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1.
Folahan O. Ayorinde Chukwuma P. Nwaonicha Voneil N. Parchment Kent A. Bryant Mahmoud Hassan Marcella T. Clayton 《Journal of the American Oil Chemists' Society》1993,70(2):129-132
cis-12,13-Epoxy-cis-octadecenoic (vernolic) acid occurs in triglycerides of the seed oil ofVernonia galamensis. The seeds also contain a lipase capable of hydrolyzing the triglycerides. Previous investigators incubated the seed ofVernonia anthelmintica and isolated 5.6% yield of 1,3-divernoloyl glycerol. We used crude lipase extract fromV. galamensis seed to synthesize 1,3-divernoloyl glycerol from vernonia oil in pentane at 40% yield. A 94% conversion of the 1,3-divernoloyl
glycerol to pure vernolic acid (5.34% oxirane = 98.9% purity) was achieved by a low-energy saponification process. The carbon-13
nuclear magnetic resonance (NMR) spectrum of the 1,3-divernoloyl glyceride indicates a potential for using carbon-13 NMR spectroscopy
in the identification of isomeric diglycerides. Thus the paper describes the synthesis, spectroscopic and chemical characterization
of 1,3-divernoloyl glycerol, in addition to providing quantitative carbon-13 NMR studies ofV. galamensis oil. 相似文献
2.
Folahan O. Ayorinde Boddy D. Butler Marcella T. Clayton 《Journal of the American Oil Chemists' Society》1990,67(11):844-845
A percolation extraction ofVernonia galamensis seed, affording 38.6% of crude vernonia oil is described. The dark colored crude oil was degummed with water, treated with
activated charcoal and bleached with a neutral agent, to give a light colored oil (Lovibond: 0.9 red, 3.5 yellow). Gas chromatographic/mass
spectrometric analysis of the refined oil indicates a relative fatty acid composition of 79–81% vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid, 11–12% linoleic acid, 4–6% oleic acid, 2–3% stearic acid, 2–4% palmitic acid, and a trace amount of
arachidic acid. 相似文献
3.
Melissa A. Anderson Ledelle Collier Robert Dilliplane Folahan O. Ayorinde 《Journal of the American Oil Chemists' Society》1993,70(9):905-908
Vernonia galamensis seed oil is a natural source of epoxidized triacylglycerols, which consist of 52% trivernolin and a mixture of other triacylglycerols.
Epoxidized oils are used for industrial applications, such as coatings and plastic formulations. To determine the major molecular
species present in Vernonia oil, desorption chemical ionization/mass spectrometry and mass spectrometry/mass spectrometry
were used to determine its glyceride composition. Seven triacylglycerols predominated: divernoloylarachidonate, trivernolin,
divernoloylstearate, divernoloyloleate, divernoloyllinoleate, dilinolenoyl vernolate and divernoloylpalmitate. 相似文献
4.
Eva-Sarbah-Yalley Folahan O. Ayorinde Broderick E. Eribo 《Journal of the American Oil Chemists' Society》1992,69(10):1046-1048
The biodegradability ofVernonia galamensis seed oil (VO) has been demonstrated with two environmental bacterial strains,Acinetobacter Iwoffi (HU 3955), andPseudomonas sp. (HU 4020). A time-dependent increase in the degradative activities of both bacteria species was apparent. There wasca. 60% decrease in the amount of VO over an eightday incubation period. Additionally, lipolytic activity was evident from the
amount of free fatty acid (FFA) that was generated. The percent FFA of the residual oil were 82% for thePseudomonas strain, and 62% for theAcinetobacter strain. The weight per epoxy value of the VO in the fermentation medium remained relatively constant over the incubation
period, suggesting the lack of preference for either the epoxidized or nonepoxidized acids present in VO. 相似文献
5.
