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1.
Mono- and polyestolides, made from oleic acid, meadowfoam oil fatty acids and erucic acid, were subjected to biodegradation
with mixed cultures of Penicillium verucosum, Mucor racemosus, and Enterobacter aerogenes. Fermentations were continued for 3, 5, 10, 15, 20, or 30 d. Meadowfoam oil and its fatty acids, oleic acid and soybean oil
were also biodegraded under the same conditions. After 10 d, oleic acid and soybean oil were degraded 99.8 and 99.2%, respectively;
meadowfoam oil and its fatty acids were degraded 89.0 and 97.7%, respectively. After 30 d, oleic acid-derived poly- and monoestolides
were degraded 98.6 and 90.0%, respectively, meadowfoam estolides were degraded 75.7%, and erucic acid estolides were degraded
84.0%. 相似文献
2.
Robert L. Wolff Corinne C. Bayard 《Journal of the American Oil Chemists' Society》1995,72(9):1043-1046
The fatty acid composition of seeds from seven species of the genusPinus (P. pinaster, P. griffithii, P. pinea, P. koraiensis, P. sylvestris, P. mughus, andP. nigra) was established. Pine seeds are rich in oil (31–68% by weight) and contain several unusual polymethylene-interrupted unsaturated
fatty acids with acis-5 ethylenic bond. These are thecis-5,cis-9 18:2,cis-5,cis-9,cis-12 18:3,cis-5,cis-11 20:2, andcis-5,cis-11,cis-14 20:3 acids, with a trace ofcis-5,cis-9,cis-12,cis-15 18:4 acid. Their percentage relative to total fatty acids varies from a low of 3.1% (P. pinea) to a high of 30.3% (P. sylvestris), depending on the species. The majorcis-5 double bond-containing acid is generally thecis-5,cis-9,cis-12 18:3 acid (pinolenic acid). In all species, linoleic acid represents approximately one-half the total fatty acids, whereas
the content of oleic acid varies in the range 14–36% inversely to the sum of fatty acids containing acis-5 ethylenic bond. The easily available seeds fromP. koraiensis appear to be a good source of pinolenic acid: their oil content isca. 65%, and pinolenic represents about 15% of total fatty acids. These values appear to be rather constant.Pinus pinaster, which is grown on several thousand acres in the southwest of France, is an interesting source ofcis-5,cis-11,cis-14 20:3 acid (7% in the oil, which isca. 35% of the dehulled seed weight), an acid sharing in common three double bonds with arachidonic acid. Apparently,P. sylvestris seed oil contains the highest level ofcis-5 double bond-containing acids among pine seed oils that have ever been analyzed. 相似文献
3.
The seed oil of the gymnosperm Welwitschia mirabilis was found to contain malvalic acid, a cyclopropenoic fatty acid. This is in sharp contrast to most other gymnosperms, which
contain Δ5cis-fatty acids as well as the normal set of fatty acids. The importance of this finding in relation to questions of the evolution
of the Gymnospermae and Angiospermae, the two main branches of higher plants, is briefly discussed. 相似文献
4.
Robert L. Wolff Laurent G. Deluc Anne M. Marpeau 《Journal of the American Oil Chemists' Society》1996,73(6):765-771
The seed oils from twenty-five Conifer species (from four families—Pinaceae, Cupressaceae, Taxodiaceae, and Taxaceae) have
been analyzed, and their fatty acid compositions were established by capillary gas-liquid chromatography on two columns with
different polarities. The oil content of the seeds varied from less than 1% up to 50%. Conifer seed oils were characterized
by the presence of several Δ5-unsaturated polymethylene-interrupted polyunsaturated fatty acids (Δ5-acids) with either 18
(cis-5,cis-9, 18∶2,cis-5,cis-9,cis-12 18∶3, andcis-5,cis-9,cis-12,cis-15 18∶4 acids) or 20 carbon atoms (cis-5,cis-11 20∶2,cis-5,cis-11,cis-14, 20∶3, andcis-5,cis-11,cis-14,cis-17 20∶4 acids). Pinaceae seed oils contained 17–31% of Δ5-acids, mainly with 18 carbon atoms. The 20-carbon acids present
were structurally derived from 20∶1n-9 and 20∶2n-6 acids. Pinaceae seed oils were practically devoid of 18∶3n-3 acid and did
not contain either Δ5-18∶4 or Δ5-20∶4 acids. Several Pinaceae seeds had a Δ5-acid content higher than 50 mg/g of seed. The
only Taxaceae seed oil studied (Taxus baccata) had a fatty acid composition related to those of Pinaceae seed oils. Cupressaceae seed oils differed from Pinaceae seed
oils by the absence of Δ5-acids with 18 carbon atoms and high concentrations in 18∶3n-3 acid and in Δ5-acids with 20 carbon
atoms (Δ5-20∶3 and Δ5-20∶4 acids). Δ5-18∶4 Acid was present in minute amounts. The highest level of Δ5-20∶4 acid was found
inJuniperus communis seed oil, but the best source of Δ5-acids among Cupressaceae wasThuja occidentalis. Taxodiaceae seed oils had more heterogeneous fatty acid compositions, but the distribution of Δ5-acids resembled that found
in Cupressaceae seed oils. Except forSciadopytis verticillata, other Taxodiaceae species are not interesting sources of Δ5-acids. The distribution profile of Δ5-acids among different
Conifer families appeared to be linked to the occurrence of 18∶3n-3 acid in the seed oils. 相似文献
5.
