3 and 23 times higher than that of Jebali and Testouri ecotypes, respectively. Twelve FAs were identified by GC/FID. Punicic acid was the major compounds ranged from 81.53% (Testouri) to 86.41% (Gabsi). The unsaturated/saturated FA ratios of PSO were 14.53, 15.95, and 18.68, respectively for Gabsi, Testouri, and Jebali, respectively. Phytosterols were also identified and ß-sitosterol was the major compound in PSO. In addition, the phytochemical and antioxidant properties of phenolic extracts obtained from pomegranate seeds residues were investigated. Pomegranate seeds extract (PSE) of Gabsi cultivar showed the highest content of polyphenols (64.762 mg CAE/g) and flavonoids (7.127 mg RE/g). Antioxidant potential of extracts was performed using DPPH test and total antioxidant capacity (TAC). Results revealed that Gabsi cultivar was the most reactive extract with EC50 of 0.105 mg/mL for DPPH test and 40.622 mg AA/g for TAC. Phenolic profiles of PSE were also investigated. Results showed the importance of cultivar selection in the potential use of bioactive compounds of seeds as nutraceutical ingredients in food and chemical industries. PRACTICAL APPLICATION: Three Tunisian pomegranate cultivars namely Jebali, Testouri, and Gabsi were investigated for their seeds oil and phenolic composition. Pomegranate seeds oil (PSO) are rich in bioactive polyunsaturated fatty acids and phytosterols that can be of interest in several food and chemical industrial applications. Moreover, pomegranate seeds extracts are a natural source of antioxidant components, such as phenolic compounds, that can be used by the pharmaceutical industry as promising nutraceutical ingredients. The obtained results can be used to provide guidance on cultivar selection during industrial applications.

Antioxidant activity and fatty acids quantification in Sicilian purslane germplasm.

Portulaca oleracea is an annual succulent herb in the family Portulacaceae. It is a nutritious vegetable with high antioxidant properties and, it is among the richest plant source of ω-3 fatty acids, as well as a rich source of ω-6 fatty acids, ascorbic acid, tocopherols and beta-carotene. In the present study, three purslane populations under different Mediterranean environmental conditions for two years, for future valorization as novel food sources of omega-3 fatty acids, were evaluated. In particular, biomorphological characteristics, total phenols and fatty acids content were determined. The antioxidant activities were evaluated using 2,2-diphenyl-1-picrylhydrazyl assay. The population "Cas" appears to have higher antioxidant activity than the other two populations ("Cal" and "S. Ven").The saturated fatty acid content is influenced only by the year of collection, while the polyunsaturated fatty acid by the populations. The most abundant unsatured fatty acids are linoleic and linolenic acids and "Cas" attained the highest contents.

Fatty Acid Composition and Applications of Eriobotrya japonica Seed Oil.

The loquat (Eriobotrya japonica) is commonly found in Japan. Its fruits are consumed raw or used in processed foods, and its leaves are used as a traditional medicine and in the manufacturing of cosmetics. Additionally, its seeds have several industrial applications. Therefore, this study aimed to estimate the fatty acid composition of loquat seed oil, and to evaluate its potential application as a deodorant. Palmitic acid, linoleic acid, behenic acid, and lignoceric acid were found to be the primary fatty acids present in the seeds, among which linoleic acid was involved in the deodorization of allyl methyl sulfide. Based on these results, loquat seed oil has potential for use in deodorant production.

"Dicranin" in the Membrane Phospholipids of a Dicranaceae and Pottiaceae Moss Member of the Eastern Himalayan Biodiversity Hotspot.

