ENZYMATIC MODIFICATION OF BORAGE OIL: INCORPORATION OF EICOSAPENTAENOIC ACID

Borage oil ( Borago officinalis L.) fatty acid composition was modified to incorporate eicosapentaenoic acid (EPA), with an immobilized nonspecific SP435 lipase from Candida antarctica as biocatalyst. Transesterification, between borage oil and EPA ethyl ester (EEPA) was carried out in hexane. Incorporation increased with increasing concentration of EEPA. An enzyme concentration of 20% gave 31% EPA incorporation into borage oil. As the incubation time increased, EPA incorporation was also increased up to 36 h.     

Gamma-linolenic acid enrichment from Borago officinalis and Echium fastuosum seed oils and fatty acids by low temperature crystallization

Solvent winterization of seed oil and free fatty acids (FFAs) was employed to obtain gamma-linolenic acid (GLA; 18:3omega6) concentrates from seed oils of two Boraginaceae species, Echium fastuosum and Borago officinalis. Different solutions of seed oils and FFAs from these two oils at 10%, 20% and 40% (w/w) were crystallized at 4 degrees C, -24 degrees C and -70 degrees C, respectively, using hexane, acetone, diethyl ether, isobutanol and ethanol as solvents. Best results were obtained for B. officinalis FFAs in hexane, reaching a maximum GLA concentration of 58.8% in the liquid fraction (LF). In E. fastuosum, the highest GLA concentration (39.9%) was also achieved with FFAs in hexane.     

Canarium zeylanicum seed oil: an edible oil with beneficial qualities

The quality parameters, fatty acid composition, phenolic compounds and antioxidant properties of the seed oil of Canarium zeylanicum were determined. The results indicate that the seed oil of Canarium zeylanicum is an excellent source of essential fatty acids which contains C18:2 (49.35 ± 0.35%) and C18:3 (19.09 ± 0.01%). The total phenol contents of the seed oil and the seed hull of Canarium zeylanicum were 66 ± 6 and 2014 ± 14 mg kg⁻¹respectively. The identified phenolic acids in the methanolic extracts of seed oil include 3,4-dihydroxybenzoic acid, p -hydroxybenzoic acid, vanillic acid and ellagic acid. Diphenyl-2-picrylhydrasyl radical scavenging activity, inhibition of deoxyribose degradation and the reducing power of the methanolic extracts of seed oil and seed hull of Canarium zeylanicum are comparable with those of butylated hydroxytoluene solutions.     

Chemical Composition and Antioxidant Capacity of Brazilian Passiflora Seed Oils

The seed oils of different varieties of 4 Passiflora species cultivated in Brazil were analyzed and compared regarding their physicochemical parameters, fatty acid composition and the presence of minor components, such as phytosterols, tocopherols, total carotenoids, and phenolic compounds. The antioxidant capacities of the oil extracts were determined using the 2,2'azinobis [3‐ethylbenzothiazoline‐6‐sulfonic acid] and oxygen radical absorbance capacity methods. The results revealed that all studied Passiflora seed oils possessed similar physicochemical characteristics, except for color, and predominantly contained polyunsaturated fatty acids with a high percentage of linolenic acid (68.75% to 71.54%). Other than the total phytosterol content, the extracted oil from Passiflora setacea BRS Pérola do Cerrado seeds had higher quantities (% times higher than the average of all samples), of carotenoids (44%), phenolic compounds (282%) and vitamin E (215%, 56%, 398%, and 100% for the α‐tocopherol, β‐tocopherol, γ‐tocopherol, and δ‐tocopherol isomers, respectively). The methanolic extracts from Passiflora setacea BRS Pérola do Cerrado seed oil also showed higher antioxidant activity, which was positively correlated with the total phenolic, δ‐tocopherol, and vitamin E contents. For the first time, these results indicate that Passiflora species have strong potential regarding the use of their seeds for oil extraction. Due to their interesting composition, the seed oils may be used as a raw material in manufacturing industries in addition to other widely used vegetable oils.     

