On‐line LC‐NMR‐MS characterization of sesame oil extracts and assessment of their antioxidant activity

Sesame lignans were isolated by solvent extraction and subsequently purified by solvent crystallization from crude, unroasted sesame oil, and a sesame oil deodorizer distillate. In addition, an aliquot of the purified sesame oil extract was treated with camphorsulfonic acid to obtain a sesaminol‐enriched extract. The sesame lignan composition of the extracts was characterized by on‐line liquid chromatography nuclear magnetic resonance spectroscopy mass spectrometry coupling (LC‐NMR‐MS). The effect of the sesame oil extracts as well as pure sesame lignans and γ‐tocopherol on the oxidative stability of sunflower oil (lignan‐free) was studied by the Rancimat assay. The Rancimat assay revealed the following oxidative stability order: sesame oil extract < sesame oil deodorizer distillate < sunflower oil (no added sesame oil extracts) < sesamol < sesaminol‐enriched sesame oil extract. In addition, the radical‐scavenging capacity of these extracts was assessed by the Trolox® equivalent antioxidant capacity (TEAC) assay. The TEAC assay revealed a slightly different AOX activity order: sesamin < sesame oil extract < sesaminol‐enriched sesame oil extract < sesamol. In conclusion, the sesaminol‐enriched extract revealed strong antioxidant activity and is therefore suitable to increase the oxidative stability of edible oils high in polyunsaturated fatty acids.     

Variation of Oil,Sesamin, and Sesamolin Content in the Germplasm of the Ancient Oilseed Crop Sesamum indicum L.

Currently, genetic improvement in oil and lignan content is a major objective in sesame breeding. As a prerequisite to meet the objective, the diversity of these traits of sesame germplasm was examined. Solvent extraction of the harvested seeds demonstrated variation in oil content ranging from 39% to 49% across the sesame accessions tested. High performance liquid chromatography of oil samples showed sesamin and sesamolin as the only lignans present in the oil, with their amount in the range of 2.74–10.55 g L⁻¹ and 2.49–13.78 g L⁻¹, respectively. Coefficient of variation for oil content remained the highest in brown and black seeded accessions, whereas it remained at maximum for sesamin and sesamolin in white seeded ones. Pearson analysis showed a positive correlation between oil and lignan content. It was concluded that Indian sesame accessions exhibit considerable variation in oil and lignans content. The S. indicum varieties with a desirable composition of oil and/or lignans have been identified and recommended for incorporation in breeding programs, as well as for specific human use.     

Lipase‐mediated hydrolysis of flax seed oil for selective enrichment of α‐linolenic acid

Polyunsaturated fatty acids (PUFA) are important ingredients of human diet because of their prominent role in the function of human brain, eye and kidney. α‐Linolenic acid (ALA), a C18, n‐3 PUFA is a precursor of long chain PUFA in humans. Commercial lipases of Candida rugosa, Pseudomonas cepacea, Pseudomonas fluorescens, and Rhizomucor miehei were used for hydrolysis of flax seed oil. Reversed phase high performance liquid chromatography followed by gas chromatography showed that the purified oil contained 12 triacylglycerols (TAGs) with differences in fatty acid compositions. Flax seed oil TAGs contained α‐linolenic acid (50%) as a major fatty acid while palmitic, oleic, linoleic made up rest of the portion. Among the four commercial lipases C. rugosa has preference for ALA, and that ALA was enriched in free fatty acids. C. rugosa lipase mediated hydrolysis of the TAGs resulted in a fatty acid mixture that was enriched in α‐linolenic to about 72% yield that could be further enriched to 80% yield by selective removal of saturated fatty acids by urea complexation. Such purified ALA can be used for preparation of ALA‐enriched glycerides. Practical applications : This methodology allows purifying ALA from fatty acid mixture obtained from flax seed oil by urea complexation.     

