Borage and evening primrose oil

The paper gives a short overview about the production and composition of borage (Borago officinalis) and evening primrose (Oenothera biennis) oil considering special aspects of the production as cold‐pressed oil. Both oils are characterized by a remarkable amount of γ‐linolenic acid, which has some nutritional advantages. The fatty acid composition of evening primrose oil is dominated by linoleic acid with about 72% and about 13% γ‐linolenic acid, while borage oil consists of twice the amount of γ‐linolenic acid and only 38% linoleic acid. The amount of saturated fatty acids is higher in borage oil. The tocopherol composition of both oils is dominated by γ‐tocopherol, with borage oil containing twice the amount compared to evening primrose oil.     

Kinetics of supercritical carbon dioxide extraction of borage and evening primrose seed oil

In the present work, high‐pressure extraction of borage (Borago officinalis L.) and evening primrose (Oenothera biennis L.) seed oil, containing the valuable γ‐linolenic acid (GLA), has been investigated. Extraction was performed with supercritical carbon dioxide on a semi‐continuous flow apparatus at pressures of 200 and 300 bar, and at temperatures of 40 and 60 °C. A constant flow rate of carbon dioxide in the range from 0.17 to 0.20 kg/h was maintained during extraction. The extraction yields obtained using dense CO₂ were similar to those obtained with conventional extraction using hexane as solvent. The composition of extracted crude oil was determined by GC analysis. The best results were obtained at 300 bar and 40 °C for both seed types extracted, where the quality of oil was highest with regard to GLA content. The evening primrose seed oil extracted with supercritical fluid extraction was particularly rich in unsaturated fatty acids: up to 89.7 wt‐% of total free fatty acids in the oil. The dynamic behavior of the extraction runs was analyzed using two mathematical models for describing the constant rate period and the subsequent falling rate period. Based on the experimental data, external mass transfer coefficients, diffusion coefficients and diffusivity in solid phase were estimated. Results showed good agreement between calculated and experimental data.     

Supercritical extraction of evening primrose oil: Experimental optimization via response surface methodology

Supercritical carbon dioxide (CO₂) effective extraction parameters (pressure, temperature, static extraction time, and dynamic extraction time) of oil recovery from evening primrose seeds were optimized via response surface methodology (RSM). The results of this study indicated that the linear terms of static and dynamic time and the quadratics of temperature and pressure, as well as the interactions of temperature and static time, pressure and temperature had a significant effect on the oil recovery. The optimum extraction conditions of 14.2 MPa, 47.3°C, 30 min (static extraction time) and 150 min (dynamic extraction time) were obtained. Applying the optimum conditions, a mean experimental recovery of 92.98% (triplicate experiment) was achieved, which is well compatible with the RSM‐predicted value (93.61%). The fatty acid composition of extracted evening primrose oil using supercritical CO₂ was compared with that obtained by Soxhlet method in which minor difference was observed. © 2011 American Institute of Chemical Engineers AIChE J, 2011     

Supercritical carbon dioxide extraction of evening primrose oil

The oil extracted from the seeds ofOenothera biennis L. (evening primrose) is a major commercial source of gamma-linolenic acid, a fatty acid having potential therapeutic value in the treatment of several diseases. This fatty acid is prone to oxidation and thermal rearrangement; therefore, the conventional recovery of the oil via mechanical expression and hexane extraction must be carried out under very mild and controlled conditions. In this study, supercritical fluid extraction with carbon dioxide has been employed as an alternative method to recover evening primrose oil (EPO). Extractions were performed over the pressure range of 20–70 MPa and at temperatures from 40 to 60°C, with a CO₂ mass flow rate of 18 g/min. The experimental data permitted the determination of EPO solubility in supercritical CO₂ at the tested extraction conditions. Supercritical fluid Chromatographic analysis of fractions collected during the extraction showed a subtle shift in the triglyceride composition. Fatty acid methyl ester analysis on similar fractions indicated that the fatty acid content was invariant with respect to extraction time. The mention of firm names or trade products does not imply that they are endorsed or recommended by the U.S. Department of Agriculture over other firms or similar products not mentioned.     

Enrichment of γ-linolenic acid from evening primrose oil and borage oilvia lipase-catalyzed hydrolysis

Lipase-catalyzed selective partial hydrolysis of evening primrose (Oenothera biennis L.) seed oil and borage (Borago officinalis L.) seed oil led to an increase in the level of γ-linolenic acid (GLA; 18∶3n−6) in the unhydrolyzed acylglycerols. Thus, in evening primrose oil, the GLA level could be raised from 9.4% in the starting material to 46.5% in the unhydrolyzed acylglycerols by means of a lipase fromCandida cylindracea. Selective hydrolysis of borage oil with Pancreatin led to an increase in the GLA content from 20.4% in the oil to 33.5% in the unhydrolyzed acylglycerols. Partial hydrolysis of borage oil with lipase fromC. cylindracea raised the GLA content of the acylglycerols to 47.8%.     

