Lipid Fractions,Fatty Acid Profiles,and Bioactive Compounds of Lithospermum officinale L. Seeds

Seeds of Lithospermum officinale L. from different climatic zones were analyzed for new sources of γ-linolenic acid (GLA, 18:3n-6) and stearidonic acid (SDA, 18:4n-3). Cultured Borago officinalis was also analyzed for comparative purposes. Analyses were conducted for fatty acid (FA) profiles of the glyceride oils from the seeds and in the neutral and polar lipids by gas chromatography (GC); lipid classes by open column chromatography and preparative thin layer chromatography (TLC); and tocopherols, sterols, and phenolic compounds by high-performance liquid chromatography with diode array detection (HPLC-DAD), and the later compounds were confirmed by liquid-chromatography-mass spectrometry (LC–MS). L. officinale from St. Petersburg Botanical Garden showed the highest percentage of GLA (17.9% of total FA), while wild-growing L. officinale from the Rostov region contained the highest percentage of SDA (17.2% of total FA). Total FA content ranged from 11.3 to 20.8% of seed weight. Neutral and polar lipids accounted for ~98 and 2.27%, respectively, of total lipids. Five neutral lipid classes were identified (% of NL): triterpene esters (1.3), triacylglycerols (93.1), free FA (1.8), diacylglycerols (1.4), and monoacylglycerols (2.4). The highest tocopherol content was found in samples from Chechen Republic (35.7 mg/100 g), in which the δ isomer was the main component. Samples from the Rostov region had the highest amounts of sterols (83.8 mg/100 g), and Δ⁵-avenasterol was the predominant compound in all samples. L. officinale seeds contain high amounts of phenolic compounds (389.9 mg/100 g as upper limit), in which rosmarinic acid is highlighted. Overall, all data suggest the possibility of using L. officinale seed oil in pharmaceutical and cosmetic formulae and as functional food.     

Fatty Acid Profile of Kenaf Seed Oil

The fatty acid profile of kenaf (Hibiscus cannabinus L.) seed oil has been the subject of several previous reports in the literature. These reports vary considerably regarding the presence and amounts of specific fatty acids, notably (12,13-epoxy-9(Z)-octadecenoic (epoxyoleic) acid, but also cyclic (cyclopropene and cyclopropane) fatty acids. To clarify this matter, two kenaf seed oils (from the Cubano and Dowling varieties of kenaf) were investigated regarding their fatty acid profiles. Both contain epoxyoleic acid, the Cubano sample around 2 % and the Dowling sample 5-6 % depending on processing. The cyclic fatty acids malvalic and dihydrosterculic were identified in amounts around 1 %. Trace amounts of sterculic acid were observed as were minor amounts of C17:1 fatty acids. The results are discussed in the context of the fatty acid profiles of other hibiscus seed oils.     

Physicochemical Properties and Fatty Acid Profile of Phoenix Tree Seed and its Oil

Various components of Phoenix tree (Firmiana simplex) seed were determined. Oil, protein, moisture, ash, and fiber accounted for 27.8 ± 0.3, 19.7 ± 0.4, 7.5 ± 0.2, 4.4 ± 0.3, and 31.23 ± 0.93 % (w/w) of the seed, respectively. The acid value, peroxide value, saponification value, and unsaponifiable matter content of Phoenix tree seed oil extracted using the Soxhlet method were 3.73 ± 0.02 mg KOH/g, 1.97 ± 0.21 mmol/kg, 183.74 ± 2.37 mg KOH/g, and 0.90 ± 0.05 g/100 g, respectively. The total tocopherol content was 54.5 ± 0.5 mg/100 g oil, which consisted mainly of δ‐tocopherol (29.5 ± 0.6 mg/100 g oil) and γ‐tocopherol (13.8 ± 0.8 mg/100 g oil). Linoleic acid (L, 30.2 %), oleic acid (O, 22.2 %), and sterculic acid (S, 23.2 %) were the main unsaturated fatty acids of Phoenix tree seed oil. The saturated fatty acids included palmitic acid (17.4 %) and stearic acid (St, 2.9 %). The work shows the first report of sterculic acid in seeds of this species. This oil can be used as a raw material to produce sterculic acid.     

