Zusammensetzung einiger koreanischer Samenöle

Composition of Some Korean Seed Oils Seeds of some Korean plants, used in popular medicine, were investigated for oil content, fatty acid composition and sterol composition. Two seed oils of conifers contained unusual polyenoic acids having 18 and 20 C-atoms. cis-5, cis-9, cis-12-Octadecatrienoic acid was identified as one of the major component fatty acids in the seed oil of Pinus koraiensis. Apart from their medicinal use, some of the investigated seeds of angiosperms, such as perilla, sesame or rape, are used mainly for oil extraction. The oils in the varieties cultivated in Korea do not differ in their fatty acid composition from the figures considered as average composition in Europe.     

Specific gravities of rapeseed and canbra oils

New varieties of rapeseed oils grown in Canada have bess than 1% erucic (cis-13-docosenoic) acid and also a reduction in cis-11-eicosenoic acid. The replacement of these acids with C₁₈ acids increased the specific gravity (25 C/25 C) from 0.9123 for an oil with 23.1% erucic acid to 0.9171 for an oil with 0.7% erucic acid. Soybean oil data are presented for comparison.     

The fatty acid composition of various cruciferous seeds

Seeds from 26 Cruciferae species in 7 genera have been investigated for fat content and fatty acid composition of the oil. The GLC retention data have been verified by mass spectrometry. The oil from Cardamine graeca contained 54% of cis-15-tetracosenoic acid; it is the highest content of this acid so far reported in any seed fat.     

Fatty acids of canola Brassica campestris var candle seed and oils at various stages of refining

Fatty acids of oil of a current variety of canolaBrassica campestris var Candle, at 3 stages of commercial production and refining, were compared with authentic seed oils, and with the oil ofB. napus var Tower. The proportion ofcis- 9, cis- 12, trans- 15 andtrans- 9, cis-12, cis-lS-octadecatrienoates relative to the all-cis isomer was lower than that previously observed in processed oils. The minor C₁₄, C₁₅, C₁₇ fatty acids previously documented for Tower were also found in the same proportions in the Candle oil. The proportion of 22:1ω7 isomer (1.1% of a total 1.2% 22:1) was intermediate to that of a high erucic variety (0.9% out of 23% 22:1) and the very low 22:1 Tower (2.3% out of 0.1% 22:1). Thus the proportion of ω7 isomers is governed by total 22:1 present.     

Studies on Herbaceous Seed Oils XI

Seeds from eight species were analysed by standard procedures for oil and protein contents. The fatty acid composition of the oils was determined by GLC. Five species were found to contain oils above 20% and none of them is rich in protein. Some of the oils have a composition fairly similar to the oils at present in common use. Five seed oils are interesting in having more than 50% of saturated acids of the total fatty acids. T. involucrata seed seems to be a promising species because of its high oil and linoleic acid (61.7%) contents.     

Chemical survey and erucic acid content of commercial varieties of nasturtium,Tropaeolum majus L.

Nasturtium (Tropaeolum majus L.) oil contains the highest levels of erucic acid of known seed oils (75–80%). A significant portion of the acid is attached to the 2-position of the glycerol, and trierucin is a major component (ca. 50%) of the oil. Seeds from eleven varieties of commercially available garden nasturtium (T. majus) were screened for oil content, erucic acid levels and fatty acid distribution. Oil contents ranged fromca. 6 to 11%, and erucic acid levels in the oils ranged from 62 to 80%. One sample ofT. speciosum was also analyzed, and contained 28% oil, fatty acids from C₁₆ to C₂₈ and triglycerides up to C₇₂.     

Oil Content and Fatty Acid Composition in Seeds of Three Safflower Species

Seeds of six safflower (C. tinctorius L.) genotypes and 19 accessions of two wild species were analyzed for oil and fatty acid composition. Oil content ranged from 29.20 to 34.00, 20.04 to 30.80 and 15.30 to 20.80% in C. tinctorius, C. oxyacantha Bieb. and C. lanatus L., respectively. The main fatty acids of oleic, linoleic, palmitic and stearic acids composed 96–99% of the total fatty acids in all species. The sum of myristic, palmitoleic, arachidic, and behenic fatty acids in oil of the species ranged from 0.43 to 0.57%. The oleic acid in seed oil of C. tinctorius, C. oxyacantha and C. lanatus ranged from 12.24 to 15.43, 14.11 to 19.28 and 16.70 to 19.77%, respectively. The corresponding ranges for linoleic acid were 71.05 to 76.12, 63.90 to 75.43 and 62.47 to 71.08%. Palmitic acid in seed oil varied from 5.48 to 7.59% in C. tinctorius, 6.09 to 8.33% in C. oxyacantha and 7.44 to 8.78% in C. lanatus. The stearic acid of the seed oil showed a variation of 1.72 to 2.86, 2.50 to 4.87 and 3.14 to 4.79% in genotypes of these species, respectively. The fatty acids composition of oil among the cultivated and wild species were not considerably different, indicating that seed oil of the wild safflower is possibly suitable for human consumption and industrial purposes.     

