Genetics,characteristics, and utilization of oil in caryopses of oat species

For oats to be an economically feasible oilseed crop in Iowa, the oil percentage would have to be increased to ca. 16%. A survey of the oil percentage in 445 oat cultivars and collections gave a range of 2.0–11.0%. The oil percentage was only slightly affected by growing oats in 5 different locations in Iowa. Inheritance studies indicated that oil percentage was inherited polygenically, and there was a tendency for high oil percentage to be partially dominant. Analysis of 64 cultivars and collections showed a wide variation of fatty acid composition: palmitic, 14–23%; stearic, <1–4%; oleic, 29–53%; linoleic, 24–48%; linolenic, < 1–5%. The oil percentage was positively correlated with oleic acid and negatively correlated with linoleic and linolenic acids. Oats contained a lipase that made extraction of oil with low acid values difficult. The lipase was strongly affected by moisture and was most active in oat doughs containing 25–50% moisture. There was at least a 20-fold variation in lipase activity in oat cultivars and collections. Whole oats may be kept in dry storage for several years without significant lipolysis, but in broken or crushed caryopses, lipolysis occurs even at low moisture levels. The lipase may be inactivated by heat or 95% ethanol treatments.     

Measurement of fatty acids in whole soybeans with near infrared spectroscopy

Improvement of nutritional and/or functional properties of soybean oil by modification of soy fatty acid composition is one of the objectives of plant breeders. A major element of breeding is rapid identification and tracking of traits in seed samples. This discussion summarizes the progression of whole‐soybean fatty acid calibration developments at Iowa State University. Emphasis was placed on linolenic acid (18:3) and total saturates (16:0 + 18:0). Normal soybeans have 12–20% (of the oil) saturated fats; modified low saturate soybeans have 6–8% saturated fats. Normal soybeans have 6–12% linolenic acid; modified low linolenic soybeans have 1–3% linolenic acid. Infratec 122x/1241 and Bruins OmegaG NIRS units were calibrated to measure fatty acid levels as a percentage of total oil content, in whole soybeans. The first Infratec calibrations (in 1998) did not remain accurate as soybean genetics changed. Iterations of the calibration process yielded calibrations for total saturates and linolenic acid with standard errors of prediction (on 2005 crop samples not included in the calibration pool) of 1.0% percentage points and 0.8% points, respectively. These were sufficient to classify modified versus normal concentrations of the two fatty acids. The NIRS units could not determine the specific percentages within the classes of modified and normal soybeans.     

Glyceride structure variation in soybean varieties: I. Stereospecific analysis

Stereospecific analysis of soybeans and related species showed that there was little palmitic or stearic acid on thesn-2-position, and thesn-1-position is consistently richer in palmitic, stearic, and linolenic acids than thesn-3-position. Thesn-3-position is enriched in oleic acid and thesn-2-position with linoleic. Plots of the percentage of fatty acids on the glycerol positions vs. the percentage in the whole oil revealed a soybean variety that had a deviant distribution that is probably genetically controlled. Journal Paper No. J-8837 of the Iowa Agriculture and Home Economics Experiment Station, Ames IA. Project No. 2143.     

Variability in seed oil composition of 43Linum species

Analyses of the seed oil of 43Linum species showed great variability in fatty acid composition. The species can be grouped in two broad categories on the basis of seed oil composition: 1) Those with high linolenic, low linoleic and low oleic acid content, and 2) Those with high linoleic, low linolenic and low oleic acid content. A positive correlation was observed between iodine value and linolenic acid content, and a negative correlation between linolenic and linoleic acid content. There was no correlation between fatty acid composition and chronosome number. No. 1722, University of California Citrus Research Center and Agriculture Experiment Station, Riverside, California.     

Degradation of α-linolenic acid during heating

Degummed bleached rapeseed oil was heated at 210, 220, and 230°C for up to 86 h under reduced pressure with nitrogen stripping. No significant change of total linoleic acid content was found, but a decrease of the total linolenic acid content was observed under extreme conditions. The degradation rate of linolenic acid is described as a function of heating time and operating temperature. Linolenic acid degradation can be predicted for any set of conditions by the established model. No significant degradation of linolenic acid can occur under standard deodorization conditions. Lesieur and Cereol are divisions of Eridania Béghin-Say Group.     

