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Previous studies indicated that tomato is a rich source of phytochemicals that act on different tumours. In this research, the phytochemical composition of selected tomato varieties was assessed by GLC and UHPLC/HPLC-MS, as well as their anti-tumour activities on HT-29 colorectal cancer cells.; Results: Significant differences were found among tomato varieties; lycopene was high in Racimo, phenolics in Pera, sterols in Cherry, and linoleic acid predominated in all varieties. The MTT and LDH assays showed significant time- and concentration-dependent inhibitory/cytotoxic effects of all tomato varieties on HT-29 cells. Furthermore, the joint addition of tomato carotenoids and olive oil to HT-29 cell cultures induced inhibitory effects significantly higher than those obtained from each of them acting separately, while no actions were exercised in CCD-18 normal cells.; Conclusion: Tomato fruits constitute a healthy source of phytochemicals, although differences exist among varieties. In vitro, all of them inhibit colorectal cancer cell proliferation with Racimo variety at the top, and exercising a selective action on cancer cells by considering the lack of effects on CCD-18 cells. Furthermore, synergy was observed between olive oil and tomato carotenoids in inhibiting HT-29 cancer cell proliferation; conversely, phenolics showed no significant effects and hindered carotenoids actions. © 2016 Society of Chemical Industry.; © 2016 Society of Chemical Industry.

Summary The aim of this work was to determine the seasonality of nutrient profiles of dusky grouper (Epinephelus marginatus Lowe, 1834) cultured in a cage to improve knowledge on its nutritional composition. Fish (n = 735) were reared in a circular polyethylene floating cage for a 19-month experimental period and provided a commercial pelleted feed once a day with a total daily ration of 1% wet body weight. Fish were sampled every 3–4 months, and biometric parameters as well as muscle composition were determined. The edible proportion of fish increased slightly with culture time. The flesh showed low lipid content, similar to those reported for wild grouper. Biometric indices, muscle proximate composition and fatty acid profiles were significantly affected by seasonality, that is lipids and monounsaturated fatty acids increased during summer, in parallel with the decline of polyunsaturated fatty acids.

Docosahexaenoic acid (DHA) is a well-known dietary n-3 polyunsaturated fatty acid (PUFA) found in marine fish and organisms whose beneficial effects for human health are widely reported. However, the supply of food containing DHA is currently becoming critical due to the overexploitation of fisheries worldwide. Consequently, searching for alternative sources of DHA is a relevant issue nowadays. Viscera from cultured fishes is considered a by-product by the fishery industry and therefore discarded after fish processing. In this work, viscera from farmed marine fish (Sparus aurata and Dicentrarchus labrax) and also oil extracted from such by-products have been studied to assess their suitability as DHA sources by obtaining their fatty acid profiles. Viscera oil was used as a source for DHA purification by a simple and easily scalable chromatographic method. As a result, a highly purified DHA fraction (>99.0% DHA on total fatty acids) was obtained. Practical applications: This DHA concentrate obtained from viscera oil could be potentially used for alimentary or pharmaceutical purposes due to its lower cholesterol content compared with other known marine sources and also because only safe and legally allowed food-grade solvents have been used throughout the whole process. This way, by obtaining a high added-value product, a revaluation is given to fish by-products which are usually discarded. Fatty acid profile of whole viscera oil (11.1% DHA of total FA) (left) and chromatogram of the DHA fraction after chromatographic purification (>99.0% DHA of total FA) (right) by using food-grade solvents as the mobile phase.

In this work, several oils and PUFA-producing species have been analyzed to know the positional distribution of fatty acids within the triacylgycerol structure. Positional distribution was determined in terrestrial oils by means of enzymatic hydrolysis, while 13C-NMR was used for marine and processed oils, which contain long-chain PUFA. In addition to several already known sources, other new ones have been characterized; i.e., α-linolenic acid was high in the subcutaneous fat of Galician horse (34.5% of total FAs in sn-2); γ-linolenic acid in Echium gentianoides and Symphytum caucasicum (47.7 and 40.1% of total FAs in sn-2, respectively); stearidonic acid in E. plantagineum (20.8% of total FAs in sn-2); eicosapentaenoic acid in cod liver oil (13.7% of total FAs in sn-2); docosahexaenoic acid in salmon, cod liver, hake roe, DHASCO© and MARINOL© oils (23.0, 20.9, 19.7, 47.0 and 55.9% of total FAs in sn-2, respectively); and arachidonic acid in ARASCO© oil (53.0% of total FAs in sn-2). Bioavailability of some valuable PUFA has been shown to be high in some of the studied samples compared to commonly consumed oils, according to their triacylglycerol positional distribution values. Practical applications: The positional distribution of PUFAs on the glycerol backbone of triacylglycerols is crucial for their bioavailability, since PUFA esterified at sn-2 position are better absorbed than those located at sn-1,3 positions. In this work, we have assessed the positional distribution of essential fatty acids in several fats and oils, both obtained from traditional sources as well as from edible species not yet prospected. Some of them might be exploited to be used as dietary PUFA sources. The positional distribution (PD) of essential fatty acids (EFAs) within the triacylglycerol structure determines their bioavailability, since EFAs esterified at sn-2 position are better absorbed than those located at sn-1,3 positions. In this work, the PD of EFAs in several fats and oils, obtained from traditional sources as well as from edible species not yet prospected, has been assessed. Bioavailability of valuable EFAs has been shown to be high in some of the newly studied oils compared to commonly consumed oils, as their triacylglycerol PD indicates.

