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1.
Joseph Gresti Corinne Mignerot Jean Bézard Robert L. Wolff 《Journal of the American Oil Chemists' Society》1996,73(11):1539-1547
Purified triacylglycerols (TAG) fromPinus koraiensis andP. pinaster seed oils, which are interesting and commercially available sources of Δ5-olefinic acids (i.e.,cis-5,cis-9,cis-12 18:3 andcis-5,cis-11,cis-14 20:3 acids) were fractionated by reversed-phase high-performance liquid chromatography, and each fraction was examined
by capillary gas-liquid chromatography for its fatty acid composition. A structure could be assigned to more than 92% of TAG
from both oils. In both instances, ca. 48% of the TAG were shown to contain at least one δ5-olefinic acid. In the great majority
of TAG, our data showed that there is only one molecule of δ5-olefinic acid per molecule of TAG. This is compatible with theoretical
calculations based on the proportion of total δ5-olefinic in the oils. Thecis-5,cis-9,cis-12 18:3 acid (14.2 and 8.6% of total fatty acids in the seed oils ofP. koraiensis andP. pinaster, respectively) and thecis-5,cis-11,cis-14 20:3 acid (1.1 and 8.1% of total fatty acids in the seed oils ofP. koraiensis andP. pinaster, respectively) are preferentially associated with two molecules of linoleic acid, and to a lesser extent, to one molecule
of linoleic acid and one molecule of oleic acid, or two oleic acid molecules. However, several other combinations occur, each
in low amounts. The distribution of δ5-olefinic acids in TAG is evidently not random. Combining these results with the known
preferential esterification of δ5-olefinic acids to the 1,3-positions of TAG would suggest that most of these acids are present
at only one of these positions at a time. 相似文献
2.
Methyl esters from seed oils of four Chenopodiaceae species are unusual in that they contain methylcis-5-hexadecenoate (4.6–12%) and methyl 5-octadecenoate (1.1–1.2%). There are indications of small amounts of 18∶25,9 and 18∶35, 9, 12 along with unsaturated acids commonly found in seed oils-oleic (14–21%), linoleic (53–57%) and linolenic (3.5–7.8%). Fatty
acid composition of the oils was determined by gas chromatography, and positions of the double bonds were established by application
of gas chromatography-mass spectrometry to the methoxylated methyl esters.
N. Market. Nutr. Res. Div., ARS, USDA. 相似文献
3.
Robert L. Wolff Eric Dareville Jean-Charles Martin 《Journal of the American Oil Chemists' Society》1997,74(5):515-523
Triacylglycerols (TAG) were purified from the storage lipids extracted from the seeds of several conifer species (Taxus baccata, Larix decidua, Sciadopytis verticillata, and Juniperus communis), each species belonging to one of the four families Taxaceae, Pinaceae, Taxodiaceae, and Cupressaceae, respectively. Each
species was characterized by a high content of 5,9-18:2, 5,9,12-18:3, 5,11,14-20:3, or 5,11,14,17-20:4 acids, respectively.
TAG were partially deacylated with ethylmagnesium bromide, and the resulting 1,2-, 2,3-diacylglycerols (DAG), and 2-monoacylglycerols
(MAG) were purified by thin-layer chromatography. 1,2- and 2,3-DAG were further fractionated by chiral column high-performance
liquid chromatography of the 3,5-dinitrophenylurethane derivatives. Alternately, TAG were subjected to porcine pancreatic
lipase, and the resulting 2-MAG were purified for further analysis. Gas-liquid chromatography of fatty acid methyl esters
prepared from the separated DAG and MAG, coupled with appropriate calculations, indicated that the Δ5-olefinic acids, irrespective
of the species, chainlengths and number of ethylenic bonds, were considerably enriched in the sn-3 position of TAG where they accounted for ca. 35 to 74 mole% of fatty acids esterified to this position (depending on the initial level of total Δ5-olefinic acids in TAG),
which corresponded to 79–94% of Δ5-olefinic acids esterified to the three positions. On the other hand, Δ5-olefinic acids
were less than 10% in the sn-2 position and less than 6% in the sn-1 position of TAG. This specific enrichment of Δ5-olefinic acids in the sn-3 position thus appears to be a general characteristic of conifer seed TAG. These results were extended to TAG from the seeds
of two pine species (Pinus koraiensis and P. pinaster) that are rich in Δ5-olefinic acids and available commercially on a ton-scale. 相似文献
4.
