Betula platyphylla var.japonica Seed Oil: A rich source of linoleic acid

Component fatty acids of the oil extracted fromBetula platypbylla Sukatchev var.japonica Hara (Betulaceae) seeds were analyzed by gas liquid chromatography. The predominant fatty acid was linoleic acid (87%), and together with oleic and linolenic acids the 18-carbon unsaturated acids amounted to 97% of the total acids.     

Fatty acid composition of oleaster pulp and pit oils

Fatty acid compositions of oleaster pulp and pit oils were determined by gas chromatography in 4 samples of different varieties. Pit oils were highly unsaturated, containing >90% linoleic, oleic, and linolenic acids, as well as traces of palmitoleic acid. Saturated fatty acids consisted of palmitic and stearic acids with traces of arachidic acid. Pulp oils showed fatty acid compositions entirely different from that of pit oils. They contained 9 saturated fatty acids, C₁₂ to C₂₄, some of them with high quantities, up to 34.9%, of the total fatty acids. Unsaturated fatty acids, mainly oleic and linoleic, with low quantities of palmitoleic and linolenic acids composed about one-third of the total fatty acids.     

Association of seed size with genotypic variation in the chemical constituents of soybeans

Ten soybean genotypes grown in 1992 with seed size ranging from 7.6 to 30.3 g/100 seeds and maturity group V or VI were selected and tested for oil and protein content and for fatty acid composition. In these germplasm, protein varied from 39.5 to 50.2%, oil, 16.3 to 21.6%, and protein plus oil, 59.7 to 67.5%. Percentages of individual fatty acids relative to total fatty acids varied as follows: palmitic, 11.0 to 12.8; stearic, 3.2 to 4.7; oleic, 17.6 to 24.2; linoleic, 51.1 to 56.3 and linolenic, 6.9 to 10.0. Seed size showed no significant correlations with individual saturated fatty acids, protein or oil content. However, significant correlations were found between seed size and individual unsaturated fatty acids: positive with oleic, and negative with linoleic and linolenic. Oil and protein content were negatively correlated with each other. Among the major fatty acids, only the unsaturated were significantly correlated with each other: negative between oleic and linoleic or linolenic, and positive between linoleic and linolenic. A subsequent study with soybeans grown in 1993 generally confirmed these findings. Variation in relative percentages of unsaturated fatty acids andr values for most pairs of relationships were even higher than those obtained from the 1992 crop. Presented at the 85th AOCS Annual Meeting and Expo, Atlanta, Georgia, May 8–12, 1994.     

Performance of near-infrared reflectance spectroscopy (NIRS) in routine analysis of C18 unsaturated fatty acids in intact rapeseed

This study was aimed to evaluate the performance of near-infrared reflectance spectroscopy (NIRS) in the analysis of the oil composition for fatty acids like oleic (C18:1), linoleic (C18:2) and linolenic (C18:3) in zero-erucic acid rapeseed (Brassica napus L.). Intact-seed samples of 1094 lines from a breeding programme for high-oleic acid rapeseed were analyzed by both NIRS and gas chromatography (GC). Previously developed calibration equations were initially used for NIRS analyses. The accuracy of NIRS was considerably improved by including some samples of the actual breeding population into the original calibration set and developing new calibration equations. The inclusion of twenty randomly selected samples led to a reduction of the standard error of performance (SEP) from 2.6% to 1.9% for oleic, from 3.8% to 2.0% for linoleic, and from 1.1% to 0.9% for linolenic acid. The application of the new equations to the remaining population of 1074 samples resulted in coefficients of correlation between NIRS and GC values of 0.95 for oleic, 0.92 for linoleic, and 0.90 for linolenic acid. Furthermore, the effectiveness of a selection for high oleic, high linoleic, or low linolenic acid content based on NIRS data was demonstrated. The results of this study will help potential users to choose the optimal selection strategy in routine analysis of C18 unsaturated fatty acids by NIRS within a breeding programme.     

