Cyclopropenoic Fatty Acids of Malvaceae Seed Oils by Gas-Liquid Chromatography

Fatty acid composition of seed oils from sixteen species of Malvaceae belonging to sic genus (Abutilon, Gossypium, Hibiscus, Kosteletzkya, Thespesia and Urena) were determined. The main fatty acids were palmitic (7–24% oleic (5–20%) and linoleic (17–69%) acids. Each of the seed oils contains varying amounts of malvalic (0.1–3.9%) and sterculic (tr?3.3%) acids. Dihydrosterculic acid was also detected by GLCat low levels in most of these oils.     

Studies on Herbaceous Seed Oils III

Seed oils from seven species belonging to four botanical families have been analysed for their fatty acid composition by using chromatographic and spectroscopic techniques. Oils from six species are very interesting in containing high percentage (63.7–84.0%) of C₁₈ unsaturated acids. Chemical screening of seed oils reveals that the species producing highly unsaturated oils merit attention for evaluation as perspective crops.     

Free Fatty Acids in Commercial Krill Oils: Concentrations,Compositions, and Implications for Oxidative Stability

The concentrations and pro-oxidative effects of free fatty acids in commercial krill oil are not well defined. We now report that krill oil free fatty acids account for 2–13% of total lipids in commercial krill oil (n = 8) that these compounds are enriched in eicosapentaenoic acid (+7.1%) and docosahexaenoic acid (+6.3%) relative to whole oils; and that this composition make them highly pro-oxidizing in marine triacylglycerol oils, but not in krill oil, which derives oxidative stability from both its phospholipids, and neutral lipids (the latter because of astaxanthin). Specific fatty acid esterification patterns showed that krill oil free fatty acids predominantly (88–93%) originated from phospholipids, mainly from the sn-2 position, which was eight-fold more hydrolyzed than the sn-1 position. Lipolysis was not ongoing in stored oils. Adding small amounts of krill oil (1–5%) to marine triacylglycerol oils significantly increased their oxidative stability and also their resistance to free fatty acid-mediated pro-oxidative effects.     

Studies on Herbaceous Seed Oils XI

Seeds from eight species were analysed by standard procedures for oil and protein contents. The fatty acid composition of the oils was determined by GLC. Five species were found to contain oils above 20% and none of them is rich in protein. Some of the oils have a composition fairly similar to the oils at present in common use. Five seed oils are interesting in having more than 50% of saturated acids of the total fatty acids. T. involucrata seed seems to be a promising species because of its high oil and linoleic acid (61.7%) contents.     

Composition and physicochemical properties of Combretum collinum,Combretum micranthum,Combretum nigricans,and Combretum niorense seeds and seed oils from Burkina Faso

Combretum collinum, Combretum micranthum, Combretum nigricans, and Combretum niorense are abundant unconventional seed oils of the African savannah. In this study, the proximate, mineral, amino acid, fatty acid, and triacylglycerol compositions of the four seed oils were quantified, and the oxidative and physicochemical properties were investigated. The amino acid, fatty acid, and triacylglycerol compositions were determined by using high performance liquid chromatography (HPLC) and gas chromatography respectively. Carbohydrates (57.35%–64.20%) followed by crude oils (20.07%–22.60%), proteins (11.95%–15.86%), and ashes (3.78%–6.19%) were the main constituents of the four seed species. The highest ash, crude fat, and protein contents were found in C. collinum, C. nigricans, and C. niorense, respectively. All four seed species were rich in Ca, K and Mg, and poor in methionine, cysteine, and lysine. The four seed oils had high saponification values (198.46–202.71 mgKOH/g), low acidity (1.12–2.26 mg of KOH/g of oil), and peroxide values (1.19–1.98 mEqO₂/kg of oil). The seed oils of C. micranthum and C. collinum exhibited the highest thermal oxidative stability (8.10 and 9.79 h at 160°C). Oleic (40.49%–56.69%), palmitic (15.17%–24.27%) and linoleic (9.49%–14.50%) acids were the predominant fatty acids of the four seed oils. The results showed that the four seed species and seed oils had good chemical composition and physicochemical properties making them suitable for food and non-food application.     

The fatty acid composition of edible marine fish oils

The body oils of 13 species of marine edible fishes found around the Karachi-Makran coast were studied by gas-liquid chromatography (GLC) for their fatty acid composition. The analyses showed the presence of fatty acids with chain lengths from 10 to 24 carbon atoms and with zero to six double bonds. The oils were found to be rich in polyunsaturated acids, particularly the penta- and hexaenoic. Certain major fatty acids were found to vary widely among the species: myristic acid 2.3 to 13.7%; palmitic 11.6 to 41.2%; stearich 7.2 to 23.2%; oleic 6.9 to 29.6%; eicosapentaenoic 1.4 to 19.0%; docosapentaenoic zero to 10.2%; and docosahexaenoic zero to 36.4%. The linoleic and linolenic acids were present in small amounts in some of the fish oils, and arachidonic acid was present in all of them.     