Extraction and Characterization of Seed Oil from Naturally Grown Chinese Tallow Trees

Seeds were collected from locally and naturally grown Chinese tallow trees (CTT) and characterized for general physical and chemical properties and fatty acid composition of the lipids. The effects of four different solvents (petroleum ether, hexane, diethyl ether, and 95 % ethanol) and two extraction methods (supercritical carbon dioxide (SC-CO₂) and conventional Soxhlet) on the properties of the CTT seed oil, including Chinese vegetable tallow (CVT) and stillingia oil (SO), were also investigated. In general, the yields of CVT and SO did not vary based on solvent for Soxhlet extraction and solvent-free SC-CO₂ extraction, except that the yield of CVT from SC-CO₂ extraction was substantially lower. Nevertheless, the CTT seed oil, extracted by SC-CO₂ displayed better quality than those extracted by Soxhlet extraction in terms of color, residual precipitation, and acid value of the oils. The pretreatment of CTT seed by 3 % aqueous sodium bicarbonate solution likely promoted the hydrolysis of triglyceride and caused the high acid value in the CVT samples. The iodine value at around 180 indicated that the SO is a highly unsaturated drying oil. Palmitic (76 %) and oleic (23 %) are two dominant fatty acids in CVT while linolenic (43 %), linoleic (31 %), and oleic (13 %) are the dominant fatty acids in SO.     

Some minor fatty acids of rapeseed oils

A number of minor unsaturated fatty acids of rapeseed oil (fromBrassica napus orcampestris) have been isolated by combinations of distillation preparatve gas liquid chromatography and silver nitrate thin layer chromatography, and were further identified by oxidative fission in BF₃-MeOH. Among the shorter chain, all-cis polyunsaturated fatty acids described are 16:3ω3, 16:2ω6 and 14:2ω6. A ubiquitous minor component inunproceessed oils was found to becis-9, cis-12, trans-15-octadecatrienoic acid, with lesser proportions of thetrans-9, cis-12, cis-15 isomer. Among others identified werecis-14:1ω9 and 15:1ω10, the latter accompanied by half as muchtrans-15:1ω10. Particular attention was paid to the proportions of the minor monoethylenic fatty acids of the ω7 series relative to the longer chain major ω9 monoethylenic fatty acids which have been reduced by plant breeding.     

Characterization of yam bean (Pachyrhizus spp.) Seeds as potential sources of high palmitic acid oil

Seeds from 22 accessions of the yam bean species Pachyrhizus ahipa (14 accessions), P. erosus (5), and P. tuberosus (3) were investigated for oil and protein contents, fatty acid composition of the seed oil, and the total tocopherol content and composition. Plants from the accessions were grown under greenhouse conditions during one (P. erosus and P. tuberosus) or two years (P. ahipa). The pattern of the investigated seed quality traits was very similar in the three species. Yam bean seeds were characterized by high oil (from about 20 to 28% in one environment) and protein contents (from about 23 to 34%). Seed oil contained high concentrations of palmitic (from about 25 to 30% of the total fatty acids), oleic (21 to 29%), and linoleic acids (35 to 40%). Levels of linolenic acid were very low, from about 1.0 to 2.5%. Total tocopherol content was relatively low in P. erosus (from 249 to 585 mg kg⁻¹ oil) and P. tuberosus (from 260 to 312 mg kg⁻¹ oil) compared with the levels found in P. ahipa grown under identical conditions (508 to 858 mg kg⁻¹ oil). In all the samples, γ-tocopherol was predominant, accounting for more than 90% of the total tocopherol content. The combination of high oil and protein contents, together with high palmitic acid, low linolenic acid, and high γ-tocopherol concentration, makes these crops an interesting alternative as sources of high palmitic acid oil for the food industry.     

Variation in fatty acid composition of the different acyl lipids in seed oils from fourSesamum species

Seeds from different collections of cultivatedSesamum indicum Linn. and three related wild species [specifically,S. alatum Thonn.,S. radiatum Schum and Thonn. andS. angustifolium (Oliv.) Engl.] were studied for their oil content and fatty acid composition of the total lipids. The wild seeds contained less oil (ca. 30%) than the cultivated seeds (ca. 50%). Lipids from all four species were comparable in their total fatty acid composition, with palmitic (8.2–12.7%), stearic (5.6–9.1%), oleic (33.4–46.9%) and linoleic acid (33.2–48.4%) as the major acids. The total lipids from selected samples were fractionated by thin-layer chromatography into five fractions: triacylglycerols (TAG; 80.3–88.9%), diacylglycerols (DAG; 6.5–10.4%), free fatty acids (FFA; 1.2–5.1%), polar lipids (PL; 2.3–3.5%) and steryl esters (SE; 0.3–0.6%). Compared to the TAG, the four other fractions (viz, DAG, FFA, PL and SE) were generally characterized by higher percentages of saturated acids, notably palmitic and stearic acids, and lower percentages of linoleic and oleic acids in all species. Slightly higher percentages of long-chain fatty acids (20∶0, 20∶1, 22∶0 and 24∶0) were observed for lipid classes other than TAG in all four species. Based on the fatty acid composition of the total lipids and of the different acyl lipid classes, it seems thatS. radiatum andS. angustifolium are more related to each other than they are to the other two species.     

