Fatty acids in lipids of maturing wheat

Two varieties of hard red winter wheat were sampled at various stages of maturity. The lipids in those samples were fractionated into free polar, free nonpolar and bound lipids. Fatty acids of those fractions were determined. Major acids present were palmitic, oleic, linoleic and linolenic. Both wheat samples showed similar qualitative, but not quantitative patterns in distribution of fatty acids during maturation. In the free polar lipid fraction, the palmitic acid content decreased with maturation while the linoleic acid content increased. The free nonpolar fractions showed a slight increase in linoleic acid; the concentration of other acids decreased slightly as the wheat matured. The bound lipid fraction showed a marked increase in linoleic acid, accompanied by decreases in the other major fatty acids, especially linolenic. Cooperative investigations of Kansas Agricultural Experiment Station and Crops Research Div., ARS, USDA.     

Variation in fatty acid composition of the different acyl lipids in seed oils from fourSesamum species

Seeds from different collections of cultivatedSesamum indicum Linn. and three related wild species [specifically,S. alatum Thonn.,S. radiatum Schum and Thonn. andS. angustifolium (Oliv.) Engl.] were studied for their oil content and fatty acid composition of the total lipids. The wild seeds contained less oil (ca. 30%) than the cultivated seeds (ca. 50%). Lipids from all four species were comparable in their total fatty acid composition, with palmitic (8.2–12.7%), stearic (5.6–9.1%), oleic (33.4–46.9%) and linoleic acid (33.2–48.4%) as the major acids. The total lipids from selected samples were fractionated by thin-layer chromatography into five fractions: triacylglycerols (TAG; 80.3–88.9%), diacylglycerols (DAG; 6.5–10.4%), free fatty acids (FFA; 1.2–5.1%), polar lipids (PL; 2.3–3.5%) and steryl esters (SE; 0.3–0.6%). Compared to the TAG, the four other fractions (viz, DAG, FFA, PL and SE) were generally characterized by higher percentages of saturated acids, notably palmitic and stearic acids, and lower percentages of linoleic and oleic acids in all species. Slightly higher percentages of long-chain fatty acids (20∶0, 20∶1, 22∶0 and 24∶0) were observed for lipid classes other than TAG in all four species. Based on the fatty acid composition of the total lipids and of the different acyl lipid classes, it seems thatS. radiatum andS. angustifolium are more related to each other than they are to the other two species.     

Tissue culture of cocoa bean (Theobroma cacao L.): changes in lipids during maturation of beans and growth of cells and calli in culture

Callus cultures ofTheobroma cacao L., initiated from explants of immature cocoa bean cotyledons, contained 5.3%–6.4% lipids (dry wt basis). The major fatty acids were palmitic, oleic and linoleic acids. Cell suspensions contained 5.7–7.7% total lipids which had a higher polyunsaturated fatty acid content than total lipids of the calli. Phospholipids and glycolipids were the predominant lipid classes of calli and cell suspensions. Immature cocoa beans at early stages of development contained much higher polyunsaturated fatty acids, higher polar lipids and lower triglycerides than did mature ripe beans. Ripe cocoa beans contained 54% total lipids of which 96.8% where triglycerides. The fatty acid composition of total lipids of calli and cell suspensions were similar to those of the immature cocoa beans.     

The seed lipids of the palm family

The majority of palms, represented byElaeis guineensis, contained mainly neutral lipids (triglycerides) in their seed fats with lauric and myristic acids as the major acids. In certain others, symbolized by theRaphia palms, polar lipids dominated, with the unsaturated acids, oleic and linoleic acids constituting the major fatty acids. Contrary to established belief, lauric and myristic acids were not the principal fatty acids in all palms.     

Tissue culture of cocoa bean (Theobroma cacao L.): Incorporation of fatty acids into lipids of cultured cells

Suspension cell cultures of cocoa bean rapidly incorporated palmitic, stearic, oleic and linoleic acids into cellular lipids. Thus, 75 and 20% of [1-¹⁴C] palmitic acid was incorporated into polar lipids and triglycerides, respectively, after 48 hr. When [1-¹⁴C] oleic and [1-¹⁴C] linoleic acid were added separately, polar lipids consistently contained most of the radioactive fatty acids. Ca. 60% of the stearic acid accumulated as unesterified fatty acid in the cells. Palmitic and stearic acid were not desaturated, but oleic acid and linoleic acid were further desaturated. The kinetics of conversion of oleic acid and linoleic acid suggested a sequential desaturation pathway of 18∶1→18∶2→18∶3 in cocoa bean cell suspensions.     