Comparative rates of formation of fatty acids in the soybean seed during its development

Summary Lincoln soybeans harvested at successive stages of maturity showed continuous increases in amounts present of each of the fatty acids: saturated, oleic, linoleic, and linolenic. The iodine value and linolenic acid percentage of the oil decreased somewhat during the early stages of seed development. The linoleic acid and total oil percentage in the bean increased continuously until the 50th day then remained constant. Oleic and saturated acids fluctuated. No evidence for dehydrogenation of saturated fatty acids was obtained either in the oil analyses or in tests of soybean tissues for dehydrogenase activity. Journal Paper No. 717 of the Purdue Agricultural Experiment Station, Lafayette, Ind.     

The plant geneticist’s contribution toward changing lipid and amino acid composition of soybeans

Interest in changing composition of soybeans focuses on linolenic acid in the oil. Available germ plasm includes no lines with less than about 3.5% linolenic acid in the oil. Some breeding lines have been obtained with iodine values of about 115, reflecting higher oleic acid and somewhat lower than normal linoleic and linolenic acid levels. Radiation and other mutagenic agents have been investigated to a limited extent for potential usefulness in inducing a mutation in the direction of low linolenic acid. No such mutant has yet been found, and the task of identifying one is formidable. There is no research known at this time with the objective of altering amino acid distribution in soybeans. One of seven papers presented at the Symposium, “The Plant Geneticist’s Contribution Toward Changing the Lipid and Amino Acid Composition of Oilseeds,” AOCS Meeting, Houston, May 1971.     

An emulsion method for the sensory evaluation of edible oils

The flavor intensity of soybean oils was evaluated in emulsions stabilized with gum acacia. A 10-point scale was used with a blank to establish the bland end of the scale and a standard diacetyl solution to establish a point near midscale. Tasting oils in emulsion gave significantly different scores than tasting oil directly. Evaluation in emulsion decreased panel error for poor quality oils but not for very bland oils. At least six samples could be tasted in emulsion without casusing panel fatigue or reducing accuracy. The concentration of oil in the emulsion could be adjusted to increase sensitivity to weak flavors or improve the evaluation of intensely flavored oils. Soybean oils containing various amounts of linolenic acid were evaluated by the emulsion method, and those with lesser amounts of linolenic acid were shown to be more stable. A gas Chromatographic total volatile method was shown to correlate fairly well with sensory evaluation of oils tasted in emulsions under conditions where both flavors scores and total volatiles changed significantly with time. Journal Paper no. J-10442 of the Iowa Agriculture and Home Economics Experiment Station, Ames. Project no. 2143.     

Characterization of naturally occurring α-hydroxylinolenic acid

The seed oil ofThymus vulgaris L. (Labiatae) contains 13% of a new unsaturated hydroxy fatty acid which has been characterized as α-hydroxylinolenic acid. This oil also contains the previously unknown norlinolenic (all-cis-8,11,14-heptadecatrienoic) acid (2%) and linolenic acid (55%). The co-occurrence of these three acids suggests that the C₁₇ acid is biosynthesized by α-oxidation of linolenic acid. Presented at the AOCS-AACC Joint Meeting, Washington, D. C., April 1968. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Variability of linolenic and linoleic acids in soybean oil

Summary Soybean oil from all locations and varieties of Uniform Test Groups II, III, and IV have been analyzed for linolenic and linoleic acid by an improved spectrophotometric method. Location composites in Group II varied from 5.9% to 8.3% in linolenic acid and from 45.3% to 50.4% in linoleic. Variety composites varied from 5.4% to 8.0% in linolenic and from 43.9% to 51.6% in linoleic. The location variability was shown to be closely associated with maximum temperature during seed development. Temperature appears to be the most important environmental factor affecting these acids, especially linolenic. The percentages of the two acids are positively correlated with each other. Publication No. 291 of the U. S. Regional Soybean Laboratory, Urbana, Ill.     