Physicochemical,Antioxidative, and Sensory Properties of Refined Rapeseed Oils

Physicochemical characteristics, antioxidant capacity (AC), and sensory quality of rapeseed oils available on the Polish market were analyzed and compared. The fatty acid composition (saturated fatty acids = 6.91–7.58%, monounsaturated fatty acids = 64.14–66.14%, and polyunsaturated fatty acids = 27.22–30.17%), color (T420 = 54.5–83.8%), amounts of free fatty acids (0.02–0.07%), primary (PV = 0.04–2.04 meq O₂ kg⁻¹) and secondary (AV = 1.02–3.21) oxidation products, phosphorus (0.38–1.62 mg kg⁻¹), chlorophyll (0.002–0.068 mg kg⁻¹), and polycyclic aromatic hydrocarbons (Σ4PAH = 0.00–2.50 μg kg⁻¹) in the commercial rapeseed oils meet the requirements of the European Food Regulation and Codex Alimentarius standards. Moreover, total phenolic content (TPC = 40.3–467.9 mg SA kg⁻¹) in the studied oils significantly differs from each other. However, the AC of rapeseed oils was analyzed using the novel iron oxide nanoparticle-based (IONP = 5552.1 − 18,510.2 μmol TE/100 g) method and the modified ferric reducing antioxidant power (FRAP = 55.7–280.3 μmol TE/100 g), cupric reducing AC (CUPRAC = 79.6–784.0 μmol TE/100 g), 2,2-diphenyl-1-picrylhydrazyl (DPPH = 185.7–516.7 μmol TE/100 g), and 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS = 465.6–2142.6 μmol TE/100 g) assays. Principal component analysis (PCA) and hierarchical cluster analysis (HCA) were applied for discrimination of the refined rapeseed oils based on fatty acid composition, physicochemical parameters, AC, and sensory properties.     

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.     

Chemical Compositions and Oxidative Stabilities of Ginkgo biloba Kernel Oils from Four Cultivated Regions in China

Ginkgo biloba is a living fossil and traditionally known as a source of pharmaceuticals and cosmetics, largely because of the lipids in the kernels. In the present study, fatty acids, triacylglycerols, micronutrients, and oxidative stabilities of G. biloba kernel oils from four major different cultivated regions in China were systematically analyzed. The results showed that the kernel oils contained more than 26 triacylglycerol species with high contents of linoleic acid (42.04–43.01%), oleic acid (14.33–18.00%), and trans-vaccenic acid (15.13–16.86%). Functional fatty acids such as trans-vaccenic acid, palmitoleic acid, and podocarpic acid were particularly enriched in the oils. In addition, high levels of tocopherols (173.41–272.18 mg/100 g) and 304.09–673.26 mg/100 g of phytosterols in the oils contributed to significantly improve their oxidative stabilities. In particular, α-tocopherol (106.63–127.35 mg/100 g), γ-tocopherol (41.41–133.65 mg/100 g), campesterol (53.22–139.88 mg/100 g), and β-sitosterol (245.50–522.62 mg/100 g) were the dominant micronutrients; while γ-tocopherol significantly affected oxidative stabilities of the four oils from different regions. It is suggested that the G. biloba kernel oils are ideal sources for high-valued usages in skin care purpose, physical therapy, functional food, and nutritional supplements.     

Studies on Herbaceous Seed Oils V

Seeds from seven species of plants belonging to less familiar botanical families were analysed for oil and protein, and the fatty acid composition of the oils was determined by gas liquid chromatography. Oils from five species are interesting in containing high percentage (71.9–83.7%) of C₁₈ unsaturated acids. Seeds from Tropaeolum majus contain oil which, on the basis of chromatographic analysis, appears to be a suitable industrial source of cis-11-eicosenoic and cis-13-docosenoic (erucic) acids.     