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.     

Lipid composition of beef and human pituitary glands

The lipid composition of beef and human pituitary was determined by chromatographic and spectrophotometric methods. Beef pituitary lipid contained about 25% nonpolar lipids and 75% phospholipids whereas nonpolar lipids made up approximately 60% of the total in human pituitaries. The main nonpolar (i.e., low polarity) lipids in human pituitary were triglycerides, cholesterol, free fatty acids and an unidentified component in the triglyceride fraction. Cholesterol was the major nonpolar lipid component in freshly collected beef anterior and posterior pituitary, but the amount of free fatty acids appeared to increase during storage. Preliminary investigation of the unknown nonpolar lipid in human pituitaries suggested that it was an unsaturated hydroxy compound with no carbonyl functions. Thin layer chromatography indicated that it was also present in smaller amounts in freshly collected beef pituitaries. The main phospholipids of beef anterior, posterior and human pituitary were phosphatidyl ethanolamine, phosphatidyl choline, phosphatidyl inositol, phosphatidyl serine and sphingomyelin. The fatty acid composition of total nonpolar lipids, free fatty acids, total phospholipids, phosphatidyl ethanolamine and phosphatidyl choline of beef anterior and posterior pituitary was determined by gas liquid chromatography. Mixtures of saturated and unsaturated fatty acids ranging from C₁₂ to C₂₂ were present; the main fatty acids were palmitic, stearic, oleic, linoleic and arachidonic.     

Effect of the nature and amount of dietary energy on lipid composition of rat bone marrow

The effect of the nature and amount of dietary calories on the lipid composition of bone marrow of rats was studied. Male weanling rats were fed 3 isocaloric diets, containing high carbohydrate, normal protein, and high protein, and a fourth high fat diet for 49 days. Feeding of the high carbohydrate, high protein, and high fat diets caused a significant increase in the level of total lipids compared to the normal protein diet. This increase of total lipids was due primarily to the increase in the level of triglycerides. There was no significant difference in fatty acid composition of either nonpolar or polar lipids of bone marrow among rats fed high carbohydrate diet and those fed normal protein diet. A comparison of fatty acid compositions between bone marrow lipids of rats fed high protein diet and the other 2 isocaloric diets revealed that the proportion of palmitic acid was higher and the proportion of oleic acid was lower in animals fed high protein diet than in animals fed the other 2 diets. Compared to the 3 isocaloric low fat diets, dietary feeding of high fat diet caused a decrease in the proportion of palmitic and palmitoleic acids and an increase in the proportion of oleic and linoleic acids in total fatty acids of both nonpolar and polar lipids.     

Composition of the neutral and phospholipid fractions from ginkgo nuts (Ginkgo biloba) and fatty acid composition of individual lipid classes

The purified lipid fraction (1.26% on the wet weight basis) from the nuts ofGinkgo biloba was found to be 90.6% neutral lipids, 7.5% polar lipids, and a very small amount of glycolipids. Main fatty acids in the triglyceride fraction were oleic and linoleic acids, and those in the phospholipid fraction were palmitic acid in addition to these unsaturated acids. The enzymic hydrolysis of the triglyceride and individual phospholipid fractions showed that only the triglyceride and phosphatidylcholine fractions contained relatively large amounts of unsaturated acids in their β-positions. The gas liquid chromatography-mass spectrometric analysis of the fatty acids of the steroid ester fraction indicated the presence of lignoceric, cerotic, montanic, and melissic acids as well as a lactone and compounds suspected to be phenolic acids containing long chain diols.     

