Physicochemical characterisation and radical-scavenging activity of Cucurbitaceae seed oils

Oils extracted from Cucurbitaceae seeds were characterised for their fatty acid and tocopherol compositions. In addition, some physicochemical characteristics, total phenolic contents and the radical-scavenging activities were determined. Oil content amounted to 23.9% and 27.1% in melon and watermelon seeds, respectively. Physicochemical characteristics were similar to those of other edible oils and the oils showed significant antioxidant activities. Fatty acid composition showed total unsaturated fatty acid content of 85.2–83.5%, with linoleic acid being the dominant fatty acid (62.4–72.5%), followed by oleic acid (10.8–22.7%) and palmitic acid (9.2–9.8%). The oils, especially watermelon seed oil, showed high total tocopherol and phenolic contents. The γ-tocopherol was the predominant tocopherol in both oils representing 90.9 and 95.6% of the total tocopherols in melon and watermelon seed oils, respectively. The potential utilisation of melon and watermelon seed oils as a raw material for food, chemical and pharmaceutical industries appears to be favourable.     

Determination of fatty acids in the seeds of Lepidium apetalum Willdenow,Descurainia sophia (L.) Webb ex Prantl,and Draba nemorosa L. by ultra-high-performance liquid chromatography equipped with a charged aerosol detector

Both the contents of fatty acids and the ratios of unsaturated to saturated fatty acids are important parameters for determining the nutritional values of oils. Thus, we herein evaluated the fatty acids present in the seed oils of Lepidium apetalum Willdenow, Descurainia sophia (L.) Webb ex Prantl, and Draba nemorosa L. as sources of Lepidii seu Descurainiae Semen seeds in Northeast Asian Countries. We developed a method based on ultra-high-performance liquid chromatography using a charged aerosol detector for the quantitative analysis of fatty acids in the seed oils. This technique is less time-consuming than previous methods as derivatization of the oils is not required. Our method was developed though the comparison of a UV detector with a charged aerosol detector, and various stationary phases and gradient programs were tested. In addition, method validation was carried out according to the International Conference on Harmonization guidelines with respect to linearity, precision, and accuracy. We found that the quantities of unsaturated fatty acids (6.051–282.376?mg/g) were higher than those of saturated fatty acids (0.855–12.548?mg/g) in all plant seed oils. The proposed method is reproducible and convenient, and therefore, is suitable for the quantitative analysis of fatty acids in plant oils.     

Chemical characterisation of old cabbage (Brassica oleracea L. var. acephala) seed oil by liquid chromatography and different spectroscopic detection systems

We report an extensive chemical characterisation of fatty acids, triacylglycerols, tocopherols, carotenoids and polyphenols contained in the oil extracted from old cabbage (Brassica oleracea L. var. acephala) by cold-pressing of the seeds. Analyses were performed by GC-FID combined with mass spectrometry, HPLC with photodiode array, fluorescence and mass spectrometry detection. The 94% of the total fatty acids were unsaturated, rappresented by erucic acid (more than 50%) followed by linoleic, linolenic and oleic acids accounting for approximately 10% each. The most abundant triacylglycerols (>13%) were represented by erucic–gadolenic–linoleic, erucic–eruci–linoleic and erucic–erucic–oleic. Among tocopherols, γ-tocopherol accounted for over 70% of the total content. Thirteen carotenoids and 11 polyphenols were identified and measured. In particular, the total content in carotenoids was 10.9 ppm and all-E-lutein was the main component (7.7 ppm); among polyphenols, six hydroxycinnamic acids and five flavonoids, were identified by combining information from retention times, PDA and MS data.     