Marine-derived fatty acids of fish oils as raw materials for fatty acids manufacture

Fish oils, often an abundant source of C₂₀ and C₂₂ fatty acids, could supplement rapessed oil in the manufacture of long chain saturated fatty acids. Herring oil, traditionally the fish oil of choice, is in very short supply due to depletion of fishery stocks. Menhaden oil, when made from fish caught in the Atlantic, could furnish a steady supply with long chain acids at about the 30% level. Oil made from other species such as anchovy or pilchard need further data on fatty acid content and variability. Manufacture of polyunsaturated fatty acids from fish oils is hampered by lack of suitable procedures. Potential markets for fish oil polyunsaturates especially in the pharmaceutical field seem promising.     

Oil content and fatty acid composition of chia (Salvia hispanica L.) from five northwestern locations in Argentina

Any new crop for which there is a market, and which appears to be adapted to the region, would be attractive to replace nonprofitable traditional crops in Northwestern Argentina. Chia (Salvia hispanica L.) is especially attractive because it can be grown to produce oil for both food and industry. The fatty acids of chia oil are highly unsaturated, with their main components being linoleic (17–26%) and linolenic (50–57%) acids. Seeds from a chia population harvested in Catamarca were sown in five Northwestern Argentina locations. The oil from the chia seeds produced under these five field conditions was measured. Linolenic, linoleic, oleic, palmitic, and stearic fatty acid contents of the oil were determined by gas chromatographic analysis. The results showed variations in oil content, and the oleic, linoleic, and linolenic fatty acid concentrations of the oil were significantly affected by location.     

γ-Linolenic and stearidonic acids in Mongolian Boraginaceae

Seeds of nine Central Asian species of Boraginaceae were investigated for the first time for their oil content and for the fatty acid composition of their seed oils by capillary gas chromatography. Levels of γ-linolenic acid ranged from 6.6 to 13.0% and levels of stearidonic acid ranged from 2.4 to 21.4% of total seed fatty acids. The seed oil ofHackelia deflexa exhibited the highest stearidonic acid content (21.4%) that has been found so far in nature. Other high contents of this fatty acid were in threeLappula species (17.2 to 18.1%). Seed oils ofCynoglossum divaricatum andAmblynotus rupestris contain considerable amounts ofcis-11-eicosenoic (5.3 to 5.8%) andcis-13-docosenoic acid (7.0 to 9.7%) besides γ-linolenic (10.2 to 13.0%) and stearidonic acid (2.4 to 6.5%), which distinguish these oils from those of other Boraginaceae genera. This paper was presented as a poster at 10th Minisymposium and Workshop on Plant Lipids, Sept. 3–6, 1995, in Berne, Switzerland.     

Sonchus oleraceus Seed Oil-Characterization of HBr-Reactive Oxygenated Acid

Seed oil of Sonchus oleraceus (Compositae) contains cis-12, 13-epoxyoctadec-cis-9-enoic acid (Vernolic, 13.7%). Structural details of this HBr-reactive acid are obtained through comparative chromatographic, spectral and chemical data with those of pure vernolic acid isolated from Vernonia anthelmintica seed oil. GLC analysis of the esters of S. oleraceus also showed a C₁₄:1 acid (1.6%).     

Preparation of deuterium-labelled methyl linoleate and its geometric isomers from natural seed oils

