Antioxidant activity of essential oil of oregano species from Argentina in relation to their chemical composition

The purpose of this work was to determine chemical composition and antioxidant activity of essential oil of different oregano species from Argentina: ‘Cordobes’, ‘Criollo’, ‘Mendocino’ and ‘Compacto’. The essential oil composition was determined by gas–liquid chromatography and mass spectrometry. Scavenging activity was analysed by DPPH test. The antioxidant activity of the essential oils was determined by an accelerated oxidation test in canola oil. Thirty‐nine compounds were identified in the oregano essential oils. The oregano species showed differences in their chemical composition, radical scavenging activity and antioxidant activity. The main compounds in the studied oregano species were thymol and trans‐sabinene hydrate followed by γ‐terpinene, terpinen‐4‐ol and α‐terpinene. The oregano, ‘Criollo’, was rich in γ‐terpinene and had lower thymol and trans‐sabinene hydrate and higher α‐terpinene and carvacrol contents than the other oregano species. ‘Mendocino’ had higher trans‐sabinene hydrate and limonene than the other oregano species. ‘Cordobes’ and ‘Compacto’ had higher thymol content, radical scavenging activity and antioxidant activity in canola oil.     

Loss of essential oil of tarragon (Artemisia dracunculus L.) due to drying

The effect of hot air‐drying on the essential oil constituents and yield in French and Russian tarragon (Artemisia dracunculus L.) leaves was studied. The tarragon leaves were dried at air temperatures ranging from 40 to 90 °C. The drying stopped when the moisture content of the samples reached 10% or for some of the treatments reached 7, 20 and 30%. The essential oil of the fresh and dried leaves was isolated by hydrodistillation and analysed by capillary gas chromatography and gas chromatography–mass spectrometry. The decrease of oil during the drying process was highest at 60 °C drying temperature. For French tarragon the decrease in the amount of oil was significantly lower at 90 °C. The effect of the relative humidity of the drying air at each temperature was not significant. The main compounds were estragole in French tarragon (69%) and sabinene in Russian tarragon (40%). The drying process changed the relative percentage of the constituents in the oil; for instance, the relative percentages of estragole decreased and sabinene increased in French tarragon. Copyright © 2006 Society of Chemical Industry     

Modulation of salt (NaCl)‐induced effects on oil composition and fatty acid profile of sunflower (Helianthus annuus L.) by exogenous application of salicylic acid

BACKGROUND: Salicylic acid (SA) is a potential endogenous plant hormone that plays an important role in plant growth and development. Since sunflower yield and its seed oil yield are adversely affected by salinity, in this study the role of SA in modulating salt (NaCl)‐induced effects on various yield and oil characteristics of sunflower was investigated. For this purpose a greenhouse experiment comprising two sunflower hybrid lines (Hysun‐33 and SF‐187), two NaCl levels (0 and 120 mmol L^?1) and four SA levels (0, 100, 200 and 300 mg L^?1) was conducted. RESULTS: Salt stress markedly reduced yield, oil content, linoleic acid and δ‐tocopherol in both sunflower lines, while it increased linolenic acid, palmitic acid, stearic acid and α‐ and γ‐tocopherols. However, increasing levels of foliar‐applied SA resulted in improved achene yield and hundred‐achene weight in both lines. Foliar‐applied SA caused a significant decrease in oil stearic acid and α‐ and γ‐tocopherols in both lines under non‐saline and saline conditions. CONCLUSION: Salt‐induced harmful effects on achene yield and oil characteristics of sunflower could be alleviated by exogenous application of SA. High doses of SA caused a marked increase in sunflower achene oil content as well as some key fatty acids. Copyright © 2010 Society of Chemical Industry     

An improved gas chromatography-based approach for characterisation of fatty acids in fresh basil seed oil

An improved gas chromatography-based analytical method for the simultaneous separation of seventy-two fatty acids was developed. Twenty-six types of trans fatty acids and conjugated linoleic acids were separated and identified with this method, especially trans C18 isomers. This method was confirmed to be high throughput and have high sensitivity and a low detection limit. It was successfully applied to separate and identify fatty acids in fresh basil seed oil. The linolenic acid content (51.67 g/100 g) was highest in basil seed oil, followed by linoleic acid (20.16 g/100 g) and oleic acid (12.70 g/100 g). These unsaturated fatty acids in fresh basil seed oil were transformed into trans fatty acids, conjugated linoleic acids and saturated fatty acids after heating to a certain temperature for an adequate duration, and the formation mechanisms were characterised.     