5.
Seed oil ofXeranthemum annuum (family Compositae) contains a number of unusual fatty acids in addition to palmitic, stearic, oleic, linoleic and linolenic.
These acids includecis-5,cis-9,cis-12-octadecatrienoic, 5%;cis-9-l,10-l-epoxyoctadecanoic, 3%;cis-9-l,10-l-epoxy-cis-12-octadecenoic (coronaric), 8%; andcis-12-d,13-d-epoxy-cis-9-octadecenoic (vernolic), 2%; as well as a mixture of two hydroxy acids, 11%. The absolute configurations of the two 9,10-epoxy
acids are established for the first time.
Presented in part at the AOCS Meeting in Cincinnati, October 1965.
No. Utiliz. Res. Dev. Div., ARS, USDA. 相似文献
6.
Masaki Kaneniwa Kazuo Miyashila Toru Takagi 《Journal of the American Oil Chemists' Society》1988,65(9):1470-1474
Autoxidation rates of the 5-olefinic monoenoic and dienoic fatty acids from sea urchin lipids and meadow-foam oils were compared
with those of normal monoenoic and dienoic fatty acids by gas-liquid Chromatographic determination of the unoxidized fatty
acid methyl esters remaining through the autoxidation period. The fatty acids are classified into five groups shown below
according to the oxidation rate of their methyl esters: I 5-olefinic monoenoic acids (c5-18:l, c5-20:l and c5-22:1), II normal
monoenoic acids (c9-18:l, cll-18:l, c9-20:1, cl3-20:l and cl3-22:l), III 5-olefinic dienoic acids (c5,cll-20:2, c5,cl3-20:2
and c5,cl3-22:2), IV 7-olefinic dienoic acids (c7,cl3-22:2 and c7,cl5-22:2) and V normal dienoic acids (c6,c9-18:2, c9,cl2-18:2
and cll,cl4-20:2). The oxidation rates of these groups increased during autoxidation in order from I to V. These results show
that the 5-olefinic monoenoic and dienoic acids are more stable to autoxidation than the normal monoenoic and dienoic acids,
respectively. The higher stabilities of the 5-olefinic monoenoic and dienoic acids in organisms are shown from these results. 相似文献
7.
Ricardo Schuch Faslh Ahmad Kumar D. Mukherjee 《Journal of the American Oil Chemists' Society》1986,63(6):778-783
The seed lipids of Munguba (Bombax munguba Mart., Bombacaceae) were found to contain substantial proportions (ca. 30%) of cyclopropene acyl moieties (sterculoyl and malvaloyl). In a novel approach to the analysis of glycerolipids containing cyclopropene acyl moieties, the triacylglycerols of Munguba seed were first treated with silver nitrate in acetonitrile-acetone (1:1, v/v), in order to convert the cyclopropene groups to the correspondingα,β-unsaturated ketones. The resulting triacylglycerols were fractionated by thin layer chromatography into molecular species containing none, one and two keto (corresponding to none, one and two cyclopropene) acyl moieties per molecule. Each of these molecular species was further fractionated according to carbon numbers by gas chromatography, and the positional distribution of the acyl moieties in each species was determined. Both sterculoyl and malvaloyl moieties were found predominantly at thesn-2 position of the triacylglycerols. The major triacylglycerols of Munguba seed were found to be 1,3-dipalmitoyl-2-oleoylglycerol, 1,3-dipalmitoyl-2-linoleoylglycerol and 1,3-dipalmitoyl-2-sterculoylglycerol. 相似文献
8.
J. R. Vickery F. B. Whitfield G. L. Ford B. H. Kennett 《Journal of the American Oil Chemists' Society》1984,61(3):573-575
Of 12 Gymnospermae seed and leaf oils, only 2 contained cyclopropene fatty acids. All-cis 5, 11, 14, 17-eicosatetraenoic acid occurred in concentrations up to 11.9% in 6 seed oils, and up to 61% in 2 leaf oils.
The structure of this acid, as its methyl ester, was established by the combination of physical (UV, IR,1H- and13C-NMR and mass spectra) and chemical techniques. Arachidonic acid also occurred in 2 seed oils. 相似文献
9.
