Seed Oil Fatty Acids of Mongolian Compositae: The trans‐Fatty Acids of Heteropappus hispidus,Asterothamnus centrali‐asiaticus and Artemisia palustris

Seed oils from the Compositae plant family are known to contain a variety of unusual fatty acids. Subsequent to the recent discovery of γ‐linolenic acid in Saussurea and Youngia, further Mongolian Compositae species were investigated for their seed oil fatty acid composition. A number of δ3trans‐fatty acids (16 : 1δ3t, 18 : 1δ3t and 18 : 3δ3t, 9c, 12c) were found in the seed oils of Heteropappus hispidus and Asterothamnus centrali‐asiaticus. The latter fatty acid, but not the trans‐monoenes, was also found in one species of Artemisia. These unusual fatty acid isomers were characterized by capillary gas‐liquid chromatographic (GLC) separations in combination with other chromatographic techniques (analytical thin layer chromatography, TLC and preparative argentation TLC), and infrared spectrocsopy (IR). Their identity was further confirmed by co‐chromatography with other seed oils known to contain these trans‐fatty acids. The fact that within the Compositae plant family there are apparently two or three distinct groups of genera containing δ3trans‐fatty acids is discussed.     

Separation of highly unsaturated triacylglycerols by reversed phase HPLC with short wavelength UV detection

Reversed phase HPLC with short wavelength UV detection is a useful alternative to conventional separation systems, with RI detection, for the analysis of the triacylglycerols of highly unsaturated vegetable oils, including γ-linolenic acid-containing oils and technical drying oils. γ-Linolenic acid-containing triacylglycerols can be identified and separated from their α-linolenic analogs. The triacylglycerol fingerprints obtained by this technique from many γ-linolenic acid-containing oils and technical oils are highly characteristic, as is apparent from chromatograms obtained from the seed oils of Oenothera biennis, Borago officinalis, Ribes nigrum, Primula florindae, and Sapium sebiferum. Characteristic peak area ratios aid the identification of these oils, and estolide peaks are seen in Sapium seed kernel oils. The high detector response for triacylglycerols containing linoleate and/or linolenate residues may present additional advantages, e.g. in the detection of such triacylglycerols in olive oil.     

Physico-chemical properties of Tecoma stans Linn. seed oil: a new crop for vegetable oil

Tecoma stans Linn. is known to have various medicinal and therapeutic properties. However, to our knowledge, no information is available regarding their seed oils. In this study, the fatty acid (FA) compositions, physico-chemical properties and antioxidant capacities of T. stans seed oils (TSOs) were investigated. The oil content of the seeds was 15%. The FAs of the TSOs were analysed by GC–MS. α-Linolenic (45.47%), oleic (23.56%), linoleic (11.48%), palmitic (6.09%) and stearic (4.12%) acids were the major detected FAs. γ-Linolenic acid and stearidonic acid, unusually FAs, were also present (1.04% and 6.65%, respectively). The total tocol content in the TSOs was found to be 266.06 mg/100 g. The main component was γ-tocopherol (78.93%). The total phenolic content (168.69 mg GAE/100 g oil) and total flavonoid content (5.54 mg CE/g oil) were also determined in the TSOs.     

Unusual Δ5cis-fatty acids in seed oils of Cimicifuga species

A range of unusual fatty acids with cis-5-unsaturation had been reported in the seed oil of Caltha palustris. Seed oils of Cimicifuga spp. have now been found to contain the same unusual fatty acids as are present in Caltha, plus several other minor fatty acids to give a more complex and more unsaturated seed oil fatty acid pattern. The gas chromatographic fatty acid patterns found seem to be consistent and chemotaxonomically significant, because essentially the same pattern was found in several species of the genus Cimicifuga. These findings may shed a new light on the relation of Cimicifuga to Caltha, and to other genera in the plant family Ranunculaceae. The situation is illustrated by capillary GLC seed oil fatty acid methyl ester “fingerprints” obtained from Cimicifuga and Caltha, and is discussed in relation to other genera. The occurrence in nature of several of these unusual fatty acids, and their chemotax-onomic significance is discussed. The close relation of GLC fatty acid patterns of Caltha and Cimicifuga could indicate monophyly and/or their belonging to the same tribe or subtribe. These observations are not in accordance with the phylogenetic systematic schemes of the genera in this plant family as published by various authors.     

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.     

Chemical characterization of unconventional palm oils from Hyophorbe indica and two other endemic Arecaceae species from Reunion Island

Abstract

Chemical characteristics of novel seed oils, yet not investigated, from three endemic Arecaceae (palm) species from Reunion Island are described. Fatty acid profiles are performed using two-dimensional gas chromatography-mass spectrometry. Carotenoid contents are determined by high performance liquid chromatography-mass spectrometry. The results of the investigations emphasize the particular composition of the unconventional red seed oil from Hyophorbe indica. Characteristic features of this oil reveal a high degree of unsaturation (50% of polyunsaturated fatty acids, with a high content (17%) of omega-3), which is possibly a unique fatty acid composition in the Arecaceae family. The two other palm oils from Dictyosperma album and Latania lontaroides contain high level of saturated fatty acids very similar to that of the edible palm oil. H. indica oil is also very rich in valuable carotenoids; in particular, lutein, β-carotene and lycopene are detected in a high content (respectively 45, 23 and 35?mg.kg^?1 in oil).     