Comparative Study of Bioactive Constituents in Turkish Olive Oils by LC-ESI/MS/MS

The purpose of this research was to evaluate and compare the differences in the phenolic composition, antioxidant properties, and fatty acids of virgin olive oils from the Ayvalik, Gemlik, and Memecik olive varieties cultivated in their respective growing areas over two harvest years. The phenolic composition of olive oils was carried out by liquid chromatography coupled with diode array detection and electrospray ionization mass spectrometry analysis and the fatty acid composition was determined by gas chromatography analysis. Fourteen phenolic compounds were identified and, among these, the most dominant were elenolic acid, tyrosol, and hydroxytyrosol. For olives from both years, the highest total phenolic content was determined in Memecik followed by Ayvalik and Gemlik. 2,2-diphenyl-1-picryl hydrazyl and 2,2′-azino-bis- (3-ethyl-benzothiazoline-6-sulphonic acid) methods were used to determine the antioxidant capacity of the olive oil extracts. In both methods, the antioxidant capacity values were higher for oil from cv. Ayvalik. Thirteen fatty acids were identified and quantified in all samples. Oleic acid was the highest concentration and this acid was more dominant in Gemlik oils.     

Central composite design for the optimization of supercritical carbon dioxide fluid extraction of fatty acids from Borago officinalis L. flower

Abstract: In the present study, fatty acids and essential oils of the flower of borage (Borago officinalis L.) were obtained by supercritical carbon dioxide fluid extraction under different conditions. The extracts obtained were compared to oils of borage flower oil isolated by hydrodistillation. The obtained oils were analyzed by gas chromatography mass spectrometry. The compounds were identified according to their retention indices and mass spectra. The experimental parameters of supercritical fluid extraction (SFE) were optimized using a central composite design after a full factorial experimental design. Extraction yields based on SFE varied in the range of 0.02% to 1.96% (w/w), and the oil yield based on the hydrodistillation was 0.05% (v/w). The optimum conditions of SFE were obtained at a pressure of 350 atm, a temperature of 65 °C, a methanol modifier volume of 100 μL, and static and dynamic extraction time of 10 min. Main components of the extracts under optimum SFE conditions were palmitic acid, linoleic acid, γ‐linolenic acid, and oleic acid. The results indicated that by using the suitable extraction conditions, SFE is more effective than the conventional hydrodistillation method in the extraction of fatty acids and the preservation of its quality. Practical Application: SFE is a good technique for the extraction of oils from plants. The extraction yields by SFE are more than the conventional method. SFE is used on a large scale for production of essential oils and pharmaceutical products from plants.     

Fatty acid composition,oxidative stability,antioxidant and antiproliferative properties of selected cold-pressed grape seed oils and flours

Cold-pressed chardonnay, muscadine, ruby red, and concord grape seed oils and their defatted flours were studied for their fatty acid composition, oxidative stability and antioxidant and antiproliferative activities. The phenolic profiles of the seed flours were also measured. The most abundant fatty acid in the oils was linoleic acid, ranging from 66.0 g/100 g of total fatty acids in ruby red seed oil to 75.3 g/100 g of total fatty acids in concord seed oil. The oils were also high in oleic acid and low in saturated fat. Ruby red grape seed oil recorded the highest oxidative stability index of 40 h under the accelerated conditions. Total phenolic content (TPC) was up to 100 times lower in the oils than in the flours. Lutein, zeaxanthin, cryptoxanthin, β-carotene, and α-tocopherol levels were also measured. DPPH radical-scavenging capacity ranged from 0.07 to 2.22 mmol trolox equivalents (TE)/g of oil and 11.8 to 15.0 mmol TE/g of flour. Oxidative stability of menhaden fish oil containing extracts of the seed flours was extended by up to 137%. HPLC analysis was conducted to determine the levels of free soluble, soluble conjugated and insoluble bound phenolics in the seed flours. The phenolic compounds analyzed included catechin, epicatechin, epicatechin gallate, quercetin, gallic acid, and procyanidins B1 and B2. Antiproliferative activity was tested against HT-29 colon cancer cells. All of the seed flours and muscadine seed oil registered significant (P < 0.05) inhibition of cancer cell growth. The results from this study demonstrate the potential of developing value-added uses for these seed oils and flours as dietary sources of natural antioxidants and antiproliferative agents for optimal health.     