The phospholipids of two moss samples Oreoweisia laxifolia (Hookf.) Kindb. (family-Dicranaceae Schimp.) and Leptodontium viticulosoides (P. Beauv.) Wijk & Margad (family-Pottiaceae Schimp.) of the Eastern Himalayan Biodiversity Hotspot were investigated to find out any peculiarity in their fatty acid profiles. Detailed analysis of phospholipid classes and the respective fatty acids was performed using high-performance thin-layer chromatography and gas chromatography-mass spectrometry. An array of different saturated and unsaturated fatty acids were detected in both the samples. Although it has been proposed previously that acetylenic fatty acids are associated only with triacylglycerol of storage lipids, the most striking observation of the present investigation is the abundance of an acetylenic fatty acid, octadeca-6-yn-9,12,15-trienoic acid (18:4a), or Dicranin, in the phospholipids of both the mosses. The position of the triple bond in the hydrocarbon chain of the fatty acids was confirmed by dimethyloxazoline derivatization of fatty acids and their characteristic mass fragmentation pattern. The occurrence of Dicranin in phospholipids and in the Pottiaceae family is reported for the first time, with substantial explanations of the observed results. This may raise the issue of rethinking "Dicranin" as a chemotaxonomic marker of Dicranaceae.

Compositional Analyses and Shelf-Life Modeling of Njangsa (Ricinodendron heudelotii) Seed Oil Using the Weibull Hazard Analysis.

This study investigated the compositional characteristics and shelf-life of Njangsa seed oil (NSO). Oil from Njangsa had a high polyunsaturated fatty acid (PUFA) content of which alpha eleostearic acid (α-ESA), an unusual conjugated linoleic acid was the most prevalent (about 52%). Linoleic acid was also present in appreciable amounts (approximately 34%). Our investigations also indicated that the acid-catalyzed transesterification of NSO resulted in lower yields of α-ESA methyl esters, due to isomerization, a phenomenon which was not observed under basic conditions. The triacylglycerol (TAG) profile analysis showed the presence of at least 1 α-ESA fatty acid chain in more than 95% of the oil's TAGs. Shelf-life was determined by the Weibull Hazard Sensory Method, where the end of shelf-life was defined as the time at which 50% of panelists found the flavor of NSO to be unacceptable. This was determined as 21 wk. Our findings therefore support the potential commercial viability of NSO as an important source of physiologically beneficial PUFAs.

High Content of Dicranin in Anisothecium spirale (Mitt.) Broth., a Moss from Eastern Himalayas and Its Chemotaxonomic Significance.

Chemical investigation of Anisothecium spirale (Mitt.) Broth. (Family Dicranaceae), an epiphytic moss from the Darjeeling district hill region of the Eastern Himalayas was performed for the first time. Analysis of neutral lipid and phospholipid classes as well as their respective fatty acids revealed the presence of a significantly high content of octadeca-6-yn-9,12,15-trienoic acid, an acetylenic fatty acid commonly known as dicranin. Dicranin and a less abundant acetylenic fatty acid were detected in neutral lipids. The unique nature of the fatty acid signature supports the view of considering dicranin as chemotaxonomic marker for Dicranaceae members.

Ethyl linolenate is elevated in meconium of very-low-birth-weight neonates exposed to alcohol in utero.

BACKGROUND: The health implications of in utero alcohol exposure have been difficult to study in very-low-birth-weight newborns (VLBW) because of an inability to identify maternal alcohol exposure. Fatty acid ethyl esters (FAEEs) are elevated in meconium of alcohol-exposed term newborns. We hypothesized that meconium FAEEs would be similarly elevated in alcohol-exposed VLBW premature newborns. METHODS: In a retrospective cohort study of 64 VLBW neonates, newborns were classified into Non-Exposed, Any Exposure, or Weekly Exposure groups based on an in-depth structured maternal interview. Meconium FAEE concentrations were quantified via gas chromatography mass spectrometry. RESULTS: Alcohol exposure during Trimester 1 (Any Exposure) occurred in ~30% of the pregnancies, while 11% of the subjects reported drinking ≥ 1 drink/week (Weekly Exposure). Meconium ethyl linolenate was higher in Any Exposure (P = 0.01) and Weekly Exposure groups (P = 0.005) compared to the Non-Exposed VLBW group. There was a significant positive correlation between Trimester 1 drinking amounts and the concentration of meconium ethyl linolenate (P = 0.005). Adjusted receiver operating characteristic (ROC) curves evaluating ethyl linolenate to identify alcohol-exposed VLBW newborns generated areas under the curve of 88% with sensitivities of 86-89% and specificities of 83-88%. CONCLUSION: Despite prematurity, meconium FAEEs hold promise to identify the alcohol-exposed VLBW newborn.