Folahan O. Ayorinde Eisa Elhilo Caswell Hlongwane Kamal A. Saeed 《Journal of the American Oil Chemists' Society》1999,76(10):1217-1221
Matrix-assisted laser desorption/ionization (MALDI) time-of-flight (TOF) mass spectrometry (MS) has been used to identify
eight triacylglycerols (TAG) in Vernonia galamensis oil (VO). The TAG include trivernolin, divernoloylstearoylglycerol, divernoloyloleoylglycerol, vernoloyllinoleoylstearoylglycerol,
vernoloyllinoleoyloleoylglycerol, and vernoloyldilinoleoylglycerol. Samples for the MALDI/TOF/MS analysis were prepared with
alpha-cyano-4-hydroxycinnamic acid (matrix) in an acetonitrile/tetrahydrofuran solvent system. A mol ratio of matrix/VO (44:1)
gave reproducible composite spectra, resulting in resolutions greater than 8,000 and signal-to-noise ratios of above 1000
for the most abundant molecular species. 1,3-Dioleoyl-2-stearoylglycerol and 1,2-dioleoyl-3-palmitoylglycerol were used as
calibration standards. 相似文献
6.
Synthesis and isolation of epoxy secondary amidesvia direct amidation ofVernonia galamensis seed oil
Kent A. A. Bryant Chukwuma P. Nwaonicha Mahmoud Hassan Melissa A. Anderson Folahan O. Ayorinde 《Journal of the American Oil Chemists' Society》1993,70(5):457-460
Vernonia galamensis oil, containing naturally epoxidized triglycerides, was reacted withn-butylamine,n-pentylamine andn-hexylamine to afford high yields of epoxidized secondary amides. Three reaction conditions were investigated: (i) reflux
with amines as solvents, (ii) reflux with hexane as the solvent and (iii) room temperature with the amines as solvents. Reactions
with amines as refluxing solvents were completed in 1–5 h, while those with hexane went to completion within 2 to 5 d. Room
temperature reactions were onlyca. 80% complete after several days. Reactivity was increased with higher amine homologs at both reflux and room temperature
reaction conditions. Isolated yields of epoxy-containing amides were about 80% with purity exceeding 96% in all cases. Spectroscopic
characterization of the previously unreported alkyl-vernolamides is provided. 相似文献
7.
Kent A. A. Bryant Chukwuma P. Nwaonicha Melissa A. Anderson Folahan O. Ayorinde 《Journal of the American Oil Chemists' Society》1992,69(10):1023-1026
We have demonstrated the potential ofVernonia galamensis seed oil as a source of hydroxy alkoxy fatty esters. Reaction of the oil with various alcohols (methanol, ethanol, 1-propanol
and 2-propanol), under acidic conditions, resulted in transesterification as well as epoxy ring opening in all cases. The
major products, the hydroxy alkoxy fatty esters, constituted approximately 80% of the product mixtures, of which the 12-hydroxy-13-alkoxy
isomers were the major constituents. These derivatives were isolated by solvent extraction and/or column chromatography to
afford 78–80% of pure isomers. Alcoholysis with butanol resulted in a poor yield of the hydroxy butoxy esters. A discussion
of the isolation and mass-spectrometric characterization of these new esters is provided. 相似文献
8.
9.
Bart G. Muuse F. Petrus Cuperus Johannes T. P. Derksen 《Journal of the American Oil Chemists' Society》1994,71(3):313-317
Dimorphotheca pluvialis is increasingly recognized as an interesting industrial new oilseed crop because it contains up to 60% of the unusual fatty
acid dimorphecolic acid (9-hydroxy,10t,12t-18∶2) (DA) for which new applications are being developed. In this paper, the yield, composition and quality are evaluated
for dimorphotheca oils (DMO) which were recovered by pressing, conventional solvent extraction and supercritical carbon dioxide
extraction (SCE). Mechanical pressing of the seeds required high temperatures and resulted in an oil recovery of only 40%,
whereas the extraction protocols yielded more than 95%. Oil recovery by pressing of winged seed was even more difficult than
that of unwinged seeds; hence, solvent extraction of winged seeds was preferred. The dark-colored DMO, recovered by expelling
or by extraction with organic solvents, needed further refining to remove pigments and gums, whereas the light yellow-colored
SCE DMO did not require further refining. SCE oil had a low phospholipid content (11 mg P/kg). Pressed oil (95 mg P/kg) and
hexaneor pentane-extracted DMO (200 mgP/kg) had much higher phospholipid contents. Peroxide andp-anisidine values were low for freshly recovered oils, but increased after storage, especially in the SCE oil, due to the
low concentration of natural antioxidants in SCE DMO, such as tocopherols. The DA content of the oils recovered by the various
techniques showed only minor differences, except that supercritical carbon dioxide had slightly decreased solubilizing power
for tri- and di-dimorphecolin as compared to hexane and pentane. 相似文献
10.