Earl G. Hammond Daniel Duvick Tong Wang Hortense Dodo R. N. Pittman 《Journal of the American Oil Chemists' Society》1997,74(10):1235-1239
Peanut (Arachis hypogaea) plant introductions (732) were analyzed for fatty acid composition. Palmitate varied from 8.2 to 15.1%, stearate 1.1 to
7.2%, oleate 31.5 to 60.2%, linoleate 19.9 to 45.4%, arachidate 0.8 to 3.2%, eicosenoate 0.6 to 2.6%, behenate 1.8 to 5.4%,
and lignocerate 0.5 to 2.5%. The eicosenoate was shown to be cis-11-eicosenoate. In addition, epoxy fatty acids were found in many plant introductions in percentages ranging as high as 2.5%.
These were tentatively identified as chiefly 9,10-epoxy stearate and coronarate with smaller amounts of vernolate. The percentage
of palmitate was shown to be correlated positively with linoleate and negatively with oleate, eicosenoate, and lignocerate.
Stearate was highly correlated with arachidate and negatively with eicosenoate and lignocerate. Oleate and linoleate, the
two major fatty acids, were negatively correlated. Arachidate was negatively correlated with eicosenoate, and eicosenoate
was positively correlated with lignocerate. Behenate and lignocerate were positively correlated. Epoxy esters were positively
correlated with palmitate and negatively with oleate. Segregation of the plant introductions by axis flower, growth habit,
and pod types showed significant differences that reflected the same fatty acid groupings revealed by the correlations. 相似文献
6.
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
7.
G. Lakshminarayana R. Subbarao Y. Sita Rama Sastry T. Chandrasekhara Rao Vijay Kale P. Vijayalakshmi 《Journal of the American Oil Chemists' Society》1982,59(5):238-240
The composition (wt %) of the fatty acids obtained by decomposition of castor oil fatty acid estolides and distillation was
determined by a combination of spectroscopic (ultraviolet, nuclear magnetic resonance, infrared), chromatographic (thin layer
on Silica Gel G modified with silver nitrate and ammonium hydroxide, gas liquid) and chemical (partial reduction and periodate/permanganate
oxidation) techniques and found to be 16:0, 2.7; 18:0, 2.6; 18:1, 5.2; conjugatedcis,trans (trans,cis)-18:2, 34.4; conjugatedcis,cis-18:2, 9.7; conjugatedtrans,trans-18:2, 3.9; 9-cis,12-trans-18:2, 20.8; 9-trans,12-cis-18:2, 2.3; and 9-cis,-18:2, 18.4. 相似文献
8.
C. D. Daulatabad G. M. Mulla A. M. Mirajkar K. M. Hosamani 《Journal of the American Oil Chemists' Society》1992,69(2):188-189
A keto fatty acid (9-oxo-cis-12-octadecenoic acid) has been isolated in appreciable amounts (45.9%) fromCryptolepis buchnani seed oil. The identification was based on chemical and spectroscopic methods. 相似文献
9.
Kallappa M. Hosamani 《Journal of the American Oil Chemists' Society》1995,72(4):489-492
Pithecollobium dulce, Benth (syn.Inga dulcis, Willd) seed oil, belonging to the Leguminosae plant family, contains minor amounts of vernolic acid (12,13-epoxy-octadec-cis-9-enoic acid, 10.0%), malvalic acid [7-(2-octacyclopropen-1-yl)heptanoic acid, 3.2%], and sterculic acid [8-(2-octacyclopropen-1-yl)octanoic
acid, 2.0%]. The other normal fatty acids are palmitic (12.1%), stearic (4.2%), behenic (10.6%), oleic (34.1%), and linoleic
(23.8%). These fatty acids have been characterized by Fourier transform infrared,1H nuclear magnetic resonance, mass spectrometry and gas-liquid chromatography techniques and by chemical degradations. 相似文献
10.
