Hibiscus mutabilis Seed Oil – Characterization of HBr-Reactive Acids

The seed oil of Hibiscus mutabilis (Chameleon rose) (Malvaceae) contains three HBr-reactive fatty acids. These are found to be cis-12, 13-epoxyoleic (vernolic) acid, 5.9%; 9,10-methylene-octadec-9-enoic (sterculic) acid. 7.3%; as well as 8,9-methylene-heptadec-8-enoic (malvalic) acid, 14.0%. Co-occurrence of these acids was established by combined spectroscopie, chromatographic and chemical techniques.     

Abutilon indicum Seed Oil — Characterisation of HBr-Reactive Acids

The seed oil of Abutilon indicum (Malvaceae) contains three HBr-reactive fatty acids. These are shown to be cis-12,13-epoxyoleic (vernolic) acid, 1.6% 9,10-methylene-octadec-9-enoic (sterculic) acid, 0.9%; as well as 8,9-methylene-heptadec-8-enoic (malvalic) acid, 2.3%. Quantitative results are obtained by combining informations about the HBr-titration, the preparative thin layer separation of oxygenated and non-oxygenated acids, and gas liquid chromatographic analysis.     

Sonchus oleraceus Seed Oil-Characterization of HBr-Reactive Oxygenated Acid

Seed oil of Sonchus oleraceus (Compositae) contains cis-12, 13-epoxyoctadec-cis-9-enoic acid (Vernolic, 13.7%). Structural details of this HBr-reactive acid are obtained through comparative chromatographic, spectral and chemical data with those of pure vernolic acid isolated from Vernonia anthelmintica seed oil. GLC analysis of the esters of S. oleraceus also showed a C₁₄:1 acid (1.6%).     

Hibiscus esculentus Seed Oil – A Reinvestigation

Seed oil of H. esculentus contains both cyclopropene (malvalic 0.9% and sterculic 0.3%) and cis-12,13-epoxyoleic (10.1%0 acids besides the other usual fatty acids. Characterization of HBr-reactive acids was done by the use of chromatographic, spectroscopic and chemical methods. Quantitation of cyclopropene and vernolic acids has been done collectively by the HBr titration, preparative TLC and GLC analysis. Seed oils of Vernonia anthelmintica and Sterculia foetida were used reference samples.     

Steaming,boiling after pre-frying,and stir-frying influence the fatty acid profiles and oxidative stability of soybean oil blended with docosahexaenoic acid algal oil

The objective of this study was to improve the content of docosahexaenoic acid (DHA) and obtain the blended oils used for different cooking methods (steaming, boiling, and stir-frying) by blending 0%–15% DHA algal oil into soybean oil. It was shown that the addition of DHA algal oil increased saturated fatty acid (SFA) (1.57%) but decreased monounsaturated fatty acid (MUFA) (0.76%) and polyunsaturated fatty acid (PUFA) (0.68%). Various cooking methods significantly changed the fatty acid (FA) compositions. Steaming is a more effective way to prevent DHA loss and the production of trans-fatty acid than boiling and stir-frying. Besides, a positive result from free fatty acid (FFA) and peroxide value also demonstrated that steaming was a better way to protect oils. Overall, the soybean oil blended with 3% DHA algal oil with better oxidative stability and could be recommended for daily application by steaming.     

The Interaction of the Soybean Seed High Oleic Acid Oil Trait With Other Fatty Acid Modifications

Oil value is determined by the functional qualities imparted from the fatty acid profile. Soybean oil historically had excellent use in foods and industry; the need to increase the stability of the oil without negative health consequences has led to a decline in soybean oil use. One solution to make the oil stable is to have high oleic acid (>70%) and lower linolenic acid content in the oil. Other fatty acid profile changes are intended to target market needs: low‐saturated fatty acid and high stearic acid content in the oil. The objective of this study is to determine the interaction of the high oleic acid oil trait with other alleles controlling fatty acid profiles. Soybean lines containing high oleic acid allele combinations plus other fatty acid modifying alleles were produced, and the seed was produced in multiple field environments over 2 years. Stable high oleic acid with low linolenic acid (<3.0%) was achieved with a 4‐allele combination. The target of >20% stearic acid in the seed oil was not achieved. Reducing total saturated fatty acids below 7% in a high oleic acid background was possible with mutant alleles of both an acyl‐ACP thioesterase B and a β‐ketoacyl‐[acyl‐carrier‐protein] synthase III gene. The results identified allele combinations that met the target fatty acid profile thresholds and were most stable across environments.     

