Fatty Acid Profiles of Garuga floribunda,Ipomoea pes‐caprae,Melanolepis multiglandulosa and Premna odorata Seed Oils

The fatty acid profiles of the seed oils of four species from four plant families for which no or only sparse information on the fatty acid profiles is available are reported. The four seed oils are Garuga floribunda of the Burseraceae family, Ipomoea pes‐caprae, of the Convolvulaceae family, Melanolepis multiglandulosa of the Euphorbiaceae family, and Premna odorata of the Labiatae (Lamiaceae) family. Linoleic acid is the most abundant in three seed oils, except I. pes‐caprae in which oleic acid is most abundant. These two acids are overall the most abundant in all four seed oils studied. Of the four seed oils investigated, only G. floribunda contains minor amounts of a cyclic fatty acid (dihydrosterculic acid).     

Eicosenoic acid and other fatty acids ofSapindaceae seed oils

The seed oils of 11 species ofSapindaceae were examined, and their fatty acid composition was determined.cis-11-Eicosenoic acid was identified as the major fatty acid ofKoelreuteria paniculata. It was present in nine of the 11 species in amounts from 8–60% of the total fatty acids and is evidently a common component of oils of this plant family. Arachidic acid was present in amounts up to 11%. Only three of the oils had acids of chain length greater than C-20. Seed oils of certain species ofKoelreuteria andCardiospermum are good potential sources of 11-eicosenoic acid. N.R. C. No. 9537.     

Chemical composition ofacacia seeds

The seeds of 12 species ofAcacia, although rich in C-18 unsaturated acids (47.9–93.5%), have low oil content (2.5–10.2%). Highest concentration of octadecatrienoic acid was inA. lenticularis (80.3%),A. suma (76.8%) andA. tortilis (71.7%) oils.A. mollissima was rich in octadecadienoic (69.1%) andA. senegal in octadecenoic (42.5%) acids. All the seed oils showed the presence of epoxy 18:1 acid, 0.6–3.8%. The protein content of the processed seed meals ranged from 13.4–37.2%, the highest being inA. senegal. Fiber content varied from 8.8–11.9%.     

Different metabolism of saturated and unsaturated long chain plasma free fatty acids by intestinal mucosa of rats

During fat absorption, unsaturated long chain fatty acids are esterified at a higher rate than saturated fatty acids of similar chain length. This phenomenon has been attributed to differences in the binding affinity of fatty acids to a cytosolic fatty acid-binding protein. As intestinal mucosa utilizes plasma free fatty acids as well, we investigated whether long chainplasma free fatty acids of different degree of saturation are metabolized also at different rates.³H-Palmitic and¹⁴C-linoleic acid complexed to rat serum were injected rapidly into a tail vein of fasting rats. One, 2 and 4 min later there was no difference between³H and¹⁴C-radioactivity in intestinal mucosa, suggesting equal initial uptake of the two labeled fatty acids from plasma. Despite their equal uptake, the incorporation of the isotopes into ester lipids was significantly different, however: at 2 min, 53.1±3.9% of³H and 73.8±4.6% of¹⁴C were recovered in ester lipids. Phospholipids and triglycerides accounted for most of the mucosal³H and¹⁴C. At 4 min, a similar distribution of isotopes in intestinal mucosal metabolites was found. These data show that despite equal initial uptake by intestinal mucosa unsaturated long chain fatty acids taken up from plasma are esterified to a higher and oxidized to a lower extent than saturated plasma free fatty acids. Unsaturated plasma free fatty acids, therefore, may provide a more important source of fatty acids for endogenous intestinal lipoprotein lipids than saturated plasma free fatty acids. It is speculated that the fatty acid binding protein might be operative not only in the intracellular transport and metabolism of luminal fatty acids but of plasma free fatty acids as well.     

Cis-5-monoenoic fatty acids ofCarlina (Compositae) seed oils

Seed oils ofCarlina corymbosa L. andC. acaulis L. containcis-5-octadecenoic acid as a major fatty acid (21–24%). This acid has not been previously reported as a constituent of Compositate seed oils. The predominant fatty acid in theCarlina oils is linoleic (50–52%); lesser amounts (≦10% each) of palmitic, stearic and oleic acids are also present. The oil ofC. acaulis has almost 2% ofcis-5-hexadecenoic acid;C. corymbosa oil includes minor amounts of some oxygenated fatty acids. Presented at the AOCS Meeting, New York, October 1968. No. Utiliz. Res. Dev. Div., ARS, USDA.     

