Fatty Acid Composition and Oil Yield in Fruits of Five <Emphasis Type="Italic">Arecaceae</Emphasis> Species Grown in Cuba

The present study targeted the whole-fruit oil yield and fatty acid composition from five of the most abundant Arecaceae species grown in Cuba. The oil yields (% dry weight), determined by the Soxhlet extraction technique with hexane, were 25.5, 5.3, 6.9, 5.4, and 6.4% for Roystonea regia, Colpothrinax wrightii, Sabal maritima, Sabal palmetto and Thrinax radiata, respectively. The free fatty acid (FFA) content varied from 2.7 to 6.8%. Fatty acid (FA) profiles of the oils indicated that lauric acid (13.7–44.4%), myristic acid (9.4–22.4%) and palmitic acid (9.2–17.1%) as major saturated FA; whereas oleic acid (9.6–42.7%) and linoleic acid (9.3–17.0%) as major unsaturated FA. R. regia fruit seemed the most promising among Arecaceae grown in Cuba because of its high oil yield and low oil FFA content.     

Minor component fatty acids of common vegetable oils

A combination of gas-liquid chromatography (GLC) and oxidative cleavage on fractions isolated by mercury derivative chromatography has shown the presence of previously unreported minor component fatty acids in olive, soybean, cottonseed, corn, peanut, rapeseed and safflower oil. All of the oils examined contain small amt of saturated acids above arachidic, some as high as hexacosanoic acid.Cis-11-octadecenoic acid was found in amt ranging from 0.5~2.0%.Cis-11-eicosenoic acid is present in the 0.04~1.4% range (rapeseed oil excluded). The tetracosenoic acid present in rapeseed (0.4%) and safflower oil (0.1%) has been identified as thecis-15-tetracosenoic acid. No unusual polyenoic species were detected with the exception of those in rapeseed oil, which contains 0.6% of both 11,14-eicosadienoic and 13,16-docosadienoic acid.     

Synthesis of fatty acid esters from acid oils using lipase B from Candida antarctica

Esterification of corn and sunflower acid oils with straight‐ and branched‐chain alcohols were conducted using lipase B from Candida antarctica (Novozym 435) in n‐hexane. Sunflower acid oil consisted of 55.6% free fatty acids and 24.7% triacylglycerols, while the free fatty acids and triacylglycerols contents of corn acid oil were 75.3% and 8.6%, respectively. After 1.5 h of methanolysis of sunflower acid oil, the highest fatty acid methyl ester content (63.6%) was obtained at 40 °C and the total fatty acid/methanol molar ratio was 1/1, using 15% enzyme based on acid oil weight. The conversion of both acid oils with straight‐ and branched‐chain alcohols was not significantly affected by the chain length of the alcohols. However, the lowest fatty acid methyl ester content (50%) was obtained in the reaction of corn acid oil with methanol. Sunflower acid oil was converted to fatty acid esters using primer alcohols such as n‐propanol, i‐ and n‐butanol, n‐amylalcohols, n‐octanol, and a mixture of amylalcohol isomers, resulting in a fatty acid ester content of about 70% at 40 °C.     

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.     

Molecular Finger Printing of Nutra-Coconut Oil with Improved Health Protective Phytoceuticals and its Efficacy as Frying Medium

Coconut oil is rich in medium chain triglycerides but lacks polyunsaturated fatty acids (PUFA) and bio‐active phytoceuticals. In the present work nutra‐coconut oil was prepared by blending coconut oil and flaxseed oil (70:30) and adding 3000 ppm of flaxseed cake concentrate using ethanol, methanol and 20 % aqueous ethanol. The concentrate prepared from flaxseed was from ethanol as it gave maximum yield. The different bio‐active molecules in flaxseed concentrate observed are polyphenols (39.04 %), tocopherols (4.37 %), ferulic acid (0.17 mg g^?1), p‐coumaric acid (2.24 mg g^?1), chlorogenic acid (16.11 mg g^?1), gallic acid (8.58 mg g^?1), sinapic acid (0.64 mg g^?1) and secoisolariresinol (30.13 mg g^?1). The nutra‐coconut oil was found to have polyphenols (2.86 %), tocopherols (442.96 ppm) and antiradical activity (94 %). The PUFA content was found to increase in nutra‐coconut oil significantly (p < 0.05) (2–22 %). The FT‐IR spectra of nutra‐coconut oil revealed that the peak at 3009 and 1651 cm^?1 was associated with the presence of unsaturated fatty acids. There was no significant (p > 0.05) difference observed in sensory attributes of snack food fried using coconut oil and nutra‐coconut oil indicating that the later could be used as a frying medium and useful for food processing industries.     