Oil content and fatty acid composition of chia (Salvia hispanica L.) from five northwestern locations in Argentina

Any new crop for which there is a market, and which appears to be adapted to the region, would be attractive to replace nonprofitable traditional crops in Northwestern Argentina. Chia (Salvia hispanica L.) is especially attractive because it can be grown to produce oil for both food and industry. The fatty acids of chia oil are highly unsaturated, with their main components being linoleic (17–26%) and linolenic (50–57%) acids. Seeds from a chia population harvested in Catamarca were sown in five Northwestern Argentina locations. The oil from the chia seeds produced under these five field conditions was measured. Linolenic, linoleic, oleic, palmitic, and stearic fatty acid contents of the oil were determined by gas chromatographic analysis. The results showed variations in oil content, and the oleic, linoleic, and linolenic fatty acid concentrations of the oil were significantly affected by location.     

Selective Synthesis of Diacylglycerols of Conjugated Linoleic Acid

Quasi-quantitative selective production of diacylglycerols (DAG) rich in polyunsaturated fatty acids (PUFA) was demonstrated using a Penicillium camembertii lipase. Under optimal initial conditions [60 °C, 10% (w/w) biocatalyst based on total reactants, 5:1 molar ratio of free conjugated linoleic acid (CLA) to hydroxyl groups in partial glycerides consisting of ca. 90% (w/w) monoacylglycerols (MAG) and ca. 10% (w/w) diacylglycerols (DAG)], reaction for only 4.5 h gave 98.62% DAG and 1.38% MAG. The DAG contained >95% unsaturated fatty acid residues. Predominant DAG were LnLn, LnL and LL, although LO and LP were also significant (Ln = linolenic; L = linoleic; O = oleic; P = palmitic). Effects of the acylating agent (free CLA), solvent, and temperature on undesirable side reactions were determined. Reaction selectivities were similar in n-hexane and solvent-free media. The re-esterified products contained less than 7% saturated fatty acids and a higher ratio of unsaturated to saturated fatty acid residues (19.00) than the precursor soybean oil (5.22). The biocatalyst retained 55% of its initial activity after use in three consecutive reaction/extraction cycles.     

An improved micro-extraction cell for supercritical fluid extraction and chromatography of fatty acids

An improved supercritical fluid micro-extraction cell of increased reliability was designed for on-line supercritical fluid extraction and chromatography (SFE/SFC) of food and other lipid-related samples. The key components in the modified cell include a Swagelok stainless steel reducing union with a dual ferrule as the cell, with polyetherether-ketone (PEEK) ferrules and nuts to connect the cell to the control valve. The new cell did not leak under all conditions examined (100–500 atmospheres, 40–80°C), even after numerous extractions (>250). The quantitative performance of the cell was evaluated with fatty acid standard solutions, technical grade fatty acid sources and wheat flour. The percent relative error (%RE) for the fatty acid standards and technical-grade fatty acid samples was ≤6.0% for oleic, linoleic and linolenic acid. The %RE for oleic and linoleic acid in the whole-wheat samples was ≤10%. The results demonstrate that the new extraction cell can be used for quantitative extractions and that the sensitivity of the SFE/SFC technique is excellent. Similar SFE/SFC methods could prove useful in studying the interaction of free fatty acids with various food components such as enzymes, amylose and proteins.     

Chemical Composition and Characteristics of <Emphasis Type="Italic">Commiphora wightii</Emphasis> (Arnott) Bhandari Seed Oil

The seeds of Commiphora wightii (Arnott) Bhandari contain 9.8 ± 0.7% oil. The fatty acid composition and chemical properties of the extracted oil were determined. Gas liquid chromatography of the methyl esters of the fatty acids shows the presence of 46.62% saturated fatty acids and 51.40% unsaturated fatty acids. The fatty acid composition is as follows: capric acid 3.50%, myristic acid 14.51%, palmitic acid 6.68%, stearic acid 4.70%, arachidic acid 3.18%, behenic acid 14.05%, myristoleic acid 1.34%, palmitoleic acid 12.07%, oleic acid 14.15%, eicosenoic acid 0.11%, linoleic acid 22.34% and alpha linoleic acid 1.37%.     