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.     

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.     

Capillary GLC fatty acid fingerprints of seed lipids—a tool in plant chemotaxonomy?

The fatty acid composition of the seed lipids of plants, in contrast to leaf lipids, may contain highly specific unusual fatty acids, which are often correlated to plant family. For example, petroselinic acid is typical for the Apiacea family, cyclopropene fatty acids are typical for the Malvaceae family, and cyclopentene-ring containing fatty acids for the Flacourtiaceae family. Other fatty acids may be characteristic for certain sub-families or only for certain species of plants within a family or genus. γ-Linolenic acid, Δ5–18:3 and Δ5–20:3 fatty acids and others may occur in several plant families, but are still linked to certain related species only. They can be analyzed by high-resolution capillary GLC. Particularly interesting is the situation in the family Ranunculaceae. GLC fingerprints of fatty acids are shown that may indicate a closer or less close relationship between species within this family.     

Analysis of the Dynamic Decomposition of Unsaturated Fatty Acids and Tocopherols in Commercial Oils During Deep Frying

The decomposition of unsaturated fatty acids and tocopherols in 10 commercial edible oils during deep frying was investigated. The dominant tocopherol in oils rich in polyunsaturated fatty acids (PUFAs) was γ-tocopherol, except for natural perilla oil (δ-tocopherol dominant), and the main tocopherol in oleic acid-rich oils was α-tocopherol. The PUFA-rich oils had higher tocopherol contents than the oleic acid-rich oils. Both the reduction rate of total unsaturated fatty acid (TUFA) and total tocopherol (TToc) were linear with frying time (t). The decomposition rate of TToc is faster than that of TUFA since the slope values obtained from fitting equations (Y?=?k t) k_TToc (1.520–14.483) were obviously larger than for k_TUFA (0.155–0.270). By establishing a dynamic decomposition index, unsaturated fatty acids and tocopherol in oils showed dynamic decomposition over multiple frying cycles. The obtained results showed that decomposition characteristics of oils are related to their fatty acid compositions.     

Fatty acid composition of two Athamanta turbith subspecies

The fruit oils of Athamanta turbith ssp. hungarica and Athamanta turbith ssp. haynaldii were obtained by Soxhlet extraction using petroleum ether. The fatty acid composition of oils was determined by GC in the methyl ester form. Considering the composition and content of fatty acids, the examined oils were very similar. Petroselinic acid was the principal one (45.6 and 46.2%, respectively), followed by a significant amount of linoleic acid (26.9 and 29.1%, respectively). In both oils, myristic, pentadecanoic, palmitic, palmitoleic, stearic, petroselinic, oleic, linoleic, α-linolenic, arachidic, and behenic acid were identified. Lignoceric acid was detected only in A. turbith ssp. hungarica oil. Published in Khimiya Prirodnykh Soedinenii, No. 4, pp. 319–320, July–August, 2006.     

Quantitation Free Fatty Acid in Perilla Seed Oil by Capillary Gas Chromatography Combined with Column Chromatography

Perilla frutescens is a member of the Lamiaceae family. It is he first group material which are identified as both medicine and food by Health Ministry of China. Recently the high content of α-linolenic in the seed of Perilla had aroused many scientists attention. Perilla seed oil is plant oil sources of the curative and edible value, which contains high content of α-linolenic(more than 50%). The α-linolenic which is a polyunsaturated fatty acid, however, is very easy to be degradation. The product of rancidity and oxidation changes the quality of oil and some degradation products are harmful to human health.     

Investigation of kernel oils of <Emphasis Type="Italic">Quercus robur</Emphasis> and <Emphasis Type="Italic">Quercus cerris</Emphasis>

The kernel oils of Quercus robur and Quercus cerris were obtained by Soxhlet extraction using petroleum ether. Oil yields were found to be 5.2–5.6% and 4.3–4.8% for Q. robur and Q. cerris kernel, respectively (expressed in g per 100 g of dried plant material). The physical and chemical constants, unsaponifiable matter and total fatty acids were determined. The total fatty acid composition of oils was determined by GC in the methyl ester form. Considering the composition and content of fatty acids, the examined kernel oils were very similar. Seven fatty acid components were identified in both oils: palmitic, stearic, arachidic, palmitoleic, oleic, linoleic, and -linolenic. In Q. robur and Q. cerris kernel oils the principal acids were oleic (44.3% and 43.0%, respectively) and linoleic (37.2% and 32.6%, respectively), followed by a significant amount of palmitic acid.Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 347–348, September–October, 2004.     