Characterization of yam bean (Pachyrhizus spp.) Seeds as potential sources of high palmitic acid oil

Seeds from 22 accessions of the yam bean species Pachyrhizus ahipa (14 accessions), P. erosus (5), and P. tuberosus (3) were investigated for oil and protein contents, fatty acid composition of the seed oil, and the total tocopherol content and composition. Plants from the accessions were grown under greenhouse conditions during one (P. erosus and P. tuberosus) or two years (P. ahipa). The pattern of the investigated seed quality traits was very similar in the three species. Yam bean seeds were characterized by high oil (from about 20 to 28% in one environment) and protein contents (from about 23 to 34%). Seed oil contained high concentrations of palmitic (from about 25 to 30% of the total fatty acids), oleic (21 to 29%), and linoleic acids (35 to 40%). Levels of linolenic acid were very low, from about 1.0 to 2.5%. Total tocopherol content was relatively low in P. erosus (from 249 to 585 mg kg⁻¹ oil) and P. tuberosus (from 260 to 312 mg kg⁻¹ oil) compared with the levels found in P. ahipa grown under identical conditions (508 to 858 mg kg⁻¹ oil). In all the samples, γ-tocopherol was predominant, accounting for more than 90% of the total tocopherol content. The combination of high oil and protein contents, together with high palmitic acid, low linolenic acid, and high γ-tocopherol concentration, makes these crops an interesting alternative as sources of high palmitic acid oil for the food industry.     

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.     

<Emphasis Type="Italic">Oenocarpus bataua</Emphasis> Mart. (Arecaceae): Rediscovering a Source of High Oleic Vegetable Oil from Amazonia

The fatty acid (FA) composition of Oenocarpus bataua oil from 38 samples collected over a large geographical range (i.e. French Guiana and Peru) was analyzed. Fifteen fatty acids were obtained from the mesocarp of this palm species. Oleic (72.7%) and palmitic (18.1%) acids were the predominant FAs. Minor FAs were cis-vaccenic acid (2.3%), linoleic acid (1.9%), stearic acid (1.7%), palmitoleic (0.9%) and alpha-linolenic acid (0.8%). The mean lipid content of the dry mesocarp was 51.6%. The O. bataua oil samples analyzed were remarkably rich in α-tocopherol. By contrast, the other fractions of the unsaponifiable matter (sterols, carotenoids) did not show any noteworthy specificity in comparison with common vegetable oils. However, the particularly high percentage in Δ5-avenasterol of O. bataua oil could serve as a marker for its authentication. Results are discussed in terms of the potential nutritional value of O. bataua oil.     

Fractionation of blackcurrant seed oil

Blackcurrant seed oil is known to be one of the richest natural sources of γ-linolenic (allcis-6,9,12-octadecatrienoic) acid, with values of up to 20% of this acid. These concentrations are sufficient for most applications of the oil, but some utilizations require higher concentrations of γ-linolenic acid. Blackcurrant seed oil also contains up to 14%α-linolenic (allcis-9,12,15-octadecatrienoic) acid. Different fractionation techniques have been evaluated to separate γ-linolenic acid specifically from the other fatty acids present in the oil and, in particular, fromα-linolenic acid. Distillation as well as fractionated crystallization at various temperatures did not give any reasonable results. Surprisingly enough, urea fractionation in methanol gives a specific separation ofα- and γ-linolenic acid, whereas stearidonic (allcis-6,9,12,15-octadecatetraenoic) acid, which is present at around 3% in the blackcurrant seed oil, cannot be separated by urea fractionation. Stearidonic acid, like γ-linolenic acid, has a double bond in the Δ6 position, which makes these two acids unique in this respect. This most probably explains their similar behavior toward urea-occlusion. Further semi-industrial preparative HPLC separations allowed us to obtain fractions of 95% γ-linolenic acid.     

Effects of dietary triacylglycerol structure on triacylglycerols of resultant chylomicrons from fish oil- and seal oil-fed rats

We investigated the influence of the intramolecular fatty acid distribution of dietary triacyl-sn-glycerols (TAG) rich in n-3 polyunsaturated fatty acids (PUFA) on the structure of chylomicron TAG. Fish oil and seal oil, comparable in fatty acid compositions but with different contents of major n-3 PUFA esterified at thesn-2 position (20:5n-3, 46.6%, and 5.3%; 22:6n-3, 75.5%, and 3.8%, respectively), were fed to rats. Mesenteric lymph was collected and the chylomicrons were isolated by ultracentrifugation. The fatty acid composition of chylomicrons largely reflected the fatty acid composition of the oils administered. The intramolecular fatty acid distributions of the TAG fed were reflected in the chylomicron TAG as the fraction of the total contents observed in thesn-2 position of 20:5n-3 were 23.6 and 13.3%, and of 22:6n-3 were 30.6 and 5.4% for resultant chylomicrons following fish oil and seal oil administration, respectively. Thus, after seal oil administration, significant higher load of n-3 PUFA was esterified in thesn-1,3 positions of chylomicron TAG compared with fish oil administration (P<0.05).     