Anette Bysted Gunhild Hølmer Pia Lund 《Journal of the American Oil Chemists' Society》1998,75(2):225-234
The effect of trans fatty acids from partially hydrogenated soybean oil and butterfat on the formation of polyunsaturated fatty acids was investigated.
Five groups of rats were fed diets that contained 20 wt% fat. The content of linoleic acid was adjusted to 10 wt% of the dietary
fats in all diets, whereas the amount of trans fatty acids from partially hydrogenated soybean oil (PHSBO) was varied from 4.5 to 15 wt% in three of the five diets. The
fourth group received trans fatty acids from butterfat (BF), while the control group was fed palm oil without trans fatty acids. Trans fatty acids in the diet were portionally reflected in rat liver and heart phosphatidylethanolamine (PE), phosphatidylcholine
(PC), phosphatidylinositol, and phosphatidylserine. Incorporation in the sn-1 position was compensated by a decrease in saturated fatty acids. Trans fatty acids were not detected in diphosphatidylglycerol. Compared to the presence in the dietary fats, 8t- and 10t-18:1 were discriminated against in the incorporation in PE and PC from liver and heart, whereas 9t- and 12t-18:1 were preferred. The formation of 20:4n-6 was not influenced by 4.5 wt% trans fatty acids (from PHSBO) but apparently was by 10 wt% in liver. In contrast, even a content of 2.5 wt% trans fatty acids from BF reduced the formation of 20:4n-6. The inhibitory effect of trans isomers on linoleic acid conversion was reflected less in heart than in liver and less for PE than for PC. Groups with trans fatty acids showed increased 22:6n-3 and 22:5n-3 deposition in liver and heart PE and PC. 相似文献
11.
Nikolaus Weber Klaus Vosmann Eberhard Fehling Kumar D. Mukherjee Dieter Bergenthal 《Journal of the American Oil Chemists' Society》1995,72(3):361-368
A novel process has been described recently for the preparation of hydroxylated fatty acids (HOFA) and HOFA methyl esters
from plant oils. HOFA methyl esters prepared from conventional and alternative plant oils were characterized by various chromatographic
methods (thin-layer chromatography, high-performance liquid chromatography, and gas chromatography) and gas chromatography-mass
spectrometry as well as1H and13C nuclear magnetic resonance spectroscopy. HOFA methyl esters obtained fromEuphorbia lathyris seed oil, low-erucic acid rapeseed oil, and sunflower oil contain as major constituents methylthreo-9,10-dihydroxy octadecanoate (derived from oleic acid) and methyl dihydroxy tetrahydrofuran octadecanoates, e.g., methyl
9,12-dihydroxy-10,13-epoxy octadecanoates and methyl 10,13-dihydroxy-9,12-epoxy octadecanoates (derived from linoleic acid).
Other constituents detected in the products include methyl esters of saturated fatty acids (not epoxidized/derivatized) and
traces of methyl esters of epoxy fatty acids (not hydrolyzed). The products that contain high levels of monomeric HOFA may
find wide application in a variety of technical products. 相似文献
12.
W. T. Roubal 《Journal of the American Oil Chemists' Society》1963,40(6):213-215
Bluefin tuna (Thunnus thynnus) is consumed in substantial amounts by humans. However, little has been reported on the fatty acid composition of bluefin
body oil and on the isomeric structures of the unsaturated fatty acids. Because of the probable nutritional significance of
unsaturated fatty acids, the present work was undertaken as an introductory study of the composition and structure of the
fatty acids of tuna. The fatty acid composition of the light and dark meats from three bluefin tuna was determined by gas-liquid
chromatography. A wide variety of saturated and polyunsaturated fatty acids were present in the oil from the meat of these
speciments. the monoemoic fatty acid fraction, which comprises 34% of the total fatty acids was isolated and the isomers determined.
Isomers found werecis-9-hexadecenoic acid,cis-9-octadecenoic acid,cis-11-octadecenoic acid,cis-9-eicosenoic acid,cis-11-eicosenoic acid,cis-11-docosenoic acid, andcis-13-docosenoic acid.