Multi-gram quantities of deuterium-labelled methyl linoleate (methyl cis-9,cis-12-octadecadienoate) and its geometric isomers are readily synthesized fromCrépis alpina (70–80% cis-9-octadecen-12-ynoic acid) andVernonia galamensis (70–80% 12,13-epoxy-cis-9-octadecenoic acid) seed oils. Methylcis- 9,cis- 12- andtrans- 9,cis- – octadecadienoate-12,13-d₂ were prepared by the Lindlar-catalyzed reduction (with D₂ gas) of methylcis- 9- and trans-9-octadecen-12-ynoates, respectively. Methyltrans- 9- octadecen-12-ynoate was synthesized by thep-toluene-sulfinic acid-catalyzed isomerization of the corresponding cis isomer. Methylcis- 9fiis- 12., trans- 9fiis- 12;cis- 9,trans- 12- andtrans- 9, frans-12-octadecadienoate-d₂, d₄ and d₆ were prepared by the Wittig coupling (with stereochemical control) of the appropriate d₂-, d₄- or de-alkyltriphenyl-phosphonium salt with methyl 12-oxo-cis-9- ortrans- 9- dodecenoate (prepared by the para-periodic acid cleavage of methyl 12,13-dihydroxy-cis-9- or trans-9-octadecenoate). Thecis dihydroxy ester was synthesized fromVernonia galamensis seed oil by acetolysis, saponification and then esterification. Thecis dihydroxy ester was isomerized by nitric acid/sodium nitrite to thetrans form and purified by silver resin chromatography. Isotopic purities ranged from 88% (for the d₆ isomers) to 99% (for the d₂ isomers). The mention of firm names or trade products does not imply that they are endorsed or recommended over other firms or similar products not mentioned.     

Variability in fatty acid composition amongArachis genotypes: A potential source of product improvement

Research on peanut (Arachis hypogeae L.) genotypes has shown a high degree of genetic variability in fatty acid composition. The two major oil fatty acids, oleic and linoleic, range between 36–69% and 14–40%, respectively, and together make up 75–85% of total fatty acids. The very long chain (C₂₀–C₂₄) fatty acids make up 4–9%, palmitic acid 7–13%, and stearic acid 2–5% of total fatty acids. Stability of oil samples as measured by length of autoxidation induction period at 60 C shows variable but statistically significant (P<0.01) correlations with levels of linoleic acid; peanut butter samples show similar patterns of stability. Selection for lower levels of linoleic acid in the development of new varieties of peanuts should results in products with significantly improved shelf life. Some genotypes show consistent differences in oil stability patterns that are not related to oil linoleic acid content. Analysis of entries from 16 wildArachis species collections revealed levels of oil linoleic acid higher than those found inA. hypogaea. One species,A. villosulicarpa, contained 49% linoleic acid and 21% very long chain acids. The range in linoleic acid withinA. hypogaea and availability of suitable techniques for measuring selection progress give scope for product improvement through breeding.     

Fatty Acid Composition of <Emphasis Type="Italic">Baccaurea courtallensis</Emphasis> Muell. Arg Seed Oil: an Endemic Species of Western Ghats,India

Baccaurea courtallensis Muell. Arg., a moderately sized evergreen tree of the Euphorbiaceae, is endemic to Western Ghats. Its fruits are edible, sour in taste, and contain 2–4 seeds. The native residents harvest the fruits for their medicinal value and for pickling. The seed weight is 0.28 g or 1.0 kg contains 3,500 seeds with a seed coat. The fruit to seed weight ratio is 34:1. Virtually, no work on the chemistry of the seeds or fruit of the species has been reported. Seeds of the species contain 22.5% oil on a dry kernel weight basis. Analysis of the composition of the oil revealed two major fatty acids palmitic acid (42.59%) and oleic acid (36.15%). Stearic acid content was 16.20% and myristic acid was 4.28% of the oil. Two minor acids present were lauric acid (0.40%) and linoleic acid (0.38%) and also including traces of linolenic acid. Physico-chemical properties of the oil showed an acid value of 1.402, a saponification value of 166.89, a refractive index of 0.4239, a specific gravity of −0.938, and an optical rotation of α at 29 °C + 0.35° (λ = 589 nm).     

Isomere Monoensäuren in Pflanzenölen

Isomeric Monoenoic Acids in Vegetable Oils In the scope of systematic studies the fatty acids of oils from seed and fruits of 38 plants are investigated for presence of isomeric monoenoic acids with 16, 18 and 20 C-atoms. All analyzed oils contain between 2 and 4 hexadecenoic, octadecenoic and icosenoic acids with different position of the double bound. Vaccenic acid, the cis-11-octadecenoic acid, is always found in low quantities. Its share depends within certain limits on the content of the oils of cis-9-hexadecenoic acid, the so-called palmitoleic acid. Petroselinic acid, cis-6-octadecenoic acid, is found in apiaceae oils and also in the seed oil of some other plant families. Besides, 14 of the investigated oils contain low quantities of ω5-monoenoic acids.     

Abutilon indicum Seed Oil — Characterisation of HBr-Reactive Acids

The seed oil of Abutilon indicum (Malvaceae) contains three HBr-reactive fatty acids. These are shown to be cis-12,13-epoxyoleic (vernolic) acid, 1.6% 9,10-methylene-octadec-9-enoic (sterculic) acid, 0.9%; as well as 8,9-methylene-heptadec-8-enoic (malvalic) acid, 2.3%. Quantitative results are obtained by combining informations about the HBr-titration, the preparative thin layer separation of oxygenated and non-oxygenated acids, and gas liquid chromatographic analysis.