Triacylglycerols from viper bugloss (Echium vulgare L.) seed bio‐oil

Triacylglycerols (TAG) in viper bugloss oil were isolated from raw pressed oil by silicic acid column chromatography. The obtained blend of TAG was separated by silver ion thin‐layer chromatography (TLC Ag⁺) into nine fractions, varying in terms of unsaturation level and molecular polarity. The composition of TAG in viper bugloss oil was determined by HPLC coupled with a diode‐array detector and an evaporative light‐scattering detector. The results showed that the first three fractions were combinations of TAG containing palmitic, oleic and linoleic acids. Fractions 4 and 6 contained TAG of a similar acid composition as above, but with the addition of γ‐linolenic acid. The remaining fractions (7–9) were the most varied in acid composition. They were found to contain 26–39% palmitic acid, 12–15% oleic acid, 13–41% linoleic acid 8–24% γ‐linolenic acid, 1.5–5.5% α‐linolenic acid and 1–5% stearidonic acid. The analysis of fatty acid allocation in TAG of viper bugloss lipids revealed that linoleic acid (ranging from 2 to 100%) was the only acid found in all isolated fractions. In the investigated oil, the predominant TAG included: LnLnG (11.38%), LnLnSt (11.17%), LnGSt (7.71%), LnStSt (6.19%) and LnLnLn (5.44%). Almost 86% of the TAG contained α‐linolenic acid, while γ‐linolenic and stearidonic acids amounted to 49 and 38%, respectively.     

The Contents of Lignans in Sesame Seeds and Commercial Sesame Oils of China

In this study, the concentrations of three lignans in 100 sesame seeds and 56 sesame oils were determined using a newly developed method based on high‐performance liquid chromatography coupled with a UV/Vis detector. Total lignan contents in sesame seed and oil samples ranged from 2.52 to 12.76 and 3.38 to 11.53 mg/g, respectively. Black sesame seeds showed higher sesamin content (range 1.98–9.41 mg/g, mean 4.34 mg/g) and sesamolin content (range 1.06–3.35 mg/g, mean 1.92 mg/g) than the other three varieties of sesame seeds. Black sesame oils had higher contents of lignans than the white sesame oils, although remarkable differences were not observed. Hot pressed and small mill sesame oils expressed higher contents of sesamol, sesamin, and total lignans than the cold pressed and refined sesame oils. The results revealed that there is extensive variability in lignan concentration in sesame oils and seeds.     

Studies of Oils of Unusual Fatty Acids

Studies of linseed, castor seed and Vernonia anthelmintica seed oils have been undertaken together keeping in view their industrial importance. Linseed oil contains the highest percentage of linolenic acid (69.1%) whereas the highest percentage of hydroxy fatty acid (85.6%) and epoxy fatty acids (76.8%) has been found out in castor seed and Vernonia anthelmintica seed oils respectively as determined by the application of thin-layer and gas liquid chromatography.     

Lignan contents in sesame seeds and products

Sesame seed (Sesamum indicum L.) is a rich source of furofuran lignans with a wide range of potential biological activities. The major lignans in sesame seeds are the oil‐soluble sesamin and sesamolin, as well as glucosides of sesaminol and sesamolinol that reside in the defatted sesame flour. Upon refining of sesame oil, acid‐catalyzed transformation of sesamin to episesamin and of sesamolin to epimeric sesaminols takes place, making the profile of refined sesame oils different from that of virgin oils. In this study, the total lignan content of 14 sesame seeds ranged between 405 and 1178 mg/100 g and the total lignan content in 14 different products, including tahini, ranged between 11 and 763 mg/100 g. The content of sesamin and sesamolin in ten commercial virgin and roasted sesame oils was in the range of 444–1601 mg/100 g oil. In five refined sesame oils, sesamin ranged between 118 and 401 mg/100 g seed, episesamin between 12 and 206 mg/100 g seed, and the total contents of sesaminol epimers between 5 and 35 mg/100 g seed, and no sesamolin was found. Thus, there is a great variation in the types and amounts of lignans in sesame seeds, seed products and oils. This knowledge is important for nutritionists working on resolving the connection between diet and health. Since the consumption of sesame seed products is increasing steadily in Europe and USA, it is important to include sesame seed lignans in databases and studies pertinent to the nutritional significance of antioxidants and phytoestrogens. It is also important to differentiate between virgin, roasted and refined sesame oils.     

Composition of Catalpa ovata Seed Oil and Flavonoids in Seed Meal as Well as Their Antioxidant Activities

In view of the growing demand for vegetable oil, currently exploration of some non‐conventional oils is of great concern. This study firstly analyzed the contents of fatty acids, phytosterols, and tocopherols in Catalpa ovata seed oil collected from four different Provinces in China. Then the composition of flavonoids as well as their antioxidant activities in defatted seed meal was determined. The results showed that the relative oil content in C. ovata seeds ranged from 24.0 to 36.0 % and seed oil was mainly composed of fatty acids linoleic acid (43.4–50.1 %), α‐linolenic acid (23.8–24.4 %), and oleic acid (13.1–16.2 %). The content of unsaturated fatty acids was up to 85.0 %. Sterol in seed oil mainly contained campesterol, stigmasterol, and β‐sitosterol. β‐sitosterol accounted for 74.0 % of the total sterol. The tocopherol content was 173.0–225.7 mg/100 g. Defatted seed meal from Hubei Province showed the highest content of total flavonoids (11 mg/g) and the strongest activities for DPPH radicals scavenging, ABTS radicals scavenging, and ferric reducing antioxidant power compared with other defatted seed meal in this study. Seven flavonoids were identified from C. ovata seed meal. These results suggest that C. ovata seeds may be developed as a new source of oil and can also be properly used in pharmaceuticals and cosmetics.     