Tridocosahexaenoyl glycerol (tri-DHA) has been identified and purified from the commercial oil DHASCO®, a natural and renewable source of DHA with 7.48 wt% of tri-DHA, by means of a gravimetric normal-phase chromatographic column and silver nitrate-silica gel as stationary phase. This method allows the purification of a highly enriched tri-DHA fraction from DHASCO® (84.4% of the total tri-DHA contained in DHASCO®), and DHA accounting for 79.8% of the total fatty acids of the purified fraction. Subsequently, the whole process was scaled up to 10 times with satisfactory results. Practical applications: This work was conducted to obtain a valuable form of DHA from a natural resource. The whole process, in which the use of unsafe solvents is avoided, has been designed to allow the potential use of the DHA-enriched fraction in the food and pharmaceutical industries as nutritional supplement, as well as for use in laboratory research using animal models.

The aim of this work was to establish the richness in γ-linolenic acid (GLA, 18:3n-6) and stearidonic acid (SDA, 18:4n-3) of the seed oil of several restricted-range Boraginaceae species, in a search for new valuable oils as advantageous alternatives to the commercially available sources of both polyunsaturated fatty acids. To this end, seeds of selected Boraginaceae species were collected and analyzed. The highest GLA contents (% total fatty acids) were found in the seed oils of Symphytum caucasicum M.Bieb. (22.9 %), Anchusa undulata subsp. undulata (Ten.) Cout. (22.0 %), Anchusa puechii Valdes (20.0 %), Glandora nitida Thomas (19.2 %), Echium pininana Webb & Berth. (17.1 %) and Pentaglottis sempervirens (L.) L. H. Bailey (17.0 %). With regard to SDA, the highest percentage was found in the seed oil of Echium cantabricum (M. Lainz) Fdez. Casas & M. Lainz (14.7 %), followed by Lappula patula (Lehm.) Asch ex Gurke (13.6 %). It is noticeable that several GLA-enriched species stand under a great threat of extinction, thus revealing the importance of the preservation of the natural ecosystems for endangered species.

Purification of arachidonic acid (AA, 20:4n-6) from different sources has been previously reported, but in most cases AA is obtained after triacylglycerol (TAG) hydrolysis. In this work, gravimetric normal-phase chromatography with gradient elution has been used to purify an AA-enriched fraction of TAG from the commercial single cell oil named ARASCO (38–44% AA content). A TAG fraction with more than 90% AA content was obtained, employing appropriate solvents for alimentary processing. The process was scaled up with satisfactory results. Due to the use of food-safe solvents in the whole process, it could be applied with alimentary or pharmaceutical purposes.

HPLC analysis of Echium plantagineum seed oil shows a complex triacylglycerol (TAG) profile. TAG species were separated on an analytical scale by HPLC and their fatty acid (FA) composition is reported. GLC analyses showed that some TAG fractions reached a stearidonic acid (SDA, 18:4n-3) percentage significantly higher than that in the original oil. TAG separation on a bigger scale was also essayed, by means of a gravimetric normal-phase chromatographic column, using silver ion-silica gel as stationary phase. Gradient elution with solvents of increasing polarity was applied, allowing the separation of valuable TAG species containing γ-linolenic acid (GLA, 18:3n-6), α-linolenic acid (ALA, 18:3n-3) and SDA as the main constituents (more than 85% of the total FA). An enzymatic hydrolysis reaction showed the distribution of FA in the isolated species of TAG. SDA was the major FA in the sn-2 position (more than 50% of total FA), followed by ALA (19%) and GLA (18.5%).