Seed Quality Traits Can Be Predicted with High Accuracy in Brassica napus Using Genomic Data.

Improving seed oil yield and quality are central targets in rapeseed (Brassica napus) breeding. The primary goal of our study was to examine and compare the potential and the limits of marker-assisted selection and genome-wide prediction of six important seed quality traits of B. napus. Our study is based on a bi-parental population comprising 202 doubled haploid lines and a diverse validation set including 117 B. napus inbred lines derived from interspecific crosses between B. rapa and B. carinata. We used phenotypic data for seed oil, protein, erucic acid, linolenic acid, stearic acid, and glucosinolate content. All lines were genotyped with a 60k SNP array. We performed five-fold cross-validations in combination with linkage mapping and four genome-wide prediction approaches in the bi-parental population. Quantitative trait loci (QTL) with large effects were detected for erucic acid, stearic acid, and glucosinolate content, blazing the trail for marker-assisted selection. Despite substantial differences in the complexity of the genetic architecture of the six traits, genome-wide prediction models had only minor impacts on the prediction accuracies. We evaluated the effects of training population size, marker density and phenotyping intensity on the prediction accuracy. The prediction accuracy in the independent and genetically very distinct validation set still amounted to 0.14 for protein content and 0.17 for oil content reflecting the utility of the developed calibration models even in very diverse backgrounds.

Impact of Cultivar on Profile and Concentration of Lipophilic Bioactive Compounds in Kernel Oils Recovered from Sweet Cherry (Prunus avium L.) by-Products.

Lipophilic bioactive compounds in oils recovered from the kernels of seven sweet cherry (Prunus avium L.) cultivars, harvested at single location in 2013, were studied. Oil yield in sweet cherry ranged between 30.3-40.3 % (w/w) dw. The main fatty acids were oleic acid (39.62-49.92 %), linoleic acid (31.13-38.81 %), α-eleostearic acid (7.23-10.73 %) and palmitic acid (5.59-7.10 %), all four represented approximately 95 % of the total detected fatty acids. The ranges of total tocochromanols and sterols were between 83.1-111.1 and 233.6-419.4 mg/100 g of oil, respectively. Regardless of the cultivar, the γ-tocopherol and ß-sitosterol were the main lipophilic minor bioactive compounds. The content of the carotenoids and squalene were between 0.38-0.62 and 60.9-127.7 mg/100 g of oil, respectively. Three significant correlations were found between oil yield and total contents of sterols (r = -0.852), tocochromanols (r = -0.880) and carotenoids (r = -0.698) in sweet cherry kernel oils. The oil yield, as well as the content of lipophilic bioactive compounds in oil was significantly affected by the cultivar.

Fatty acid profile of milk and Cacioricotta cheese from Italian Simmental cows as affected by dietary flaxseed supplementation.

The study aimed to determine the effects of adding flaxseed to the diet on the fatty acid profile of the milk of Italian Simmental cows and on the Cacioricotta cheese thereby produced. The experiment involved 24 Italian Simmental cows divided into 2 groups of 12 animals according to the diet fed: a control diet (CO) with no flaxseed supplementation, and a diet supplemented with whole flaxseed (FS). Milk yield and composition was not significantly changed by diet, whereas saturated fatty acids, monounsaturated fatty acids (MUFA), and polyunsaturated fatty acids (PUFA) were increased by flaxseed supplementation. Cows fed flaxseed showed higher percentages of long-chain fatty acids: in particular, linolenic acids, mainly represented by C18:3n-3, and n-3 series were higher in the FS group than in the CO group. The percentage of MUFA was higher by about 12% in FS than in CO, mainly due to the contribution of C18:1 cis-9. The percentage of conjugated linoleic acid (CLA) in milk was not significantly changed by flaxseed supplementation. Furthermore, atherogenic and thrombogenic indices were lower by about 30 and 16%, respectively, in the FS group compared with the CO group. The fatty acid profile of Cacioricotta cheese produced using Italian Simmental cow milk showed higher levels of MUFA, PUFA, and n-3, and improved atherogenic and thrombogenic indices in FS than in CO, confirming the ability to transfer beneficial molecules from milk into cheese. In particular, cheese-making technology contributed to the increased CLA content in Cacioricotta cheese.