Virgin hemp seed oil: An interesting niche product

Virgin hemp seed oil is not widespread on the market, although it is characterised by an interesting fatty acid composition with a high content of polyunsaturated fatty acids. Linoleic acid is the predominant fatty acid, which comes, together with α‐linolenic acid (18:3n‐3), to approximately 80% of the total fatty acids. From a nutritional point of view, up to 7% γ‐linolenic acid (18:3n‐6) and 2.5% stearidonic acid (18:4n‐3) are very interesting. The total amount of tocopherols is high between 80 and 110 mg/100 g, with γ‐tocopherol as the main tocopherol (85%). Due to the high amount of unsaturated fatty acids, hemp seed oil is very susceptible to oxidative deterioration, which results in a fast impairment of the oil during storage. In addition, the high amounts of chlorophyll in the oil due to harvesting of high amounts of immature seeds require light protection, which is often neglected because of merchandising purposes. The virgin oil is characterised by a nutty taste with a slightly bitter aftertaste. The use of virgin hemp seed oil is recommended during mild processing of food without heat.     

Variation in Fatty Acid Composition in Indian Germplasm of Sesame

A germplasm collection of 33 entries comprising 22 sesame (Sesamum indicum L.) cultivars, 4 landraces of S. mulayanum and 7 other accessions of 4 wild species were analyzed for the fatty acid compositions of their seed oil. The entries varied widely in their fatty acid compositions. The percentage content of oleic, linoleic, palmitic and erucic acids ranged between 36.7–52.4, 30.4–51.6, 9.1–14.8 and 0.0–8.0, respectively. Linolenic and arachidonic acids were the minor constituents but varied widely in wild species. Oleic and linoleic were the major fatty acids with mean values of 45.9 and 40.5%, respectively and the mean of their combined values was 86.4%. The polyunsaturated fatty acid (PUFA) compositions ranged from 30.9 to 52.5% showing high variation in PUFA in the germplasm. Linoleic acid content was very high in one landrace (47.8) and one accession each of three wild species, S. mulayanum (49.3), S. malabaricum (48.2) and S. radiatum (51.6%). Use of fatty acid ratios to estimate the efficiency of biosynthetic pathways resulted in high oleic and low linoleic desaturation ratios and consequently high linoleic and very low linolenic acid contents in seed oil. The results of this study provided useful background information on the germplasm and also identified a few accessions having high linoleic acid which can be used for developing cultivars with desirable fatty acid compositions.     

Genetic diversity of fatty acids in sesame and its relatives in Nigeria

The genetic diversity in seed lipid and fatty acid composition in nine accessions of sesame, comprising six cultivated and three wild relatives, was studied and compared. Seed oil content was 53.23–55.12% in cultivated and 53.35–58.56% in wild accessions. The principal fatty acids in the accessions were palmitic, stearic, oleic (OLE), linoleic (LIN) and linolenic (LIL) acids, of which lower OLE and higher LIN acids were observed in all the accessions. Principal component analysis revealed that OLE acid, total unsaturated fatty acids, total saturated fatty acids (SFAs), LIN acid and the unsaturated to SFA ratio had the highest loading in the first component, which accounted for 54.01% of the total variation. For the second principal components, lauric, palmitoleic, capric, lignoceric, arachidic and LIL acids had the highest loading, accounting for 26.94% of the total variation. Three principal components explained 89.01% of the total variation. The dendrogram generated by the UPGMA cluster analysis grouped the nine accessions into five distinct clusters, indicating genetic diversity; this can be used to plan crosses and maximise the expression of heterosis. Practical applications : This research work provides information on the fatty acid profile of seed oil from nine morphologically distinct accessions of sesame selected from thirty‐three accessions collected in 2003. This is intended to establish genetic diversity on the basis of fatty acid profile, identify accessions with high seed oil quality that may be adopted for large scale cultivation in Nigeria and justify the suitability of the nine accessions in serving as base materials in the ongoing breeding efforts for sesame seed oil quantity and quality improvement.     