Southern French thyme oils: chromatographic study of chemotypes

Oils obtained from seven chemotypes (thymol, linalool, geraniol, borneol, (E)‐sabinene hydrate/terpinene‐4‐ol, p‐cymene and carvacrol) of Thymus vulgaris (thyme) that exist in the South of France were analysed by gas chromatography/mass spectrometry (GC/MS) and characterised. Wild thyme growing in three departments (Bouches du Rhone, Var and Vaucluse) of Provence and in a fourth neighbouring department (Gard) was also studied. This is often the result of a mixture of three chemotypes: thymol, carvacrol and p‐cymene. Linalool and (E)‐sabinene hydrate/terpinene‐4‐ol were observed as minor chemotypes. GC/MS was also used to monitor seasonal variations in the composition of the oil obtained from thyme harvested at the same location (Gemenos, near Marseille, Bouches du Rhone) during the plant vegetative and life cycles (19 samples). Four components were determined: the phenols thymol and carvacrol and the monoterpene hydrocarbon precursors p‐cymene and γ‐terpinene. Results showed maximum oil (34.1 mL kg⁻¹ dry matter) and phenolic terpenoid (95.4 mmol kg⁻¹ dry matter) contents occurring in May, the period of flowering and harvesting. In contrast, in December the oil displayed a higher level of phenolic precursors (p‐cymene and γ‐terpinene, 72.8 mmol kg⁻¹ dry matter) than phenolic terpenoids. Depending on the harvesting date, the oils isolated from southern French thyme (T. vulgaris) could have different potential biological activities. Copyright © 2005 Society of Chemical Industry     

Effect of salinity on seed oil content and fatty acid composition of safflower (Carthamus tinctorius L.) genotypes

Safflower (Carthamus tinctorius L.) is a species moderately tolerant to salt stress and is cultivated in dry areas where salinity can be a serious threat. We examined effects of salinity stress on seed oil content and fatty acid composition in 64 safflower genotypes grown under saline and non-saline (control) field experiments in two growing seasons. The results showed significant effects of genotype, salinity and their interactions on most of the characteristics examined. Salt tolerant genotypes were less affected by salinity than salt-sensitive ones for oil quantity and quality. The overall reductions of 7.7% oil content and 29% oil yield were observed due to salinity stress. Salinity stress caused a significant increase in oleic acid (C18:1) and significant decreases in linoleic (C18:2) and linolenic (C18:3) acids. These results suggest inhibition of oleic acid desaturase and differential responses of salt-tolerant and salt-sensitive genotypes under salinity stress.     

Hydrogenation for Low Trans and High Conjugated Fatty Acids

Hydrogenated vegetable oils contain of trans fatty acids. Because of the increased health concern about trans fatty acids, new hydrogenations have been studied to seek ways for substantial reduction of the trans fatty acids in the hydrogenated vegetable oils. This paper reviews new hydrogenation processes such as electrocatalytic hydrogenation, precious catalyst hydrogenation, and supercritical fluid state hydrogen, which have shown promising results for the reduction of trans fatty acids below the level of 8%. This paper also reviews the recently introduced hydeogenation technique for high accumulation of conjugated linoleic acids, beneficiary functional components. The hydrogenated vegetable oils with high quantity conjugated linoleic acid might provide the possibility for the utilization of hydrogenated oils as health‐prompting food ingredients.     