Structural Determination and Occurrence in Ahiflower Oil of Stearidonic Acid Trans Fatty Acids

Several marine oils and seed oils on the market contain relevant quantities of stearidonic acid (18:4n‐3, SDA). The formation of 18:4n‐3 trans fatty acids (tFA) during the refining of these oils necessitates the development of a method for their quantification. In this study, 18:4n‐3 was isolated from Ahiflower and isomerized to obtain its 16 geometric isomers. The geometric isomers of 18:4n‐3 were isolated by silver ion HPLC (Ag⁺‐HPLC) and characterized by partial reduction with hydrazine followed by gas chromatography analysis. The elution order of all 16 isomers was established using a 100 m × 0.25 mm 100% poly(biscyanopropyl siloxane) capillary column and at the elution temperature of 180 °C. The 4 mono‐trans‐18:4n‐3 isomers produced during the refining of oils rich in 18:4n‐3 were chromatographically resolved from each other, but c6,t9,c12,c15‐18:4 coeluted with the tetra‐cis isomer. These 2 fatty acids (FA) were resolved by reducing the separation temperature to 150 °C, but this change caused tetra‐cis‐18:4n‐3 to coelute with t6,c9,c12,c15–18:4. Combining the results from 2 isothermal separations (180 and 150 °C) was necessary to quantify the 4 mono‐trans 18:4n‐3 FA in Ahiflower oil.     

Chemical Composition and Fatty Acid Profile of Khat (Catha edulis) Seed Oil

The proximate, physicochemical, and fatty acid compositions of seed oil extracted from khat (Catha edulis) were determined. The oil, moisture, crude protein, crude fiber, crude carbohydrate, and ash content in seeds were 35.54, 6.63, 24, 1.01, 30.4 %, and 1.32 g/100 g DW respectively. The free fatty acids, peroxide value, saponification value, and iodine value were 2.98 %, 12.65 meq O₂/kg, 190.60 mg KOH/g, and 145 g/100 g oil, respectively. Linolenic acid (C_18:3, 50.80 %) and oleic (C_18:1, 16.96 %) along with palmitic acid (C_16:0, 14.60 %) were the dominant fatty acids. The seed oil of khat can be used in industry for the preparation of liquid soaps and shampoos. Furthermore, high levels of unsaturated fatty acids make it an important source of nutrition especially as an animal product substitute for omega‐3 fatty acids owing to the high content of linolenic acid.     

Methyl Esters (Biodiesel) from and Fatty Acid Profile of Gliricidia sepium Seed Oil

Increasing the supply of biodiesel by defining and developing additional feedstocks is important to overcome the still limited amounts available of this alternative fuel. In this connection, the methyl esters of the seed oil of Gliricidia sepium were synthesized and the significant fuel‐related properties were determined. The fatty acid profile was also determined with saturated fatty acids comprising slightly more than 35 %, 16.5 % palmitic, 14.5 % stearic, as well as lesser amounts of even longer‐chain fatty acids. Linoleic acid is the most prominent acid at about 49 %. Corresponding to the high content of saturated fatty acid methyl esters, cold flow is the most problematic property as shown by a high cloud point of slightly >20 °C. Otherwise, the properties of G. sepium methyl esters are acceptable for biodiesel use when comparing them to specifications in biodiesel standards but the problematic cold flow properties would need to be observed. The ¹H‐ and ¹³C‐NMR spectra of G. sepium methyl esters are reported.     