The production of fish oils enriched in polyunsaturated fatty acid-containing triglycerides

A simple concentration technique was developed and used for the production of fish oils highly enriched with respect to the polyunsaturated triglycerides. The method involves the rapid solidification of fish oil droplets in liquid nitrogen followed by extraction with acetone at −60°C. The combined percentage ofcis-5,8,11,14,17-eicosapentaenoic acid (20:5) andcis-4,7,10,13,16,19-docosahexaenoic acid (22:6) after enrichment of a crude South African Anchovy (Engraulis capensis) oil was 57.4. A maximum percentage of 66.0 was attained for n-3 fatty acids after enrichment of a crude Chilean fish oil. A maximum yield of 26.0% was achieved for a crude sardine (Sardina pilchardus) oil. Triglycerides containing only saturated fatty acids or a combination of saturated and monoenoic acids were totally removed by the process, as assessed by silver-ion high-performance liquid chromatography of the triglyceride oils. This process permits the production of significant quantities of highly unsaturated triglycerides, which may be used in physiological and oxidative studies or for structural analysis of these triglycerides, many of which are present at extremely low concentrations in the original oils.     

Fatty Acid Profiles of Some Fabaceae Seed Oils

The fatty acid profiles of six seed oils of the Fabaceae (Leguminosae) family are reported and discussed. These are the seed oils of Centrosema pubescens, Clitoria ternatea, Crotalaria mucronata, Macroptilium lathyroides, Pachyrhizus erosus, and Senna alata. The most common fatty acid in the fatty acid profiles of these oils is linoleic acid with palmitic, stearic, oleic and linolenic acids usually completing the most prominent fatty acids in these species. Long‐chain saturated fatty acids were observed in all oils. Centrosema pubescens and Macroptilium lathyroides exhibited the greatest amounts of long‐chain saturated fatty acids exceeding the amount of stearic acid in these oils. C. pubescens exhibited slightly more that 6 % C24:0 together with some fatty acids >C25 and M. lathyroides approximately 4 % C22:0 and 3 % C24:0. The results are comparatively discussed to previous data on the fatty acid profiles of Fabaceae species.     

The fungicidal activity of the unsaturated fatty acids and quaternary salts prepared from fish oils

Summary Saturated and unsaturated fatty acids and 10 unsaturated fatty acid fractions and ethyl esters of unsaturated fatty acid fractions prepared from fish oils were tested on their inhibitory activity againstCandida albicans. Oxidation of highly unsaturated fractions from fish oil and ethyl esters of unsaturated fatty acid fractions of menhaden, pilchard, and cod liver oils increases their antifungal activity. Saturated and unsaturated quaternaries were tested for their antifungal activity. Hexadecyltriethylammonium bromide and hexadecylpyridinium bromide showed the highest activity againstCandida albicans, Aspergillus niger, andRhyzopus nigricans. Any lengthening of the carbon chain more than C₁₆ weakened the activity of both saturated triethylammonium bromide and pyridinium bromide. An increase of unsaturation enhanced it. The antifungal activity of quaternaries prepared from fish oils was about 4,000 times stronger than that of oxidized highly unsaturated fatty acid fractions prepared from fish oils. The decisive factor in the highly inhibitory activity of quaternaries against fungi might depend on their positively charged portion since the surface of microorganisms is, as a rule, negatively charged. Aided by a grant from the Collett-Week Company, Ossining, N. Y.     

Heat treatment of vegetable oils. II. GC-MS and GC-FTIR spectra of some isolated cyclic fatty acid monomers

Gas liquid chromatography coupled with mass spectrometry (GC-MS) showed that the cyclic fatty acid monomers (CFAM) isolated from a heated linseed oil have two ethylenic bonds, while the CFAM isolated from heated sunflower oils were saturated and monoethylenic isomers. GC-MS studies also showed the presence of cyclohexenic derivatives in the case of linseed oil. GLC coupled with Fourier transform infrared spectrometry (GC-FTIR) studies indicated that the CFAM isolated from linseed oil were ofcis (Z),trans (E) structures except two components which werecis,cis (Z,Z) dienoic acids. The unsaturated CFAM isolated from sunflower oils werecis (Z) andtrans (E) monoethylenic isomers. For sunflower oils, the major CFAM were isomers having acis (Z) ethylenic bond. The saturated CFAM isolated from a heated sunflower oil had molecular weights of 296 and 294. The latter could correspond to some bicyclic isomers.     