γ-Linolenic acid concentrates from borage and evening primrose oil fatty acidsvia lipase-catalyzed esterification

γ-Linolenic acid (GLA, all-cis 6,9,12-octadecatrienoic acid) has been enriched from fatty acids of borage (Borago officinalis L.) seed oil to 93% from the initial concentration of 20% by lipase-catalyzed selective esterification of the fatty acids withn-butanol in the presence ofn-hexane as solvent. The immobilized fungal lipase preparation, Lipozyme, used as biocatalyst, preferentially esterified palmitic, stearic, oleic and linoleic acids and discriminated against GLA, which was thus concentrated in the unesterified fatty acids fraction. In the absence of hexane, concentrate containing about 70% GLA was obtained. When the reaction conditions, optimized for borage oil fatty acids, were applied to fatty acids of evening primrose (Oenothera biennis L.) oil, concentrates containing 75% GLA were obtained. From both oils, GLA concentrates were prepared efficiently in short reaction times (1–3 h) at 30–60°C. The process can be applied for the production of GLA concentrates for dietetic purposes.     

Antioxidant activity of evening primrose phenolics in sunflower and rapeseed oils

Crude ethanol/ethyl acetate extracts of industrial evening primrose (Oenothera biennis L.) seed meal were separated into six fractions using the Sephadex LH‐20 column chromatography and 96% aqueous ethanol as a mobile phase. Their antioxidant activities were tested in sunflower and rapeseed oils by using an Oxidograph apparatus at a temperature of 110 °C. Only the fractions III and IV displayed a pronounced antioxidant activity while the other fractions were either inactive or even pro‐oxidative. The active fractions contained phenolic acids and their esters; gallic acid, methyl and ethyl gallates, protocatechuic acid and its methyl ester were identified by GC/MS. Catechin was present, too, but exhibited only moderate antioxidant activity in sunflower oil.     

Oxidative stability of stripped and nonstripped borage and evening primrose oils and their emulsions in water

Oxidative stability of stripped and nonstripped borage and evening primrose oils and their emulsions in water was evaluated. The results indicated that column chromatographic techniques provide an effective means for stripping vegetable oils of their minor components. However, some minor components may be retained in the stripped oils. The minor components in borage and evening primrose oils significantly (P<0.05) influenced their oxidative stability in the dark. In contrast, the behavior of endogenous antioxidants in borage and evening primrose oil-in-water emulsions, according to the “polar paradox” theory, was difficult to evaluate. Correlations existed between peroxide value (PV) and conjugated dienes (CD) (P<0.05) as well as 2-thiobarbituric acid-reactive substances (TBARS) and hexanal content (P<0.01) for most oils and emulsion systems. Therefore, CD and TBARS may generally be used to assess the oxidative stability of borage and evening primrose oils and their oil-in-water emulsions in addition to or in place of PV and headspace volatiles, respectively.     

Enzymatic modification of evening primrose oil: Incorporation of n−3 polyunsaturated fatty acids

Immobilized lipase SP435 fromCandida antaractica was used as a biocatalyst for the modification of the fatty acid composition of evening primrose oil by incorporating n−3 polyunsaturated fatty acid (PUFA) and eicosapentaenoic acid (EPA). Transesterification (ester-ester interchange) was conducted in organic solvent or without solvent, with EPA ethyl ester (EEPA) as the acyl donor. Products were analyzed by gas-liquid chromatography (GLC). After 24-h incubation in hexane, the fatty acid composition of evening primrose oil was markedly changed to contain up to 43% EPA. The amount of 18:2n−6 PUFA was reduced by 32%, and the saturated fatty acid content was also reduced. The effects of incubation time, molar ratio, enzyme load, and reaction medium on mol% EPA incorporation were also studied. Generally, as the incubation time (up to 24 h), molar ratio, and enzyme load increased, EPA incorporation also increased. Evening primrose oil, containing EPA and γ-linolenic acid (18:3n−6) in the same glycerol backbone, was successfully produced and may be more beneficial for certain applications than unmodified oil.     

Effect of evening primrose extracts on oxidative stability of sunflower and rapeseed oils

Antioxidative activities of evening primrose seed meal extracts in sunflower and rapeseed oils were compared with that of commercially used antioxidants, namely butylated hydroxytoluene (BHT), ascorbylpalmitate as well as Grindox‐118. The study was carried out under Schaal oven conditions at 60 °C and the weight gain was followed up by p‐anisidine value measurement following the oxidation. An Oxidograph apparatus monitored the oxidation of oils at 110 °C. Among the examined extracts, the ethyl acetate extract (0.2%), containing only 87 mg/g of total phenolics, exhibited a stronger antioxidant activity than BHT (0.01%) and effectively stabilised both oils. A strong antioxidative effect was also noted for the ethanol‐ethyl acetate extract (168 mg/g of total phenolics). The study showed that addition of ethyl acetate and ethanol‐ethyl acetate extracts could extend the sunflower and rapeseed oils shelf‐life by protecting oils from further decomposition that naturally occurs during thermal treatments.     