香榧种子含油量及脂肪酸组成对比研究

为探究不同品种香榧种子含油量及组成的差异,对同一产地不同品种的11种香榧（旋纹榧、茄榧、大圆榧、米榧、象牙榧、芝麻榧、普通榧、木榧、小圆榧、炭盆榧和寸金榧）种子的含油量以及种子油脂肪酸组成进行了对比研究,结果表明：不同品种的香榧种子含油量及种子油脂肪酸类型都表现出明显差异。11种不同香榧种子含油量约2%~14%,普通榧最高（13.4%）,炭盆榧最低（2.2%）;脂肪酸种类最少8个,最多13个（寸金榧和木榧）。香榧种子油以不饱和脂肪酸为主,其总量超过66%。普通榧不饱和脂肪酸总量达到85.87%,其中主要成分油酸、亚油酸总量超过72%。所有品种的香榧种子油都含有超过6.90%的特殊脂肪酸金松酸,而且以普通榧中含量最高,达到10.41%。     

Uptake and Incorporation of Pinolenic Acid Reduces n-6 Polyunsaturated Fatty Acid and Downstream Prostaglandin Formation in Murine Macrophage

Many reports have shown the beneficial effects of consumption of pine seeds and pine seed oil. However, few studies have examined the biological effect of pinolenic acid (PNA; ∆5,9,12–18:3), the main fatty acid in pine seed oil. In this study, using murine macrophage RAW264.7 cells as a model, we examined the effect of PNA on polyunsaturated fatty acid (PUFA) metabolism, prostaglandin (PG) biosynthesis and cyclooxygenase-2 (COX-2) expression. Results showed that PNA was readily taken up, incorporated and elongated to form eicosatrienoic acid (ETrA, ∆7,11,14–20:3) in macrophage cells. A small portion of this elongated metabolite was further elongated to form ∆9,13,16–22:3. The degree of incorporation of PNA and its metabolites into cellular phospholipids varied with the length of incubation time and the concentration of PNA in the medium. Incubation of PNA also modified the fatty acid profile of phospholipids: the levels of 18- and 20-carbon PUFA were significantly decreased, whereas those of 22-carbon fatty acids increased. This finding suggests that PNA enhances the elongation of 20-carbon fatty acids to 22-carbon fatty acids. The syntheses of PGE₁ from dihomo-γ-linolenic acid (DGLA, ∆8,11,14–20:4) and PGE₂ from arachidonic acid (ARA, ∆5,8,11,14–20:4) were also suppressed by the presence of PNA and its metabolite. As the expression of COX-2 was not suppressed, the inhibitory effect of PNA on PG activity was attributed in part to substrate competition between the PNA metabolite (i.e., ∆7,11,14–20:3) and DGLA (or ARA).     

Comparative Effects of Sandalwood Seed Oil on Fatty Acid Profiles and Inflammatory Factors in Rats

The aim of the present study was to investigate the effect of sandalwood seed oil on fatty acid (FA) profiles and inflammatory factors in rats. Fifty male Sprague–Dawley rats were randomly divided into five different dietary groups: 10 % soybean oil (SO), 10 % olive oil (OO), 10 % safflower oil (SFO), 10 % linseed oil (LSO) and 8 % sandalwood seed oil blended with 2 % SO (SWSO) for 8 weeks. The SWSO group had a higher total n-3 polyunsaturated fatty acids (PUFA) levels but lower n-6:n-3 PUFA ratios in both adipose tissue and liver than those in the SO, OO and SFO groups (p < 0.05). Although the SWSO group had a much lower 18:3n-3 level (4.51 %) in their dietary lipids than the LSO group (58.88 %), the levels of docosahexaenoic acid (DHA: 22:6n-3) in liver lipids and phospholipids of the SWSO group (7.52 and 11.77 %) were comparable to those of the LSO group (7.07 and 13.16 %). Ximenynic acid, a predominant acetylenic FA in sandalwood seed oil, was found to be highly incorporated into adipose tissue (13.73 %), but relatively lower in liver (0.51 %) in the SWSO group. The levels of prostaglandin F_2α, prostaglandin E₂, thromboxane B₂, leukotriene B₄, tumor necrosis factor-α and interleukin-1β in both liver and plasma were positively correlated with the n-6:n-3 ratios, suggesting that increased n-6 PUFA appear to increase the formation of pro-inflammatory cytokines, whereas n-3 PUFA exhibit anti-inflammatory activity. The present results suggest that sandalwood seed oil could increase tissue levels of n-3 PUFA, DHA and reduce the n-6:n-3 ratio, and may increase the anti-inflammatory activity in rats.     