Stefania Vichi Lorena Pizzale Lanfranco S. Conte 《European Journal of Lipid Science and Technology》2007,109(1):72-78
The positional distribution of fatty acids (FA) in triacylglycerols (TAG) of 47 virgin olive oils from diverse cultivars grown in distinct areas of North‐Eastern Italy was studied. Few data were previously available on oils from these geographical areas. The effects of climatic and geographical conditions on the stereospecific distribution of TAG in olive oil were confirmed. Moreover, the results of the stereospecific analysis were used to evaluate the preferential esterification position of each FA on the basis of the degree of unsaturation and the chain length. The data of the stereospecific analysis of olive oil TAG can contribute to the determination of the selectivity of olive fruit acyltransferases for distinct FA. 相似文献
10.
Interesting differences were found in oils from two samples ofStenachaenium macrocephalum (Compositae) seed with dissimilar storage histories. One contained significant amounts of epoxy acids (6.5%) and hydroxy
conjugated dienoic acids (5.6%), but the other contained no more than 1% of these oxygenated acids. Characterization of components
in the former oil established that the principal epoxy acid (4.0%) is the previously unknowncis-9, 10-epoxy-trans-3,cis-12-octadecadienoic acid. The conjugated dienols include two additional new acids with Δ3 unsaturation (2.5%): 9-hydroxy-trans-3,-trans-10,cis-12-octadecatrienoic and 13-hydroxy-trans-3,cis-9,trans-11-octadecatrienoic acoids. The nonoxygenated acids, except for the large amount (40%) oftrans-3,cis-9,cis-12-octadecatrienoic, are those that commonly occur in seed oils.
Presented at the AOCS Meeting, San Francisco, April 1969.
No. Utiliz. Res. Dev. Div., ARS, USDA. 相似文献
11.
Cis-hexadecenoates isolated from rat liver and hepatoma 7288CTC lipids were analyzed for positional isomers by ozonolysis and
capillary gas liquid chromatography. In addition to the Δ6, Δ7, Δ9 and Δ11 isomers found in both tissues, the hepatoma neutral
and polar lipids contained relatively high percentages of Δ12 and Δ14 hexadecenoates that were virtually absent from liver.
The occurrence of these unusual fatty acids may result from an error in lipid metabolism in the hepatoma. 相似文献
12.
Marcel S. F. Lie Ken Jie M. S. K. Syed Rahmatullah 《Journal of the American Oil Chemists' Society》1995,72(2):245-249
Enrichment ofcis-5 polyunsaturated fatty acids [20:3(5c,11c,14c), 4.3% and 20:4(5c,11c,14c,17c), 11.3%] fromBiota orientalis seed oil was carried out by lipase-catalyzed selective esterification and hydrolysis reactions. Lipases fromRhizomucor miehei (Lipozyme),Candida cylindracea and porcine pancreas were used. Lipozyme-catalyzed esterification ofBiota fatty acids withn-butanol inn-hexane allowed 20:3 and 20:4 (as fatty acids) to be enriched to a maximum level of 52.9%, and in the presence ofC. cylindracea lipase 61.5% enrichment was achieved. Esterification with pancreatic lipase was poor with low levels of enrichment of 20:3
and 20:4 (22%). A multigram scale esterification of the free fatty acids fromBiota seed oil by repeated treatment of the isolated fatty acid fraction withn-butanol inn-hexane in the presence ofC. cylindracea lipase furnished an enrichment yield of 72.5% of a mixture of 20:3 and 20:4 fatty acids. Urea fractionation of the free fatty
acids ofBiota oil gave an initial enriched fraction of 20:3 (9.5%) and 20:4 (25.2%) which, upon treatment withC. cylindracea lipase inn-butanol andn-hexane, gave an enriched fraction of 85.3% of 20:3 and 20:4 fatty acids. Partial hydrolysis of the triglycerides ofBiota oil byC. cylindracea lipase in potassium phosphate buffer at 25°C resulted in a 2.8-fold enrichment ofcis-5 polyunsaturated fatty acids (40.8% of 20:3 and 20:4) as contained in the unhydrolyzed acylglycerol fractions. 相似文献
13.