Gas chromatography with tandem differential mobility spectrometry of fatty acid alkyl esters and the selective detection of methyl linolenate in biodiesels by dual-stage ion filtering.

Alkyl esters of fatty acids (FAAEs) with carbon numbers from 8 to 20 formed protonated monomers and proton bound dimers through atmospheric pressure chemical ionization reactions and these gas ions were characterized for their field dependent mobility coefficients using differential mobility spectrometry (DMS). Separation of ion peaks with a vapor modifier was achieved for ions with masses of 317-1033 Da though the differences in these coefficients and the resolution of ion peaks decreased proportionally with increased ion mass. Differences in dispersion curves were sufficient to isolate ions from specific FAAEs in the effluent of a gas chromatograph by dual stage ion filtering using a tandem DMS detector. Methyl linolenate was isolated from nearby eluting methyl oleate, methyl stearate and methyl linoleate within analysis times of 10s without measureable complications from charge suppression in the ion source or leakage in filtering of ions with close proximity of dispersion behavior.

Punica granatum cv. Dente di Cavallo seed ethanolic extract: antioxidant and antiproliferative activities.

This paper aims to provide a solid base for the utilisation of pomegranate whole seed ethanolic extract (PSEE) as a nutraceutical/functional food ingredient. PSEE was tested for its antioxidant and antiproliferative activities against different human cancer cell lines. Bioactive lipid compounds were identified by studying the PSEE lipid portion. PSEE exhibited a protection of lipid peroxidation threefold higher than a positive control. PSEE showed a promising antiproliferative activity against hormone dependent prostate carcinoma LNCaP, with an IC50 value 3 times lower than the positive control vinblastine, and against human breast cancer cell lines (IC50=9.6 µg/ml). PSEE contained lipid bioactive compounds, such as neutral lipids, consisting of 72.8% punicic acid, glycolipids and phospholipids rich in essential fatty acids (α-linoleic and α-linolenic acids). Due the presence of bioactive compounds and the remarkable antiproliferative activity, the use of PSEE as a value-added ingredient in formulations of products aimed to prevent diseases, especially cancer, could be promoted.

Characterization of white Mahlab (Prunus mahaleb L.) seed oil: a rich source of α-eleostearic acid.

UNLABELLED: Seed oils with high polyunsaturated fatty acid content are used in various industries including the food and pharmaceutical industries. White mahlab (Prunus mahaleb L.) seed was found to contain 31% oil. The oil was highly polyunsaturated and abundant in α-eleostearic (38.32%), oleic (31.29%), and linoleic (22.96%) acids, which together comprised 93.91% of the total fatty acids. The α-eleostearic acid was identified and characterized based on (1)H-NMR, UV, and FTIR spectroscopy. The oil was characterized by a relatively high quantity of tocopherols with γ-tocopherol as the major tocopherol isomer. The physicochemical characteristics of the white mahlab seed and seed oil were also determined. The thermogravimetric analysis indicated that the oil was thermally stable up to 350 °C and began to decompose at 520 °C. This study demonstrated that these seeds may be reused and their oil incorporated into other food products, a beneficial practice considering that the compounds present in the seeds and oils have positive effects on human health. PRACTICAL APPLICATION: In this study, mahlab seed oil was found to have potentials to become a new edible oil source as it contained a high level of polyunsaturated fatty acids especially, α-eleostearic acid, which is a conjugated fatty acid rarely found in vegetable oils and has a beneficial effects on human health.

Coordinate changes in gene expression and triacylglycerol composition in the developing seeds of oilseed rape (Brassica napus) and turnip rape (Brassica rapa).