Frying quality and stability of low-and ultra-low-linolenic acid soybean oils

To determine effects of very low levels of linolenic acid on frying stabilities of soybean oils, tests were conducted with 2% (low) linolenic acid soybean oil (LLSBO) and 0.8% (ultra-low) linolenic acid soybean oil (ULLSBO) in comparison with cottonseed oil (CSO). Potato chips were fried in the oils for a total of 25 h of oil use. No significant differences were found for either total polar compounds or FFA between samples of LLSBO and ULLSBO; however, CSO had significantly higher percentage of polar compounds and FFA than the soybean oils at all sampling times. Flavor evaluations of fresh and aged (1, 3, 5, and 7 wk at 25°C) potato chips showed some differences between potato chips fried in different oil types. Sensory panel judges reported that potato chips fried in ULLSBO and aged for 3 or 7 wk at 25°C had significantly lower intensities of fishy flavor than did potato chips fried in LLSBO with the same conditions. Potato chips fried in ULLSBO that had been used for 5 h and then aged 7 wk at 25°C had significantly better quality than did potato chips fried 5 h in LLSBO and aged under the same conditions. Hexanal was significantly higher in the 5-h LLSBO sample than in potato chips fried 5 h in ULLSBO. The decrease in linolenic acid from 2 to 0.8% in the oils improved flavor quality and oxidative stability of some of the potato chip samples.     

Oil Quality Improvement in Soybeans-Glycine max (L.) Merr.

Plant breeding was used to reduce the linolenic acid content of soybean oil and improve oil stability. By crossing strains with the lowest linolenic acid content available, it was possible to produce offspring with amounts of linolenic acid 1 to 1.5% lower than the best parental strain. The selection of desirable strains was greatly accelerated by growing plants in Puerto Rico during the winter. Mutagenic agents (X-rays and ethyl methylsulfonate) were used in an attempt to introduce more variability for fatty acid composition into the population. Seed source has a small effect on the amount of linolenic acid produced in the next generation of seeds. A late planting date significantly increased the amount of linolenic and stearic acid in soybeans. There was a significant negative correlation between linolenic acid and both oleic and stearic acid.     

Effects of Vegetable Oil Composition on Epoxidation Kinetics and Physical Properties

In this article, we investigate the role of triacylglycerol composition on the properties of epoxidized vegetable oils and the kinetics of the epoxidation process under conditions comparable to commercial epoxidation. Commodity soybean oil (24% oleic acid, 50% linoleic acid, and 7% linolenic acid), high‐oleic soybean oil (75% oleic acid, 8% linoleic acid, and 2.5% linolenic acid), and linseed oil (11% oleic acid, 15% linoleic acid, and 64% linolenic acid) were each epoxidized to various extents. Epoxidation rate, viscosity, differential calorimetry, and X‐ray diffraction data are presented for these oils and interpreted in the context of their fatty acid profile (mostly oleic, linoleic, or linolenic). While fully epoxidized soybean oil is widely commercially available and used in an increasing array of industrial applications, information relating to partially epoxidized oils and epoxidized oils of other cultivars is less well known.     

Borage and evening primrose oil

The paper gives a short overview about the production and composition of borage (Borago officinalis) and evening primrose (Oenothera biennis) oil considering special aspects of the production as cold‐pressed oil. Both oils are characterized by a remarkable amount of γ‐linolenic acid, which has some nutritional advantages. The fatty acid composition of evening primrose oil is dominated by linoleic acid with about 72% and about 13% γ‐linolenic acid, while borage oil consists of twice the amount of γ‐linolenic acid and only 38% linoleic acid. The amount of saturated fatty acids is higher in borage oil. The tocopherol composition of both oils is dominated by γ‐tocopherol, with borage oil containing twice the amount compared to evening primrose oil.     