Comparative study on fatty acid composition of olive (Olea europaea L.), with emphasis on phytosterol contents

The present study was designed to determine the fatty acid composition and phytosterol contents of Turkish native olive cultivars, namely Kilis Yağlık and Nizip Yağlık cv. In this context, olive fruits from 34 locations were sampled and then screened for their components in comparison. Fifteen different fatty acids were found in both olive oils. In the order of abundance, the most important ones were oleic acid (18:1) > palmitic acid (16:0) > linoleic acid (18:2) > stearic acid (18:0). Significant differences were observed in the contents of oleic acid (18:1), palmitic acid (16:0), linoleic acid (18:2) but not for stearic acid content in comparison both oils (p < 0.01). There were significant differences in terms of unsaturated fatty acids, saturated fatty acids and polyunsaturated fatty acids (p < 0.01). The seven phytosterols – cholesterol, campesterol, stigmasterol, β ‐sitosterol, Δ‐5‐avenasterol, Δ‐7‐stigmastenol and Δ‐7‐avenasterol – were studied in both oil sources. The predominant sterols were β ‐sitosterol, Δ5‐avenasterol and campesterol in the samples analysed. However, no significant differences were found in the levels of the phytosterols between the two olive cultivars.     

Fatty Acid Composition of Seed Oils of Twelve Salvia Species Growing in Turkey

Seed oils of 12 Salvia species collected from different regions in Turkey (S. Albimaculata Hedge & Hub.-Mor., S. Candidisima Vahl., S. Cedronella Boiss., S. Cryptantha Montbret & Aucher ex Bentham, S. Forskahlei L., S. Fruticosa Miller (Sin. S. Triloba L. Fil), S. Halophila Hedge, S. Hypargeia Fisch. & Mey., S. Sclarea L., S. Tomentosa Miller, S. Tchihatcheffii (Fisch. & Mey.) Boiss., S. Virgata Jacq.) were obtained by Soxhlet apparatus using hexane. The oil yields were found to be between 2.0% and 20.9%. Fatty acids in the oils were converted to methyl esters and determined by GC/MS in methyl ester form. The main fatty acid components of S. halophila, S. Hypargeia, and S. Sclarea are unsaturated oleic, linoleic, and linolenic acids. In others except S. Candidissima, the dominant acids are oleic, linoleic and palmitic acids.     

Fatty acid composition of some Astragalus species from Turkey

In this study, the fatty acid contents of some Astragalus L. (Fabaceae) species from Turkey were determined by GC and GC-MS techniques. The seed oils of Astragalus sp. (A. echinops Aucher ex. Boiss., A. subrobustos Boriss., A. jodostachys, Boiss. & Buhse., A. falcatus Lam., A. fraxinifolius DC.) contained linolenic (between 23–41.%), linoleic (23–37%), and oleic acids (8–19%) as the major components. Fatty acid composition of the studied Astragalus taxa showed uniform fatty acid patterns. Palmitic and stearic acids were the major saturated fatty acids in the seed oils. The amounts of unsaturated fatty acids were higher than saturated fatty acids. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 526–528, November–December, 2006.     

Cytotoxicity of new secondary metabolites,fatty acids and tocols composition of seeds of Ducrosia anethifolia (DC.) Boiss

Two new monoterpene Ducrosin A (1) and sesquiterpene Ducrosin B (2) were isolated along with three known compounds, stigmasterol (3) and two furanocoumarins (4 and 5), from the dichloromethane extract of the seeds of Ducrosia anethifolia (DC.) Boiss. Their structures were determined using extensive 1D and 2D NMR, (ES)-HRMS and IR spectroscopic analyses and by comparison with literature data. Gas chromatography analysis of the fatty acids (FAs) of D. anethifolia seed oils (DAOs) showed high percentages of elaidic acid (C18:1 Δ9t) 65% and oleic acid (C18:1 Δ9c) 15%. The total tocopherol (tocols) content in DAOs was found to be 164 mg/100 g. The cytotoxic effect of the isolates was also evaluated using the MTT assay against the HCT-116 and SKOV-3 cell lines. The results showed that compound 2 was the most cytotoxic agent followed by compounds 1 and 4, which has an epoxide moiety that most likely contributes to its activity.     