Extraction and Characterization of Montmorency Sour Cherry (Prunus cerasus L.) Pit Oil

Montmorency sour cherry (Prunus cerasus L.) pit oil (CPO) was extracted and characterized by various methods including: GC, LC–MS, NMR, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and X‐ray powder diffraction (XRD). The oil gave an acid value of 1.45 mg KOH/g, saponification value of 193 mg KOH/g and unsaponifiable matter content of 0.72 %. The oil contained oleic (O) and linoleic (l ) acids as the major components with small concentrations of α‐eleostearic acid (El, 9Z,11E,13E‐octadecatrienoic acid) and saturated fatty acid palmitic (P) acid. The CPO contained six major triacyglycerols (TAG), OOO (16.83 %), OLO (16.64 %), LLO (13.20 %), OLP (7.25 %), OOP (6.49 %) and LElL (6.16 %) plus a number of other minor TAG. The TAG containing at least one saturated fatty acid constitute 33 % of the total. The polymorphic behavior of CPO as studied by DSC and XRD confirmed the presence of α, β′ and β crystal forms. The oxidative induction time of CPO was 30.3 min at 130 °C and the thermal decomposition temperature was 352 °C.     

Synthesis of azelaic acid and suberic acid fromVernonia galamensis oil

We have demonstrated the potential ofVernonia galamensis seed oil as a source of dibasic acids. Reaction of nitric acid withV. galamensis oil afforded a homologous series of dibasic acids that include butanedioic acid, pentanedioic acid, hexanedioic acid (adipic), heptanedioic acid (pimelic), octanedioic acid (suberic), nonanedioic acid (azelaic), decanedioic acid (sebacic), and undecanedioic acid. Using a combination of chloroform extraction and subsequent water crystallizations, we have isolated suberic acid (∼95% purity by GC) and azelaic acid (∼95% purity by GC). The isolated yield of suberic acid is 15% and of azelaic acid is 11%. Reported reaction of nitric acid with ricinoleic acid (from castor oil) gave 8.8% suberic acid and 7.2% of a mixture of suberic and azelaic acids.     

Acacia albida Seed Oil: Characterization of Coronaric Acid

Coronaric acid makes up 7.8% of Acacia albida (leguminosae) oil triglycerides. Direct acetolysis of the oil followed by saponification gave cis-9,10-dihydroxyoctadec-cis-12-enoic acid which was characterized by various spectroscopic studies and chemical transformations. Quantitation of the coronaric acid was done by gas-liquid chromatography. Chrysanthemum coronarium seed oil was used as the reference standard throughout the study.     

Black Raspberry Seed Oil Improves Lipid Metabolism by Inhibiting Lipogenesis and Promoting Fatty‐Acid Oxidation in High‐Fat Diet‐Induced Obese Mice and db/db Mice

The objective of this study was to evaluate the beneficial effect of α‐linolenic acid‐rich black raspberry seed (BRS) oil on lipid metabolism in high‐fat diet (HFD)‐induced obese and db/db mice. Five‐week‐old C57BL/6 mice were fed diets consisting of 50% calories from lard, 5% from soybean, and 5% from corn oil (HFD), or 50% calories from lard and 10% from BRS oil (HFD + BRS oil diet) for 12 weeks. Six‐week‐old C57BL/KsJ‐db/db mice were fed diets consisting of 16% calories from soybean oil (standard diet), 8% from soybean, and 8% from BRS oil, or 16% from BRS oil for 10 weeks. The BRS oil diets lowered the levels of triacylglycerol, nonesterified fatty acids, and total cholesterol in serum and liver of both of the obese and db/db mice as compared with the HFD and standard diet, respectively. mRNA levels of lipogenesis markers including cluster of differentiation 36, fatty‐acid‐binding protein 1, sterol regulatory element binding protein 1c, fatty‐acid synthase, and solute carrier family 25 member 1 in the liver of the BRS oil groups were lower than those in the liver of the HFD and standard groups in the obese and db/db mice, respectively. On the other hand, fatty‐acid oxidation markers including carnitine palmitoyltransferase 1A, acyl‐CoA dehydrogenase, hydroxylacyl‐CoA dehydrogenase α, and acyl‐CoA oxidase in the liver of the BRS oil groups were higher than those in the liver of the HFD and standard groups in the obese and db/db mice, respectively. Peroxisome proliferator‐activated receptor α mRNA and protein levels increased in the liver and epididymal adipose tissue of the obese and db/db mice fed BRS oil compared with HFD and standard diet, respectively. BRS oil might improve lipid metabolism by inhibiting lipogenesis and promoting fatty‐acid oxidation in HFD‐induced obese and db/db mice.     