Fatty acid composition of the oil of winged beans,Psophocarpus tetragonolobus (L.) DC

The fatty acid composition of the oils of five varieties of winged beans,Psophocarpus tetragonolobus (L.) DC, was determined and found to be similar to peanut oil. The total unsaturated fatty acids ranged from 53.8% to 68.5% (mean, 62.0%). Oleic acid and linoleic acids were the major unsaturated fatty acids. The major saturated fatty acids were behenic, palmitic and stearic acids. Parinaric acid, a toxic fatty acid, previously reported to occur in winged beans, was not present in the oil of the winged beans analyzed. Taken in part from the Ph.D. dissertation of V.V. Garcia whose present address is Department of Food Science and Technology, University of the Philippines at Los Banos, College, Laguna, Philippines.     

Chemical and physical analyses of oils from four species of cucurbitaceae

The seed oils ofCucumeropsis mannii, two varieties ofLagenaria sicceraria andTelfairia occidentalis were evaluated. The oil contents by mechanical expression were 33.2%, 33.4%, 34.2% and 32.8% from the roasted kernels ofC. mannii, L. sicceraria var. 1,L. sicceraria var. 2 andT. occidentalis, respectively. Lower oil contents (26.4-28.6%) were obtained from unroasted kernels of the species. The difference in oil yield between the unroasted and roasted kernels was significant (p ≤ 0.05). Roasting of the kernels did not affect the quality factors of the oils, except for the color. The color of oil from roasted kernels was golden, whereas that from unroasted kernels was pale yellow. The predominant fatty acids were palmitic, stearic, oleic and linoleic. The oils from the varieties ofL. sicceraria were more unsaturated (80.2-80.3%) than the oils fromC. mannii (71.4%) andT. occidentalis (69.3%). The smoke (149.5-180.1°C) and flash (204.8-291.5°C) points varied considerably among the oils.Cucumeropsis mannii andT. occidentalis kernel oils failed a cold test, while the oils fromL. sicceraria passed.     

Seasonal Variation of the Chemical Content and Fatty Acid Composition of Mantle and Tentacle of Male and Female Sepia officinalis

The goal of this study was to evaluate the chemical composition and the fatty acid profile of mantle and tentacle of male and female Sepia officinalis, sampled at four seasons from the Mediterranean sea of Tunisia. S. officinalis were found to be rich in glycogen, protein and oil, and significant differences were observed between samples. The level of saturated fatty acid and unsaturated fatty acid showed significant variability among sex and during seasons. DHA and EPA, as polyunsaturated fatty acids, were the most abundant in all samples (14.8–27.8 % and 10.4–18.3 %, respectively). Oleic acid was the most abundant monounsaturated fatty acids (1.63–4.52 %). Σn3 and Σn6 was remarkably different between seasons and among sex. This study could be suitable for the development of reliable guide of fatty acid accumulation in cephalopod.     

The fatty acid composition of three unicellular algal species used as food sources for larvae of the American oyster (Crassostrea virginica)

The total lipid and fatty acid content of 3 algal species,Pyramimonas virginica, Pseudoisochrysis paradoxa andChlorella sp., which have been successful as food sources for rearing larvae of the American oyster,Crassostrea virginica, was determined. Of the fatty acids of ω6 and ω3 families which have been shown to be essential fatty acids for normal growth in many animals, only the ω6 fatty acids were found to be higher in these 3 species of algae than in the traditional oyster larvae diet which consists of the algaeMonochrysis lutheri andIsochrysis galbana. The major fatty acid constituents of the total lipids of the 3 species were the C12, C14, C16 and C18 saturated fatty acids and the C16 and C18 mono- and polyunsaturated acids. These components constituted 70–93% of the total lipid in cultures of all ages. There were modest amounts of C20 and C22 polyunsaturated acids; some of these existed only in trace amounts. InP. virginica andChlorella sp., hexadecanoic acid was dominant (23–39%). The presence of large quantities of tetradecanoic acid (22–26%) and oleic acid (17–21%) was characteristic ofP. paradoxa. Chlorella sp. had the highest proportion of octadecatrienoic acid (18∶3ω3) which accounted for up to 17% of the total lipids. γ-Linolenic acid (18∶3ω6) was found only inChlorella sp., but in the 5th-day culture only. The lowest proportion of total polyethylenic acid was inP. paradoxa; however, lipid analyses showed this alga had the most lipid/individual cell. Some variations were observed in the fatty acid composition with age of the culture. Contribution No. 883 of the Virginia Institute of Marine Science, Gloucester Point, VA 23062.     