Selective hydrogenation of soybean oil in the presence of copper catalysts

Many investigators associate the poor keeping properties of soybean oil with its linolenic acid content. On the other hand the high linoleic acid content is a desired property from a nutritional point of view. We have therefore developed a process for the preferential reduction of the linolenic acid content by selective hydrogenation. Conventional catalysts for the hydrogenation of fats have a rather low selectivity in this respect. When linolenic acid in soybean oil is hardened (e.g., with a nickel catalyst), most of the linoleic acid is converted into less unsaturated acids. It was found that linolenic acid is hydrogenated much more preferentially in the presence of copper catalysts than in that of nickel and other hydrogenation catalysts. At a linolenic acid content of 2%, soybean oil hardened with nickel catalyst contained about 28% linoleic acid, whereas with copper catalyst the hardened soybean oil contained 49% linoleic acid. By means of our process it is possible to manufacture a good keepable oil of, e.g., I.V. 115 and containing 1% linolenic acid and 46% linoleic acid. The storage stability of this product is comparable with that of sunflower-seed oil. A liquid phase yield of 86% is obtained after winterization at 5C for 18 hr. The high selectivity for linolenate reduction of copper catalysts must be ascribed to the copper part of the catalyst. Investigations into the structure of the catalyst indicate that the active center consists of copper metal crystallites; whether these centers are promoted by the carrier or traces of other substances is under investigation.     

Performance evaluation of hexane-extracted oils from genetically modified soybeans

Soybeans produced by induced mutation breeding and hybridization were cracked, flaked and hexane-extracted, and the recovered crude oils were processed to finished edible oils by laboratory simulations of commercial oil-processing procedures. Three lines yielded oils containing 1.7, 1.9 and 2.5% linolenic acid. These low-linolenic acid oils were evaluated along with oil extracted from the cultivar Hardin, grown at the same time and location, and they were processed at the same time. The oil from Hardin contained 6.5% linolenic acid. Low-linolenic acid oils showed improved flavor stability in accelerated storage tests after 8 d in the dark at 60°C and after 8h at 7500 lux at 30°C, conditions generally considered in stress testing. Room odor testing indicated that the low-linolenic oils showed significantly lower fishy odor after 1 h at 190°C and lower acrid/pungent odor after 5 h. Potatoes were fried in the oils at 190°C after 5, 10 and 15 h of use. Overall flavor quality of the potatoes fried in the low-linolenic oils was good and significantly better after all time periods than that of potatoes fried in the standard oil. No fishy flavors were perceived with potatoes fried in the low-linolenic oils. Total volatile and polar compound content of all heated oils increased with frying hours, with no significant differences observed. After 15 h of frying, the free fatty acid content in all oils remained below 0.3%. Lowering the linolenic acid content of soybean oil by breeding was particularly beneficial for improved oil quality during cooking and frying. Flavor quality of fried foods was enhanced with these low-linolenic acid oils.     

Cardiopathogenicity of rapeseed oils and oil blends differing in erucic,linoleic, and linolenic acid content

Male Wistar rats were fed semipurified diets containing 20% fat for 25 weeks. Ten different oils or oil blends were employed, including rapeseed oils, simulated rapeseed-type oils, and modified rapeseed-type oils. Safflower, soybean, and hydrogenated coconut oils served as control oils. Histopathological examination of the cardiac tissue was conducted at the end of the study and an incidence-severity rating assigned to the lesions induced by each fat. Oils containing high levels of erucic acid (26–30%) induced the most severe cardiac necrosis, irrespective of the source of erucic acid (rapeseed oil or nasturtium oil). Increasing the linoleic: linolenic acid ratio of the high erucic oils to that of soybean oil failed to reduce necrosis, but the absence of linolenic acid from a high erucic acid oil blend resulted in a markedly reduced lesion incidence-severity rating, comparable to those obtained for low erucic acid rapessed oil and soybean oil which were similar. Lowest lesion incidence was obtained with safflower oil and hydrogenated coconut oil. We have postulated that linolenic acid plays a role in the etiology of cardiac necrosis observed when rats are fed diets containing low erucic acid rapeseed oils.     