Conjugated linoleic acid content in fermented goat milk as affected by the starter culture and the presence of free linoleic acid

The effect of yoghurt starter cultures and probiotic Lactobacillus casei on the formation of conjugated linoleic acid (CLA) and microbial populations of fermented goat milk was investigated during 35 days of cold storage. The addition of hydrolysed sunflower oil as a source of free linoleic acid was investigated. The fermentation process enhanced the content of the cis9, trans11‐CLA isomer in milk, whereas the trans10, cis12‐CLA isomer was not detected in goat milk or control fermented milks. The use of both starters generated trans10, cis12‐CLA only when hydrolysed sunflower oil was supplemented. Populations of streptococci and lactobacilli were affected by the presence of hydrolysed sunflower oil.     

c9t11‐Conjugated linoleic acid‐rich oil fails to attenuate wasting in colon‐26 tumor‐induced late‐stage cancer cachexia in male CD2F1 mice

Scope: Cancer cachexia is characterized by muscle and adipose tissue wasting caused partly by chronic, systemic inflammation. Conjugated linoleic acids (CLAs) are a group of fatty acids with various properties including anti‐inflammatory cis9, trans11 (c9t11)‐CLA and lipid‐mobilizing trans10, cis12 (t10c12)‐CLA. The purpose of this study was to test whether dietary supplementation of a c9t11‐CLA‐rich oil (6:1 c9t11:t10c12) could attenuate wasting of muscle and adipose tissue in colon‐26 adenocarcinoma‐induced cachexia in mice. Methods and results: Loss of body weight, muscle and adipose tissue mass caused by tumors were not rescued by supplementation with the c9t11‐CLA‐rich oil. In quadriceps muscle, c9t11‐CLA‐rich oil exacerbated tumor‐induced gene expression of inflammatory markers tumor necrosis factor‐α, IL‐6 receptor and the E3 ligase MuRF‐1 involved in muscle proteolysis. In epididymal adipose tissue, tumor‐driven delipidation and atrophy was aggravated by the c9,t11‐CLA‐rich oil, demonstrated by further reduced adipocyte size and lower adiponectin expression. However, expression of inflammatory cytokines and macrophage markers were not altered by tumors, or CLA supplementation. Conclusion: These data suggest that addition of c9t11‐CLA‐rich oil (0.6% c9t11, 0.1% t10c12) in diet did not ameliorate wasting in mice with cancer cachexia. Instead, it increased expression of inflammatory markers in the muscle and increased adipose delipidation.     

Chemical composition and in vitro antimicrobial activity of the essential oil of Origanum minutiflorum O Schwarz & PH Davis

The essential oil obtained by hydrodistillation from the aerial parts of Origanum minutiflorum O Schwarz & PH Davis, an endemic species in Turkey, was analysed for its antimicrobial activity in vitro. Gas chromatography/mass spectrometry analysis of the essential oil resulted in the identification of 34 constituents accounting for 961.5 mL L^?1 of the oil, the major compounds present being carvacrol (793.4 mL L^?1), p‐cymene (32.6 mL L^?1) and γ‐terpinene (21.4 mL L^?1). The in vitro antimicrobial activity of the essential oil was investigated in order to evaluate its efficacy against 16 bacteria and two yeasts, using disc diffusion and minimum inhibitory concentration methods. The essential oil showed strong antimicrobial activity against all test micro‐organisms except Pseudomonas aeruginosa. Its main components carvacrol and p‐cymene were also assayed for their antimicrobial activities. Carvacrol exhibited comparable activity to the crude oil, proving it to be the main component responsible for the biological activity observed. This study demonstrates the in vitro antimicrobial activity of the essential oil of this endemic remedy against a wide spectrum of clinically important micro‐organisms, including pathogenic yeasts, being the first report on the anticandidal properties of the essential oil of O. minutiflorum. Copyright © 2006 Society of Chemical Industry     

Volatile compounds and oxidative stability of Pinus halepensis Mill. seed oil under heating conditions