月苋草油制备共轭亚油酸的研究

GC—MS分析月苋草油中脂肪酸的组成,其亚油酸含量很高。探讨制备和富集提纯亚油酸反应条件,研究在高压条件下金属催化剂对亚油酸共轭化的影响。     

Phenolic acids of borage (<Emphasis Type="Italic">Borago officinalis</Emphasis> L.) and evening primrose (<Emphasis Type="Italic">Oenothera biennis</Emphasis> L.)

The composition of phenolic acids, both free and liberated from esters and glycosides, was determined in evening primrose and borage seeds by GC and MS. The free phenolic acid fraction was predominant in these seeds. Protocatechuic acid was the principal phenolic acid of the free and esterified phenolic acids in evening primrose seeds. Ferulic acid represented a high proportion of the free phenolic acids, but hydroxycaffeic acid was the major constituent of phenolic acids liberated from esters of borage seeds.     

A rapid microozonolysis-GLC procedure for locating unsaturation in olefinic acids,including trienes and tetraenes

Increased versatility has been achieved in the identification of unknown olefinic fatty acids by ozonolysis. The method has been applied to purified methyl esters containing up to four double bonds. Aldehydic fragments, obtained from esters by the Stein-Nicolaides procedure (2), were determined by GLC on two columns of different polarity. Equivalent chain lengths of each fragment on the two columns provide identification. For monoenoic esters the location of the double bond is clearly indicated by the aldehyde and aldehyde-ester fragments. Dienes are identified by the aldehyde and aldehyde-ester fragments when the original chain length of the ester is known; the dialdehyde fragment provides confirmatory evidence. Trienes and tetraenes are analyzed by interrupting the ozonolysis at various times, thereby producing unsaturated, as well as saturated, aldehydes and aldehyde-esters. Unsaturated fragments locate the central or interior double bonds. Presented at the AOCS Meeting, Chicago, October 1967. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Determination of conjugated linolenic acid content of selected oil seeds grown in Turkey

Seeds originating from some Turkish sources were analyzed with respect to their characteristics and FA compositions. These seeds represented pomegranate (Punica granatum L.), bitter grourd (Momordica charantia L.), pot marigold (Calendula officinalis L.), catalpa (Catalpa bignonoides), bourdaine (Rhamnus frangula L.), Oregon grape (Mahonia aquifolium), sarsaparilla (Smilax aspera), mahaleb (Prunus mahaleb L.), black-thorn (Prunus spinosa L.), cherry laurel (Prunus laurocerasus L.), and firethorn (Pyracantha coccinea). Bitter gourd and bourdaine seeds contain more than 20% oil. Catalpa, bourdaine, Oregon grape, blackthorn, and cherry laurel seed oil contents ranged from 15 to 20%. In the seeds from plants belonging to the Rosacea family, oil content ranged from 4.5 to 18.5%. Among the seed oils analyzed, pot marigold had one of the lowest oil contents (5.9%). Pomegranate contained the highest amount of total conjugated linolenic acid (CLNA) (86.0%). Seed oils of bitter grourd, pot marigold, mahaleb, and catalpa were rich in CLNA: 60.0, 29.5, 27.6, and 27.5%, respectively. Bourdaine, Oregon grape, and sarsaparilla seeds contained low amounts of CLNA. On the other hand, mahaleb, bourdaine, catalpa, Oregon grape, sarsaparilla, cherry laurel, blackthorn, and firethorn seed oils are basically oleic and linoleic acid-rich oils and therefore have little drying ability (semidrying oil). The results show a potential for the use of endogenous Turkish seeds as a source of CLNA.     

Vitamin D and Evening Primrose Oil Administration Improve Glycemia and Lipid Profiles in Women with Gestational Diabetes