G. Üstun L. Kent N. Çekin H. Civelekoglu 《Journal of the American Oil Chemists' Society》1990,67(12):958-960
Three commercially cultivatedNigella sativa seed varieties of Turkish origin were analyzed, and the characteristics and constituents of the seed oils were reported.
Presence of lipase enzyme in seed results in enzymatic hydrolysis at ordinary temperature; the free acid content of oil may
increase up to 40% or higher. Black cumin seed oil might serve as a source of semi-drying oil and fatty acids of technical
grade, and the removal of free fatty acids from oil and the recovery of fatty acids were investigated. 相似文献
11.
The process of grinding soybeans to a fine flour and extracting the flour with hexane was studied on a pilot plant scale.
The crude oil from the pilot plant study had 15 ppm phosphorus and was suitable for physical refining after a light acid pretreatment
and bleaching. The refined oil showed a Lovibond color of 1.4 yellow and 0.3 red. The pilot plant study also showed that grinding
of the soybeans and the separation of solid from miscella were the most difficult steps in solvent extraction with fine flour.
A laboratory study on separation of miscella from meal by aqueous ethanol reduced the hold-up volume, but it did not remove
all the miscella. A test with betacarotene showed that only the miscella outside the flour particles was displaced.
Aqueous ethanol solutions used as a second solvent extracted additional nontriglyceride materials (primarily phospholipids)
from the meal. Also, the free fatty acid content of the oil was increased with aqueous ethanol solution wash. The quality
of the extracted crude oil was lowered by using a second solvent, but it had the advantage of needing only one centrifugation
to separate miscella from meal. 相似文献
12.
In a previous report [Zúñiga, M.E., J. Concha, C. Soto, and R. Chamy, Effect of the Rose Hip (Rosa aff. rubiginosa) Oil Extraction Cold-Pressed Process, in Proceedings of the World Conference and Exhibition on Oilseed Processing, and Utilization, edited by R.F. Wilson, AOCS Press, Champaign, 2001, pp. 210–213], the authors showed that an enzymatic pretreatment of rose-hip seeds, prior to oil extraction by cold pressing, improves the oil yield. In this work, we studied the effects of temperature and moisture during the enzymatic hydrolysis stage using two previously selected mixtures of commercial enzymes: (i) Olivex (mainly pectinase) plus Cellubrix (mainly cellulase), and (ii) Finizym (mainly β-glucanase) plus Cellubrix (mainly cellulase) (all from Novozymes A/S, Madrid, Spain). In addition, we evaluated the effect of enzymatic hydrolysis on the oil extraction pressing rate at different operational pressures. Samples hydrolyzed enzymatically by either of the two commercial enzyme mixtures at 45°C and 30–40% moisture showed oil extraction yields up to 60%, an increase of greater than 50%, as compared with control samples in which the enzyme solutions were replaced by water. Both the oil extraction rate and yield by pressing increased when enzymatic pretreatment was applied. The oil extraction yield increased slightly when the operation pressure was elevated; however, when the sample was preheated, the oil extraction yield was greatly increased, especially for enzyme-treated samples. Results confirmed the importance of temperature and moisture as enzymatic hydrolysis parameters that improve rose-hip oil extraction yields in the cold-pressing process. When pressing was carried out after preheating enzymatically treated samples, it was possible to increase the oil extraction yield to 72% compared with the control without preheating, which resulted in a 46% oil yield. 相似文献
13.