Extraction of pollen lipids by SFE‐CO2 and determination of free fatty acids by HPLC

Rape bee pollen lipids obtained by petrol ether extraction (PEE) or supercritical fluid (carbon dioxide) extraction (SFE) were compared with regard to their free fatty acid (FFA) components. Optimal SFE conditions were selected by carrying out the Taguchi method with an OA9 (3³) matrix design, and are as follows: extraction pressure at 35 MPa, temperature at 45 °C, and dynamic extraction time at 90 min. The lipid yield based on PEE was 7.42 wt‐% and the extracts of the desired analytes based on SFE varied in the range of 3.23–5.58 wt‐% under different conditions. With the optimized procedure, the lipid yield was 6.09 wt‐%. The FFA in the lipids were separated with a pre‐column derivation method and 1‐[2‐(p‐toluenesulfonate) ethyl]‐2‐phenylimidazole [4,5‐f]9,10‐phenanthrene as labeling regent, followed by high‐pressure liquid chromatography (HPLC) with fluorescence detection. HPLC analysis shows that the lipids contain abundant unsaturated fatty acids (UFA) in high to low concentrations as follows: linolenic acid (18:3), oleic acid (18:1), linoleic acid (18:2), nervonic acid (24:1), and lignoceric acid (20:4). The UFA contents in the SFE extracts were higher than those after PEE. The results indicated that SFE under suitable conditions is more selective than conventional PEE with regard to lipid extraction and preservation of their quality.     

Effect of resin components on the degradation of guayule rubber

All natural rubbers are likely to contain some long chain fatty acids or their esters. The individual effect of the four C₁₈ fatty acids (stearic, oleic, linoleic, and linolenic acid) present in the guayule resin on the degradation of guayule rubber has been investigated concurrently by stress–relaxation of radiation cured rubber networks and by gel permeation chromatography studies on the raw rubber in the temperature zone 70–125°C. C₁₈ unsaturated fatty acids enhance the degradation of rubber several fold. The rate of degradation follows the order: rubber ≤ rubber + stearic acid < rubber + oleic acid < rubber + linoleic acid < rubber + linolenic acid. The thermal degradation is slower than the thermooxidative. The rate of degradation monotonically increased with the number of conjugated double bonds and is first order with respect to acid concentration. The activation energy for the chain scission for both thermal and thermooxidative degradation has been found to be 95 ± 10 kJ/mol. The mechanism of degradation of guayule rubber in the presence of fatty acids is discussed.     

Determination of the fatty acid profile by 1H‐NMR spectroscopy

The common unsaturated fatty acids present in many vegetable oils (oleic, linoleic and linolenic acids) can be quantitated by ¹H‐nuclear magnetic resonance spectroscopy (¹H‐NMR). A key feature is that the signals of the terminal methyl group of linolenic acid are shifted downfield from the corresponding signals in the other fatty acids, permitting their separate integration and quantitation of linolenic acid. Then, using the integration values of the signals of the allylic and bis‐allylic protons, oleic and linoleic acids can be quantitated. The procedure was verified for mixtures of triacylglycerols (vegetable oils) and methyl esters of oleic, linoleic and linolenic acids as well as palmitic and stearic acids. Generally, the NMR (400 MHz) results were in good agreement with gas chromatographic (GC) analyses. As the present ¹H‐NMR‐based procedure can be applied to neat vegetable oils, the preparation of derivatives for GC would be unnecessary. The present method is extended to quantitating saturated (palmitic and stearic) acids, although in this case the results deviate more strongly from actual values and GC analyses. Alternatives to the iodine value (allylic position equivalents and bis‐allylic position equivalents) can be derived directly from the integration values of the allylic and bis‐allylic protons.     