Occurrence of mixtures of geometrical isomers of conjugated octadecatrienoic acids in some seed oils: Analysis by open-tubular gas liquid chromatography and high performance liquid chromatography

Analytical methods to obtain the detailed compositions of the fatty acids in oils containing more than one conjugated octadecatrienoic acid by open-tubular gas liquid chromatography (GLC) and by reversed-phase high performance liquid chromatography (HPLC) were established. Effective GLC separations ofcis,trans,trans-9,11,13-octadecatrienoic acid (ctt-9,11,13–18∶3),ctc-9,11,13–18∶3,ttc-9,11,13–18∶3,ttt-9,11,13–18∶3,ttc-8,10,12–18∶3, andttt-8,10,12–18∶3 were obtained with an opentubular column coated with the nonpolar liquid phase OV-1 using an instrument having all-glass carrier gas pathways. The HPLC method also gave satisfactory separations for the isomeric conjugated octadecatrienoates on the basis of number of thecis andtrans double bonds. Two or three minor conjugated trienoic acids were found along with the principal conjugated trienoic acid in tung oil, and seed oils of cherry,Prunus sp., Momordica charantia, Trichosanthes anguina, Punica granatum, Catalpa ovata, andCalendula officinalis. The mechanism for the formation of the conjugated trienoic acid mixtures in the seed oils is discussed. TheC. ovata seed oil also containedct andtt-9,12-octadecadienoic acids. Thett isomer is presumed to be a precursor ofttc-9,11,13–18∶3, the main conjugated trienoic acid in this oil.     

Determination of the length of polymethylene chains in salts of saturated and unsaturated fatty acids by infrared spectroscopy

The length of polymethylene chains is determined by counting the number of, or measuring the position of, methylene vibration peaks in the 1070–710 cm⁻¹ and/or the 1380–1170cm⁻¹ regions of the IR spectrum of salts of fatty acids. Plotting this peak position against the phase relationship of the vibration in adjacent methylenes gives a curve which is independent of the chain length. (Thephase relationship, Φ/π=k/(m+1); where φ is the phase difference in radians between adjacent methylenes in a chain;m is the number of methylenes in the chain;k=1,2,3,…m, withk=1 generally assigned to the in-phase vibration.) Separate curves are obtained for methylene wagging and for two arrays of coupled twisting-rocking vibrations. Coupled twisting-rocking vibrations give as many as one peak per methylene group in the 1070–710 cm⁻¹ region with silver, sodium, potassium and barium salts of saturated acids. Lead salt peaks split. These peaks show the total length of salts of both saturated andtrans-unsaturated acids, but only the length of the carboxylate segment in salts ofcis-unsaturated acids. (The carboxylate segment comprises the carbons from the carboxylate carbon to the first unsaturated carbon, inclusive.) Wagging vibrations in the 1380–1170 cm⁻¹ region show the total chain length of saturated salts and the length of the carboxylate segment in unsaturated salts, bothcis andtrans. This region also has peaks for twisting-rocking vibrations, and they are most conspicuous in the spectra of silver and barium salts. Presented in part at the AOCS meeting in Toronto, Canada, 1962.     

Composition of fatty acids and structure of triglycerides in medium and low erucic acid rapeseed

Total triglycerides in medium (MEAR) and low (LEAR) erucic acid cultivars of rapeseed were fractionated by argentation chromatography into twelve and ten fractions, respectively. Gas liquid chromatography of the fatty acids in the triglyceride fractions and their 2-monoglycerides was used to evaluate the structural characteristics of the individual fractions. Fractionation occurred on the basis of degree of unsaturation, molecular weight and positional characteristics. The most mobile fractions contained 34–50% of saturated fatty acids while the less mobile had 59–65% of polyunsaturated fatty acids. In the medium erucic acid oil, long chain fatty acids (C20–C22) were found in all fractions, but four fractions of low erucic acid oil were essentially free of long chain acids. Two of these fractions in the latter oil, which represented 44% of the total triglycerides, were glycerol trioleate and dioleoyllinoleoylglycerol. The majority of the 2-positions were occupied by unsaturated C18 fatty acids, generally in the order of linoleic ≥linolenic> oleic acids. The saturated and long chain fatty acids occurred predominantly in the 1-and 3-positions. The various fractions of medium and low erucic acid oils were similar in structural composition except that eicosenoic and erucic acids substituted for oleic acid in some external positions. Erucic acid did not appear to substitute directly for oleic acid in the 2-position.     