The fatty acid composition of lipids from muscle and adipose tissues of pigs fed various oil mixtures differing in their ratio between oleic acid and linoleic acid

High concentrations of polyunsaturated fatty acids (PUFA) in meat have detrimental effects on its technical properties. The present study was carried out to investigate whether PUFA levels in pork can be reduced by increasing the concentrations of oleic acid in pig diets. To this end a bifactorial experiment was carried out with 48 female growing finishing pigs. Six different diets were used with two different concentrations of linoleic acid (12 vs. 24 g/kg) and three different concentrations of oleic acid (12 vs. 18 vs. 24 g/kg). The experiment started at a body weight (BW) of 58 kg and continued until 115 kg BW. The fatty acid composition of total lipids of backfat, perirenal fat and musculus (m.) longissimus dorsi was analysed. Concentrations of linoleic acid and total PUFA in backfat and perirenal fat were affected only by the dietary linoleic acid content but not at all by the dietary oleic acid content. Increasing the dietary concentration of oleic acid raised the level of oleic acid in those tissues at the expense of saturated fatty acids, suggesting competition between monounsaturated fatty acids and saturated fatty acids for incorporation into triglycerides. At the low dietary linoleic acid concentration, the percentages of linoleic acid and total PUFA in total lipids of m. longissimus dorsi were also unaffected by the dietary oleic acid content. In contrast, at the high dietary linoleic acid concentration, percentages of linoleic acid and total PUFA of the m. longissimus dorsi were reduced by increasing the dietary concentration of oleic acid, suggesting that oleic acid and linoleic acid compete for incorporation into muscle lipids. Thus, at high dietary linoleic acid levels the fatty acid composition of the m. longissimus dorsi was favourably affected by high dietary oleic acid concentrations; in backfat and perirenal fat, however, no beneficial effect of high dietary oleic acid levels was seen.     

Canavalia ensiformis neutral lipids,a rich source of lupeol

The composition of the neutral lipids ofCanavalia ensiformis, which represent 2.21% of whole seeds, has been investigated. The fatty acid composition is characterized by the presence of palmitic (15%), oleic (54%), linoleic (7%) and linolenic (8%) acids. The unsaponifiable matter (7.9% of the neutral lipids), was examined for sterol, 4α-methylsterol and triterpene alcohols. The occurrence of lupeol in high amount in the last fraction (96%) constitutes an interesting source for this compound.     

The lipid composition of karaka seeds (corynocapus laevigatus)

The kernels of karaka seeds(Corynocapus laevigatus) contained 9.6% oil by wt. The lipid constituents were characterized by silicic acid column chromatography and thin layer chromatography, and their individual fatty acid compositions by gas liquid chromatography. Of the seed oil, triacylglycerol was the major component which contained high proportions of linoleic (45%) and oleic (26%) acids. The major component of husk oil (0.9% of husk by wt) was polar lipid (glycolipids and pigments).     

Oviposition response ofLobesia botrana females to long-chain free fatty acids and esters from its eggs

Avoidance of occupied ovisposition sites supposes that females perceive information related to their own progency. Fatty acids identified from egg extracts have been reevaluated using a different extraction method, and we have investigated the dose-dependent oviposition response of European grape vine moths (Lobesia botrana) to myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, methyl palmitate, methyl oleate, and ethyl palmitate; all except ethyl palmitate have been identified from eggs ofL. botrana. A methylene dichloride extract of eggs fromL. botrana revealed the presence of saturated free fatty acids (myristic, palmitic, and stearic) and unsaturated acids (palmitoleic, oleic, linoleic, and linolenic) in amounts ranging from 3.9 ng/egg equivalent for myristic acid to 30 ng/egg equivalent for palmitic and oleic acids. The extract also contained traces of methyl palmitate and methyl stearate. The greatest avoidance indexes were observed in response to palmitic, palmitoleic, and oleic acids. All the other compounds tested caused weaker responses. A reduction in the number of eggs laid was observed when moths were exposed to each of the esters applied at 0.3 µg per application spot. Reduction in eggs laid was also observed at a 10-fold higher dose of oleic acid. The present results confirm that general and simple molecules can be involved in the regulation of oviposition site selection and that they may participate in chemical marking of the eggs.     

