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.     

Fatty Acid Profile of Kenaf Seed Oil

The fatty acid profile of kenaf (Hibiscus cannabinus L.) seed oil has been the subject of several previous reports in the literature. These reports vary considerably regarding the presence and amounts of specific fatty acids, notably (12,13-epoxy-9(Z)-octadecenoic (epoxyoleic) acid, but also cyclic (cyclopropene and cyclopropane) fatty acids. To clarify this matter, two kenaf seed oils (from the Cubano and Dowling varieties of kenaf) were investigated regarding their fatty acid profiles. Both contain epoxyoleic acid, the Cubano sample around 2 % and the Dowling sample 5-6 % depending on processing. The cyclic fatty acids malvalic and dihydrosterculic were identified in amounts around 1 %. Trace amounts of sterculic acid were observed as were minor amounts of C17:1 fatty acids. The results are discussed in the context of the fatty acid profiles of other hibiscus seed oils.     

Acacia suma Seed Oil-Characterization of a HBr-Reactive Acid

The seed oil of Acacia suma (Leguminosae) was found to have a HBr-reactive fatty acid along with other usual fatty acids. On the basis of chemical, spectroscopic and chromatographic techniques the HBr-reactive acid was identified as cis-9, 10-epoxy-cis-12-octadecenoic (coronaric) acid. This acid makes up 10.6% of the total oil triglycerides.     

Epoxy oils from plant seeds

Epoxy acids have been reported in seed oils from more than 60 species in 12 plant families. The discovery of 9,10-epoxyoctadec-12-ynoic and 9,10-epoxy-trans-3,cis-12-octadecadienoic acids brings to six the number of natural epoxy acids now known to occur in seed oils. These latest epoxy acids and 15,16-epoxy-cis-9,cis-12-octadecadienoic acid have been found in only one species each and at levels lower than 5% of the oil. Coronaric (9,10-epoxy-cis-12-octadecenoic) acid and 9,10-epoxystearic acid have been encountered in several seed oils, the first as much as 15% of the oil and the latter in only small amounts. Vernolic (12,13-epoxy-cis-9-octadecenoic) acid, which has been identified in numerous oils, is the only epoxy acid known to occur in seed oils at levels above 15%, and it may constitute as much as 75%. On the basis of data available to date,Vernonia anthelmintica appears to have the best potential for commercial production of an epoxy oil. Although one improved line has been selected, continued improvement is needed. Formation of epoxy acids in oilseeds during storage after harvest has been demonstrated, and may be partly responsible for the small amounts of epoxide detected in oils from a wide variety of seeds. Presented at the AOCS Meeting, New Orleans, April 1970. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Rapid transesterification and mass spectrometric approach to seed oil analysis

Fatty acid composition of seed oil is determined in less than one hr using a quantitative one-vial technique. The method of analysis requires alcoholic solutions of sodium methoxide mild enough for epoxy and polyunsaturated oils. Separation and characterization of component fatty acids were accomplished by high resolution gas chromatography-mass spectrometry. Using this method,Vernonia galamensis seed oil is shown to contain 79–80% vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid.Amaranthus cruentus, a West African vegetable crop, is shown to contain 17.3% palmitic acid, 3.2% stearic acid, 22.7% oleic acid, 54.7% linoleic acid and 2.1% linolenic acid.     

Minor Seed Oils XVI: Examination of Fifteen Seed Oils

Fifteen seed oils from nine plant families have been examined. Oleic acid is the major component in all the oil samples, maximum being in Amaranthus tricolor (91.0%), except in the seed oil of Physalis maxima. All the samples contain arachidic and behenic acids. The oil samples from Ipomoea species and from Physalis maxima contain the lower fatty acids (caprylic and capric). Linolenic acid is found in eleven samples and lauric acid in all the seed oils except the seed oil of Celosia cristata.     

The abundance ofcis-5-octadecenoic acid inDioscoreophyllum cumminsii seed oil

Oil fromDioscoreophyllum cumminsii (Stapf) Diels containscis-5-octadecenoic acid as 84% of its total fatty acids. The unsaturated acids normally found in seed oils are present in small amounts (oleic, 1%, linoleic 5.2%; and linolenic, 0.3%). Other unusual acids present, in minor amounts, arecis-5-hexadecenoic (0.6%), 11-octadecenoic (0.9%) and two polyenoic acids which are probably unsaturated at the 5 position. N. Market. Nutr. Res. Div., ARS, USDA.     

