Compositions of the seed oil of the Borago officinalis from Iran

In order to investigate the composition of borage (Borago officinalis L.) seed oil, this research was performed under the field conditions at Shahriyar and Garmsar zones, Iran during the 2012 planting year. The oil yield of borage was 31.46% and 33.7% at Shahriyar and Garmsar zone, respectively, and nine and eight fatty acids were identified in the seed oil of borage at Shahriyar and Garmsar, respectively – palmitic, linoleic, stearic and γ-linolenic acids were dominant in the seed oil of borage from both zones. Unsaturated fatty acid content was more than the saturated fatty acids in both zones. The ratio of linoleic acid and α-linolenic acid in the borage cultivated at Shahriyar and Garmsar zones was 2.13 and 2.29. The fatty acid profile of Garmsar borage, oleic and oleic/linoleic acid ratio, increased. Locations with different ecological conditions resulted in changes in both seed oil content and fatty acid profile of borage.     

The Thermostability of Two Kinds of Recombinant ∆6-Fatty Acid Desaturase with Different N-Terminal Sequence Lengths in Low Temperature

Two recombinant Rhizopus stolonifer ?6-fatty acid desaturase enzymes with different-length N-termini were cloned and expressed in Saccharomyces cerevisiae strain INVScl: LRsD6D begins with the sequence of the N-terminal of the R. stolonifer ?6-fatty acid desaturase native, encoding a deduced polypeptide of 459 amino acids (M-S-T-L-D-R-Q-S-I-F-T-I-K-E-L-E-S-I-S-Q-R-I-H-D-G-D-E-E-A-M-K-F), whereas SRsD6D begins with the amino acid sequence of the predicted ORF, encoding a deduced polypeptide of 430 amino acids (M-K-F) and LRsD6D is longer than SRsD6D by 29 amino acids (M-S-T-L-D-R-Q-S-I-F-T-I-K-E-L-E-S-I-S-Q-R-I-H-D-G-D-E-E-A). Bioinformatic analysis characterized the two recombinant ?6-fatty acid desaturase enzymes with different-length N-termini, including three conserved histidine-rich motifs, hydropathy profile, and a cytochrome b5-like domain in the N-terminus. When the coding sequence was expressed in S. cerevisiae strain INVScl, the coding produced ?6-fatty acid desaturase activity exhibited by RsD6D, leading to a novel peak corresponding to γ-linolenic acid methyl ester standards, which was detected with the same retention time. The residual activity of LRsD6D was 74 % at 15 °C for 4 h and that of SRsD6D was 43 %. Purified recombinant LRsD6D was more stable than SRsD6D, indicating that the N-terminal extension, containing mostly hydrophobic residues, affected the overall stability of recombinant LRsD6D.     

Overexpression of Δ12-Fatty Acid Desaturase in the Oleaginous Yeast <Emphasis Type="Italic">Rhodosporidium toruloides</Emphasis> for Production of Linoleic Acid-Rich Lipids

Under nutrient-limited conditions, the red yeast Rhodosporidium toruloides can accumulate neutral lipids, of which the compositional fatty acids are mainly saturated and mono-unsaturated ones with 16 or 18 carbon atoms. To improve the linoleic acid content in the lipids, we enabled galactose-inducible expression of the gene encoding Δ12-fatty acid desaturase (FADS) from Mortierella alpina or Fusarium verticillioides by integration of the corresponding expression cassettes into the genome of R. toruloides haploid and diploid strains. The relative linoleic acid content increased up to fivefold and the final linoleic acid titer reached 1.3 g/L under flask culture conditions. Our results suggested that R. toruloides may be further explored as cell factory for production of high-valued lipids and other fatty acid derivatives as bio-based chemicals and fuels.     