Determination of vernolic acid content in the oil ofEuphorbia lagascae by gas and supercritical fluid chromatography

Determination of the content of vernolic acid (12,13-epoxy-9c-octadecenoic) in the oil ofEuphorbia lagascae has been performed by gas chromatography of the fatty acid methyl ester derivatives of the triacylglycerols in the oil and by supercritical fluid chromatography (SFC) of the raw oil and the fatty acid derivatives of the oil. The content of vernolic acid was found to be 55 wt%. The three methods were compared, and SFC analysis of the fatty acid derivatives was found to be the most accurate method.     

Modulation of cyclic nucleotide phosphodiesterase by dietary fats in rat heart

Feeding oils of different fatty acid composition modifies the fatty acid composition of cardiac membrane phospholipids, thereby inducing changes in cardiac contractility and altering response of adenylate cyclase to catecholamines. In the present study, the effect of such dietary manipulations on cyclic nucleotide phosphodiesterase, which is involved in the control of cyclic nucleotide intracellular levels and in the control of cardiac contractility, was investigated. Rats were fed either a saturated fatty acid-enriched diet (8 weight percent [%] coconut oil +2% sunflower oil), an n−6 fatty acid-enriched diet (10% sunflower oil) or an n−3 fatty acid-enriched diet (8% fish oil +2% sunflower oil). The fatty acid composition of cardiac phospholipids, as well as the nonesterified fatty acid content of heart were markedly altered by the diets. The 18∶2n−6 and 20∶4n−6 content of cardiac phospholipids was markedly (−49%) depressed by fish oil as compared with sunflower oil feeding, but the nonesterified fatty acid level of heart membrane was lowest in coconut oil-fed rats. In addition, fish oil feeding more drastically depressed the n−6/n−3 fatty acid ratio in the nonesterified fatty acid pool than in cardiac phospholipids. Cyclic AMP phosphodiesterase activity was the lowest in both the particulate and soluble fractions of heart from rats fed sunflower oil, whereas cyclic GMP phosphodiesterase activity was not altered by the diets. Cyclic AMP phosphodiesterase activity was decreased by 18 and 12% in heart membranes of the sunflower oil group as compared to that of the coconut oil and fish oil groups, respectively. In heart cytosol, the activity decreased by 30% when compared with the activity of the coconut oil group. Additionalin vitro experiments showed that polyunsaturated fatty acids were more potent inhibitors of cyclic AMP phosphodiesterase than saturated fatty acids. These results suggest that polyunsaturated fatty acid-enriched diets might decrease heart cyclic AMP phosphodiesterase activity by increasing non-esterified polyunsaturated fatty acids, especially those of the n−6 series, but more complex and indirect mechanisms are very likely to be involved.     

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.     

Studies in interesterification. II. Acidolysis of some vegetable oils with lauric acid