Minor Seed Oils XVIII: Examination of Twelve Seed Oils

Twelve seed oils from ten plant families have been examined. Except three the seed oils are reported to be medicinal. Oleic acid is the major component in the seed oils from Celosia pyramidalis, Cryptostegia grandiflora, Gomphrena globosa, Isotoma longiflora, Jasminum officinale Var. grandiflorum and Sida humilis. The remaining six seed oils contain linoleic acid as the major component. All the samples contain arachidic and behenic acids. The oil sample from Sida humilis contains lauric acid. Linolenic acid is found in five samples and myristic in seven samples.     

Occurrence ofCis-6-hexadecenoic acid as the major component ofThunbergia alata seed oil

An unusual series of monoenoic fatty acids constitutes about 85% of the total acids in seed oil fromThunbergia alata. The major component in the oil,cis-6-hexadecenoic acid (82%), is accompanied by the homologous 4-tetradecenoic (ca. 0.2%) and 8-octadecenoic (1.8%) acids. Another homologous series is represented by 5-tetradecenoic (ca. 0.2%), 7-hexadecenoic (1.8%) and the familiar 9-octadecenoic (4.4%) acids. Traces (<0.1%) of three other acids, 6-tetradecenoic and 10- and 11-octadecenoic, are also present along with palmitic (5.8%), stearic (0.6%) and linoleic (2.2%) acids. Some of the monoenoic acids have not previously been known to occur in seed oils. Presented at the Fifth Great Lakes Regional Meeting of the American Chemical Society, Peoria, Illinois, 1971. No. Market. Nutr. Res. Div., ARS, USDA.     

Minor components responsible for flavor reversion of soybean oil

Edible refined, bleached and deodorized (RBD) soybean oil was fractionated by silicic acid column chromatography to identify minor components responsible for flavor reversion. Minor components from oil eluted with diethyl ether/n-hexane (1:1) were compared with those from corn and canola oils. All vegetable oils contain free fatty acids, diglycerides and sterols as major ingredients in this fraction. However, unusual triglycerides consisting of 10-oxo-8-octadecenoic acid and 10-and 9-hydroxy octadecanoic acids were detected in RBD and crude soybean oils.     

Lipids containing isoricinoleoyl (9-hydroxy-cis-12-octadecenoyl) moieties in seeds ofWrightia species

Composition of lipids in mature seeds ofWrightia tinctoria andWrightia coccinea, which contain large proportions of isoricinoleic acid (9-hydroxy-cis-12-octadecenoic acid) as constituent fatty acid beside the common long chain fatty acids, is reported. The major classes of acyl lipids in the seeds of the twoWrightia species, identified by chromatographic and mass spectrometric analyses, are found to be triisoricinoleoylglycerol and diisoricinoleoylacylglycerols. Phospholipids and glycolipids contain only small proportions of isoricinoleoyl moieties. Among two possible precursors for the biosynthesis of isoricinoleic acid, 9-hydroxystearic acid, but notcis-12-octadecenoic acid, is detectable in the seed lipids.     

Chromatographischer und spektroskopischer Vergleich des Autoxidationsprozesses von Öl- und Elaidinsäure

Chromatographic and Spectroscopic Comparison of the Autoxidation Process of Oleic and Elaidic Acid The autoxidation process of cis-9-octadecenoic and trans-9-octadecenoic acid was studied using thin-layer chromatography, gasliquid chromatography, nuclear magnetic resonance spectroscopy and infra-red spectroscopy. On the basis of results obtained and by comparison with the “classical methods”, such as the course of peroxide value, and changes in acid value and iodine value, a scheme has been proposed to characterize the initial phase of the autoxidation process of oleic and elaidic acids.     

Acetylenic acids ofAlvaradoa amorphoides seed oil

Oil from the seed ofAlvaradoa amorphoides Liebm. (Simaroubaceae) collected in Mexico contains two acetylenic fatty acids previously unknown in seed oils, 15% of 17-octadecen-6-ynoic and a trace amount of 6-eicosynoic acid. The predominant fatty acid (58%) in the oil is 6-octadecynoic (tariric). Both the δ6 and δ9 series of hexadecenoic, octadecenoic, octadecadienoic, and octadecatrienoic acids were found, but only the δ6 isomer of eicosenoic acid (1.4%) was detectec. The mono- and dienoic acids make up about 19% of the total oil. The remainder consists mostly of saturated acids (6.3%). Techniques used in isolation and identification of the acids included thin layer and gas chromatography, IR, UV, NMR and mass spectroscopy, and ozonolysis coupled with gas chromatography. Presented at the 7th Great Lakes Regional American Chemical Society Meeting, Kalamazoo, Mich., June, 1973. ARS, USDA     

γ-Linolenic acid inAcer seed oils

The octadecatrienoic acids inAcer negundo L. (maple family) seed oil include both 9,12,15- (1%) and 6.9,12-(7%) isomers. The chief monoenoic acids identified were 9-octadecenoic (21%), 11-eicosenoic (7%), 13-docosenoic (15%), and 15-tetracosenoic (7%). Also present is a considerable amount of 9,12-octadecadienoic acid. Investigation of ten other Aceraceae revealed their seed oils to have a similar fatty acid composition.     