Phospholipid Composition of <Emphasis Type="Italic">Jatropha curcus</Emphasis> Seed Lipids

Jatropha curcus L. oil has emerged as one of the most important raw materials for biodiesel production. However, no detailed study has been reported on characterizing the lipid constituents of jatropha oil. The present study revealed that the total oil content of jatropha seeds was 32% with a composition of 97.6% neutral lipids, 0.95% glycolipids and 1.45% phospholipids. The fatty acid composition of total lipids, neutral lipids, phospholipids and glycolipids was also determined and found to contain oleic acid (18:1) and linoleic acids (18:2) as major fatty acids. The phospholipids fraction was further characterized and quantified and found to contain phosphatidyl choline (PC) 60.5%, phosphatidyl inositol (PI) 24% and phosphatidyl ethanolamine (PE) 15.5%. The fatty acid composition and the positional distribution of the fatty acids of individual phospholipids were also reported.     

Comparison of the Structures of Triacylglycerols from Native and Transgenic Medium-Chain Fatty Acid-Enriched Rape Seed Oil by Liquid Chromatography–Atmospheric Pressure Chemical Ionization Ion-Trap Mass Spectrometry (LC–APCI-ITMS)

The sn position of fatty acids in seed oil lipids affects physiological function in pharmaceutical and dietary applications. In this study the composition of acyl-chain substituents in the sn positions of glycerol backbones in triacylglycerols (TAG) have been compared. TAG from native and transgenic medium-chain fatty acid-enriched rape seed oil were analyzed by reversed-phase high performance liquid chromatography coupled with online atmospheric-pressure chemical ionization ion-trap mass spectrometry. The transformation of summer rape with thioesterase and 3-ketoacyl-[ACP]-synthase genes of Cuphea lanceolata led to increased expression of 1.5% (w/w) caprylic acid (8:0), 6.7% (w/w) capric acid (10:0), 0.9% (w/w) lauric acid (12:0), and 0.2% (w/w) myristic acid (14:0). In contrast, linoleic (18:2n6) and alpha-linolenic acid (18:3n3) levels decreased compared with the original seed oil. The TAG sn position distribution of fatty acids was also modified. The original oil included eleven unique TAG species whereas the transgenic oil contained sixty. Twenty species were common to both oils. The transgenic oil included trioctadecenoyl-glycerol (18:1/18:1/18:1) and trioctadecatrienoyl-glycerol (18:3/18:3/18:3) whereas the native oil included only the latter. The transgenic TAG were dominated by combinations of caprylic, capric, lauric, myrisitic, palmitic (16:0), stearic (18:0), oleic (18:1n9), linoleic, arachidic (20:0), behenic (22:0), and lignoceric acids (24:0), which accounted for 52% of the total fat. In the original TAG palmitic, stearic, oleic, and linoleic acids accounted for 50% of the total fat. Medium-chain triacylglycerols with capric and lauric acids combined with stearic, oleic, linoleic, alpha-linolenic, arachidic, and gondoic acids (20:1n9) accounted for 25% of the transgenic oil. The medium-chain fatty acids were mainly integrated into the sn-1/3 position combined with the essential linoleic and alpha-linolenic acids at the sn-2 position. Eight species contained caprylic, capric, and lauric acids in the sn-2 position. The appearance of new TAG in the transgenic oil illustrates the extensive effect of genetic modification on fat metabolism by transformed plants and offers interesting possibilities for improved enteral applications.     

Egg yolk lipids and maternal diet in the nutrition of turkey embryo

Turkey hens were fed diets containing no added fat nor diets supplemented with soybean oil or neatsfoot oil. The composition of neutral and polar lipid fatty acids present in the unincubated turkey egg yolk was compared with that of those present in the yolk sac of the developing turkey embryo at different stages of development. Comparisons were made of the fatty acid fractions in the entire embryo homogenates, except liver and heart, which were analyzed separately. Changes in the relative amounts of the fatty acids are reported as affected by age of the embryo and by dietary lipids. The fatty acids from both the neutral and polar lipids which were utilized to the greatest extent for embryonic development were palmitoleic, oleic, linoleic, and linolenic, regardless of the dietary supplements. Arachidonic, tetracosenoic, and docosahexaenoic acids also were metabolized by the embryo. Saturated fatty acids, used by the embryo as development progressed, were palmitic, stearic, and arachidic acids. Analyses of the liver fatty acids showed that the C16∶0 C16∶1, C18∶0, C18∶1, and C20∶4 acids in the neutral and polar lipids decreased with embryonic development and varied with the type of diet. The heart contained low levels of myristic, palmitic, stearic, arachidic, and arachidonic acids in the neutral lipids and palmitoleic and oleic acids in the polar lipids.     