Fifteen roes from different marine fish species available in Spain were analyzed in order to determine their fatty acid (FA) composition, especially the eicosapentaenoic acid (20:5n-3, EPA) and docosahexaenoic acid (22:6n-3, DHA) contents. Roes from Atlantic bonito (Sarda sarda), European squid (Loligo vulgaris), cuttlefish (Sepia spp.), lumpfish (Cyclopterus lumpus), European hake (Merluccius merluccius), Atlantic salmon (Salmo salar) and gonads of male Atlantic mackerel (Scomber scombrus) reached EPA + DHA amounts higher than 30% of the total FA, and among them, roes from lumpfish, European hake and salmon provide different FA type ratios that could make them adequate as dietary sources of EPA and DHA.

Gravimetric normal-phase silver ion–silica gel column chromatography has been used for the novel application of purification of GLA-containing triglycerides (GLA-TGs) from evening primrose seed oil (EPO). Gradient elution with increasing polarity enabled separation of valuable TG species containing γ-linolenic acid (GLA, 18:3n-6). Enzymatic hydrolysis revealed the distribution of fatty acids (FAs) in the isolated TG species, with GLA in the sn-2 position in different percentages, depending on the degree of unsaturation. A novelty of this work was the successful use of the procedure to improve the purification of raw GLA species from EPO up to preparative scale, thus enabling use of this methodology for industrial purposes.

Summary Several oil sources of gamma-linolenic acid (GLA) were extracted from their corresponding seeds using several extracting systems: A, supercritical fluid extraction (CO2-SFE); B, methanol/acetyl chloride/hexane (1:0.05:0.5, v/v/v); C, chloroform/methanol/water (1:2:0.8, v/v); D, hexane/diethyl ether (1:1.5, v/v); E, hexane/ethanol (96%) (1:0.9, v/v); F, hexane/ethanol (96%) (1:2.5, v/v); G, 1-butanol; H, ethanol (96%); I, ethanol (96%)/water (1:1, v/v); J, potassium hydroxide/ethanol (96%) (0.0223:1, p/v). It is noticeable that the total fatty acids extracted by the solvent system I was significantly lower than the amounts obtained by the other extracting systems (P

Stearidonic acid (SA, 18:4n-3) is a polyunsaturated fatty acid (PUFA) that constitutes the first metabolite of α-linolenic acid (ALA, 18:3n-3) in the metabolic pathway leading to C20–22 PUFA, such as eicosapentaenoic acid (EPA, 20:5n-3), and docosahexaenoic acid (DHA, 22:6n-3), which recently have received much attention because of their various physiological functions in the human body. Recently, several studies indicated that dietary SA increased EPA more efficiently than ALA. Thus, vegetable oils containing SA may become a dietary source of n-3 fatty acids that is more effective in increasing tissue n-3 PUFA concentrations than the current ALA-containing vegetable oils. Nevertheless, few SA sources occur in nature, although there are still a large number of species untested to date. SA has been detected in variable amounts in several species of algae, fungi and animals tissues, but the seeds of some plant families seem to be better sources of SA, especially Echium (Boraginaceae) species. This work reviews the nutritional significance, medical uses and natural occurrence of SA.

The fatty acids (FA) eicosapentaenoic acid (20:5ω-3; EPA) and docosahexaenoic acid (22:6ω-3; DHA), which have several health benefits, have been concentrated from mako shark liver (Isurus oxyrinchus). The process was carried out in one single step, in which fish liver oil was simultaneously extracted, saponified and concentrated. Additionally, the polyunsaturated fatty acids (PUFA) concentrate was winterized to crystallize the remaining saturated FA, resulting in a further increase in the concentration of DHA and EPA. Two variables, temperature and water concentration in the saponification mixture, were optimized to increase the concentration of ω-3 PUFA. Best results were obtained at 12 °C and 0% water content in the mixture, obtaining 17.8% purity and 77.6% yield of EPA; DHA purity and yield were 33.3 and 82.2%, respectively.

Seeds from 20 species belonging to Boraginaceae, subfamilies Boraginoideae and Heliotropioideae, were surveyed in a search for new sources of γ-linolenic acid (GLA) and stearidonic acid (SDA). Seed oil content ranged from 7.5% in Echium humile ssp. pycnanthum to 28.8% in Anchusa undulata. GLA ranged from 0.2% of total fatty acids in Heliotropium undulatum to 20.2% in Lithodora maroccana. This last species may be considered as new source of GLA. GLA content was also tested in other Lithodora species from the south east of Spain, to compare GLA percentages among related taxa. GLA amounts in all Echium species reached approximately 12%, in good agreement with previous findings in other European Echium species. SDA ranged from an absence in several Cynoglossum species to 16.2% in Echium humile ssp. pycnanthum, which may be considered as a new source of this fatty acid.