Deacidification of black cumin seed oil by selective supercritical carbon dioxide extraction 总被引:1,自引:0,他引:1
Selma Türkay Mark D. Burford M. Kemal Sangün Ekrem Ekinci Keith D. Bartle Anthony A. Clifford 《Journal of the American Oil Chemists' Society》1996,73(10):1265-1270
The deacidification of high-acidity oils from Black cumin seeds (Nigella sativa) was investigated with supercritical carbon dioxide at two temperatures (40 and 60°C), pressures (15 and 20 MPa) and polarities
(pure CO2 and CO2/10% MeOH). For pure CO2 at a relatively low pressure (15 MPa) and relatively high temperature (60°C), the deacidification of a highacidity (37.7
wt% free fatty acid) oil to a low-acidity (7.8 wt% free fatty acid) oil was achieved. The free fatty acids were quantitatively
(90 wt%) extracted from the oil and left the majority (77 wt%) of the valuable neutral oils in the seed to be recovered at
a later stage by using a higher extraction pressure. By reducing the extraction temperature to 40°C, increasing the extraction
pressure to 20 MPa, or increasing the polarity of the supercritical fluid via the addition of a methanol modifier, the selectivity
of the extraction was significantly reduced; the amount of neutral oil that co-extracted with the free fatty acids was increased
from 23 to 94 wt%. 相似文献
14.
A. Chaudhry R. Kleiman K. D. Carlson 《Journal of the American Oil Chemists' Society》1990,67(11):863-866
Routine analysis of fatty ester fractions ofLesquerella fendleri oil suggested the presence of epoxy compounds and other minor components. By a combination of open silica column and high
performance liquid chromatography (HPLC) fractionations of the methyl esters prepared from the oil, these constitutents were
isolated and then characterized by thin-layer chromatography-mass spectrometry (GC-MS—electron ionization, EI, and chemical
ionization, CI) and nuclear magnetic resonance (NMR—1H and13C). Three epoxy acids, 15,16-epoxy-9,12-octadecadienoic, 9,10-epoxy-12-octadecenoic and 9,10-epoxy-octadecanoic, were found.
Hydroxy acids present included a C-22 homologue of lesquerolic acid (16-hydroxy-12-docosenoic acid) and 14,15-dihydroxy-tricosanoic
acid. Other minor ocmponents included four sterols, brassicasterol, campesterol, β-sitosterol and stigmasterol, and a series
of saturated and unsaturated fatty acids up to C30.
Visiting postdoctoral scientist sponsored by the government of India. 相似文献
15.
Vernonia galamensis is a potential new industrial oilseed crop from the Asteraceae family. The interest in this species is due to the presence
of a high vernolic acid content of its seed oil, which is useful in the oleochemical industry for paints and coatings. The
development of a rapid, precise, robust, nondestructive, and economical method to evaluate quality components is of major
interest to growers, processors, and breeders. NIR reflectance spectroscopy (NIRS) is routinely used for the prediction of
quality traits in many crops. This study was conducted to establish a rapid analytical method for determining the quality
of intact seeds of V. galamensis. A total of 114 Vernonia accessions were scanned to determine seed weight, FA composition, oil, and protein contents using NIRS. Conventional chemical
analysis for FA composition, total oil, and protein contents were performed by GC, Soxhlet extraction, and the Dumas combustion
method, respectively. Calibration equations were developed and tested through cross-validation. The coefficient of determination
in cross-validation for FA ranged from 0.47 (linoleic acid) to 0.55 (vernolic acid), and for oil, protein, and seed weight
from 0.71 (oil) to 0.86 (seed protein). It was concluded that NIRS calibration equations developed for seed weight and seed
quality traits can be satisfactorily used as early screening methods in V. galamensis breeding programs. 相似文献
16.
H. L. Bhardwaj A. A. Hamama D. A. Dierig 《Journal of the American Oil Chemists' Society》2007,84(4):393-397
Vernonia galamensis [(Cass.) Less.] is a native of Ethiopia and Eritrea. Seed of vernonia contain substantial quantities of naturally epoxidized
oil, which is used in the paint industry to reduce emissions of volatile organic compounds that produce smog resulting from
the use of petroleum-based (alkyd-resin) paint. Epoxidized oil is also used in the manufacture of plasticizers, additives
to polyvinyl chloride, polymer blends and coatings, and cosmetic and pharmaceutical applications. Previous research has indicated
that vernonia has potential for commercialization in the mid-Atlantic region of the United States. This study characterized
fatty acids in oil from vernonia grown in this latter region. Vernonia oil, from 14 vernonia lines grown during 1995 and 1996
under field conditions in Virginia, contained 3.3, 3.0, 5.0, 15.0, 0.2, 0.5, 0.4, and 72.7%, respectively, of C16:0, C18:0,
C18:1, C18:2, C18:3, C20:0, C20:1, and vernolic (C18:1 epoxy) fatty acids. Effects of genotypes on vernonia oil quality were
generally not significant whereas the effects of years were significant. The concentration of vernolic acid was positively
correlated with oil concentration but negatively correlated with concentrations of all individual fatty acids, except for
C18:3.