Determination of fatty acids in the seeds of Lepidium apetalum Willdenow,Descurainia sophia (L.) Webb ex Prantl,and Draba nemorosa L. by ultra-high-performance liquid chromatography equipped with a charged aerosol detector

Both the contents of fatty acids and the ratios of unsaturated to saturated fatty acids are important parameters for determining the nutritional values of oils. Thus, we herein evaluated the fatty acids present in the seed oils of Lepidium apetalum Willdenow, Descurainia sophia (L.) Webb ex Prantl, and Draba nemorosa L. as sources of Lepidii seu Descurainiae Semen seeds in Northeast Asian Countries. We developed a method based on ultra-high-performance liquid chromatography using a charged aerosol detector for the quantitative analysis of fatty acids in the seed oils. This technique is less time-consuming than previous methods as derivatization of the oils is not required. Our method was developed though the comparison of a UV detector with a charged aerosol detector, and various stationary phases and gradient programs were tested. In addition, method validation was carried out according to the International Conference on Harmonization guidelines with respect to linearity, precision, and accuracy. We found that the quantities of unsaturated fatty acids (6.051–282.376?mg/g) were higher than those of saturated fatty acids (0.855–12.548?mg/g) in all plant seed oils. The proposed method is reproducible and convenient, and therefore, is suitable for the quantitative analysis of fatty acids in plant oils.     

The Effects of Selenium on Polyunsaturated Fatty Acids of Diasporangium jonesianum

Fungi had become the main resource of polyunsaturated fatty acids, especially linoleic acid. The research studied the effects and mechanism of selenium on polyunsaturated fatty acids of Diasporangium jonesianum. The results showed that selenium could significantly increase the yields of linoleic acid. In contrast, the growth and γ-linolenic acid yield of D. jonesianum was decreased under selenium treatments. Δ6-Fatty acid desaturase gene of D. jonesianum was investigated in this research. Sequence analysis indicated that this cDNA sequence encoded 235 amino acids. The conserved region of Δ6-fatty acid desaturase included three conserved histidine-rich domain, hydropathy profile, and was rich in disulfide bonds. This study showed that selenium may in discriminatively substitute S and incorporate selenium-amino acids into the desaturase that the conformation of enzyme active sites was impacted which leaded to the inhibition of the convert of linoleic acid to γ-linolenic acid and the over accumulation of linoleic acid. Selenium might enhance the fatty acid contents of fungi through influencing the desaturase structure.     

Fatty acid composition of some Astragalus species from Turkey

In this study, the fatty acid contents of some Astragalus L. (Fabaceae) species from Turkey were determined by GC and GC-MS techniques. The seed oils of Astragalus sp. (A. echinops Aucher ex. Boiss., A. subrobustos Boriss., A. jodostachys, Boiss. & Buhse., A. falcatus Lam., A. fraxinifolius DC.) contained linolenic (between 23–41.%), linoleic (23–37%), and oleic acids (8–19%) as the major components. Fatty acid composition of the studied Astragalus taxa showed uniform fatty acid patterns. Palmitic and stearic acids were the major saturated fatty acids in the seed oils. The amounts of unsaturated fatty acids were higher than saturated fatty acids. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 526–528, November–December, 2006.     

Analytical Characterization of Fatty Acids Composition of Datura alba Seed Oil by Gas Chromatography Mass Spectrometry

Methyl ester derivatives of fatty acids were analyzed for the determination of the constituents of Datura alba seed oil. Gas chromatography coupled to mass spectrometer was used for these analyses. Results delivered that there were saturated as well as unsaturated fatty acids in Datura alba seed oil. Total of 15 different fatty acid components were identified and quantified. Methyl linoleate was found in highest concentration (16.22%) among the identified analytes of interest. In addition methyl esters of Palmitic acid (6.59%), Oleic acid (5.41%) and Stearic acid (1.35%) were found. Concentrations of rest of the detected fatty acids were less than 1%. From the literature it appears that no such work has been performed for the determination of fatty acids in Datura alba seed oil.     

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.     

Fatty Acid Composition of Seed Oils of Twelve Salvia Species Growing in Turkey

Seed oils of 12 Salvia species collected from different regions in Turkey (S. Albimaculata Hedge & Hub.-Mor., S. Candidisima Vahl., S. Cedronella Boiss., S. Cryptantha Montbret & Aucher ex Bentham, S. Forskahlei L., S. Fruticosa Miller (Sin. S. Triloba L. Fil), S. Halophila Hedge, S. Hypargeia Fisch. & Mey., S. Sclarea L., S. Tomentosa Miller, S. Tchihatcheffii (Fisch. & Mey.) Boiss., S. Virgata Jacq.) were obtained by Soxhlet apparatus using hexane. The oil yields were found to be between 2.0% and 20.9%. Fatty acids in the oils were converted to methyl esters and determined by GC/MS in methyl ester form. The main fatty acid components of S. halophila, S. Hypargeia, and S. Sclarea are unsaturated oleic, linoleic, and linolenic acids. In others except S. Candidissima, the dominant acids are oleic, linoleic and palmitic acids.