Heating conditions of Pinus halepensis seed oil were monitored to evaluate the effect of thermo‐oxidation processes on the bioactive compounds contained in the samples. The following parameters were monitored: ultra violet absorption at 232 and 270 nm, fatty acid composition, oxidative stability, antiradical activity and aromatic profiles. Under thermo‐oxidation process, trans fatty acids (TFA) increased and conjugated linoleic acid isomers appeared. The antiradical activity significantly decreased from 73.3% to 52.5% after 120 min of heating. Oxidative stability decreased (r = ?0.70). The volatile profile was heavily influenced by heating with the formation of new volatile compounds, such as the two isomers (E,Z)‐2,4‐decadienal and (E,E)‐2,4‐decadienal. α‐pinene, and the main terpene compound was very vulnerable to heating conditions. Despite its peculiar pleasant aroma and nutritional value, the P. halepensis seed oil should not be used for cooking. Indeed, under frying conditions, its antioxidant properties and oxidative stability are lost and potential toxic compounds, such as TFA and unsaturated aldehydes, are formed.     

Salt-induced modulation in inorganic nutrients, antioxidant enzymes, proline content and seed oil composition in safflower (Carthamus tinctorius L.)

BACKGROUND: Safflower (Carthamus tinctorius L.) has gained considerable ground as a potential oil‐seed crop. However, its yield and oil production are adversely affected under saline conditions. The present study was conducted to appraise the influence of salt (NaCl) stress on yield, accumulation of different inorganic elements, free proline and activities of some key antioxidant enzymes in plant tissues as well as seed oil components in safflower. Two safflower accessions differing in salt tolerance (Safflower‐33 (salt sensitive) and Safflower‐39 (salt tolerant)) were grown under saline (150 mmol L^?1) conditions and salt‐induced changes in the earlier‐mentioned physiological attributes were determined. RESULTS: Salt stress enhanced leaf and root Na⁺, Cl^? and proline accumulation and activities of leaf superoxide dismutase, catalase and peroxidase, while it decreased K⁺, Ca²⁺ and K⁺/Ca²⁺ and Ca²⁺/Na⁺ ratios and seed yield, 100‐seed weight, number of seeds, as well as capitula, seed oil contents and oil palmitic acid. No significant effect of salt stress was observed on seed oil α‐tocopherols, stearic acid, oleic acid or linoleic acid contents. Of the two safflower lines, salt‐sensitive Safflower‐33 was higher in leaf and root Na⁺ and Cl^?, while Safflower‐39 was higher in leaf and root K⁺, K⁺/Ca²⁺ and Ca²⁺/Na⁺ and seed yield, 100‐seed weight, catalase activity, seed oil contents, seed oil α‐tocopherol and palmitic acid. Other attributes remained almost unaffected in both accessions. CONCLUSION: Overall, high salt tolerance of Safflower‐39 could be attributed to Na⁺ and Cl^? exclusion, high accumulation of K⁺ and free proline, enhanced CAT activity, seed oil α‐tocopherols and palmitic acid contents. Copyright © 2011 Society of Chemical Industry     

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     

Enrichment of ω‐3 fatty acids in flax seed oil by alkaline lipase of Aspergillus fumigatus MTCC 9657

Flax seed oil obtained from the seeds of flax plant (Linum usitatissimum, L.) is an unexploited source which contains ω‐3 and ω‐6 fatty acids. Flax seed oil is hydrolysed with a novel alkaline lipase from Aspergillus fumigatus MTCC 9657 for the removal of unwanted fatty acids and enrichment of ω‐3 fatty acids. An appropriate balance of ω‐3 and ω‐6 polyunsaturated fatty acids and enzymatic enrichment of polyunsaturated fatty acids in diet promote nutrition and health. Fatty acid composition shows that flax seed oil contains about 26.80%, 13.5% and 25.45% of ω‐3 and ω‐6 fatty acids in triglyceride (TG), diglyceride (DG) and monoglyceride (MG), respectively. After 8 h of hydrolysis, ω‐3 content was increased to 39% in TG, showing that unwanted saturated fatty acids are removed. ω‐6 content of triglycerides in flax seed oil also showed 54.76% increase after 8 h of hydrolysis. An enzymatic method of hydrolysis by fungal lipase was developed by this study and achieved to concentrate the essential fatty acids linoleic acid (LA) and α‐linoleic acids (ALA).     