Studies on Minor Seed Oils XII

Physico-chemical analysis of seven seeds of indigenous species of plants belonging to six different botanical families have been carried out with the help of UV, IR, TLC-GLC techniques. All the seed oils were found in agreement with the simple fatty acid composition i.e. linoleic-oleic-palmitic type. The chief components among unsaturated acids in the six seed oils are oleic and linoleic acids together forming 40.0-86.0 %. Polygonum sp. surprisingly is found to have combined content of oleic and linoleic acid 13.3 % only but having unexpected high amount of linolenic acid (37.8 %). Among saturated acids, palmitic acid was predominant acid found in the range of 10.0-483 %. This chemical screening of seed oils reveals that the species producing highly unsaturated oils merit attention for utilization as minor seed oils.     

Varietal difference in lipid content and fatty acid composition of highbush blueberries

Lipids from five cultivars of highbush blueberries (Vaccinium corymbosum L.) were extracted and fractionated into neutral lipids (60–66%), glycolipids (20–22%) and phospholipids (14–18%). The major fatty acids in all fractions were palmitic (16∶0), oleic (18∶1), linoleic (18∶2), and linolenic (18∶3) acids. All lipid classes had a large concentration of C₁₈ polyunsaturated acids (84–92%), indicating that blueberries are a rich source of linoleic and linolenic acids. Changes in the fatty acid composition of neutral lipids and phospholipids were not significantly different among the five cultivars, but significant differences were noted in the ratios of linoleic and linolenic acids in the glycolipids fraction.     

Distribution of fatty acids during germination of soybean seeds

Gas chromatographic determination of the fatty acids in the seeds of soybean (Glycine max) showed mainly linoleic, oleic and palmitic acids with linoleic acid being the major component. Changes in the distribution of fatty acids were measured during germination in the cotyledons and roots. A decrease in palmitic and oleic acids was observed in the cotyledons from 6 to 12 days, while linoleic acid increased during the same period. In roots also, the major fatty acid was linoleic acid, while palmitic and linolenic acids were higher in roots in comparison with the cotyledons. During the 3–12 days of germination period, no major changes in the distribution pattern of fatty acids were observed in the roots. The possible significance of these changes is discussed.     

Lipid Profile and Fatty Acid Composition of Moth Bean (Vigna aconitefolia) Seeds

The seeds of moth bean (Vigna aconitefolia) were found to contain 4.5 % of lipid. Fractionation of this lipid by silicic acid column chromatography yielded 44.5 % neutral lipids (NL), 23.4 % glycolipids (GL) and 32.1 % phospholipids (PL). Fatty acid composition of the total lipid and lipid fractions showed that palmitic acid (37.3-54.7 %), stearic acid (7.8-8.0%) oleic acid (6.8-13.9 %) linoleic acid (23.1-35.6 %) and linolenic acid (3.0-10.0%) are the major fatty acids. The phospholipid fraction was found to be different from the rest in containing higher palmitic acid (54.7%) and lower unsaturated fatty acids.     

The abundance ofcis-5-octadecenoic acid inDioscoreophyllum cumminsii seed oil

Oil fromDioscoreophyllum cumminsii (Stapf) Diels containscis-5-octadecenoic acid as 84% of its total fatty acids. The unsaturated acids normally found in seed oils are present in small amounts (oleic, 1%, linoleic 5.2%; and linolenic, 0.3%). Other unusual acids present, in minor amounts, arecis-5-hexadecenoic (0.6%), 11-octadecenoic (0.9%) and two polyenoic acids which are probably unsaturated at the 5 position. N. Market. Nutr. Res. Div., ARS, USDA.     