Acidolysis reactions of cottonseed oil, peanut oil, mahua oil (Madhuca latifolia), and palm oil with lauric acid were investigated with special reference to the influence of catalysts and the relative proportions of oil and lauric acid on the extent and type of fatty acids displaced from an oil. Catalysts such as sulfuric acid, zinc oxide, calcium oxide, magnesium oxide, aluminum oxide, and mercuric sulfate were used. The reaction generally was carried out by heating oil and lauric acid at 150C±2 for 3 hr. The reaction products were separated and then analyzed by UV spectrophotometry and GLC. Sulfuric acid was found to be the best catalyst with 1 part of oil and 1.2 parts of the displacing acid (lauric acid) for displacement of high-molecular-weight fatty acids from an oil by low-molecular-weight fatty acids. The nature of the displacement of fatty acids varied from oil to oil, depending on their compositions. It was further indicated that linoleic acid was displaced preferentially over oleic acid in an amount dependent on its initial content in an oil with a corresponding increase in saturated acids content. A broad similarity in displacement patterns, in general, was noted; the fatty acids above C₁₈ were not displaced as in the case of peanut oil. The results demonstrate the feasibility of introducing lauric acid in the vegetable oils for the production of interesting oils with vastly different physical and chemical properties.     

Identification of Minor Acylglycerols Less Polar than Triricinolein in Castor Oil by Mass Spectrometry

Acylglycerols in castor oil less polar than triricinolein were identified by electrospray ionization–mass spectrometry using the lithium adducts of the acylglycerols in the HPLC fractions of castor oil. Thirty four new molecular species of acylglycerols containing hydroxy fatty acids in castor oil were identified by MS. The chain lengths of fatty acid substituents were C16, C18, C20, C22 and C23. The numbers of double bonds of the fatty acids were from zero to three. The numbers of hydroxyl groups on the fatty acid chains were from zero to three as previously reported. The structure of fatty acid, OH18:2, was proposed as 12-hydroxy-9,13-octadecadienoic acid. An unusual odd-numbered long-chain fatty acid, 23:0 (tricosanoic acid), was identified. Some new estolides and tetraacylglycerols, were identified as (12-ricinoleoylricinoleoyl)-ricinoleoyl-linoleoyl-glycerol (RRRL), (12-ricinoleoylricinoleoyl)-ricinoleoyl-oleoyl-glycerol (RRRO), (12-ricinoleoylricinoleoyl)-ricinoleoyl-palmitoyl-glycerol (RRRP), (12-ricinoleoylricinoleoyl)-ricinoleoyl-stearoyl-glycerol (RRRS) and (12-ricinoleoylricinoleoyl)-ricinoleoyl-linolenoyl-glycerol (RRRLn). The normal fatty acid (non-hydroxylated) of these tetraacylglycerols were directly attached to the glycerol backbone. The biosynthetic pathway of castor oil is proposed.     

Biooxidation of fatty acid distillates to dibasic acids by a mutant of Candida tropicalis

Fatty acid distillates (FADs) produced during physical refining of vegetable oil contains large amount of free fatty acid. A mutant of Candida tropicalis (M20) obtained after several stages of UV mutation are utilized to produce dicarboxylic acids (DCAs) from the fatty acid distillates of rice bran, soybean, coconut, palm kernel and palm oil. Initially, fermentation study was carried out in shake flasks for 144 h. Products were isolated and identified by GLC analysis. Finally, fermentation was carried out in a 2 L jar fermenter, which yielded 62 g/L and 48 g/L of total dibasic acids from rice bran oil fatty acid distillate and coconut oil fatty acid distillate respectively. FADs can be effectively utilized to produce DCAs of various chain lengths by biooxidation process.     

Incorporation of n-3 fatty acids into plasma lipid fractions, and erythrocyte membranes and platelets during dietary supplementation with fish, fish oil, and docosahexaenoic acid-rich oil among healthy young men