山茱萸籽油的理化性质及脂肪酸组成分析

主要对山茱萸籽的组成、山茱萸籽油的理化性质及脂肪酸组成进行了分析.结果表明:山茱萸籽中还原糖、总糖、粗蛋白和粗脂肪含量分别为29.2％、64.7％、21.7％和13.1％.山茱萸籽油酸值(KOH)、碘值(Ⅰ)、过氧化值及皂化值(KOH)分别为0.97 mg/g、113.8 g/100 g、8.9 mmol/kg、186.5 mg/g.山茱萸籽油中饱和脂肪酸以棕榈酸(10.40％)为主,其次是硬脂酸(3.49％)和山嵛酸(3.32％);不饱和脂肪酸中油酸(35.80％)和亚油酸(34.60％)含量较高,还含有5.51％的芥酸.     

不同超声波处理方式辅助三相分配法提取琉璃苣籽油的比较

采用三相分配法(TPP)提取琉璃苣籽油,以琉璃苣籽油得率为指标,对提取时间、料液比、硫酸铵加量、水相与叔丁醇体积比进行了研究;同时比较了超声波预处理辅助三相分配法(UPTPP)和超声波辅助三相分配法(UTPP)对琉璃苣籽油提取效果的影响。结果表明:采用TPP,在料液比1∶15、提取时间20 min、硫酸铵加量0.35 g/mL、水相与叔丁醇体积比1∶2时,琉璃苣籽油得率最大,为31.26%;采用超声波作为过程强化方法,可缩短TPP的提取时间,且UPTPP优于UTPP,在超声波预处理时间160 s、超声功率100 W、占空比50%时,琉璃苣籽油得率为33.57%,比TPP提高了2.31个百分点。因此,超声波预处理后采用三相分配法是一种有效的油脂提取方法。     

Distribution of fatty acids in edible organs and seed fractions of borage (Borago officinalis L.)

BACKGROUND: Borage (Borago officinalis L.) is currently used as a vegetable in the north of Spain. The edible parts of the plant are the petioles, leaves and stems. The objective of this study was to determine the oil and fatty acids content in the edible tissues (leaves, petioles and stems) and seed fractions (endosperm + cotyledon, seed coat and elaiosome) of white‐ and blue‐flowered borage accessions. RESULTS: Leaves showed higher mean values of oil content (2.7%) than petioles and stems (1.1% and 1.4%, respectively) in both, blue‐ and white‐flowered material. The most abundant fatty acids in leaves were palmitic, linoleic, α‐linolenic and stearidonic acids (about 75% of the total fatty acids), while in petioles and stems myristic and linoleic acids were most abundant (about 60% of the total fatty acids). Palmitic, oleic, linoleic and γ‐linolenic (GLA) acids were the major fatty acids of seed coat and endosperm + cotyledon in borage seeds (85% of the total fatty acids), while palmitic, stearic, oleic and linoleic acids were the most abundant fatty acids of elaisome in borage seeds (80% of the total fatty acids). CONCLUSION: This paper shows that green parts of borage contain substantial amounts of omega‐3 and omega‐6 fatty acids, which are essential fatty acids for animal and human nutrition. Thus, borage could be a ‘power food’ of the future because of its content of unsaturated fatty acids, particularly the essential fatty acids, which have great potential to prevent cardiovascular disease, cancer and infectious diseases. Copyright © 2007 Society of Chemical Industry     

Effect of endogenous antioxidants of sesame seeds and sesame oil to the thermal stability of edible vegetable oils