Chemical Composition and Nutritional Characteristics of the Seed Oil of Wild <Emphasis Type="Italic">Lathyrus</Emphasis>, <Emphasis Type="Italic">Lens</Emphasis> and <Emphasis Type="Italic">Pisum</Emphasis> Species from Southern Spain

The fatty acid composition of the seed oil of 19 wild legume species from southern Spain was analyzed by gas chromatography. The main seed oil fatty acids ranged from C_14:0 to C_20:0. Among unsaturated fatty acids, the most abundant were linoleic, oleic and linolenic acids, except for Lathyrus angulatus, L. aphaca, L. clymenum, L. sphaericus and L. nigricans where C_18:3 contents were higher than C_18:1 contents. Palmitic acid was the most abundant saturated acid in studied species, ranging from 11.6% in Lathyrus sativus to 19.3% in Lens nigricans. All studied species showed higher amounts of total unsaturated fatty acids than saturated ones. Among studied species, the ω6/ω3 ratio was variable, ranging from 2.0% in L. nigricans to 13.8% in L. sativus, there being eight species in which the ω6/ω3 ratio was below 5. The fatty acids observed in these plants supports the use of these plants as a source of important dietary lipids.     

Crystallization at low temperatures as a technique in the analysis of oils

Summary 1. A rapid method for determining the saturated, oleic, linoleic and linolenic acids in a 1-gram sample of fat has been described. 2. Saturated fatty acids were separated by quantitative crystallization from acetone solution at −40° C. 3. The three unsaturated acids, oleic, linoleic and linolenic, were calculated from the iodine and thiocyanogen values of the remaining liquid acids. 4. Analysis of known mixtures of fatty acids demonstrated the accuracy of the method to be approximately ±2 units percent. 5. Duplicate determinations of the fatty acid distribution in natural oils agreed within 0 to 4 units percent. 6. Data on the oleic, linoleic, and linolenic acid content of 15 seed oils were presented. Published with the approval of the Director of the Wisconsin Agricultural Experiment Station, Madison, Wisconsin. This work was supported in part by funds furnished by the Lever Brothers Company, Cambridge, Massachusetts, and the Wisconsin Alumni Research Foundation.     

混合脂肪酸的分离

以一般油脂加工副产物十八碳混合脂肪酸为原料,采用配合结晶梯度冷冻反萃取分离技术,不经任何热处理以避免聚合作用的发生,使混合脂肪酸中的饱和脂肪酸与不饱和脂肪酸分离,同时将不饱和脂肪酸分成油酸和(亚油酸+亚麻酸)两组分。后者含量可达95%以上。     

Characterization of Turkish <Emphasis Type="Italic">Quercus</Emphasis> L. Taxa Based on Fatty Acid Compositions of the Acorns

Total oil content and the composition of fatty acids were analyzed in the acorns of 16 Quercus taxa from Turkey. The range of total fat varied between 0.7 and 7.4%. Oleic (10.2–54.4%), linoleic (24.2–49.1%), palmitic (13.4–30.4%), alpha linolenic (1.5–8.6%) and stearic acid (1.5–4.5%) were major fatty acids for all taxa. Significantly differences at section level were found (p < 0.05) for palmitic, stearic and oleic acid concentration. Saturated (17.0–38.6%), mono unsaturated (11.0–55.5%) and unsaturated fatty acids (57.4–81.6%) in total oil were also significantly different between section Quercus, Cerris and Ilex (p < 0.05). In addition, sectional differences were significant (p < 0.02) for the relative concentrations of saturated fatty acids compared to mono, poly and total unsaturated fatty acids. Considerable variation of individual fatty acid levels were observed in related species and varieties. The species from section Ilex Loudon exhibited the highest levels of saturated fatty acid while the lowest levels were found in Q. brantii, Q. libani and Q. trojana from section Cerris Loudon. These species also had the highest levels of unsaturated fatty acids. Whereas the lowest values were detected in the species of section Ilex. Both varieties of Q. cerris showed significant differences (p < 0.05) from the other species in section Cerris for all parameters, except for stearic acid and exhibited little variations among their individual populations. Different concentrations of fatty acids may be useful biochemical markers for the characterization of Quercus at the infrageneric level. Interesting ratios of linoleic:α-linolenic acid especially in Q. robur ssp. robur, Q. hartwissiana, Q. vulcanica, Q. ithaburensis ssp. macrolepis and Q. libani also were detected with respect to dietary reference for fatty acid intake.