高产花生四烯酸产生菌干菌体中脂肪酸成分的气相色谱-质谱分析

将高产生花生四烯酸（AA）脂肪酸产生菌的干菌体经三氟化硼－甲醇方法甲酯化后,用毛细管气相色谱和质谱进行分析。结果表明干菌体中含有饱和不饱和脂肪酸,其中不饱和脂肪数中以花生四烯酸的含量（70．20％）最高,另外还含有少量的亚油酸和γ-亚麻酸等不饱和脂肪酸,同时给出了各个脂肪酸组分的相对含量。     

Polyunsaturated fatty acids of <Emphasis Type="Italic">Cortusa turkestanica</Emphasis> seed oil

The composition of free and bound lipids from seeds of Cortusa turkestanica A. Lozinsk (Primulaceae) was studied. The fatty acid composition of principal acyl-containing classes was established using GC/MS. It was found that triacylglycerines isolated from free and bound lipids contained the usual acids and rarely encountered polyunsaturated 18:3 ω-6 (γ-linolenic, 8.8 and 3.2%) and 18:4 ω-3 (stearidonic, 0.7 and 0.4%) acids and were enriched in linoleic acid (18:2, ω-6, 58.2 and 60.8%, respectively). It was found that polyunsaturated 18:3 ω-6 and 18:4 ω-3 acids were missing in the free form and were found among polar substances of bound lipids.     

Ionic Liquid-Based Extraction of Fatty Acids from Blue-Green Algal Cells Enhanced by Direct Transesterification and Determination Using GC × GC-TOFMS

Blue-green algae commonly referred to as cyanobacteria are known to grow in freshwater bodies when they are provided with suitable growth conditions such as nutrients, temperature and light. Algae biomass is known to contain a large amount of lipids, such as saturated and unsaturated fatty acids. In this study, fatty acids from algal cells were extracted using a newly developed extraction protocol using ionic liquid enhanced by direct transesterification at an elevated temperature. The identification and quantification of fatty acids was performed using gas chromatography coupled to a time-of-flight mass spectrometer (GC × GC-TOFMS). The extracted fatty acids were dominated by those with carbon chain of C16 and C18; [i.e. 7-hexadecenoic acid (C16:1) and hexadecanoic acid (C16:0) for C16, whereas C18 includes γ-linolenic acid (γ-C18:3); linoleic acid (C18:2); linolenic acid (C18:3); 6,9,12,15-octadecatetraenoic acid (C18:4); oleic acid (C18:1) and octadecanoic acid (C18:0)]. The obtained fatty acid composition was then compared with that obtained by organic solvent extraction using a mixture of chloroform and methanol. Statistical evaluation was performed using one-way ANOVA and found that there was no statistically significant difference (P = 0.908) between the two extraction methods, a finding which indicates the usefulness of ionic liquid as a solvent to replace volatile organic solvent to minimize environmental pollution.     

Antibacterial study and fatty acid analysis of lipids of the sponge <Emphasis Type="Italic">Myrmekioderma granulata</Emphasis>

The composition of the lipophilic extract of the sponge Myrmekioderma granulata (Esper) collected from 13 m depth of the Bay of Bengal of the Orissa coast was investigated. Fatty acids as well as volatiles and sterols were identified. 4,8,12-Trimethyltridecanoic acid was identified for the first time along with the important PUFAs such as linoleic acid (n-6, C18:2), dihomo-γ-linolenic acid (n-6, C20:3), 5,8,11,14-eicosatetraenoic acid (n-3, C20:4), and 5,8,11,14,17-eicosapentaenoic acid (EPA) (n-3, C20:5) from this species. The branched polyunsaturated fatty acids like br-C26:2, 25-methyl-5,9-heptacosadienoic acid and 24-methyl-5,9heptacosadienoic acid were also identified by GC-MS. The lipid extract exhibited limited activity against different pathogens.     

Fatty acids of Rhodobryum ontariense (Bryaceae)

The chemical composition of Rhodobryum ontariense (Kindb.) Kindb. has not been previously investigated. Fatty acids of this moss were analysed qualitatively and quantitatively with an aim to identify its corresponding pattern. A total of eight fatty acids were identified including two acetylenic ones: 9,12,15-octadecatrien-6-ynoic acid (42.26%), α-linolenic acid (20.32%), palmitic acid (14.31%), 9,12-octadecadienoic-6-ynoic acid (13.31%), linoleic acid (5.25%), oleic acid (2.47%), stearic acid (1.14%) and γ-linolenic acid (0.92%). To our knowledge, this is the first record of acetylenic fatty acids in the genus Rhodobryum. In general, acetylenic fatty acids vary considerably among different moss groups and have been used as a chemotaxonomic character in bryophyte classifications. Other species of Rhodobryum from Asia have been traditionally used in ethno medicine by indigenous cultures. Two fatty acids of those reported here, 9,12,15-octadecatrien-6-ynoic and α-linolenic acid, have known cardio protective activity, which supports respective claims of traditional herbal use of these mosses.     