<Emphasis Type="Italic">cis</Emphasis>-, <Emphasis Type="Italic">trans</Emphasis>- and Saturated Fatty Acids in Selected Hydrogenated and Refined Vegetable Oils in the Indian Market

The fatty acid composition of 27 samples of commercial hydrogenated vegetable oils and 23 samples of refined oils such as sunflower oil, rice bran oil, soybean oil and RBD palmolein marketed in India were analyzed. Total cis, trans unsaturated fatty acids (TFA) and saturated fatty acids (SFA) were determined. Out of the 27 hydrogenated fats, 11 % had TFA about 1 % where as 11 % had more than 5 % TFA with an average value of about 13.1 %. The 18:1 trans isomers, elaidic acid was the major trans contributor found to have an average value of about 10.8 % among the fats. The unsaturated fatty acids like cis-oleic acid, linoleic acid and α-linolenic acid were in the range of 21.8–40.2, 1.9–12.2, 0.0–0.7 % respectively. Out of the samples, eight fats had fatty acid profiles of low TFA (less than 10 %) and high polyunsaturated fatty acids (PUFA) such as linoleic and α-linolenic acid. They had a maximum TFA content of 7.3 % and PUFA of 11.7 %. Among the samples of refined oils, rice bran oil (5.8 %) and sunflower oil (4.4 %) had the maximum TFA content. RBD palmolein and rice bran oils had maximum saturated fatty acids content of 45.1 and 24.4 % respectively. RBD palmolein had a high monounsaturated fatty acids (MUFA) content of about 43.4 %, sunflower oil had a high linoleic acid content of about 56.1 % and soybean oil had a high α-linolenic acid content of about 5.3 %.     

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.     

Fatty acid compositions of seed oils of sevenhibiscus species of malvaceae

The seeds of sevenHibiscus (Malvaceae) species, viz.,H. surattensis, H. vitifolius, H. hirtus, H. punctatus, H. zeylanicus, H. micranthus andH. solandra, contained 13–17% oil. Linoleic acid predominated (43.9–67.6%) in the component fatty acids of all the oils, followed by palmitic (15.1–30.1%) and oleic acids (5.9–24.8%), while malvalic, sterculic, dihydrosterculic and epoxy acids were present in small concentrations (1.7–8.4, 0.6–3.9, trace-2.1, trace-0.5%, respectively).     

Cyclopropene fatty acids of selected seed oils from bombacaceae,malvaceae, and sterculiaceae

Fatty acid compositions of seed oils from three species of Bombacaceae, eleven from Malvaceae, and six from Sterculiaceae were determined. Each of the seed oils contains varying amounts of both malvalic and sterculic acids accompanied by one or both of the corresponding cyclopropane fatty acids. In addition, the seed oil ofPachira aquatic Aubl. (Bombacaeae) contains 12.8% α-hydroxysterculic acid.     

Fatty acid composition of seed oils from sixAdansonia species with particular reference to cyclopropane and cyclopropene acids

The oil content of sixAdansonia species (Bombacaceae family) of Madagascar (Adansonia grandidieri, A. za, A. digitata, A. fony, A. madagascariensis andA. suarenzensis) and Africa (A. digitata) ranges from 8 to 46%. All the oils give a positive response to the Halphen test. Malvalic, sterculic and dihydrosterculic acids were detected using gas liquid chromatography-mass spectrometry (GLC-MS). Epoxy or hydroxy fatty acids were not found in these oils. Fatty acid composition was determined by GLC using glass capillary columns coated with BDS and Carbowax 20 M. Results obtained for cyclopropenic fatty acids (CPEFA) were compared to those given by glass capillary GLC after derivatization with silver nitrate in methanol, by hydrogen bromide titration and by proton magnetic resonance (PMR). Good agreement was observed for the results given by the various methods. Malvalic acid content ranges from 3 to 28%, sterculic acid from 1 to 8% and dihydrosterculic acid from 1.5 to 5.1%. Odd-numbered fatty acids (Pentadecanoic and hepatadecanoic) were also observed in minute amounts (0.1–1.1%). Among the normal fatty acids, we observed mainly palmitic (21–46%), oleic (15–40%) and linoleic (12–32%). The relationship between fatty acid composition andAdansonia species is discussed.     

Changes in triacylglycerol molecular species and thermal properties of blended and interesterified mixtures of coconut oil or palm oil with rice bran oil or sesame oil

Blended oils were prepared by mixing appropriate amounts of coconut oil (CNO) or palm oil (PO) with rice bran oil (RBO) or sesame oil (SESO) to get approximately equal proportions of saturated/monounsaturated/polyunsaturated fatty acids in the oil. These blended oils were subjected to interesterification reactions using lipase to randomize the fatty acid distribution on the glycerol molecule. The fatty acid compositions of the modified oils were evaluated by gas chromatography while changes in triacylglycerol molecular species were followed by HPLC. The triacylglycerol molecular species of the blended oils reflected those present in the parent oil. Interesterification of the blended oils resulted in the exchange of fatty acids within and between the triacylglycerol molecules, resulting in alterations in the existing triacylglycerol molecules. Emergence of new triacylglycerol molecular species following interesterification was also observed. The thermal profiles of the native, blended and interesterified oils were determined by differential scanning calorimetry. Thermal behaviour, melting and crystallization properties of the modified oils showed significant changes reflecting the changes in the triacylglycerol molecules present in the oil. Therefore, interesterification of oils introduces significant changes in the physical properties of oils, even though the overall fatty acid composition of blended and interesterified oils remains the same.     