Lipase-catalyzed incorporation of oleic acid into melon seed oil

The ability of lipase PS30 (Pseudomonas sp.) to modify the fatty acid profile of melon seed oil by incorporation of oleic acid (18:1n-9) was investigated. The transesterification was carried out in hexane in an orbital shaking water bath at 55°C for 24 h with methyl oleate (70% pure) as acyl donor. Oleic acid content increased from 13.5% to 53%, and linoleic acid (18:2n-6) content decreased from 65% to 33%. The incorporation of oleic acid into melon seed oil by Pseudomonas sp. lipase helped balance the fatty acid profile of the oil in terms of monounsaturated (18:1n-9) and essential fatty acids (18:2n-6).     

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.     

Tetra-acid triglycerides containing a new hydroxy eicosadienoyl moiety inLesquerella auriculata seed oil

The seed oil ofLesquerella auriculata contains 32% of a previously unknown fatty acid, 14-hydroxy-cis-11,cis-17-eicosadienoic acid; we propose for it the trivial name “auricolic acid.” In addition, the oil contains 2% densipolic (12-hydroxy-cis-9,cis-15-octadecadienoic) acid, 10% lesquerolic (14-hydroxy-cis-11-eicosenoic) acid and 5% ricinoleic acid. The oil ofL. auriculata is also unusual, because a large part of the total oil consists of triglycerides containing more than three acyl groups. These components were characterized by various chromatographic, spectroscopic and lipolytic techniques. Presented in part at the AOCS Meeting, New Orleans, April 1970. ARS, USDA.     

Frying stability of soybean and canola oils with modified fatty acid compositions

Pilot plant-processed samples of soybean and canola (lowerucic acid rapeseed) oil with fatty acid compositions modified by mutation breeding and/or hydrogenation were evaluated for frying stability. Linolenic acid contents were 6.2% for standard soybean oil, 3.7% for low-linolenic soybean oil and 0.4% for the hydrogenated low-linolenic soybean oil. The linolenic acid contents were 10.1% for standard canola oil, 1.7% for canola modified by breeding and 0.8% and 0.6% for oils modified by breeding and hydrogenation. All modified oils had significantly (P<0.05) less room odor intensity after initial heating tests at 190°C than the standard oils, as judged by a sensory panel. Panelists also judged standard oils to have significantly higher intensities for fishy, burnt, rubbery, smoky and acrid odors than the modified oils. Free fatty acids, polar compounds and foam heights during frying were significantly (P<0.05) less in the low-linolenic soy and canola oils than the corresponding unmodified oils after 5 h of frying. The flavor quality of french-fried potatoes was significantly (P<0.05) better for potatoes fried in modified oils than those fried in standard oils. The potatoes fried in standard canola oil were described by the sensory panel as fishy.     

Fatty acid variation in seed oil amongOcimum species

Content, fatty acid composition, and glyceride profile of oil from seeds of seven basil (Ocimum sp.) chemotypes were determined. The species studied includedO. basilicum, O. canum, O. gratissimum, andO. sanctum. The oil content ranged from 18 to 26%, with triglycerides comprising between 94 and 98% of extracted neutral lipids. The major acylated fatty acids were linolenic (43.8–64.8%), linoleic (17.8–31.3%), oleic (8.5–13.3%), and palmitic acid (6.1–11.0%). Linolenic acid was similar among the fourO. basilicum chemotypes (57–62%), highest inO. canum (65%), and lowest inO. sanctum (44%). Basil seed oil appears suitable as an edible oil or can be used for industrial purposes, and could be processed in the same way as linseed oil. Preliminary calculations estimate that a hectare of basil could produce from 300 to 400 kg of seed oil.     

Optically active trihydroxy acids ofChamaepeuce seed oils

Two trihydroxy acids have been isolated fromChamaepeuce afra (Jacq.) DC, seed oil and identified as (+)-threo-9,10,18-trihydroxyoctadecanoic (phloionolic) acid (9%) and (+)-threo-9,10-,18-trihydroxy-cis-12-octadecenoic acid (14%). The unsaturated acid has not previously been found in nature. Nuclear magnetic resonance, infrared, thin-layer chromatography, optical rotation, and identification of the oxidative cleavage products show that these two trihydroxy components have the structures indicated.Chamaepeuce hispanica DC. seed oil and the seed oil of an unidentifiedChamaepeuce species apparently contain these same two acids but in different proportions fromC. afra oil. Presented at the AOCS Meeting, Philadelphia, October 1966. No. Utiliz, Res Dev. Div., ARS, USDA.