The Fatty Acid Profile and Phenolic Composition of Descurainia sophia Seeds Extracted by Supercritical CO2

Oil and phenolics were extracted from Descurainia sophia (Sophia) seeds by a supercritical CO₂ system. Extractions were conducted in two sequential steps, first using 100 % CO₂ and then adding 10 % ethanol as co‐solvent. The extracts were collected in each step using two separate collectors operating at different pressures. The extraction run was 3 and 4 h for the first period, and 2 h for the second period. The majority of the oil was collected in the first extraction period while phenolic compounds were obtained in the second extraction period. A combined mode of static/dynamic extraction (3 h running and 1 h soaking in CO₂) was also used in the first extraction period, which enhanced the total extraction yield (29.3 ± 0.5 %) and was comparable to the 4 h extraction yield (31.4 ± 0.1 %). The total fatty acid (FA) content of oil in collector 1 (0.94 g) was nearly twice that in collector 2 (0.60 g). The oil contained 14 FAs with α‐linolenic being predominant (48.5 %), with a total 91.1 % unsaturated FAs, a ω3/ω6 ratio of 2.7, and an erucic acid content of 6.2 %. More than 10 phenolic compounds were detected by HPLC in the Sophia seed extracts of which sinapic acid was the dominant compound. Sophia seed extracts showed high levels of antioxidant activity. These results suggest that Sophia seed oil and phenolics have the potential for functional food and pharmaceutical applications.     

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.     

Supercritical Carbon Dioxide Extraction,Fatty Acid Composition,Oxidative Stability,and Antioxidant Effect of Torreya grandis Seed Oil

Torreya grandis seed oil (TGSO) extraction with supercritical carbon dioxide was explored from the extraction conditions, fatty acid composition, its oxidative stability and antioxidant activity in a bench‐scale apparatus. An L₉(3⁴) orthogonal design was applied to optimize extraction parameters. The results demonstrated that the maximum yield of 94.57 % was obtained at 45 MPa, 4 h and 50 °C. There were 18 kinds of compounds found within TGSO; the predominant ingredient was linoleic acid (42.02 %), followed by oleic acid (32.14 %) and dihomo‐γ‐linolenic acid (9.80 %). The IC₅₀ values for 1,6‐bis(diphenylphosphino) hexane radical (DPPH), hydroxyl radical (HO?) and superoxide radical (O₂^·?) were 5.61, 3.16 and 4.20 mg/mL, respectively.     

Eco-friendly Pretreatment of Oil with High Free Fatty Acid Content Using a Sulfamic Acid/Ethanol System

In recent years, sulfamic acid (SA, NH₂SO₃H) has emerged as a novel green catalyst for organic synthesis because of several advantages, including its non‐volatility, non‐hygroscopicity, non‐corrosivity, and low cost. This work reports the use of sulfamic acid as a catalyst in the pretreatment of oil with a high content of free fatty acids (10 and 20 % FFA) in ethanol or methanol. The process (esterification reaction) used in the pretreatment of the oil was carried out under a variety of conditions, initial fatty acid content, temperature, type of alcohol, and % catalyst. The experiments using an NH₂SO₃H/ethanol system resulted in a high fatty acid ethyl ester conversion, 88.53 % (±0.95) from an initial acidity of 40 mg KOH/g (20 % FFA), using 8 % NH₂SO₃H as the catalyst. According to the results, the methodology using sulfamic acid and ethanol demonstrated elevated potential for a environmentally‐friendly means of biodiesel production.     