Preparation of Omega-3 PUFA Concentrates from Fish Oils via Urea Complexation

The effect of weight ratio of urea to fatty acids and the urea-fatty acid adduct crystallization temperature on the enrichment of eicosapentaenoic acid from marine oil fatty acids was studied. The optimum ratio of urea to fatty acids was found to be 3 : 1 for laboratory scale preparations and the optimum temperature for the formation of urea-fatty acid adduct was 1°C. At very low temperatures (?12, ?18, ?35°C) the recovery efficiency for EPA was reduced. Using these optimum values, enrichment of EPA and other n-3 polyunsaturated fatty acids via urea complexation was carried out on a pilot plant scale in a variety of North Atlantic and North Pacific fist oils and a seal oil. Irrespective of hte type of starting oil, all the oils gave a concentrate with 69–85% total n-3 PUFA with an overall yield of 17–20%. Menhaden is clearly an ideal oil for preparation of EPA concentrate, as the starting oil usually has a higher proportion of EPA to DHA than most of the other commercial fish oils.     

Dragon Fruit (Hylocereus spp.) Seed Oils: Their Characterization and Stability Under Storage Conditions

Oil was extracted from the seeds of white-flesh and red-flesh dragon fruits (Hylocereus spp.) using a cold extraction process with petroleum ether. The seeds contained significant amounts of oil (32–34 %). The main fatty acids were linoleic acid (C18:2, 45–55 %), oleic acid (C18:1, 19–24 %), palmitic acid (C16:0, 15–18 %) and stearic acid (C18:0, 7–8 %). The seed oils are interesting from a nutritional point of view as they contain a large amount of essential fatty acids, amounting to up to 56 %. In both dragon fruit seed oils, tri-unsaturated triacylglycerol (TAG) was mainly found while their TAG composition and relative percentage however varied considerably. Therefore, they showed a different melting profile. A significant amount of total tocopherols was observed (407–657 mg/kg) in which the α-tocopherol was the most abundant (~72 % of total tocopherol content). The impact of storage conditions, cold and room temperatures, on the oxidative stability and behavior of tocopherols was monitored over a 3-month storage period. During storage, the oxidative profile changed with a favorably low oxidation rate (~1 mequiv O₂/week) whilst tocopherols decreased the most at room temperature. After 12 weeks, the total tocopherol content, however, still remained high (65–84 % compared to the initial oils). Hereto, the dragon fruit seed oils can be considered as a potential source of essential fatty acids and tocopherols, with a good oxidative resistance.     

The fatty acid composition of seed oils from ten plant families with particular reference to cyclopropene and dihydrosterculic acids

Oil contents and fatty acid compositions of 40 seed oils of the plant families Elaecarpaceae, Thymelaeceae, Malvaceae, Sterculiaceae (order Malvales); Anacardiaceae, Celestraceae, Sapindaceae (Sapindales); Ebenaceae, Sapotaceae (Ebenales) and Rhamnaceae (Rhamnales) are presented. Cyclopropene fatty acids (CPFA) occur in two families in the order malvales not hitherto assayed. CPFA contents of seed oils of 12 Australian and Pacific species of Malvaceae and Sterculiaceae are given. CPFA occur randomly in small amounts in at least six families not in the order Malvales. Dehydrosterculic acid (DHS) occurs in small amounts in many species of Anacardiaceae, Celestraceae, Elaeocarpaceae, Malvaceae, Sapindaceae, Sapotaceae and Sterculiaceae. Linoleic acid was predominant in 28 of 40 seed oils, being as high as 63.9% in two species. The sum of 18:1 and 18:2 esters exceeded 70% in 20 oils.     

Minor Seed Oils XVI: Examination of Fifteen Seed Oils

Fifteen seed oils from nine plant families have been examined. Oleic acid is the major component in all the oil samples, maximum being in Amaranthus tricolor (91.0%), except in the seed oil of Physalis maxima. All the samples contain arachidic and behenic acids. The oil samples from Ipomoea species and from Physalis maxima contain the lower fatty acids (caprylic and capric). Linolenic acid is found in eleven samples and lauric acid in all the seed oils except the seed oil of Celosia cristata.