Essential Oil and Phenolic Compounds of Artemisia herba-alba (Asso.): Composition,Antioxidant, Antiacetylcholinesterase,and Antibacterial Activities

Total phenols, flavonoids, flavonols, and flavanols of the methanolic extract of the aerial part of Artemisia herba-alba were determined. The extract was analyzed by liquid chromatography with photodiode array coupled with electrospray ionisation mass spectrometry and allowed to identify of 10 phenolic compounds. Apigenin-6-C-glycosyl flavonoids and caffeoylquinic acids were identified. Chlorogenic acid and 1,4 dicaffeoylquinic acid being the major constituents. The essential oil obtained by hydrodistillation was analyzed by gas chromatography–mass spectrometry. Twenty-three compounds, representing 97.8% of the total oil, were identified. The most abundant components were β-thujone (41.9%), α-thujone (18.4%), and camphor (13.2%). Methanolic extract and essential oil exhibited a considerable antioxidant activity as evaluated by 2,2-diphenyl-pycrilhydrazil hydrate scavenging activity, reducing power, β-carotene bleaching test, and chelating ability. The methanolic extract was found to be more efficient, while the essential oil exhibited the highest acetylcholinesterase inhibitory activity. Analysis of the antibacterial activity showed that A. herba-alba methanolic extract and essential oil are efficient against gram positive and gram negative bacteria.     

Essential fatty acids and trans contents of some oils,margarine and other food fats

Levels of polyunsaturated fatty acids (PUFA), cis, cis-methylene interrupted polyunsaturated fatty acids (i.e. essential fatty acids—EFA) and isolated trans double bonds in six crude vegetable oils, seven commercial oils, eighteen margarines, two butter fats and fats from two types each of crisps and butter biscuits have been determined. The ratios between the PUFA or EFA and the saturated fatty acids of various samples have been tabulated. Normal (i.e. high linoleic) safflower seed oil gave the highest ratio. Margarines which were estimated to contain partially hydrogenated fish oils (45–90%, on fat basis) gave high values of trans double bonds. Butter fat having a similar EFA level to that present in a ‘hydrogenated fish oil’ margarine contained a much lower level of trans isomers. Almost all the PUFA in the oils of crips, and about half the PUFA content of butter biscuits, existed as ‘true’ essential fatty acids.     

Chemical composition,antioxidative capacity and interactive antimicrobial potency of Satureja khuzestanica Jamzad essential oil and antimicrobial agents against selected food‐related microorganisms

This study aimed to determine the chemical composition, antimicrobial and antioxidative activity of Satureja khuzestanica Jamzad essential oil. The oil was analysed by GC and GC/MS. Twenty‐eight constituents were identified. The oxygenated monoterpenes (78.22%) were the principal compound group. Among them, carvacrol (53.86%) and thymol (19.84%) were the most abundant constituents. The oil exhibited an acceptable antimicrobial activity against most of the tested microorganisms. The checkerboard method was applied to determine fractional inhibitory concentration indices (FICIs) to interpret the synergetic, additive, indifference or antagonistic interactions between essential oil and each of antimicrobials (lysozyme, ciprofloxacin, fluconazole and amphotericin B) against food‐related microorganisms. The synergetic phenomenon (FICI ≤ 0.5) was observed in majority of combinations with the exception of the essential oil and lysozyme. The oil exhibited good 1,1‐diphenyl‐2‐picrylhydrazyl radical scavenging activity (IC₅₀ = 28.71 μg mL^?1). Also, the oil had strong antioxidative activity in β‐carotene‐linoleic acid assay relative antioxidant activity (RAA% = 95.45). This study demonstrated that the essential oil has beneficial biological properties and its simultaneous application with standard antimicrobials against food‐related microorganisms result in reduction in inhibitory doses of the antimicrobials in vitro.     