Unusual fatty acids in compositae: γ-Linolenic acid in Saussurea spp. seed oils

The plant family Compositae is known to produce a set of unusual fattly acids in their seed oil. Saussurea, a genus of the Compositae is less studied in respect to the fatty acid compsition of their seed oil. Only Saussurea candicans was reported to contain crepenynic acid (33%) as seed oil component. In continuation of our exploration of the portential of wild oil seeds, fatty acids in seed oils of seven Saussurea species (S. amara, S. salicifolia, S. lipschitzii, S. pseudoalpina, S. pricei, S. parviflora, and S. dorogostaiskii) growing in Mongolia a were investigated by means of capillary GLC on capiallary columns of different selectivity (Silar 5 CP and BPX 70). γ-Linolenic acid was found at levels up to 11% of the consitituent fatty acids of Saussurea spp. seed oils. This is the first time that γ-Linolenic acid has been found in members of the plant family Compositae. Moreover, the number, position and configuration of the double bonds in γ-linolenic acid and that of other fatty acids was additionally confirmed by silver ion thin layer chromatography and infrared spectroscopy. The occurence and distribution of γ-linolenic acid, which has found considerable interest for pharmaceutical and dietary use, may be of chemotaxonomical significance in the plant family Compositae.     

Fatty acid variability in three medicinal herbs of Panax species

Background

Fatty acid profiling has been widely used in the bacteria species identification, we hypothesized that fatty acid characteristics might discriminate the Panax herbs according to species. To test the hypothesis, fatty acids of Panax species, including Panax ginseng, Panax notoginseng and Panax quinquefolius, were characterized and compared using gas chromatography–mass spectrometry (GC-MS) followed by multivariate statistical analysis.

Results

The content of investigated 11 fatty acids, including myristic acid, pentadecanoic acid, palmitic acid, palmitoleic acid, heptadecanoic acid, stearic acid, oleic acid, linoleic acid, α-linolenic acid, arachidic acid and eicosadienoic acid, obviously varied among three species, suggesting each species has its own fatty acid pattern. Principal component analysis and hierarchical clustering analysis according to the absolute and relative contents of fatty acids, showed that 30 tested samples could be clearly differentiated according to the species.

Conclusions

These findings demonstrated that GC-MS-based fatty acid profiling coupled with multivariate statistical analysis provides reliable platform to classify these three Panax species, which is helpful for ensuring their safety and efficacy.     

Chemical Characterization,Antiproliferative and Antioxidant Activities of Polyunsaturated Fatty Acid-Rich Extracts from Chlorella sp. S14

Microalgae is a rich source of polyunsaturated fatty acid. This study was conducted to identify and isolate microalgal strain with the potentials for producing polyunsaturated fatty acids (PUFAs) and determine its cytotoxic effect on some cancer cells. The algal strain (Chlorella sp. S14) was cultivated using modified BG-11 media, and algal biomass obtained was used for fatty acid extraction. Gas chromatographic–mass spectrometry was used to identify and quantify the levels of the fatty acid constituents. The total content of monounsaturated fatty acids (1.12%) was low compared to polyunsaturated fatty acids (PUFAs) (52.87%). Furthermore, n-3 PUFAs accounted for (12.37%) of total PUFAs with the presence of α-linolenic acid (2.16%) and cis-11,14,17-eicosatrienoic acid (2.16%). The PUFA-rich extract did not exhibit a cytotoxic effect on normal cells. Treatment with the PUFA-rich extract (150 µg/mL) significantly reduced cell viability in MCF-7 (31.58%) and A549 (62.56%) cells after the 48 h treatment. Furthermore, treatment of MCF-7 with fatty acid extracts (125 and 150 µg/mL) showed a significant reduction in MDA levels, increase in catalase activities and decrease in GSH level compared to untreated cells. However, a slight decrease in MDA level was observed in A549 cells after the 48 h treatment. There are no significant changes in catalase activities and GSH level in treated A549 cells. However, a slight reduction of NO levels was observed in treated MCF-7 and A549 cells. These results indicate the potentials of PUFA-rich extracts from Chlorella sp. S14 to reduce viability and modulate redox status in A549 and MCF-7 cells.     