Limited data are available assessing the effects of vitamin D and evening primrose oil (EPO) administration on markers of insulin resistance and lipid concentrations in gestational diabetes mellitus (GDM). This study was designed to evaluate the effects of vitamin D and EPO administration on insulin resistance and lipid concentrations among women with GDM. In this prospective randomized, double‐blind, placebo‐controlled clinical trial, 60 participants with GDM were divided into 2 groups of either 1000 IU vitamin D3 and 1000 mg EPO or placebo for 6 weeks. At the beginning and end of the study, fasting blood samples were obtained from the participants to measure related variables. After 6 weeks of intervention, changes in fasting plasma glucose (?3.6 ± 7.5 vs. +1.5 ± 11.4 mg/dL, P = 0.04), serum insulin concentrations (?2.0 ± 5.3 vs. +4.6 ± 10.7 µIU/mL, P = 0.004), homeostasis model of assessment (HOMA) insulin resistance (?0.5 ± 1.1 vs. +1.1 ± 2.5, P = 0.003), HOMA‐B cell function (?7.7 ± 23.3 vs. +17.4 ± 42.9, P = 0.007) and the quantitative insulin sensitivity check index (+0.01 ± 0.02 vs. ?0.01 ± 0.02, P = 0.007) in the vitamin D plus EPO group were significantly different from the placebo group. In addition, compared with the placebo, vitamin D and EPO supplementation resulted in significant reductions in serum TAG (?20.0 ± 54.3 vs. +34.3 ± 38.2 mg/dL, P < 0.001), VLDL (?4.0 ± 10.9 vs. +6.9 ± 7.6 mg/dL, P < 0.001), TC (?22.1 ± 32.6 vs. +5.3 ± 20.1 mg/dL, P < 0.001), LDL concentrations (?18.0 ± 25.5 vs. +1.8 ± 15.7 mg/dL, P = 0.001) and TC/HDL (?0.3 ± 0.4 vs. +0.3 ± 0.5 mg/dL, P < 0.001). We did not observe any significant effect of vitamin D and EPO supplementation on serum HDL concentrations. Clinical trial registration number: http://www.irct.ir : IRCT201509115623N52.     

Vernolic and cyclopropenoid fatty acids in Plectranthus mollis,syn. Plectranthus incanus,link seed oil: A rich source of oil

Plectranthus mollis, syn. Plectranthus incanus Link seed oil contains the following acids: palmitic (7.2%), stearic (13.6%), oleic (21.7%), linoleic (46.5%), malvalic (2.3%), sterculic (3.2), and vernolic (6.1%).     

Physical refining of coconut oil: Effect of crude oil quality and deodorization conditions on neutral oil loss

In the present study, neutral oil loss (distillative and mechanical carry-over) during physical refining of coconut oil was quantified. Neutral oil loss seems to depend on both the crude oil quality and the process conditions during deodorization. The distillation of volatile glyceridic components (monoand diglycerides), originally present in the crude oil, was confirmed as the major cause for the neutral oil loss. The amount of these volatile components in crude coconut oils cannot be derived as such from the initial free fatty acid content. A lower deodorization pressure with less sparge steam resulted in a larger neutral oil loss than a higher pressure with more steam. A “deodorizability” test on a laboratory scale under standardized conditions (temperature=230°C, pressure=3 mbar, time=60 min, sparge steam=1%), to evaluate crude oil quality and to obtain a more accurate prediction of the expected neutral oil loss and free fatty acid content in the fatty acid distillate, is described.     

Dependence of oil stability index of fatty compounds on their structure and concentration and presence of metals

During storage and use, vegetable oil-derived industrial products such as biodiesel and biodegradable lubricants can be subjected to conditions that promote oxidation of their unsaturated components. The materials arising during oxidation and subsequent degradation can seriously impair the quality and performance of such products. Therefore, oxidative stability is a significant issue facing these vegetable oil-derived products, and enhanced understanding of the influence of various components of vegetable oils and storage parameters is necessary. In this work, the oil stability index (OSI) was used for assessing oxidation of monoalkyl esters of FA by varying several parameters. Neat fatty compounds and prepared mixtures thereof were studied for assessing the influence of compound structure and concentration. Small amounts of more highly unsaturated compounds had a disproportionately strong effect on oxidative stability. The recently developed concept of bis-allylic equivalents correlated more closely than the iodine value with the OSI times of mixtures of fatty esters. The OSI times of free acids were shorter than those of the corresponding alkyl esters. The presence of copper, iron, and nickel also reduced oxidative stability, but their effect was less than the presence of more highly unsaturated fatty compounds. Of these metals, copper had the strongest catalytic effect on OSI time. OSI may be an alternative to long-term storage tests for determining the influence of extraneous materials such as metals on oxidative stability.     

Changes of the tocopherol and fatty acid contents in rapeseed oil during refining

Among the most important metabolic compounds there are some which are not synthesized by human and animal organisms and have to be supplied in appropriate quantities in due time. Vitamin E and the essential unsaturated fatty acids have crucial physiological significance, and their greatest quantities occur in plant oils. During refining, apart from unnecessary substances, nutritionally advantageous compounds are also being eliminated. In the present paper changes of tocochromanols taking place during refining of rapeseed oil obtained from seeds of two subsequent crops were investigated. It was observed that losses of tocopherols exceeded 30%, two thirds of which resulted from distilling off during deodorization. The ratio of vitamin E to essential unsaturated fatty acids expressed as the Harris coefficient decreased in the refined oil obtained from seeds of two subsequent crops by about 28%.