α‐Eleostearic acid is more effectively metabolized into conjugated linoleic acid than punicic acid in mice

BACKGROUND: The objective of this study was to investigate the metabolism of α‐eleostearic acid (α‐ESA, cis9,trans11,trans13‐18:3) and punicic acid (PA, cis9,trans11,cis13‐18:3) and to compare the relative conversion efficiency of these fatty acids into conjugated linoleic acids (CLAs) in mice. RESULTS: Twenty‐four male ICR mice were fed either a control diet or one of two experimental diets supplemented with 10 g kg^?1α‐ESA or PA in the form of triacylglycerols for 6 weeks. The accumulation of PA in all tissues examined was significantly higher than α‐ESA; in both groups it was found that cis9,trans11‐conjugated linoleic acid (cis9,trans11‐18:2) was detected in all tissues examined. The relative conversion rate of α‐ESA into cis9,trans11‐18:2 was significantly higher than that of PA. The highest conversion rate of α‐ESA was found in adipose tissue (91.8%), spleen (91.4%) and kidney (90.7%), and the lowest in the heart (84.6%). The highest conversion rate of PA occurred in the liver (76.2%) and the lowest occurred in the heart (54.5%). CONCLUSION: The present results indicate that both α‐ESA and PA are effectively metabolized into cis9,trans11‐18:2 in mice. These conjugated dietary fatty acids might be useful sources of CLAs in tissues owing to the natural abundance of α‐ESA and PA in some seeds. Copyright © 2009 Society of Chemical Industry     

Effects of Trans and Conjugated LC N‐3 Polyunsaturated Fatty Acids on Lipid Composition and Abdominal Fat Weight in Rats

ABSTRACT: Trans and conjugated fatty acids may exhibit either beneficial or detrimental bioactive effects depending on their metabolic properties. This study was conducted to elucidate if isomerization and conjugation of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) demonstrate more favorable bioactivity on lipid metabolism compared to unmodified EPA and DHA. The effects of dietary intake of trans and conjugated forms of EPA and DHA on lipid metabolism were evaluated in animal trials and compared to a control group fed soybean oil. None of the experimental diets showed significant differences from the control in terms of body weight; however, the white adipose tissue weight of rodents fed trans DHA, conjugated EPA (CEPA), and conjugated DHA (CDHA) was significantly lower than the control. Triacylglycerol levels in plasma were significantly decreased in groups fed trans DHA (17.2 mg/dL) and CDHA (31.9 mg/dL) relative to the control (51.3 mg/dL). The total cholesterol concentrations were significantly lower than the control (68.0 mg/dL) in all experimental groups (47.3 to 53.7 mg/dL) except CEPA (58.3 mg/dL). Fatty acid compositions of lipids extracted from rodent livers were influenced by the dietary fatty acid profiles, with all groups showing higher concentrations of stearic acid and lower levels of linoleic acid compared to the control. Rodents fed trans DHA did not have detectable levels of these fatty acid isomers in their livers, suggesting either quick metabolism or a difficulty with bio‐absorption.     

Essential oil composition of sea fennel (Crithmum maritimum) form Turkey

Constituents of essential oils of sea fennel (Crithmum maritimum L.) collected in different localities of Turkey in 1997 and 1998 have been identified by GC/MS. The effects of collection time and locality on the oil content and composition have been studied. The samples were classified into groups according to the main components: sabinene, γ‐terpiene, methyl thymol and terpinen‐4‐ol; γ‐terpinene, dill apiol and sabinene; γ‐terpiene, methyl thymol and limonene; p‐cymene, methyl thymol and γ‐terpinene. (Z)‐β‐ocimene and spathulenol were found with high percentage values in some samples. cis‐p‐Menth‐4‐en‐1,2‐diol was identified in only one oil. Early collected plants yielded oil rich in p‐cymene. Effect of freezing plant did not have any important effect in oil composition.