Positional distribution of the fatty acids in the triglycerides of mango (Mangifera indica) kernel fat

Triglycerides of mango seed kernel fat contain, depending on the variety, 32.4–44.0% of stearic acid and 43.7–54.5% of oleic acid. Palmitic and linoleic acids represent, respectively, 5.9–9.1% and 3.6–6.7% of the fatty acids. The triglycerides also contain minor amounts of arachidic and linolenic acids. Palmitic, stearic and arachidic acids were almost exclusively distributed among thesn-1-andsn-3-positions. Oleic acid represented 85–89% of the fatty acids at thesn-2-position. Oleic acid at thesn-1- andsn-3-positions showed a preference for thesn-1-position. Linoleic acid was mainly esterified at thesn-2-position. The amounts of saturated fatty acids, i.e., palmitic and stearic acids, and of oleic acid, at thesn-1- and sn-3-positions, were linearly related to their respective contents in the total triglycerides.     

Linoleic acid requirement of rats fedtrans fatty acids

The amount of linoleic acid required to prevent undesirable effects of C18trans fatty acids was investigated. In a first experiment, six groups of rats were fed diets with a high content oftrans fatty acids (20% of energy [en%]), and increasing amounts of linoleic acid (0.4 to 7.1 en%). In a second experiment, four groups of rats were fed diets designed to comparetrans fatty acids with saturated andcis-monounsaturated fatty acids of the same chain length at the 2 en% linoleic acid level. After 9–14 weeks, the oxygen uptake, lipid composition and ATP synthesis of heart and liver mitochondria were determined. The phospholipid composition of the mitochondria did not change, but the fatty acid compositions of the two main mitochondrial phospholipids were influenced by the dietary fats.Trans fatty acids were incorporated in all phospholipids investigated. The linoleic acid level in the phospholipids, irrespective of the dietary content of linoleic acid, increased on incorporation oftrans fatty acids. The arachidonic acid level had decreased in most phospholipids in animals fed diets containing 2 en% linoleic acid. At higher linoleic acid intakes, the effect oftrans fatty acids on the phospholipid arachidonic acid level diminished. However, in heart mitochondrial phosphatidylethanolamine,trans fatty acids significantly increased the arachidonic acid level. Despite these changes in composition, neither the amount of dietary linoleic acid nor the addition oftrans fatty acids influenced the mitochondrial function. For rats, a level of 2 en% of linoleic acid is sufficient to prevent undesirable effects of high amounts of dietary C18trans fatty acids on the mitochondrial function.     

Seed oils from cassia fistula,C. Occidentalis,and C. Tora (Indian varieties)

Summary Fatty acids from oils of Indian varieties ofC. fistula, C. occidentalis, andC. tora were fractionated by the lead salt-alcohol and methyl ester distillation methods. Compositions were calculated from the iodine values and saponification equivalents of the ester fractions. Identities of saturated acids were established by determining the properties of the recrystallized acids. Unsaturated acids were identified as the bromo-and hydroxy-derivatives. Cassia fistula, C. occidentalis, andC. tora oils were found to contain the following percentages of fatty acids, respectively: palmitic, 16.0, 19.7, 23.5; lignoceric, 5.2, 4.3, 3.4; oleic, 30.7, 31.6, 28.1; and linoleic, 48.1, 38.1, 45.0. In addition,C. occidentialis oil contained 6.3% of linolenic acid. Chrysophanic acid was isolated in yield of 0.6% fromC. tora oil, but only traces were obtained fromC. occidentalis oil.     

Epoxidation ofLesquerella andLimnanthes (Meadowfoam) oils

Lesquerella gordonii (Gray) Wats andLimnanthes alba Benth. (Meadowfoam) are species being studied as new and alternative crops. Triglyceride oil from lesquerella contains 55–60% of the uncommon 14-hydroxy-cis-11-eicosenoic acid. Meadowfoam oil has 95% uncommon acids, includingca. 60%cis-5-eicosenoic acid. Both oils are predominantly unsaturated (3% saturated acids), and have similar iodine values (90–91), from which oxirane values of 5.7% are possible for the fully epoxidized oils. Each oil was epoxidized withm-chloro-peroxybenzoic acid, and oxirane values were 5.0% (lesquerella) and 5.2% (meadowfoam). The epoxy acid composition of each product was examined by gas chromatography of the methyl esters, which showed that epoxidizedL. gordonii oil contained 55% 11,12-epoxy-14-hydroxyeicosanoic acid, and epoxidized meadowfoam oil contained 63% 5,6-epoxyeicosanoic acid, as expected for normal complete epoxidation. Mass spectrometry of trimethylsilyloxy derivatives of polyols, prepared from the epoxidized esters, confirmed the identity of the epoxidation products and the straightforward nature of the epoxidation process. Synthesis and characterization of these interesting epoxy oils and derivatives are discussed.