Division of Industrial Research, U.S. Fish and Wildlife Service, Department of the Interior. 相似文献
13.
Nanzad Tsevegsüren Kurt Aitzetmüller 《Journal of the American Oil Chemists' Society》1996,73(12):1681-1684
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. 相似文献
14.
Eberhard Fehling 《Journal of the American Oil Chemists' Society》1995,72(3):355-359
Gel permeation chromatography of hydroxylated fatty acids (HOFA), prepared from various plant oils by a novel technical process,
showed the presence of considerable amounts of estolides formed by intermolecular esterification of the HOFA. Thin-layer chromatographic
fractionation followed by gas chromatography of the fractions revealed that the nonpolar estolides contain predominantly saturated
fatty acids esterified tothero-9, 10-dihydroxy octadecanoic acid or dihydroxy tetrahydrofuran octadecanoic acids, e.g., 9,12-dihydroxy-10, 13-epoxy octadecanoic
acid and 10,13-dihydroxy-9, 12-epoxy octadecanoic acid. The fractions of polar estolides consist mainly of intermolecular
esters of the above dihydroxy fatty acids. 相似文献
15.
The triacylglycerols of winter butterfat were fractionated according to the type and degree of unsaturation into six fractions
by silver ion high-performance liquid chromatography (Ag-HPLC). The acyl carbon number distribution of the triacylglycerols
in each fraction was elucidated by reversed-phase HPLC and mass spectrometry (MS). The MS analysis of each fraction gave deprotonated
triacylglycerol [M - H]− ions which were produced by chemical ionization with ammonia. The daughter spectrum of each of the [M - H]− ions provided information on its fatty acid constituents. Successful fractionation of triacylglycerols differing in the configuration
of one fatty acyl residue by Ag-HPLC was important because geometrical isomers could not be distinguished by the MS system
used. In addition to the fatty acid compositions, reversed-phase HPLC analysis demonstrated the purity of the collected fractions:
molecules having acis-trans difference were separated nearly to the baseline. Triacylglycerols differing in the configuration of one fatty acyl residue
were not equally distributed in relation to their acyl carbon numbers. This indicates that during the biosynthesis of triacylglycerols,cis- andtrans-fatty acids are processed differently. Although the fatty acid compositions of the corresponding molecular weight species
of disaturatedtrans- and disaturatedcis-monoenoic triacylglycerols were similar, there may be differences in the amounts of different fatty acid combinations or
in the distribution of fatty acids between the primary and secondary glycerol positions. In addition to the main components,
it was possible to analyze minor triacylglycerols, such as molecules containing one odd-chain fatty acid, by the MS system
used. 相似文献
16.
Meadowfoam fatty acids (83% monoenoic fatty acid), reacted with 0.01–0.1 mole equivalents of perchloric acid, gave 33–71% yield of estolide, an oligomeric 2° ester, resulting from self condensation. Equimolar amounts of perchloric acid to fatty acid failed to produce estolide but converted the fatty acids to a mixture of lactones, mainly γ-eicosanolactone. Temperature plays a critical role; higher temperatures (75–100°C), at the same acid concentration, provide lactones while lower temperatures (20–65°C) yield estolides. Lower acid levels (<0.1 mole equivalents) gave the best yields (≈70%) at 65°C. The estolide and monomer were characterized by nuclear magnetic resonance, infrared high-pressure liquid chromatography, gas chromatography, gas chromatography/mass spectrometry. The estolide is a mixture of oligomers with an average distribution near 1.65 ester units. The ester linkages are located mainly at the original double bond positions but have some positional isomerization to adjacent sites in accord with carbocation migration along the alkyl chain. The residual double bond of the estolide was extensively isomerized fromcis totrans and positionally along the chain. The distilled monomer is similar in structure to the unsaturated portion of the estolide with geometrical and positional double bond isomerization. In addition, a significant amount of cyclization of the fatty acids to lactone (≈30%) had occurred. 相似文献
17.