Comparative study on fatty acid composition of olive (Olea europaea L.), with emphasis on phytosterol contents

The present study was designed to determine the fatty acid composition and phytosterol contents of Turkish native olive cultivars, namely Kilis Yağlık and Nizip Yağlık cv. In this context, olive fruits from 34 locations were sampled and then screened for their components in comparison. Fifteen different fatty acids were found in both olive oils. In the order of abundance, the most important ones were oleic acid (18:1) > palmitic acid (16:0) > linoleic acid (18:2) > stearic acid (18:0). Significant differences were observed in the contents of oleic acid (18:1), palmitic acid (16:0), linoleic acid (18:2) but not for stearic acid content in comparison both oils (p < 0.01). There were significant differences in terms of unsaturated fatty acids, saturated fatty acids and polyunsaturated fatty acids (p < 0.01). The seven phytosterols – cholesterol, campesterol, stigmasterol, β ‐sitosterol, Δ‐5‐avenasterol, Δ‐7‐stigmastenol and Δ‐7‐avenasterol – were studied in both oil sources. The predominant sterols were β ‐sitosterol, Δ5‐avenasterol and campesterol in the samples analysed. However, no significant differences were found in the levels of the phytosterols between the two olive cultivars.     

Enantiomeric separation of various lipoxygenase derived monohydroxy polyunsaturated fatty acid methyl esters by high-performance liquid chromatography

Lipoxygenase derived monohydroxy polyunsaturated fatty acid methyl esters were separated by chiral high-performance liquid chromatography (HPLC) with a Chiralcel OD-H column in the normal-phase mode. Major lipoxygenase derivatives of linoleic, -linolenic and arachidonic acids are well resolved by this column, provided they have been individually purified. Our method allows an easy and rapid determination of lipoxygenases enantioselectivity. In all cases tested the R enantiomer is eluted first.     

Polyunsaturated fatty acids from several plant species of the family Boraginaceae

Lipids from seeds of the plants Cynoglossum officinale (1), Echium vulgare (2), and Lappula squarrosa (3) of the family Boraginaceae growing in the Republic of Bashkortostan were studied. Four polyunsaturated acids, linoleic (LA), γ-linolenic (GLA), α-linolenic (ALA), and stearidonic (SA), were identified among the fatty acids. The principal acids of the neutral lipids (NL) were 18:1 and 18:2 in 1, ALA in 2 and 3, and GLA in approximately equal amounts in all three samples. The highest amount of SA (16.8 %) was found in 3. Unsaponified components of NL samples were identified by GC/MS. Alkaloids were observed in the pulp and polar lipids.     

Fatty acid content of three <Emphasis Type="Italic">Cistus</Emphasis> species growing in Turkey

The seed oils of Cistus laurifolius, C. salviifolius, and C. creticus were investigated for their fatty acids by employing capillary GC and capillary GC-MS. The results of this study indicated that palmitic, linoleic, linolenic, oleic, stearic, and behenic acids were found in all of these three seed oils of Turkish origin. In addition, an important polyunsaturated fatty acid, linoleic acid, was the major fatty acid in all of these oil samples.Published in Khimiya Prirodnikh Soedinenii in No. 6, pp. 433–434, November–December.This revised version was published online in April 2005 with a corrected cover date.     

SKIN PERMEATION ENHANCEMENT BY FATTY ACIDS

The present study elucidates the skin permeation enhancement effects of a number of fatty acids, i.e. straight-chain saturated (SFA), monounsaturated (MUFA) and polyunsaturated acids (PUFA). The effects were studied using human stratum corneum (SC) and p-aminobenzoic acid (PABA) as a model permeant. The fatty acids in propylene glycol (FA/PG) were applied according to a pre-treatment/co-treatment protocol. SFA with 6 to 12 carbons exhibit a parabolic correlation between enhancement effect and chain-length, with a maximum at nonanoic-decanoic acids (with 9 and 10 carbons). All cis-6-, 9-, 11- or 13-octadecenoic acids (MUFA) enhance the permeation of PABA to the same extent. PUFA — linoleic (LA), α-linolenic (ALA) and arachidonic acids — enhance PABA permeation stronger than MUFA but additional double bonds do not further increase the degree of enhancement. The enhancement effects of fatty acids on the PABA penetration through SC are structure-dependent, associated with the existence of a balance between the permeability of pure fatty acids across SC and the interaction of the acids to skin lipids. Based on this and other studies, a set of mechanisms of action is proposed for fatty acids.     