Contribution of Virginia State University Agricultural Research Station, journal article series number 253. The use of any
trade names or vendors does not imply approval to the exclusion of other products or vendors that may also be suitable. 相似文献
17.
Charment O. Moussata Casimir C. Akoh 《Journal of the American Oil Chemists' Society》1998,75(9):1155-1159
Melon seeds are rich in oil. However, the stability of melon seed oil (MSO) is low because of its high content of the essential fatty acid, linoleic acid (18:2n-6). MSO was physically blended or enzymatically interesterified with higholeic sunflower oil (HOSO). The fatty acid composition of MSO was remarkably changed after interesterification. Palmitic (16:0), stearic (18:0), and oleic (18:1n-9) acid contents increased at the sn-2 position of triacylglycerols, whereas 18:2n-6 decreased due to interesterification. The oxidative stability of the physical and Pseudomonas sp. (PS30) lipase-interesterified blends was assessed with the Oxidative Stability Instrument, peroxide value, and conjugated diene methods. The stability of MSO increased with increased proportions of HOSO, which was the source of 18:1n-9 in the blends. The ratio of 18:1n-9/18:2n-6 improved from 0.18 in MSO to 1.47 in the enzymatically interesterified blend. Calculated oxidizability and the results of oxidation tests of the blends confirmed the improvement in MSO stability by both physical blending and enzymatic interesterification. 相似文献
18.
Charment O. Moussata Casimir C. Akoh 《Journal of the American Oil Chemists' Society》1998,75(12):1155-1159
Melon seeds are rich in oil. However, the stability of melon seed oil (MSO) is low because of its high content of the essential
fatty acid, linoleic acid (18:2n-6). MSO was physically blended or enzymatically interesterified with higholeic sunflower
oil (HOSO). The fatty acid composition of MSO was remarkably changed after interesterification. Palmitic (16:0), stearic (18:0),
and oleic (18:1n-9) acid contents increased at the sn-2 position of triacylglycerols, whereas 18:2n-6 decreased due to interesterification. The oxidative stability of the physical
and Pseudomonas sp. (PS30) lipase-interesterified blends was assessed with the Oxidative Stability Instrument, peroxide value, and conjugated
diene methods. The stability of MSO increased with increased proportions of HOSO, which was the source of 18:1n-9 in the blends.
The ratio of 18:1n-9/18:2n-6 improved from 0.18 in MSO to 1.47 in the enzymatically interesterified blend. Calculated oxidizability
and the results of oxidation tests of the blends confirmed the improvement in MSO stability by both physical blending and
enzymatic interesterification. 相似文献
19.
20.
F. Petrus Cuperus Gerard Boswinkel Bart G. Muuse Johannes T. P. Derksen 《Journal of the American Oil Chemists' Society》1996,73(12):1675-1679
The possibility of extraction ofDimorphotheca oil with supercritical carbon dioxide is demonstrated in this article. Before extraction, the seeds have to be pretreated
to improve extraction yield. Experiments showed that the best pretreatment procedure forDimorphotheca was heating the seeds under reduced pressure to 100°C for 60 min, followed by flaking or milling. To give an impression about
the efficiency of the supercritical extraction, a mathematical model has been developed to estimate the overall mass transfer
coefficient (A
p
K). Also, an empirical relation betweenA
p
K and the interstitial velocity has been found. The physical properties of the supercriticalDimorphotheca oil are in good agreement with those of conventionally extracted oil, except for a lower phospholipid content. It is expected
that further refining of supercriticalDimorphotheca oil will be marginal. 相似文献