植物油中脂肪酸不同定量方法的比较分析

比较峰面积归一化法与标准曲线法两种方法分析植物油中脂肪酸百分比含量的差异。利用气相色谱-质谱联用仪(GC-MS)检测10种市售食用植物油中的8种主要脂肪酸,峰面积归一化法和标准曲线法计算脂肪酸的百分比含量。结果表明,标准曲线法与峰面积归一化法相比,肉豆蔻酸、棕榈酸、十七烷酸、硬脂酸和棕榈油酸所占的百分比升高,而油酸、亚油酸和亚麻酸比例降低;饱和脂肪酸比例升高,不饱和脂肪酸百分比降低。利用峰面积归一化法计算植物油中脂肪酸百分比时,降低了饱和脂肪酸比例,升高了不饱和脂肪酸比例,可能对健康有潜在的不利影响。建议使用标准曲线法计算不同植物油中脂肪酸的百分比。     

Physico-chemical properties of Tecoma stans Linn. seed oil: a new crop for vegetable oil

Tecoma stans Linn. is known to have various medicinal and therapeutic properties. However, to our knowledge, no information is available regarding their seed oils. In this study, the fatty acid (FA) compositions, physico-chemical properties and antioxidant capacities of T. stans seed oils (TSOs) were investigated. The oil content of the seeds was 15%. The FAs of the TSOs were analysed by GC–MS. α-Linolenic (45.47%), oleic (23.56%), linoleic (11.48%), palmitic (6.09%) and stearic (4.12%) acids were the major detected FAs. γ-Linolenic acid and stearidonic acid, unusually FAs, were also present (1.04% and 6.65%, respectively). The total tocol content in the TSOs was found to be 266.06 mg/100 g. The main component was γ-tocopherol (78.93%). The total phenolic content (168.69 mg GAE/100 g oil) and total flavonoid content (5.54 mg CE/g oil) were also determined in the TSOs.     

大果白刺游离脂肪酸的柱前衍生高效液相色谱-荧光检测法分析

采用2-（11H-苯[a]咔唑）乙基对甲苯磺酸酯（BCETS）为柱前荧光衍生试剂,通过梯度洗脱使得18种脂肪酸在BDS-C8柱上得到良好的分离.方法应用于大果白刺不同部位中游离脂肪酸的分析,结果表明大果白刺的果皮果肉和叶子中均含有大量的不饱和脂肪酸,其总不饱和脂肪酸含量分别为70.74%和73.47%.大果白刺种子中不饱和脂肪酸的含量相对较少,仅占总脂肪酸含量的57.21%,其不饱和脂肪酸组成主要是C18∶1（油酸）和C18∶2（亚油酸）.其中,大果白刺的果皮果肉中,不饱和脂肪酸主要是C18∶1、C18∶2和C18∶3（亚麻酸）.其叶子中的不饱和脂肪酸主要是C18∶3,所占总脂肪酸比例为48.34%.首次对大果白刺中的脂肪酸进行了分析,可以为大果白刺在食品、药品中的进一步开发应用和质量控制提供一定的数据支持.     

Chromatographic Analysis for Fatty Acids and Lipid-Soluble Bioactives of Derris indica Crude Seed Oil

A combination of column chromatography (CC), gas chromatography (GC), thin layer chromatography (TLC) and liquid chromatography (LC) techniques were performed to analyze lipid classes, fatty acids and fat-soluble bioactives of Derris indica crude seed oil. Hexane extract of Derris indica oilseeds was found to be 56%. Level of neutral lipids in the crude seed oil was the highest, followed by glycolipids and phospholipids, respectively. Linoleic followed by α-linolenic, palmitic and oleic were the major fatty acids in the crude seed oil. The ratio of unsaturated fatty acids to saturated fatty acids was higher in neutral lipid classes than in the polar lipid fractions. The oil was characterized by a relatively high amount of phytosterols, wherein the sterol markers were β-sitosterol, campesterol and stigmasterol. γ-Tocopherol was the major tocopherol while the rest being α-tocopherol. In consideration of potential utilization, detailed knowledge on the composition of Derris indica oil is of major importance.     

Oxygenated Metabolites of n‐3 Polyunsaturated Fatty Acids as Potential Oxidative Stress Biomarkers: Total Synthesis of 8‐F3t‐IsoP, 10‐F4t‐NeuroP and [D4]‐10‐F4t‐NeuroP

A wide variety of metabolic products of polyunsaturated fatty acids is of paramount importance for improving our medical knowledge in the field of oxidized lipids. Two novel metabolites of n‐3 polyunsaturated fatty acids, 8‐F_3t‐IsoP and 10‐F_4t‐NeuroP as well as a deuterated derivative thereof were synthesized based on an acetylenic intermediate. An original approach achieved lateral chain insertion of 8‐F_3t‐IsoP by a ring‐closing alkyne metathesis/semi‐reduction strategy together with a temporary tether.     