The essential fatty acid g-linolenic (GLA, C18:3n-6), which has several pharmaceutical properties, has been concentrated from the seed oil of three plant species, Borago officinalis, Anchusa azurea and Echium fastuosum. The process was effected through one single and ecological step: simultaneous seed oil extraction/saponification/GLA concentration. Finally, the mother liquor containing the GLA concentrate was stored at low temperature to crystallize saturated fatty acids and further increase GLA purity. Two variables affecting the process were found: water content in the saponification mixture and filtration temperature. Best results were obtained from B. officinalis (GLA purity 68%, GLA yield 64%), although closely followed by the concentrates from the other species.

The polyunsaturated fatty acids (PUFA) eicosapentaenoic acid (EPA, 20∶5n−3) and docosahexaenoic acid (DHA, 22∶6n−3), which have several pharmaceutical properties, have been purified from cod liver oil. The process consisted of four main steps: (i) saponification of the oil, (ii) use of urea inclusion adducts method to obtain PUFA, (iii) PUFA methylation, and (iv) argentation silica gel column chromatography of the methylated PUFA. Argentation silica gel chromatography yielded highly pure DHA in the process (100% purity, 64% yiild). For EPA, the recovery in the combined process was 29.6%, and the final purity was 90.6%, owing to the simultaneous elution of other polyunsaturated fatty esters. The recovery in the urea inclusion method was strongly enhanced by application of orbital agitation during the crystallization process, in which EPA yield increased from 60–70% without agitation to 90–97% at 800 rpm; stearidonic acid (18∶4n−3) yield ranged from 60–75% without agitation to 87–95% at 800 rpm, and DHA yield varied from 53–73% without agitation to 85–99% at 800 rpm

The free fatty acids eicosapentaenoic acid (C20:5ω3, EPA) and docosahexaenoic acid (C22:6ω3), obtained from the microalgae Phaeodactylum tricornutum, and the EPA methyl ester were compared with regard to their extent of peroxidation using different storage conditions. Several series were stored according to selected variables: hexane addition versus no addition, 4 °C versus 25 °C, and antioxidant addition (octyl gallate) versus no antioxidant addition, always in the dark. Previously, the EPA and methyl EPA structures were confirmed by NMR spectra to discard the formation of conjugated dienes after the downstream process. The results showed that the stability was higher for methyl EPA than for the free fatty acid, and that peroxidation can be retarded by low temperature storage and mainly by hexane addition. The peroxidation process was evaluated by the peroxide value (spectrophotometric method by iodine absorption), although the conjugated diene absorbance and the loss in percentage of the fatty acid have been tested as good indicators of the peroxidation process. A simple kinetic model that explains the peroxidation process during the initiation and propagation steps is given.

Analyses of the nutritional composition of tender leaves of three species of Sonchus (S. asper L, S oleraceus L and S tenerrimus L) from different locations in the south east of Spain were carried out. The proximate composition, as well as the content of mineral elements (Na, K, Ca, Mg, P, Fe, Cu, Zn and Mn), fatty acids, vitamin C, carotenoids and oxalic acid were determined. The results, which referred to fresh weight, emphasised the low proportion of available carbohydrates. Vitamin C contents were high, and ranged from 457 mg kg−1 (S tenerrimus) to 779 mg kg−1 (S oleraceus). Carotenoids were found in a high proportion (158 mg kg−1) in S oleraceus. Mineral element contents were similar to other green leafy vegetables. Fibre was present in amount above 30 g kg−1 in the three species. Essential fatty acids of the ω3 series were highest in S oleraceus (44·97%). It is believed that these species of Sonchus could be used for nutritional purposes, due to the high concentrations of nutrients that they contain. © 1998 SCI.

Seeds from 50 species belonging to the family Caryophyllaceae, subfamilies Alsinoideae, Silenoideae, and Spergulaceae, were surveyed in a search for new sources of γ-linolenic acid (GLA) having low levels of other interfering PUFA and therefore appropriate for GLA purification. It was detected mainly in Alsinoideae species, with a maximum of 15.6% of total FA in Minuartia laricifolia subsp. ophiolitica. Different amounts of stearidonic acid (18∶4n−3) were present in the Alsinoideae species, ranging from undetectable levels in seven species to 3.30% of total FA in Stellaria media. An ANOVA showed a taxonomical correlation between GLA percentages and the genus/subfamily within this family.