Discrimination of Origin of Sesame Oils Using Fatty Acid and Lignan Profiles in Combination with Canonical Discriminant Analysis

The aims of this study were to investigate total fatty acid composition and lignan contents of Korean, Chinese and Indian roasted sesame oils and to differentiate the geographic origins of the oils using analytical data in combination with canonical discriminant analysis. The analytical data were obtained from 84 oil samples that were prepared from 51 Korean, 19 Chinese, and 14 Indian white sesame seeds harvested during 2010 and 2011 and distributed in Korea during the same period. Six variables selected for the discriminant analysis were the contents of three fatty acids (linoleic, oleic, and palmitic) and three lignans (sesamin, sesamolin, and sesamol). A good discrimination between sesame oils from Korea, China, and India was achieved by applying two canonical discriminant functions, with 97.6 % of the samples correctly classified into the geographic origin. When the origins of five commercial oil samples (one was prepared from Korean sesame seeds and the other four were made from imported sesame seeds) were predicted using discriminant functions, the Korean sesame oil was accurately distinguished from the others.     

Genetics,characteristics, and utilization of oil in caryopses of oat species

For oats to be an economically feasible oilseed crop in Iowa, the oil percentage would have to be increased to ca. 16%. A survey of the oil percentage in 445 oat cultivars and collections gave a range of 2.0–11.0%. The oil percentage was only slightly affected by growing oats in 5 different locations in Iowa. Inheritance studies indicated that oil percentage was inherited polygenically, and there was a tendency for high oil percentage to be partially dominant. Analysis of 64 cultivars and collections showed a wide variation of fatty acid composition: palmitic, 14–23%; stearic, <1–4%; oleic, 29–53%; linoleic, 24–48%; linolenic, < 1–5%. The oil percentage was positively correlated with oleic acid and negatively correlated with linoleic and linolenic acids. Oats contained a lipase that made extraction of oil with low acid values difficult. The lipase was strongly affected by moisture and was most active in oat doughs containing 25–50% moisture. There was at least a 20-fold variation in lipase activity in oat cultivars and collections. Whole oats may be kept in dry storage for several years without significant lipolysis, but in broken or crushed caryopses, lipolysis occurs even at low moisture levels. The lipase may be inactivated by heat or 95% ethanol treatments.     

Oxidative stability of Echium plantagineum seed oil bodies

Echium plantagineum seed contains a highly polyunsaturated oil (approximately 14% linoleic acid, 10% γ‐linolenic acid, 33% α‐linolenic acid and 14% stearidonic acid); almost half of the fatty acids are omega‐3 fatty acids, so there is an interest in the possible health benefits of this oil, which, once extracted, is prone to oxidation. For the first time in reported literature, oil bodies (OBs), the organelles that store the oil in mature seed, were recovered from E. plantagineum seeds. The oxidative stability of these organelles ex vivo, dispersed in an aqueous continuous phase, was tested against processed E. plantagineum oil emulsions stabilised with either SDS or Tween 20. For both primary and secondary oxidation products the OBs were the most stable form of dispersed oil, and the dispersed systems were all more stable than bulk E. plantagineum oil after incubating at 40°C for 7 days. The possible reasons for the enhanced chemical stability of E. plantagineum OBs are explored in this paper. Practical applications: OBs, the natural store of oil in oilseeds, can be recovered from seeds intact and are relatively stable to oxidation ex vivo. Echium seed OBs, enriched in physiologically active omega‐3 fatty acids, therefore offer an attractive alternative to traditional oil extraction methods and overcome the need to encapsulate the omega‐3 rich oil.     

Chemical Examination of Iberis odorata Seed Oil

Iberis odorata seeds of cruciferae plant family yield 26.0 percent of fatty oil which has an iodine value 107.5. The oil is investigated for its fatty acid composition by reversed phase partition chromatography. The fatty acids in the seed oil constitute 39.6% erucic, 3.5% eicosenoic and 3.2% docosadienoic acids, in addition to the usual oleic (13.6%), linoleic (25.7%) and linolenic acids (3.1%). Saturated acids (C₁₂) to (C₂₂) amount to 11.3% of the component acids.     

Lipid classes,fatty acid composition and triacylglycerol molecular species of kidney beans (Phaseolus vulgaris L.)