Differently processed sesame seeds were used for the preparation of sesamol, seed extract, oil extract or unsaponifiable matter. Analysis of these sesame extracts revealed that dehulling and roasting of seeds had an adverse effect on their lignan and phenolic compounds content. Various concentrations of the extracts were incorporated in vegetable oils and their effectiveness in retarding the oxidative deterioration of oils was evaluated. Additionally, the formation of oxidation products in these oil samples was correlated with their antioxidant activity and their sesamol and phenolic compounds content. Results indicated that decomposition of phenolic compounds present in oil samples induced a significant reduction in their linoleic acid peroxidation inhibition capacity and a corresponding increase in their oxidative rancidity. Sesame seed extract was the most effective in protecting oils from oxidation, suggesting that seed extract, especially the one prepared from coated-unroasted sesame seeds, may have potential application as a source of natural antioxidants in oil industry.     

Fatty acid profile, thymoquinone content, oxidative stability, and antioxidant properties of cold-pressed black cumin seed oils

Six different batches of cold-pressed black cumin seed oils (BCSO) were evaluated for their fatty acid profiles, thymoquinone contents, oxidative stability, and antioxidant properties. Linoleic, oleic, and palmitic acids were the major fatty acids in the tested oils. The cold-pressed BCSO samples differed in their oxidative stability measured as the oxidative stability index (OSI). The greatest OSI was about 155 h, and the lowest OSI was proximately 76 h, reflecting a 2-fold difference in their oxidative stability. These BCSO contained significant level of phenolic components with a concentration ranging from 1.02 to 1.40 mg gallic acid equivalents/g oil. In addition, BCSO contained about 3.48-8.73 mg/g thymoquinone and trace amount of dithymoquinone. Electron spin resonance (ESR) analysis showed that cold-pressed BCSO contained natural antioxidants and was able to suppress radical mediated lipid peroxidation in fish oil. The methanol extracts of BCSO could directly react with and quench DPPH radicals, which further confirmed the antioxidant property of these BCSO. The results from the present study suggest that cold-pressed black cumin seed oil may serve as an excellent dietary source of thymoquinone and natural antioxidants.     

响应曲面优化超声辅助提取山茱萸籽油工艺及其成分分析

研究以正己烷为溶剂超声辅助提取山茱萸籽油的工艺,并对其成分进行分析。采用响应曲面优化法(RSM)优化山茱萸籽油的提取工艺,确定最佳提取工艺参数为提取温度40℃、提取时间40min、液料比10:1(mL/g),在此条件下,山茱萸籽油的一次提取率为97.08%(出油率7.90%)。利用GC-MS对山茱萸籽油中脂肪酸成分进行分析,结果表明：山茱萸籽油的主要脂肪酸成分为油酸(61.89%)、硬脂酸(19.99%)、棕榈酸(7.63%)和亚油酸(6.33%)等,不饱和脂肪酸占脂肪酸总量的69.45%;采用高效液相色谱法测定,山茱萸籽油中VE含量为76.0mg/100g。     

Antioxidant capacities of phenolic compounds and tocopherols from Tunisian pomegranate (Punica granatum) fruits

This article aims to determine the phenolic, tocopherol contents, and antioxidant capacities from fruits (juices, peels, and seed oils) of 6 Tunisian pomegranate ecotypes. Total anthocyanins were determined by a differential pH method. Hydrolyzable tannins were determined with potassium iodate. The tocopherol (α-tocopherol, γ-tocopherol, and δ-tocopherol) contents were, respectively, 165.77, 107.38, and 27.29 mg/100 g from dry seed. Four phenolic compounds were identified and quantified in pomegranate peel and pulp using the high-performance liquid chromatography/ultraviolet method: 2 hydroxybenzoic acids (gallic and ellagic acids) and 2 hydroxycinnamic acids (caffeic and p-coumaric acids). Juice, peel, and seed oil antioxidants were confirmed by ferric reducing antioxidant power (FRAP) and oxygen radical absorbance capacity (ORAC) methods. The highest values were recorded in peels with 25.63 mmol trolox equivalent/100 g and 22.08 mmol TE/100 g for FRAP and ORAC assay, respectively. Results showed that the antioxidant potency of pomegranate extracts was correlated with their phenolic compound content. In particular, the highest correlation was reported in peels. High correlations were also found between peel hydroxybenzoic acids and FRAP ORAC antioxidant capacities. Identified tocopherols seem to contribute in major part to the antioxidant activity of seed oil. The results implied that bioactive compounds from the peel might be potential resources for the development of antioxidant function dietary food.     