Variation in Seed Oil Content and Fatty Acid Composition of Globe Artichoke Under Different Irrigation Regimes

Seed oil content of globe artichoke and its composition were assessed under three irrigation regimes, including irrigation at 20, 50, and 80 % depletion of soil available water. Water deficit affected the phenological characteristics, amount and the quality of the oil as well as the phenolics and antioxidant activity of the leaves and capitula. The seed oil content ranged from 18.7 % in 80 % to 22.8 % in 20 % treatment. The fatty acid composition of oil was determined using gas chromatography (GC). The predominant fatty acids in the oil were linoleic (51.68 %), oleic (34.22 %), palmitic (9.94 %), and stearic (3.58 %). Water deficit leads to reduced oil content, linoleic acid, the unsaturated/saturated fatty acid ratio and the iodine value. On the other hand, some other fatty acids such as palmitic and oleic acid and also the ratio of oleic/linoleic acid were elevated due to water deficit. Higher antioxidant activity was observed in capitula (IC₅₀ = 222.6 μg ml^?1) in comparison to the leaves (IC₅₀ = 285.8 μg ml^?1). Finally, the severe drought stress condition caused to gain higher oil stability, while the highest seed oil content and unsaturated fatty acids in the oil was obtained in non‐stress condition. Moreover, high phenolics, flavonoids and antioxidant activity as well as appreciable dry matter content were obtained in the moderate water stress condition.     

多价不饱和脂肪酸分离方法及在橡胶籽油中的应用

介绍了多价不饱和脂肪酸的分离纯化方法 ,以及在橡胶籽油中的应用前景。     

Oil Content,Oil Yield and Fatty Acid Profile of Groundnut Germplasm in Mediterranean Climates

A high amount of good-quality vegetable oil in seeds has an overwhelming contribution to the groundnut (Arachis hypogaea L.) cultivation throughout the world. In order to take into account great variation in oil characteristics in Arachis subspecies and botanical varieties, 256 groundnut genotypes including ICRISAT’s mini core collection were investigated. Significant variability in oil content (31.7–57.0%) was detected among groundnut genotypes. Oil yield varied from 9.5 to 179.3 kg da^?1 with the average being 67.7 kg da^?1. Significant genotypic differences were also observed for all the fatty acids studied. Oleic and linoleic acids accounted for the major fraction with mean values of 45.3 and 32.1% in the ranges of 35.3–60.9% and 16.1–43.6%, respectively. Significant negative correlation was observed between oleic and linoleic acid. In the present investigation, desirable values were obtained for oil traits which would be useful to develop nutritional and health-beneficial cultivars.     

Fatty Acid Composition and Antioxidant Activity of Tea (Camellia sinensis L.) Seed Oil Extracted by Optimized Supercritical Carbon Dioxide

Seeds are another product in addition to leaves (raw materials for teas) of tea (Camellia sinensis L.) plant. The great increase of tea consumption in recent years raises the challenge of finding commercial applications for tea seeds. In the present study, supercritical carbon dioxide (SC-CO(2)) extraction edible oil from tea seed was carried out, response surface methodology (RSM) was used to optimize processing parameters including time (20-90 min), temperature (35-45 °C) and pressure (50-90 MPa). The fatty acid composition and antioxidant activity of the extracted oil was also investigated. The highest yield of oil (29.2 ± 0.6%) was obtained under optimal SC-CO(2) extraction conditions (45 °C, 89.7 min and 32 MPa, respectively), which was significantly higher (p < 0.05) than that (25.3 ± 1.0%) given by Soxhlet extraction. Meanwhile, tea seed oil extracted by SC-CO(2) contained approximately 80% unsaturated fatty acids and showed a much stronger scavenging ability on the DPPH radical than that extracted by Soxhlet. SC-CO(2) is a promising alternative for efficient extraction of edible oil from tea seed. Moreover, tea seed oil extracted by SC-CO(2) is highly edible and has good antioxidant activity, and therefore may play a potential role as a health-promoting food resource in human diets.