Seed oils from five legume cultivars of Phaseolus vulgaris, grown in Japan, were extracted and classified by thin‐layer chromatography (TLC) into seven fractions: hydrocarbons (HC; 0.7–1.4 wt‐%), steryl esters (SE; 1.7–3.3 wt‐%), triacylglycerols (TAG; 33.8–45.9 wt‐%), free fatty acids (FFA; 0.6–1.5 wt‐%), sn‐1,3‐diacylglycerols (1,3‐DAG; 0.3–1.0 wt‐%), sn‐1,2‐diacylglycerols (1,2‐DAG; 0.4–1.2 wt‐%) and phospholipids (PL; 49.4–58.8 wt‐%). Fatty acids derivatized as methyl esters were analyzed by gas chromatography (GC) and a flame ionization detector. Molecular species and the fatty acid distribution of TAG isolated from the total lipids in the beans were analyzed by a combination of argentation‐TLC and GC. A modified argentation‐TLC procedure, developed to optimize the separation of the complex mixture of total TAG, provided 18 different groups of TAG, based on both the degree of unsaturation and the total length of the three acyl chains of fatty acid groups. SDT (3.2–4.2 wt‐%), M₂T (3.8–5.0 wt‐%), D₃ (4.8–5.9 wt‐%), MDT (8.0–13.9 wt‐%), D₂T (12.5–15.8 wt‐%), MT₂ (19.4–22.7 wt‐%), DT₂ (17.8–23.5 wt‐%) and T₃ (9.2–13.0 wt‐%) were the main TAG components. The dominant fatty acids of TAG were α‐linolenic (48.5–57.8 wt‐%) and linoleic (16.7–25.8 wt‐%) acids, with appreciable amounts of palmitic (8.3–13.2 wt‐%) and oleic (7.8–13.8 wt‐%) acids. The high content of α‐linolenic acid in the cultivars of P. vulgaris could very likely play a beneficial role in reducing the risk of coronary heart disease among the large populations consuming them in Japan.     

Triglyceride composition ofAmoora rohituka seed oil

The fatty acid composition ofAmoora rohituka seed oil was determined by gas-liquid chromatography. The mole percentages of individual acids were found to be palmitic, 24.8; stearic, 12.4; oleic, 20.9, linoleic, 28.5; and linolenic, 13.4. Triglyceride composition was calculated from the fatty acid composition of the native oil and of the monoglyceride produced from it by pancreatic lipase hydrolysis. This calculation gave 2.2, 28.6, 48.1, and 21.1% GS₃, GS₂U, GSU₂, and GU₃, respectively.     

Oil from calabash seed,Crescentia cujete L.

Summary The composition and characteristics of calabash,Crescentia cujete L., seed and oil have been determined. The oil was found to have the following composition calculated from the iodine and thiocyanogen values, and saturated acid content of mixed fatty acids: saturated acids 19.7%, oleic acid 59.4%, linoleic acid 19.3%, and linolenic acid 1.6%. Comparison of the composition and characteristics of calabash seed oil with those for peanut and olive oil indicate that, except for the presence of a small amount of linolenic acid in the former, the oils are similar. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Variation in Fatty Acid Compositions, Oil Content and Oil Yield in a Germplasm Collection of Sesame (Sesamum indicum L.)

The variation in oil content, oil yield and fatty acid compositions of 103 sesame landraces was investigated. The landraces varied widely in their oil quantity and quality. The oil content varied between 41.3 and 62.7%, the average being 53.3%. The percentage content of linoleic, oleic, palmitic and stearic acids in the seed oil ranged between 40.7–49.3, 29.3–41.4, 8.0–10.3 and 2.1–4.8%, respectively. Linolenic and arachidic acids were the minor constituents of the sesame oil. Linoleic and oleic acids were the major fatty acids of sesame with average values of 45.7 and 37.2%, respectively. The total means of oleic and linoleic acids as unsaturated fatty acids of sesame were about 83% which increases the suitability of the sesame oil for human consumption. The superiority of the collection was observed in oil content. The oil content of a few accessions was above 60%, proving claims that some varieties of sesame can reach up to 63% in oil content. The accessions with the highest oil content were relatively richer in the linoleic acid content while there were some landraces in which linoleic and oleic acid contents were in a proportion of almost 1:1. The results obtained in this study provide useful background information for developing new cultivars with a high oil content and different fatty acid compositions. Several accessions could be used as parental lines in breeding programmes aiming to increase sesame oil quantity and quality.     

Aphananthe aspera kernel oil: A rich source of linoleic acid

The seed kernels ofAphananthe aspera Planch. yielded 50.8% of a pale yellow oil. The fatty acid composition determined by gas liquid chromatography was: 5.3% palmitic, 0.1% hexadecenoic, 3.0% stearic, 6.1% oleic, 85.1% linoleic, and 0.4% linolenic acids.