Triacylglycerol estolides have been reported as components of the seed oil of a number of plant species and are generally associated with the presence of fatty acids containing hydroxyl groups. We have used MALDI-TOF MS to examine the intact acylglycerol species present in the seed oils of two plants that produce kamlolenic acid (18-hydroxy-Δ9cis,11trans,13trans-octadecatrienoic acid). Mallotus philippensis and Trewia nudiflora were both shown to produce seed oil rich in TAG-estolides. Analysis by MALDI-TOF MS/MS demonstrated that the TAG-estolides had a structure different to that previously proposed after enzymatic digestion of the oil. Acylglycerols containing up to 14 fatty acids were detected but fatty acid estolides were only present in a single position on the glycerol backbone, with predominantly non-hydroxyl fatty acids in the remaining two positions. Increased numbers of fatty acids per glycerol backbone were accounted for by the presence of fatty acid estolides containing a correspondingly greater number of fatty acids. For example, acylglycerols containing seven fatty acids had a fatty acid estolide of five fatty acids at one position on the glycerol backbone. Both capped and uncapped fatty acid estolides, with a free hydroxyl group, were present, with capped fatty acid estolides being more abundant in T. nudiflora and uncapped fatty acid estolides in M. philippensis. 相似文献
18.
Gerald P. McNeill Robert G. Ackman Stephen R. Moore 《Journal of the American Oil Chemists' Society》1996,73(11):1403-1407
Lipase hydrolysis was evaluated as a means of selectively enriching long-chain ω3 fatty acids in fish oil. Several lipases
were screened for their ability to enrich total ω-3 acids or selectively enrich either docosahexaenoic acid (DHA) or eicosapentaenoic
acid (EPA). The effect of enzyme concentration, degree of hydrolysis, and fatty acid composition of the feed oil was studied.
Because the materials that were enriched in long-chain ω3 acids were either partial glycerides or free fatty acids, enzymatic
reesterification of these materials to triglycerides by lipase catalysis was also investigated. Hydrolysis of fish oil by
eitherCandida rugosa orGeotrichum candidum lipases resulted in an increase in the content of total ω3 acids from about 30% in the feed oil to 45% in the partial glycerides.
The lipase fromC. rugosa was effective in selectively enriching either DHA or EPA, resulting in a change of either the DHA/EPA ratio or the EPA/DHA
ratio from approximately 1:1 to 5:1. Nonselective reesterification of free fatty acids or partial glycerides that contained
ω3 fatty acids could be achieved at high efficiency (approximately 95% triglycerides in the product) by using immobilizedRhizomucor miehei lipase with continuous removal of water. 相似文献
19.
Ching T. Hou 《Journal of the American Oil Chemists' Society》1995,72(11):1265-1270
A new microbial isolate,Flavobacterium sp. DS5, converted oleic and linoleic acids to their corresponding 10-keto-and 10-hydroxy fatty acids. The hydration enzyme
seems to be specific to the C-10 position. Conversion products from α- and γ-linolenic acids were identified by gas chromatography/mass
spectrometry, Fourier transform infrared, and nuclear magnetic resonance as 10-hydroxy-12(Z),15(Z)-octadecadienoic and 10-hydroxy-6(Z),12(Z)-octadecadienoic acids, respectively. Products from other 9(Z)-unsaturated fatty acids also were identified as their corresponding 10-hydroxy- and 10-keto-fatty acids.Trans unsaturated fatty acid was not converted. From these results, it is concluded that strain DS5 hydratase is indeed a C-10
positional-specific andcis-specific enzyme. DS5 hydratase prefers an 18-carbon monounsaturated fatty acid. Among the C18 unsaturated fatty acids, an additional double bond at either side of the 9,10-position lowers the enzyme hydration activity.
Because hydratases from other microbes also convert 9(Z)-unsaturated fatty acids to 10-hydroxy fatty acids, the C-10 positional specificity of microbial hydratases may be universal. 相似文献
20.
Eisa B. Elhilo Melissa A. Anderson Folahan O. Ayorinde 《Journal of the American Oil Chemists' Society》2000,77(8):873-878
Reduction of vernonia oil methyl esters (VOME) into epoxy fatty alcohol and diols was achieved with lithium aluminum hydride
(LAH), under reflux and room temperature conditions, by using hexane and tetrahydrofuran (THF) as solvents. The reactions
of VOME with LAH in hexane produced cis-12,13-epoxy-cis-9-octadecenol as a major product with an isolated yield of 73.6%, whereas the reaction with LAH in THF gave isomers of 12(13)-hydroxy-cis-9-octadecenol as the major products with an isolated yield of 95.1%. LAH was similarly reacted with vernonia oil (VO) to
give the same products in lower yields. 1H nuclear magnetic resonance (NMR), 13C NMR, gas chromatography-mass spectrometry, and infrared were used to characterize these products.
This study demonstrates the ability to control the reactivity of the epoxy functionality in VO or VOME with the choice of
polar or nonpolar solvents, and extends the range of oleochemicals that can be derived from vernonia oil. 相似文献