黑种草籽油的超临界CO_2萃取及其GC-MS分析

以新疆瘤果黑种草籽为原料,采用超临界CO2萃取技术(SFE-CO2)研究了瘤果黑种草籽油的萃取工艺,并对其化学成分进行了GC-MS分析。得到瘤果黑种草籽油较适宜的工艺条件为:萃取压力20 MPa,萃取温度35℃,萃取时间2 h,CO2流量20 kg/h。在该工艺条件下,黑种草籽油的得油率达36.33%。GC-MS检测出6种脂肪酸成分,主要为不饱和脂肪酸,其中,亚油酸质量分数60.95%,油酸质量分数20.54%,8,11-二十碳二烯酸质量分数2.43%,不饱和脂肪酸的质量分数近84%。     

TheTrans-6 fatty acids ofPicramnia sellowii seed oil

The C₁₈ monoenoic acids inPicramnia sellowii Planch. seed oil include bothcis-andtrans-6-octadecenoic acids, as well as oleic acid. The hexadecenoic acids are also thecis- andtrans-Δ6-isomers, and the eicosenoic acids have Δ6-unsaturation of undetermined geometric configuration. The C₁₈ polyenoic acids detected are 9,12- and 6,9-octadecadienoic and 9,12,15- and 6,9,12-octadecatrienoic acids. Partial investigation of another species,P. pentandra Sw., revealed its oil to have a similar fatty acid composition. Presented in part at AOCS Meeting, New York, October 1968. No. Utiliz. Res. Dev. Div., ARS, USDA.     

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.     

Comparison of two kinds of pumpkin seed oils obtained by supercritical CO2 extraction

The oils from two kinds of pumpkin seeds, black and white ones, were extracted by supercritical CO₂ (SC‐CO₂). The technological variables for SC‐CO₂ extraction were optimized and the resulting oils were analyzed by GC‐MS. As a result, the optimal conditions for SC‐CO₂ extraction were as follows: 25～30 MPa, 45 °C, SC‐CO₂ flow rate of 30～40 kg/h. The main compounds in the resulting oils were 9,12‐octadecadienoic acid, 9‐octadecenoic acid, stearic acid, palmitic acid for both types of pumpkin seeds, however, the black seed oil contains more unsaturated fatty acids (UFA) than the white seed oil. On the other hand, some compounds including heptadecanoic acid (0.27%), tetracosanic acid (0.1%), 9‐dodecaenoic acid (0.45%) and pentadecenoic acid (0.05%) were found in white seed oil but not in black seed oil; while eicosanic acid (0.05%), 11,14‐eicosadienoic acid (0.2%), 11‐octadecenoic acid (0.06%), 7‐hexadecenoic acid (0.02%) and 1,12‐tridecadiene (0.02%) were only found in black seed oil.     

Analysis of seed oil from ricinus communis and dimorphoteca pluvialis by gas and supercritical fluid chromatography

The seed oils from Dimorphoteca pluvialis and Ricinus communis contain hydroxy fatty acids. Dimorphoteca pluvialis contains Δ-9-hydroxy-10t, 12t-octadecadienoic acid (dimorphecolic acid) and R. communis contains Δ-12-hydroxy-9c-octadecenoic acid (ricinoleic acid). The oils were derivatized and analyzed to determine the content of hydroxy fatty acids. The trimethylsilyl fatty acid methyl ester (TMS-FAME) derivatives were analyzed by capillary gas chromatography (GC), and the free fatty acid (FFA) derivatives and the oils were analyzed by capillary supercritical fluid chromatography (SFC). Further, mass spectroscopy of the TMS-FAME derivatives was performed to check the purity of the derivatives. The results from the GC analyses of TMS-FAME corresponded to the results found by SFC analysis of the FFA. The content of ricinoleic acid in the glycerolipids of R. communis was 87.7 wt%, and the content of dimorphecolic acid in D. pluvialis was 54.0 wt%. The methods were evaluated with respect to the cost, ease, and time needed for sample preparation and analysis.     

Mexican prickly poppy seed oil

Summary Oil from the Mexican prickly poppy (Argemone mexicana) seed was found to contain the following percentages of acids: Myristic, 0.3; palmitic, 11.1; stearic, 1.8; lignoceric, 0.1; hexadecenoic, 0.8; oleic, 21.3; and linoleic, 58.6. Ricinoleic and linoleic acids, which had been reported by other investigators (2, 3) as constituents of this oil, were not found in the oil from Mexican seed. Agricultural Chemical Research Division Contribution No. 96.