The effects of n-3 fatty acid supplementation in the form of fresh fish, fish oil, and docosahexaenoic acid (DHA) oil on the fatty acid composition of plasma lipid fractions, and platelets and erythrocyte membranes of young healthy male students were examined. Altogether 59 subjects (aged 19–32 yr, body mass index 16.8–31.3 kg/m²) were randomized into the following diet groups: (i) control group; (ii) fish diet group eating fish meals five times per week [0.38±0.04 g eicosapentaenoic acid (EPA) and 0.67±0.09 g DHA per day]; (iii) DHA oil group taking algae-derived DHA oil capsules (1.68 g/d DHA oil group taking algae-derived DHA oil capsules (1.68 g/d DHA in triglyceride form); and (iv) fish oil group (1.33 g EPA and 0.95 g DHA/d as free fatty acids) for 14 wk. The fatty acid composition of plasma lipids, platelets, and erythrocyte membranes was analyzed by gas chromatography. The subjects kept 4-d food records four times during the study to estimate the intake of nutrients. In the fish diet, in DHA oil, and in fish oil groups, the amounts of n-3 fatty acids increased and those of n-6 fatty acids decreased significantly in plasma lipid fractions and in platelets and erythrocyte membranes. A positive relationship was shown between the total n-3 polyunsaturated fatty acids (PUFA) and EPA and DHA intake and the increase in total n-3 PUFA and EPA and DHA in all lipid fractions analyzed. DHA was preferentially incorporated into phospholipid (PL) and triglyceride (TG) and there was very little uptake in cholesterol ester (CE), while EPA was preferentially incorporated into PL and CE. The proportion of EPA in plasma lipids and platelets and erythrocyte membranes increased also by DHA supplementation, and the proportion of linoleic acid increased in platelets and erythrocyte membranes in the DHA oil group as well. These results suggest retroconversion of DHA to EPA and that DHA also interferes with linoleic acid metabolism.     

番荔枝籽油脂脂肪酸组成的GC-MS分析

研究了番荔枝籽油脂中脂肪酸的组成.用索氏脂肪抽提器提取番荔枝籽的油脂,并以GC-MS分析油脂脂肪酸的组成.结果表明,番荔枝籽油脂收率达29.2％;番荔枝籽油脂中含有8种脂肪酸,主要为:油酸(45.37％)、亚油酸(30.68％)、棕榈酸(13.60％)和硬脂酸(8.94％),其中不饱和脂肪酸含量达76.29％.番荔枝籽含油量高,脂肪酸种类丰富,尤其是不饱和脂肪酸含量较高,具有较高的开发利用价值.     

Comparison of Fatty Acid Profile of Specialty Maize to Normal Maize

Increasing utilization of specialty maize prompted us to evaluate its fatty acid profile. For this purpose maize germplasm, classified as low oil normal maize (group 1), high oil normal maize (group 2), quality protein maize (QPM) (group 3) and sweet corn (group 4) was evaluated for oil, starch, protein and fatty acid composition mainly palmitic, stearic, oleic and linoleic acid. High oil content was observed in sweet corn samples which might be result of shriveled grain texture because of an increased embryo to kernel ratio. Individual fatty acids showed wide differences among different groups. A slightly higher amount of palmitic acid was reported in specialty maize as compared to normal maize. In contrast, stearic acid content was significantly low in high oil normal maize (56 %), QPM (36.2 %) and sweet corn (28.4 %) in comparison to low oil normal maize. Although no significant differences were observed for oleic acid between low oil normal and high oil normal maize, but sweet corn samples showed significantly reduced oleic acid compared to low oil normal maize. However, the most important observation was the higher content of linoleic acid in specialty maize (groups 2, 3 and 4) as compared to low oil normal maize. Further, the ratio of MUFA/PUFA was also discussed. It was concluded that specialty maize possesses a better oil quality in comparison to low oil normal maize.     

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.     

Chemical Properties and Fatty Acid Composition of Thunbergia fragrans Roxb. Seed Oil

The physicochemical and fatty acid compositions of seed oil extracted from Thunbergia fragrans were determined. The oil content, free fatty acids, peroxide value, saponification value and iodine value were 21.70 %, 2.25 % (as oleic acid), 9.6 (mequiv. O₂/kg), 191.71 (mg KOH/g) and 127.84 (g/100 g oil) respectively. The fatty acid profiles of the methyl esters showed the presence of 90.16 % unsaturated fatty acids and 9.84 % saturated fatty acids. Palmitoleic acid, which is usually found in marine foods and is unique in seed oils of botanical origin, was the major component (79.24 %). The oil can also be used in industries for the preparation of liquid soaps, shampoos and alkyd resin.     