Crop production for vegetable oil in the northern latitudes utilises oilseed rape (Brassica napus subsp. oleifera) and turnip rape (B. rapa subsp. oleifera), having similar oil compositions. The oil consists mostly of triacylglycerols, which are synthesised during seed development. In this study, we characterised the oil composition and the expression levels of genes involved in triacylglycerol biosynthesis in the developing seeds in optimal, low temperature (15 °C) and short day (12-h day length) conditions. Gene expression levels of several genes were altered during seed development. Low temperature and short day treatments increased the level of 9,12,15-octadecatrienoic acid (18:3n-3) in turnip rape and short day treatment decreased the total oil content in both species. This study gives a novel view on seed oil biosynthesis under different growth conditions, bringing together gene expression levels of the triacylglycerol biosynthesis pathway and oil composition over a time series in two related oilseed species.

Enrichment of functional properties of ice cream with pomegranate by-products.

Pomegranate peel rich in phenolics, and pomegranate seed which contain a conjugated fatty acid namely punicic acid in lipid fraction remain as by-products after processing the fruit into juice. Ice cream is poor in polyunsaturated fatty acids and phenolics, therefore, this study was conducted to improve the functional properties of ice cream by incorporating pomegranate peel phenolics and pomegranate seed oil. Incorporation of the peel phenolics into ice cream at the levels of 0.1% and 0.4% (w/w) resulted in significant changes in the pH, total acidity, and color of the samples. The most prominent outcomes of phenolic incorporation were sharp improvements in antioxidant and antidiabetic activities as well as the phenolic content of ice creams. Replacement of pomegranate seed oil by milk fat at the levels of 2.0% and 4.0% (w/w) increased the conjugated fatty acid content. However, perception of oxidized flavor increased with the additional seed oil. When one considers the functional and nutritional improvements in the enrichment of the ice cream together with overall acceptability results of the sensory analysis, then it follows from this study that ice creams enriched with pomegranate peel phenolics up to 0.4% (w/w) and pomegranate seed oil up to 2.0% (w/w) could be introduced to markets as functional ice cream. Enrichment of ice creams with pomegranate by-products might provide consumers health benefits with striking functional properties of punicalagins in pomegranate peel, and punicic acid in pomegranate seed oil.

Molecular properties of the class III subfamily of acyl-coenyzme A binding proteins from tung tree (Vernicia fordii).

Acyl-CoA binding proteins (ACBPs) have been identified in most branches of life, and play various roles in lipid metabolism, among other functions. Plants contain multiple classes of ACBP genes. The most diverse group is the class III proteins. Tung tree (Vernicia fordii) contains two such genes, designated VfACBP3A and VfACBP3B. The two proteins are significantly different in length and sequence. Analysis of tung ACBP3 genes revealed significant evolution, suggesting relatively ancient divergence of the two genes from a common ancestor. Phylogenetic comparisons of multiple plant class III proteins suggest that this group is the most evolutionarily dynamic class of ACBP. Both tung ACBP3 genes are expressed at similar levels in most tissues tested, but ACBP3A is stronger in leaves. Three-dimensional modeling predictions confirmed the presence of the conserved four α-helix bundle acyl-CoA binding (ACB); however, other regions of these proteins likely fold much differently. Acyl-CoA binding assays revealed different affinities for different acyl-CoAs, possibly contradicting the redundancy of function suggested by the gene expression studies. Subcellular targeting of transiently-expressed plant ACBP3 proteins contradicted earlier studies, and suggested that at least some class III ACBPs may be predominantly targeted to endoplasmic reticulum membranes, with little or no targeting to the apoplast.

At line prediction of PUFA and biohydrogenation intermediates in perirenal and subcutaneous fat from cattle fed sunflower or flaxseed by near infrared spectroscopy.