提取方式对接骨木籽油品质的影响

目的：比较冷榨法、索式提取法、亚临界丁烷萃取法对接骨木籽油得率、理化指标、脂肪酸组成以及体外抗氧化活性的影响。方法：以接骨木籽为原料,采用冷榨法、索式提取法和亚临界丁烷萃取法3种方式提取接骨木籽油,参考国家标准测定其理化指标与体外抗氧化活性,并利用GC-MS联用技术分析其脂肪酸组成。结果：3种提取方式中,亚临界丁烷萃取法的得油率最高(28.8%),索式提取法次之(27.6%),冷榨法最低(18.8%);亚临界丁烷萃取法所得的接骨木籽油的酸价和过氧化值最低,碘值最高;3种不同提取方式所得的接骨木籽油脂肪酸组成相似,主要成分为亚麻酸、亚油酸、棕榈酸,但含量存在一定差异,亚临界丁烷萃取法所得的接骨木籽油的亚麻酸含量最高,为46.94%;3种提取方式所得的接骨木籽油均具有良好的抗氧化活性,但亚临界丁烷萃取法的DPPH自由基、ABTS自由基清除能力高于冷榨法与索式提取法。结论：不同提取方法对接骨木籽油的品质存在一定影响,亚临界丁烷萃取法对接骨木籽油有较高提取率,所得油脂品质较好,是提取接骨木籽油的理想方法。     

樟树籽油抗氧化能力及物质基础研究

植物油中天然抗氧化成分对油脂的加工、货架期及营养品质具有重要影响。为研究樟树籽油抗氧化活性及物质基础,本文分别对其脂肪酸组成、不皂化物含量、总酚含量和DPPH自由基清除率进行测定,分析总多酚及不皂化物对樟树籽油抗氧化活性的贡献率,明确樟树籽油抗氧化活性物质基础。结果表明,樟树籽油中主要为中链脂肪酸癸酸和月桂酸,二者含量占总脂肪酸的94.80%,不皂化物含量为0.55±0.01% ,总多酚含量为33.07 ±0.63 mg.kg_^-1。樟树籽油对DPPH自由基清除率的IC₅₀值为0.13 g.mL_^-1。相同质量浓度的樟树籽油、不皂化物和总多酚对DPPH自由基清除率分别为98.92±1.58%、38.49±0.66%、49.60±3.78%。因此,不皂化物及总酚对樟树籽油抗氧化贡献率分别为38.91%、50.14%。研究结果表明樟树籽油具有较强的抗氧化能力,其抗氧化活性物质主要为多酚类成分和不皂化物,二者对樟树籽油抗氧化能力的总贡献率高达89.05%。本研究初步明确了樟树籽油的抗氧化活性成分,可为樟树籽油的开发利用奠定基础。     

Essential oil extracted from peach (Prunus persica) kernel and its physicochemical and antioxidant properties

Peach kernel oil was extracted using Soxhlet extraction with different solvents (petroleum ether, ethyl ether, chloroform and hexane). The physicochemical properties (acid value, iodine value, peroxide value and saponification value), the fatty acid composition, phenolic constituents and contents, and antioxidant activities of peach kernel oil were examined. As per our results, oil extracted with hexane has better overall quality. Its acid, peroxide, iodine and saponification values were 0.895 mg KOH/g oil, 0.916 mg/g oil, 36.328 mg/100 g oil and 101.836 mg KOH/g oil, respectively. Large proportions of unsaturated fatty acid (91.27%) and high content of phenolic compounds (4.1593 mg GAE/g), which contribute to considerably strong antioxidant activity, were found in oil. The main fatty acids found in the peach kernel oil were oleic acid (61.87 g/100 g oil) and linoleic acid (29.07 g/100 g oil). The HPLC analysis of phenolic compounds showed that rutin, (-)-epicatechin gallate, hydrocinnamic acid, sinopinic acid, dithiothreitol and caffeic acid were major constituents. The results suggested that peach kernel oil is a good source of the unsaturated fatty acid, phenolic compounds with strong antioxidant activity, and has the potential to be used as nutrient rich food oil. The results also verified that peach kernel meals contained higher amounts of total phenolic and stronger antioxidant activities than oils, enabling their application as ingredients for functional or enriched foods.     