Comparative studies on composition of cardiac phospholipids in rats fed different vegetable oils

Male Sprague-Dawley rats were fed diets for 1 or 16 weeks, containing 20% by weight vegetable oils differing widely in their oleic, linoleic and linolenic acid content. No significant changes were observed in the level of the cardiac lipid classes. The fatty acid composition of the 2 major phospholipids, phosphatidylcholine and phosphatidylethanolamine, showed a remarkable similarity between diets in the concentration of total saturated, C22 polyunsaturated and arachidonic acids. Monounsaturated acids were incorporated depending on their dietary concentration, but the increases were moderate. Dietary linolenic acid rapidly substituted C22 polyunsaturated fatty acids of the linoleic acid family (n−6) with those from the linolenic acid family (n−3). The results suggest that dietary linolenic acid of less than 15% does not inhibit the conversion of linoleic to arachidonic acid but the subsequent conversion of arachidonic acid to the C22 polyunsaturates was greatly reduced. Significant amounts of dietary monounsaturated fatty acids were incorporated into cardiac cardiolipin accompanied by increases in polyunsaturated fatty acids, apparently to maintain an average of 2 double bonds/molecule. The cardiac sphingomyelins also accumulated monounsaturated fatty acids depending on the dietary concentration. It is quite evident from the results of this study that the incorporation of oleic acid and the substitution of linolenic for linoleic acid-derived C22 polyunsaturated fatty acids into cardiac phospholipids was related to the dietary concentration of these fatty acids and was not peculiar to any specific oil. Even though it is impossible to estimate the effect of such changes in cardiac phospholipids on membrane structure and function, results are discussed which suggest that the resultant membrane in the Sprague-Dawley male rat is more fragile, leading to greater cellular breakdown and focal necrosis. Contribution No. 914 from the Animal Research Institute.     

Triacylglycerols from viper bugloss (Echium vulgare L.) seed bio‐oil

Triacylglycerols (TAG) in viper bugloss oil were isolated from raw pressed oil by silicic acid column chromatography. The obtained blend of TAG was separated by silver ion thin‐layer chromatography (TLC Ag⁺) into nine fractions, varying in terms of unsaturation level and molecular polarity. The composition of TAG in viper bugloss oil was determined by HPLC coupled with a diode‐array detector and an evaporative light‐scattering detector. The results showed that the first three fractions were combinations of TAG containing palmitic, oleic and linoleic acids. Fractions 4 and 6 contained TAG of a similar acid composition as above, but with the addition of γ‐linolenic acid. The remaining fractions (7–9) were the most varied in acid composition. They were found to contain 26–39% palmitic acid, 12–15% oleic acid, 13–41% linoleic acid 8–24% γ‐linolenic acid, 1.5–5.5% α‐linolenic acid and 1–5% stearidonic acid. The analysis of fatty acid allocation in TAG of viper bugloss lipids revealed that linoleic acid (ranging from 2 to 100%) was the only acid found in all isolated fractions. In the investigated oil, the predominant TAG included: LnLnG (11.38%), LnLnSt (11.17%), LnGSt (7.71%), LnStSt (6.19%) and LnLnLn (5.44%). Almost 86% of the TAG contained α‐linolenic acid, while γ‐linolenic and stearidonic acids amounted to 49 and 38%, respectively.     

Low linolenic soybeans and beyond

Low linolenic soybean oil is the first in a series of modified oilseed products to be introduced to meet food company and consumer needs. Consumer packaged goods and foodservice companies are currently using this oil to successfully replace partially hydrogenated soybean oil, resulting in the reduction of trans fatty acids from the food supply. In addition to meeting consumer demand for healthier foods, many food processors have chosen low linolenic soybean oil based on taste, performance and cost benefits. Seed companies continue to utilize traditional breeding, marker assisted breeding and biotechnology approaches to modify oilseeds that produce oils with health and nutrition benefits. Additional modified oilseeds are at various stages of development. Soybeans with increased levels of stearic acid are being developed as an alternative to partially hydrogenated fats and high saturate fats required to provide solids and structure to food. High stability fry oils with increased levels of oleic acid, reduced levels of linolenic acid as well as a version with lower saturated fat are being developed. Soybeans are also being modified to offer more sustainable sources of omega‐3s including stearidonic acid and eicosapentaenoic acid/docosahexaenoic acid which will result in more efficacious sources of omega‐3s compared to alpha‐linolenic acid‐containing vegetable oil and improved functionality/stability compared to fish and algal oils.