Genetic diversity for lipid content and fatty acid profile in rice bran

Rice (Oryza sativa L.) bran contains valuable nutritional constituents, which include lipids with health benefits. A germplasm collection consisting of 204 genetically diverse rice accessions was grown under field conditions and evaluated for total oil content and fatty acid (FA) composition. Genotype effects were highly statistically significant for lipid content and FA profile (P<0.001). Environment (year) significantly affected oil content (P<0.05), as well as stearic, oleic, linoleic, and linolenic acids (all with P<0.01 or lower), but not palmitic acid. The oil content in rice bran varied relatively strongly, ranging from 17.3 to 27.4% (w/w). The major FA in bran oil were palmitic, oleic, and linoleic acids, which were in the ranges of 13.9–22.1, 35.9–49.2, and 27.3–41.0%, respectively. The ratio of saturated to unsaturated FA (S/U ratio) was highly related to the palmitic acid content (r ²=0.97). Japonica lines were characterized by a low palmitic acid content and S/U ratio, whereas Indica lines showed a high palmitic acid content and a high S/U ratio. The variation found suggests it is possible to select for both oil content and FA profile in rice bran.     

The effect of temperature on lipid classes and their fatty acid profiles inLipomyces starkeyi

The effect of environmental temperature on fatty acid contents of major lipid classes was determined inLipomyces starkeyi at 30, 20, and 10°C. When the temperature was reduced from 30 to 20°C, the linolenic acid content increased in phosphatidylcholine but fell with further reduction to 10°C. The relative contribution of phosphatidylcholine and phosphatidylethanolamine that contained the next lowest-melting fatty acids, palmitoleic and linoleic acids, increased on lowering the temperature from 20 to 10°C and, concomitantly, the combined phosphatidylinositol and phosphatidylserine fraction decreased, and triacylglycerols were accumulated.     

Chemical Investigations on Celastrus paniculatus Seed Oil I

Fatty acid compositions of four lipid fractions of Celastrus paniculatus seed namely normal triglycerides (20.2%), polar triglycerides (44.4%), polar nonglyceridic ester (23.5%), and nonpolar nonglyceridic ester (11.9%), have been determined by gas liquid chromatography. Percentage contents of major component acids in these fractions are: palmitic, 25.1, 42.0, 12.7, 58.2; stearic, 6.7, 4.5, 15.8; oleic, 46.1, 24.8, 4.7, 14.2; linoleic, 15.4, 14.7, 10.0; and linolenic, 3.0, 13.1, 43.0, respectively. The major molecular species constituting the normal triglycerides are: palmitooleopalmitin, 6.8%; palmitooleostearin, 5.6%; palmitodiolein, 14.7; palmitooleolinolein, 7.0%; stearodiolein, 6.1%; triolein, 8.0% and dioleolinolein 7.6%. Lipolysis of the polar triglyceride indicated as high as 59.6% of saturated acids linked to the 2-position of glycerol.     

Microbial conversion of palmitoleic acid to 9,12-hexadecadienoic acid (16:2ω4) by Trichoderma sp. AM076

Trichoderma sp. AM076, isolated from a freshwater sample, was found to accumulate 9,12-cis-hexadecadienoic acid (16:2ω4), when grown with palmitoleic acid (16: 1ω7). Methyl myristate was the best carbon source for the conversion of palmitoleic acid to 16:2ω4. The mycelial 16:2ω4 content reached 17.4 mg/g dry mycelia (443 mg/L) when the fungus was grown in a medium that contained 2.0% methyl myristate, 1.5% yeast extract, and 2.0% methyl palmitoleate, pH 6.0, for 5 d at 28°C with shaking. In both nonpolar and polar lipids from the mycelia, 16:2ω4 was detected as one of the major fatty acids when 16:1ω7 was added. It is probable that 16:1ω7 is converted to 16:2ω4 through the Δ12 desaturation reaction.