Lipid metabolism and tissue composition in Atlantic salmon (Salmo salar L.)—Effects of capelin oil, palm oil, and oleic acid-enriched sunflower oil as dietary lipid sources

Triplicate groups of Atlantic salmon (Salmo salar L.) were fed four diets containing different oils as the sole lipid source, i.e., capelin oil, oleic acid-enriched sunflower oil, a 1∶1 (w/w) mixture of capelin oil and oleic acid-enriched sunflower oil, and palm oil (PO). The β-oxidation capacity, protein utilization, digestibility of dietary fatty acids and fatty acid composition of lipoproteins, plasma, liver, belly flap, red and white muscle were measured. Further, the lipid class and protein levels in the lipoproteins were analyzed. The different dietary fatty acid compositions did not significantly affect protein utilization or β-oxidation capacity in red muscle. The levels of total cholesterol, triacylglycerols, and protein in very low density lipoprotein (VLDL), low density lipoprotein (LDL), high density lipoprotein (HDL), and plasma were not significantly affected by the dietary fatty acids. VLDL, LDL, and HDL fatty acid compositions were decreasingly affected by dietary fatty acid composition. Dietary fatty acid composition significantly affected both the relative fatty acid composition and the amount of fatty acids (mg fatty acid per g tissue, wet weight) in belly flap, liver, red and white muscle. Apparent digestibility of the fatty acids measured by adding yttrium oxide as inert marker, was significantly lower in fish fed the PO diet compared to the other three diets.     

Oil and Conjugated Linolenic Acid Contents of Seeds from Important Pomegranate Cultivars (<Emphasis Type="Italic">Punica granatum</Emphasis> L.) Grown in Turkey

In the present study, seed oil content and fatty acid composition of 15 commercially important pomegranate cultivars were determined. The oil content of pomegranate seeds ranged between 13.95 and 24.13% (d.b). Palmitic, stearic, arachidic, and behenic acid contents of the oils ranged between 2.10–2.77, 1.35–2.01, 0.33–0.48, and 0.16–0.22%, respectively. The predominant unsaturated fatty acid was punicic acid (70.42–76.17%) and a minor unsaturated fatty acid was gadoleic acid (0.42–0.75%). The analysis on unsaturated fatty acids particularly showed significant amounts of punicic acid, which is considered to enhance the oil quality and is of importance to health.     

General properties and the fatty acid composition of the oil from the mophane caterpillar, Imbrasia belina

A preliminary investigation of the bulk properties of the oil from the edible mophane caterpillar (phane), Imbrasia belina, showed a significant difference in the iodine values of the oils from mature and young phane. Detailed analysis of the fatty acid composition of the two oil samples was thus carried out by capillary gas chromatography (GC) and complemented with ¹H and ¹³C nuclear magnetic resonance (NMR) studies to investigate the degree of unstauration in the two oil samples. While these studies showed that the oil samples from the mature and young mophane caterpillar were much the same in fatty acid composition, the data revealed a significant divergence from a literature report on phane oil. This earlier report puts the ratio of total saturated to total unsaturated fatty acids at approximately 1:1 (48.2:48.8, in percentages) and estimates the fatty acid composition for the major fatty acids as 16:0 (31.9%), 18:0 (15.2%), 18:1 (20.4%), 18:2 (9.9%), and 18:3 (19%). The data collected from the present work, however, showed the fatty acid composition for total saturated and total unsaturated fatty acids to be 40.5 and 57.0%, respectively. This work estimated the fatty acid composition for the major fatty acids as 16:0 (27.2%), 18:0 (12.3%), 18:1 (16.1%), 18.2 (10.7%), and 18:3 (29.0%). Thus, linolenic acid was the most abundant fatty acid in the phane oil. The GC results of the present analysis were largely corroborated by studies of the composition of fatty acid classes in the phane oil estimated from integrals of ¹H and ¹³C NMR signals. Oils from other edible Lepidoptera larvae are also known to be much richer in unsaturated than saturated fatty acids.