Antioxidant,Antimicrobial Activities and Fatty Acid Compositions of Wild Berberis spp. by Different Techniques Combined with Chemometrics (PCA and HCA)

Interest in medicinal plants and fruits has increased in recent years due to people beginning to consume natural foods. This study aims to investigate the total phenolic flavonoid content, antioxidant activity, condensed tannin content, oil content, and fatty acid compositions of five local breeds of Berberis spp. from Bayburt, Turkey, and their antioxidant and antimicrobial activities. The fatty acid composition of samples was performed with gas chromatography-mass spectrometry (GC-MS), and the total fatty acid content of samples was between 6.12% and 8.60%. The main fatty acids in Berberis spp. samples were α-linolenic acid (32.85–37.88%) and linoleic acid (30.98–34.28%) followed by oleic acid (12.85–19.56%). Two antioxidant assays produced similar results, demonstrating that extracts of wild B. vulgaris L. had the highest ferric reducing antioxidant power (FRAP) (621.02 μmol FeSO₄.7H₂O/g) and 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) (0.10 SC₅₀ mg/mL) values. According to principal component analysis (PCA), four components were determined. In addition, two main groups were determined according to hierarchical cluster analysis (HCA), and wild and culture of B. vulgaris L. were in different subgroups. This is the first original report about the fatty acid composition and oil content of Berberis spp. grown in Bayburt, Turkey. The obtained results indicate that B. integerrima Bunge and B. vulgaris, which have especially remarkable fatty acid content, antioxidant, and antimicrobial activity, could be potential sources for these properties in different areas of use.     

Chromatographic Analysis for Fatty Acids and Lipid-Soluble Bioactives of Derris indica Crude Seed Oil

A combination of column chromatography (CC), gas chromatography (GC), thin layer chromatography (TLC) and liquid chromatography (LC) techniques were performed to analyze lipid classes, fatty acids and fat-soluble bioactives of Derris indica crude seed oil. Hexane extract of Derris indica oilseeds was found to be 56%. Level of neutral lipids in the crude seed oil was the highest, followed by glycolipids and phospholipids, respectively. Linoleic followed by α-linolenic, palmitic and oleic were the major fatty acids in the crude seed oil. The ratio of unsaturated fatty acids to saturated fatty acids was higher in neutral lipid classes than in the polar lipid fractions. The oil was characterized by a relatively high amount of phytosterols, wherein the sterol markers were β-sitosterol, campesterol and stigmasterol. γ-Tocopherol was the major tocopherol while the rest being α-tocopherol. In consideration of potential utilization, detailed knowledge on the composition of Derris indica oil is of major importance.     

Elucidation of the Lipid Composition of Hemp (Cannabis sativa L.) Products by Means of Gas Chromatography and Ultra-High Performance Liquid Chromatography Coupled to Mass Spectrometry Detection

The growing demand in natural matrices that represent a source of dietary and nutraceutical molecules has led to an increasing interest in Cannabis sativa, considered to be a multipurpose, sustainable crop. Particularly, the considerable content in essential fatty acids (FAs) makes its derived-products useful food ingredients in the formulation of dietary supplements. In this research, the FA and triacylglycerol (TAG) composition of hempseed oils and flours were investigated using gas chromatography coupled to mass spectrometry and flame ionization detection as well as liquid chromatography coupled to mass spectrometry (LC-MS), respectively. Furthermore, a recently introduced linear retention index (LRI) approach in LC was successfully employed as a useful tool for the reliable identification of TAG species. A total of 30 FAs and 62 glycerolipids were positively identified in the investigated samples. Relative quantitative analyses confirmed linoleic acid as the most abundant component (50–55%). A favorable omega6/omega3 ratio was also measured in hemp-derived products, with the α-linolenic acid around 12–14%. Whereas, γ-linolenic acid was found to be higher than 1.70%. These results confirm the great value of Cannabis sativa as a source of valuable lipids, and the further improvement of the LRI system paves the way for the automatization of the identification process in LC.