Physicochemical characteristics of the Lasiococca comberi Haines seeds

Physicochemical characteristics and fatty acid composition of Lasiococca comberi Haines (Euphorbiaceae), an endangered forest tree species, were determined for the first time. The oil, protein, crude fibre and carbohydrate contents in seeds were 41.5, 13.8, 22.2 and 11.6%, respectively. The refractive index, pH, specific gravity, saponification value, iodine value, peroxide value and p-anisidine value of seed oil were 1.4781, 6.4, 0.9, 178.4 mg KOH/g, 196 g I₂/100 g of oil, 5.1 mEq O₂/kg and 188.4, respectively. The predominant fatty acids were linolenic acid (65.3%), oleic acid (13.8%), linoleic acid (7.1%) and palmitic acid (5.3%). HPLC analysis revealed the presence of α-tocopherol (13.2 mg/100 g) and γ-tocopherol (6.3 mg/100 g) as the major tocopherols. The results indicated that L. comberi seed oil can be classified as drying oil having possible applications in different industries and as an important dietary source of omega-3 fatty acids.     

Compositions of the seed oil of the Borago officinalis from Iran

In order to investigate the composition of borage (Borago officinalis L.) seed oil, this research was performed under the field conditions at Shahriyar and Garmsar zones, Iran during the 2012 planting year. The oil yield of borage was 31.46% and 33.7% at Shahriyar and Garmsar zone, respectively, and nine and eight fatty acids were identified in the seed oil of borage at Shahriyar and Garmsar, respectively – palmitic, linoleic, stearic and γ-linolenic acids were dominant in the seed oil of borage from both zones. Unsaturated fatty acid content was more than the saturated fatty acids in both zones. The ratio of linoleic acid and α-linolenic acid in the borage cultivated at Shahriyar and Garmsar zones was 2.13 and 2.29. The fatty acid profile of Garmsar borage, oleic and oleic/linoleic acid ratio, increased. Locations with different ecological conditions resulted in changes in both seed oil content and fatty acid profile of borage.     

Fatty acid,tocopherol, and sterol content of three <Emphasis Type="Italic">Teucrium</Emphasis> species from Tunisia

In the present study analyses concerning the composition of vitamin E, sterols, triglycerides, and fatty acids of three Teucrium species (Teucrium alopecurus, T. nabli, and T. polium) seed oil were performed. Linoleic, linolenic, and palmitic were the major fatty acids. The oil was characterized by a high amount of phytosterol, wherein clerosterol, sitosterol, and stigmasterol are the main constituents. The amount of tocopherol is nearly 550 mg/kg of oil, with α-tocopherol as the major isomer. Information concerning the composition of Teucrium seed oil is very important for evaluating the therapeutic effect of this oil. Published in Khimiya Prirodnykh Soedinenii, No. 3, pp. 261–264, May–June, 2009.     

High-pressure phase equilibria of binary and ternary mixtures of carbon dioxide,triglycerides and free fatty acids: Measurement and modeling with the GC-EOS

Vapor–liquid equilibria were measured for binary systems including carbon dioxide and free fatty acids such as oleic and linoleic acid, triglycerides as triolein or vegetable oils as sunflower oil, and modelled by the Group Contribution Equation of State (GC-EoS). Binary group parameters used in the calculation and prediction of CO₂–triglycerides systems were obtained from the literature but in the case of CO₂-free fatty acids, binary group parameters were adjusted through a parameterization strategy. At the end, a unique set of parameters could be established to model systems of vegetable oils at high pressures in the presence of CO₂. Moreover, a strategy to calculate the two-phase region in a ternary diagram was also studied. The good correspondence between theoretical and experimental results suggests that the strategy and the set of binary group parameters proposed in this work can be reliable predictive tools for using GC-EoS to describe systems involving vegetable oils with a composition based mainly in free fatty acids and triglycerides, such as those which can be encountered, for example, in oil deacidification processes using supercritical CO₂.     