S. Kermasha S. Kubow M. Safari A. Reid 《Journal of the American Oil Chemists' Society》1993,70(2):169-173
Triacylglycerol (TAG) standards were separated by analytical high-performance liquid chromatography (HPLC) with laser light-scattering
detection (LLSD). A high sensitivity for TAGs was observed with LLSD whereas poor sensitivity was observed with ultraviolet
detection. The HPLC-LLSD analytical separation of butterfat TAGs showed that the TAGs were eluted according to increasing
carbon number. Preparative HPLC-LLSD was used to characterize butterfat TAGs that contained hypercholesterolemic fatty acids
(laurate, myristate, palmitate) with carbon chainlengths of 12 or greater. These TAG fractions accounted for 29.2% of the
total butterfat TAGs. Analysis of the positional distribution of fatty acids of selected butterfat TAGs containing hypercholesterolemic
fatty acids showed the presence of positional isomers in each of these fractions. These butterfat TAGs also showed the predominant
presence of hypercholesterolemic fatty acids at thesn-2 position. The characterization of the positional distribution of hypercholesterolemic fatty acids in butterfat TAGs is
the first step for the determination of the metabolic role of the positional distribution in the hypercholesterolemic effects
of butter. 相似文献
14.
The pattern of accumulation of triacylglycerols, their fatty acid compositions and the positional distribution of the fatty
acids at thesn-2- andsn-1,3-positions of the triacylglycerol molecules at progressive stages of oil palm fruit development were determined. There
was an exponential rate of increase of triacylglycerols and their fatty acids toward the end of fruit development. The fatty
acid composition of the triacylglycerols in the early stages of development, prior to active accumulation, was more or less
similar, but differed appreciably from the later stages, and the transition of fatty acid composition toward that of normal
palm oil occurred at around 16 wk after anthesis (WAA) and stabilized at 20 WAA. All fatty acids increased in terms of absolute
quantity. There was an overall consistency in fatty acid positional distribution, irrespective of development stage. More
saturated fatty acids were found to be esterified at thesn-1,3-positions and more unsaturated fatty acids at thesn-2-position of triacylglycerol. Higher rate of incorporation of 16:0 at the 1,3-positions during the active phase of triacylglycerol
synthesis was observed, while 18:1 acid exhibited a reverse trend. 相似文献
15.
F. Comes M. Farines A. Aumelas J. Soulier 《Journal of the American Oil Chemists' Society》1992,69(12):1224-1227
Cherry seed oil, from the Rosaceae family, prunoid subfamily, is characterized by the existence of about 10% α-eleostearic
acid. The structure of the acid was proven by H and13C nuclear magnetic resonance. The triacylglycerols of this oil were identified and quantitated by highperformance liquid chromatography
by means of several types of detectors. α-Eleostearic acid was not found in the seeds of previously studied prunoids (almond,
peach, apricot and plum). The main fatty acids found in the seeds of cherry and other prunoids were linoleic (L), oleic (O)
and palmitic acids, and the major triacylglycerols were LLO, LOO and OOO. These chemical data support the botanical relationship
within the prunoid subfamily and show the proximity of cherry to the Chrysobalanaceae family. 相似文献
16.
The carbon chain length distribution and the double bond positional isomer composition of the monoenoic fatty acids of the
lipids of total human brain tissue have been determined using gas chromatography and gas chromatography/mass spectrometry
of the fatty acid methyl and picolinyl esters. The even chain length monoenoic C16 to C28 fatty acids contain predominantly two positional isomer series, the n−7 and n−9cis homologues, whose relative proportion varies significantly with chain length. The odd chain length long-chain fatty acids
consist of n−8 and n−10 isomers, whereas the odd chain length very long-chain (more than 22 carbon) fatty acids are n−7 and
n−9 isomers. 相似文献
17.
Hiromi Yoshida Masayuki Saiki Yuka Tomiyama Yoshiyuki Mizushina 《European Journal of Lipid Science and Technology》2008,110(2):158-163
The fatty acid distributions of triacylglycerols (TAG) and major phospholipids (PL) obtained from adzuki beans (Vigna angularis) were investigated. The total lipids extracted from the beans were separated by thin‐layer chromatography (TLC) into eight fractions. The major lipid components were PL (63.5 wt‐%), TAG (21.2 wt‐%), steryl esters (7.5 wt‐%) and hydrocarbons (5.1 wt‐%), while free fatty acids, diacylglycerols (1,3‐DAG and 1,2‐DAG) and monoacylglycerols were also present in minor proportions (0.2–1.1 wt‐%). The major PL components isolated from the beans were phosphatidylcholine (45.3 wt‐%), phosphatidylethanolamine (25.8 wt‐%) and phosphatidylinositol (21.5 wt‐%). Phosphatidylinositol was unique in that it had the highest saturated fatty acid content among the three PL. With a few exceptions, however, the principal characteristics of the fatty acid distribution in the TAG and three PL were evident in the beans: Unsaturated fatty acids were predominantly concentrated in the sn‐2 position while saturated fatty acids primary occupied the sn‐1 or sn‐3 position in the oils of the adzuki beans. In general, these results could be useful to both consumers and producers for the manufacture of traditional adzuki foods in Japan. 相似文献
18.