Chemical analysis and preliminary toxicological evaluation of Garcinia mangostana seeds and seed oil

The chemical analysis and preliminary toxicological evaluation of Garcinia mangostana seeds and seed oil have been investigated in order to determine the possibility of using them for human and/or animal consumption. Proximate analysis showed that the seeds had high amount of carbohydrate and were rich in oil (21.68 ± 6.18%) but have a low protein content. The physical properties of the oil extracts showed the state to be liquid at room temperature (25 ± 1 °C) and the colour of the oil golden-orange. The specific gravity of the oil was 0.98 ± 0.01. Among the chemical properties of the oil extracts, acid value, saponification number, iodine value, percent free fatty acid and peroxide value compared well with those of conventional edible oils. The seed flour was found to be a good source of minerals. It contained considerable amounts of potassium (7071 mg/kg), magnesium (865 mg/kg) and calcium (454 mg/kg). Fatty acid composition of the seed oil indicated that the oil contained one essential fatty acids small proportions: linoleic acid (1.30%). The most prevalent fatty acids were palmitic acid (49.5%) and oleic acid (34.0%). Weanling albino rats appeared to suffer no toxicological effects when fed with G. mangostana seed oil in their diet for 8 weeks. Weekly monitoring of the rats showed good physical appearance and steady weight increase. Histological examination of sections of the heart, liver, kidney, spleen and lung revealed that the kidney of some of the rats had some degrees of pathology which included diffuse glomerular and tubular degeneration. No lesion was found in the heart and liver of the rats. The seed oil could be useful as an edible oil and for industrial applications.     

Characterization of Rosehip (Rosa canina L.) Seed and Seed Oil

In this study, the nutritional composition and phytochemical composition of the rosehip seed, and the fatty acid and sterol compositions of the seed oil were investigated. The rosehip seed contained valuable phytochemicals such as phenolic compounds (2554 μg/g), carotenoids (2.92 μg/g), and ascorbic acid (1798 μg/g). Furthermore, the rosehip-seed oil was rich in polyunsaturated fatty acids, linoleic acid (54.05%), linolenic acid (19.37%), and phytosterols, mainly β-sitosterol (82.1%). The rosehip seed and seed oil were found to have antioxidant activity measured by trolox equivalent antioxidant capacity assay. It can be concluded that the rosehip seed and seed oil may be utilized as a source of phytonutrients.     

茶叶籽油与油茶籽油理化性质及脂肪酸组成比较

在对茶叶籽及油茶籽的外观、含仁率、含油率等进行测定的基础上,对茶叶籽油及油茶籽油的理化性质及脂肪酸组成进行了分析。结果表明,茶叶籽及油茶籽外观相差较大,茶叶籽油与油茶籽油在折光指数、酸值、碘值和皂化值等理化性质上较接近。脂肪酸组成上,油酸、亚油酸、棕榈酸为茶叶籽油及油茶籽油中含量最多的三种脂肪酸,油酸含量分别为52.13%和73.67%,亚油酸24.32%和11.09%,棕榈酸17.36%和10.63%。茶叶籽油和油茶籽油的单不饱和脂肪酸含量分别为54.12%和75.78%,多不饱和脂肪酸含量为24.55%和11.39%。茶叶籽含油率为19.88%,茶叶籽油潜在年产量可达15余万t。其必需脂肪酸含量是油茶籽油的2.15倍;不皂化物含量为0.77%,比油茶籽油高出22%;茶叶籽油脂肪酸比例均衡,适于人体的吸收,具有开发应用的潜力。