NIRS potential to estimate the proportion of PUFA and their biohydrogenation products in adipose tissues from cattle fed sunflower or flaxseed was tested. Immediately after skinning, perirenal and subcutaneous fat samples from 63 steers were collected, scanned intact at 37°C and 33°C, respectively, over a NIR spectral range from 400 to 2498nm using benchtop equipment and then analyzed for fatty acid composition. NIRS calibrations in perirenal fat showed high predictability for total and major omega-6 and omega-3, conjugated linolenic acids, t,t-conjugated linoleic acids (CLA), non-CLA dienes and trans-monounsaturated fatty acids, with R(2) (RMSECV, %) of 0.88-0.89 (0.16-0.20), 0.89-0.91 (0.07-0.08), 0.86-0.89 (0.01-0.09), 0.82 (0.07), 0.89 (0.46) and 0.86-0.88 (0.87-1.29), respectively. NIRS predictions in subcutaneous fat were less reliable, probably due to lower fatty acid variability. The results show NIRS to be a useful technique for the early, fast and relatively inexpensive estimation of proportions of fatty acids with potential human health effects in cattle perirenal fat.

Uptake of conjugated linolenic acids and conversion to cis-9, trans-11-or trans-9, trans-11-conjugated linoleic acids in Caco-2 cells.

Dietary oils containing large amounts of conjugated linolenic acids (CLnA) may be regarded as a source of conjugated linoleic acids (CLA), which have been suspected to bear health-promoting properties. Indeed, CLnA can be converted into CLA in mammals. The objective of the present study was to investigate the uptake of CLnA and their metabolism into CLA in Caco-2 cells, as a validated in vitro model of the intestinal barrier. Caco-2 cells were incubated for 24 h in the presence of either α-eleostearic, ß-eleostearic, catalpic or punicic acid. We first observed that Caco-2 cells take these CLnA up at different rates and then convert them but with varying efficiency depending on the structure of the Δ13 double bond. Finally, the distribution of CLnA between neutral lipids (NL) and phospholipids appeared to be linked to their number of trans double bonds: the higher the number, the higher the accumulation in the NL fraction.

[Fatty acid of Rkatsiteli grape seed oil, Phellodendron lavallei oil and Amaranthus seeds oil and its comparative byological activity].

The aim of the study is individual qualitively and quantitatively identification of fatty acids in Pkatsiteli grape seed oil, Phellodendron lavallei oil and Amaranthus seed oil and prediction of its biological activity. Using high-effective liquid chromatogramphy fatty acids were franctionated. Their relative concentrations are expressed as percentages of the total fatty acid component. Identification of the fatty acids consituents is based on comparison of their retention time with that of known standards. The predominant fatty acids in the oils were palmitic, oleic and stearic acids. The investigation demonstrated that fatty acids composition takes marked part in lipid metabolism of biological necessary components. The most interesting result of the investigation was the detection of unusual for the essentain oil begenic acid.

Singlet oxygen-related photooxidative stability and antioxidant changes of diacylglycerol-rich oil derived from mixture of olive and perilla oil.

UNLABELLED: This study investigated the oxidative stability and antioxidants changes in diacylglycerol (DAG)-rich oil under singlet oxygen. DAG-rich oil was derived from triacylglycerol (TAG) oil of extra virgin olive and perilla oil mixture by hydrolysis and re-esterification using lipases. The oxidation of oils was performed at 25 °C for 48 h under singlet oxygen produced with chlorophyll b under light, and was evaluated by headspace oxygen consumption and peroxide value (POV). The oxidation of DAG-rich oil was higher and faster in the co-presence of light and chlorophyll than in their single presence. DAG-rich oil was more oxidation-susceptible than TAG oil. There was no significant change in fatty acid and lipid subclass compositions in DAG-rich oil during the photooxidation. Tocopherols were degraded, whereas polyphenols weren't during phootooxidation of DAG-rich oil. The oxidation of DAG-rich oil was well-correlated with tocopherol contents, not with polyphenol contents, indicating that tocopherols were effective antioxidants in the singlet oxygen-related phootooxidation of DAG-rich oil. The results suggested that the oxidative stability of DAG-rich oil under singlet oxygen be improved by a precise control through retention of tocopherols. PRACTICAL APPLICATION: The results of this study can be applied to the utilization of diacylglycerol oils to the area of functional edible oils with good oxidative stability.