Hiromi Yoshida Yuka Tomiyama Naoko Yoshida Yoshiyuki Mizushina 《European Journal of Lipid Science and Technology》2009,111(4):386-391
Regiospecific distributions of fatty acids of triacylglycerols (TAG) and phospholipids (PL) separated from broad beans (Vicia faba) of four cultivars (Minpo, Sanuki, Nintoku and Sanren) were investigated. The major lipid components were PL (47.5–50.5 wt‐%) and TAG (47.7–50.1 wt‐%), while steryl esters, hydrocarbons, free fatty acids, diacylglycerols and monoacylglycerols were present in minor proportions (1.6–2.4 wt‐%). The PL components isolated from the four cultivars were phosphatidylcholine (56.4–58.4 wt‐%), phosphatidylethanolamine (20.3–21.7 wt‐%) and phosphatidylinositol (16.6–18.6 wt‐%). Phosphatidylinositol was unique in that it had the highest saturated fatty acid content among these PL. The principal characteristics of the fatty acid distribution in the TAG and PL were evident in the beans: Unsaturated fatty acids were predominantly concentrated in the sn‐2 position while saturated fatty acids primarily occupied the sn‐1 or sn‐3 position in these lipids. The lipid components and fatty acid distributions were almost the same in the four cultivars and were not influenced by genetic variability and planting location. These results could be useful information to both consumers and producers for the manufacture of traditional broad bean foods in Japan. 相似文献
19.
Six oils of marine, algal, and microbial origin were analyzed for stereospecific distribution of component fatty acids. The
general procedure involved preparation ofsn-1,2-(2,3)-diacylglycerols by partial deacylation with ethylmagnesium bromide or pancreatic lipase, separation of X-1,3- andsn-1,2(2,3)-diacylglycerols by borate thin-layer chromatography, resolution of thesn-1,2- andsn-2,3-enantiomers by chiral phase high-performance liquid chromatography following preparation of dinitrophenylurethane derivatives,
and determination of the fatty acid composition by gas chromatography. Unexpected complications arose during a stereospecific
analysis of triacylglycerols containing over 33% of either 20∶4 or 22∶6 fatty acids. Thesn-1,2(2,3)-diacylglycerols made up of two long-chain polyunsaturated acids migrated with the X-1,3-diacylglycerols and required
separate chiral phase resolution. Furthermore, the enzymatic method yieldedsn-1,2(2,3)-diacylglycerols, overrepresenting the polyenoic species due to their relative resistance to lipolysis, but prolonged
digestion yielded correct composition for the 2-monoacylglycerols. The final positional distribution of the fatty acids was
established by pooling and normalizing the data from subfractions obtained by norman- and chiral-phase separation of diacylglycerols.
The molecular species of X-1,3-,sn-1,2- andsn-2,3-diacylglycerol dinitrophenylurethanes were identified by chiral-phase liquid chromatography/mass spectrometry with electrospray
ionization, which demonstrated a preferential association of the paired long-chain acids with thesn-1,2- andsn-2,3-diacylglycerol isomers. 相似文献
20.
Kohei Yamamoto Akira Shibahara Akiko Sakuma Takao Nakayama Goro Kajimoto 《Lipids》1990,25(10):602-605
The pulp lipids of jujube (Zizyphus jujuba var.inermis) fruit have been shown by chromatographic, spectrometric and chemical analyses to contain a series ofcis-monoenoic fatty acids with n−5 unsaturation as major acyl moieties. The total concentration of these n−5 fatty acids, such
as 14∶1n−5, 16∶1n−5 and 18∶1n−5, ranged from 22 to 54% of total fatty acids in the pulp lipids of 11 different sources. The
main component of the n−5 homologues was 16∶1n−5 in all cases. Other monoenoic acids with n−7 unsaturation, namely palmitoleic
(cis-9-hexadecenoic) acid andcis-vaccenic (cis-11-octadecenoic) acid, as well as with n−9 unsaturation, namely oleic acid, were also identified. In the seed lipids of jujube
fruit, none of the n−5 monoenoic acids could be detected. Thus the jujube pulp lipids are characterized by the predominance
of n−5 monoenoic acid isomers. 相似文献