Characterization of Phenolic Compounds,Vitamin E and Fatty Acids from Monovarietal Virgin Olive Oils of “Picholine marocaine” Cultivar

Olive oil is an important product in the Mediterranean diet, due to its health benefits and sensorial characteristics. Picholine marocaine is the most cultivated variety in Morocco. The present research aims to evaluate the phenolic compounds, vitamin E and fatty acids of commercial Picholine marocaine virgin olive oils (VOOs) from five different North Moroccan provinces (Chefchaouen, Taounate, Errachidia, Beni Mellal and Taza), using HPLC-photodiode array (PDA)/electrospray ionization (ESI)-MS, normal phase (NP)-HPLC/ fluorescence detector (FLD) and GC-flame ionization detector (FID)/MS, respectively. The obtained results showed an average content of 130.0 mg kg⁻¹ of secoiridoids (oleuropein aglycone, 10-hydroxy-oleuropein aglycone and ligstroside aglycone, oleocanthal and oleacein), 108.1 mg kg⁻¹ of phenolic alcohols (tyrosol and hydroxytyrosol), 34.7 mg kg⁻¹ of phenolic acids (caffeic acid, ferulic acid and elenolic acid), and 8.24 mg kg⁻¹ of flavonoids (luteolin, luteolin glucoside, apigenin). With regard to vitamin E, α-tocopherol was the most abundant vitamin E (57.9 mg kg⁻¹), followed by α-tocotrienol (2.5 mg kg⁻¹), γ-tocopherol (4.5 mg kg⁻¹) and β-tocopherol (1.9 mg kg⁻¹), while δ-tocopherol was not detected. Moreover, 14 fatty acids were found and, among them, oleic acid (76.1%), linoleic acid (8.1%) palmitic acid (8.7%) and stearic acid (2.5%) were the major fatty acids detected. Finally, heat map and principal component analysis allowed us to classify the studied provinces in terms of VOO chemical composition: Chefchaouen (tyrosol and hydroxytyrosol), Taounate (oleuropein aglycone), Errachidia (ferulic acid, w-3 and w-6), Beni Mellal (oleocanthal) and Taza (luteolin and oleic acid).     

快速气相色谱法测定食用油中的未衍生化长链脂肪酸

建立了利用短的微径色谱柱直接测定食用油中未衍生化长链脂肪酸的快速气相色谱方法。C12~C22脂肪酸在2 min之内实现基线分离，定量标准曲线的相关系数大于0.988，最低检测限（S/N=3）为2.80~9.60 mg/L,回收率为74.5%~86.5%。该方法快速、简便、准确，分析通量大，已成功地用于香油、色拉油及调和油等3种食用油中长链脂肪酸含量的测定。     

Simultaneous Determination of Six Free Fatty Acids in the Alcohol Extract of Tie Bang Chui with Gas Chromatography-Mass Spectrometry

A GC-MS method was developed for the determination of free fatty acids (FFAs) in the alcohol extract of Tie Bang Chui. Six major types of FFAs were identified. All the six FFAs identified in alcohol extract were quantified with nonadecanoic acid as an internal standard. The results showed that the alcohol extract was abundant in three types of FFAs, linoleic acid (38.14%, 8.49 ± 0.22 mg/g) was the predominant fatty acid, followed by palmitic acid and oleic acid, unsaturated FFAs amounted to 71.35% of the total FFA content, and there was no trans FFA present.     

柽柳实中挥发油和脂肪酸分析

首次研究了维药细穗柽柳(Tamarix leptostachys Bunge)实中挥发油和脂肪酸的化学成分。 分别采用药典中的挥发油提取法和索式取提法提取柽柳实中的挥发油和脂肪酸,使用气质联用技术获取总离子流图,各色谱峰相应的质谱图经过NIST2011标准谱库检索定性,并采用峰面积归一化法进行定量分析,计算各成分的相对百分含量。 两种方法分别鉴定出48种挥发油和19种脂肪酸。 挥发油主要成分为芳香类化合物(43.71%)、芳香性醛酮类(20.58%)、脂肪酸类(13.03%)、酯类(17.36%)和醇类(4.19%)等。 脂肪酸主要成分为棕榈酸(35.61%)、亚油酸(27.26%)和油酸(11.33%)等,其中不饱和脂肪酸含量占总脂肪酸含量的38.65%。 维药细穗柽柳实中富含丰富的挥发油和不饱和脂肪酸,具有很好的开发利用价值。