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1.
Casimir C. Akoh Brenda H. Jennings Dorris A. Lillard 《Journal of the American Oil Chemists' Society》1996,73(8):1059-1062
Immobilized lipase SP435 fromCandida antaractica was used as a biocatalyst for the modification of the fatty acid composition of evening primrose oil by incorporating n−3
polyunsaturated fatty acid (PUFA) and eicosapentaenoic acid (EPA). Transesterification (ester-ester interchange) was conducted
in organic solvent or without solvent, with EPA ethyl ester (EEPA) as the acyl donor. Products were analyzed by gas-liquid
chromatography (GLC). After 24-h incubation in hexane, the fatty acid composition of evening primrose oil was markedly changed
to contain up to 43% EPA. The amount of 18:2n−6 PUFA was reduced by 32%, and the saturated fatty acid content was also reduced.
The effects of incubation time, molar ratio, enzyme load, and reaction medium on mol% EPA incorporation were also studied.
Generally, as the incubation time (up to 24 h), molar ratio, and enzyme load increased, EPA incorporation also increased.
Evening primrose oil, containing EPA and γ-linolenic acid (18:3n−6) in the same glycerol backbone, was successfully produced
and may be more beneficial for certain applications than unmodified oil. 相似文献
2.
Kuan-hsiang Huang Casimir C. Akoh 《Journal of the American Oil Chemists' Society》1994,71(11):1277-1280
The ability of immobilized lipases IM60 fromMucor miehei and SP435 fromCandida antarctica to modify the fatty acid composition of selected vegetable oils by incorporation of n−3 polyunsaturated fatty acids into
the vegetable oils was studied. The transesterification was carried out in organic solvent with free acid and ethyl esters
of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) as acyl donors. With free EPA as acyl donor, IM60 gave higher
incorporation of EPA than SP435. However, when ethyl esters of EPA and DHA were the acyl donors, SP435 gave higher incorporation
of EPA and DHA than IM60. When IM60 and free acid were used, the addition of 5 μL water increased EPA incorporation into soybean
oil by 4.9%. With ethyl ester of EPA as acyl donor, addition of 2 μL water increased EPA incorporation by 3.9%. For SP435,
addition of water up to 2μL resulted in increased EPA incorporation, but the incorporation declined when the added water exceeded
this amount. The addition of water increased the EPA incorporation into Trisun 90 after 24 h reaction but not the reaction
rate at early stages of the reaction. 相似文献
3.
Lipase-catalyzed modification of phospholipids: Incorporation of n-3 fatty acids into biosurfactants
Phospholipids were successfully modified by lipase-catalyzed transesterification to incorporate n-3 polyunsaturated fatty
acids such as eicosapentaenoic acid (20:5) and docosahexaenoic acid (22:6). The phospholipid modification was carried out
in organic media with lipase fromMucor miehei (lipozyme) as biocatalyst. The parameters studied were the effect of different solvents, enzymes, acyl donor type, phospholipid
class, water, enzyme and substrate concentrations. Hydrolysis of phosphatidylcholine to yield lysophosphatidylcholine and
the synthesis of phosphatidylcholine from lysophosphatidylcholine was also carried out. The optimal conditions for the modification
of phospholipids by transesterification were obtained with phosphatidylcholine and free eicosapentaenoic acid EPA 45 as acyl
donor in the presence of 15% w/w nonimmobilizedMucor miehei lipase (lipozyme) in hexane with no added water. The maximum incorporation of EPA 45 was 17.7 mol%. Hydrolysis was easily
achieved with phospholipase A2 in benzene and Tris-HCl buffer. The synthesis of phosphatidylcholine was difficult, and when it was achieved, not enough
phosphatidylcholine was obtained for quantitation. 相似文献
4.
Lipase-catalyzed modification of borage oil: Incorporation of capric and eicosapentaenoic acids to form structured lipids 总被引:2,自引:0,他引:2
Casimir C. Akoh Charment O. Moussata 《Journal of the American Oil Chemists' Society》1998,75(6):697-701
Two immobilized lipases, nonspecific SP435 from Candida antarctica and sn-1,3 specific IM60 from Rhizomucor miehei, were used as biocatalysts for the restructuring of borage oil (Borago officinalis L.) to incorporate capric acid (10:0, medium-chain fatty acid) and eicosapentaenoic acid (20:5n-3) with the free fatty acids
as acyl donors. Transesterification (acidolysis) reactions were carried out in hexane, and the products were analyzed by gas-liquid
chromatography. The fatty acid profiles of the modified borage oil were different from that of unmodified borage oil. Higher
incorporation of 20:5n-3 (10.2%) and 10:0 (26.3%) was obtained with IM60 lipase, compared to 8.8 and 15.5%, respectively,
with SP435 lipase. However, SP435 lipase was able to incorporate both 10:0 and 20:5n-3 fatty acids at the sn-2 position, but the IM60 lipase did not. Solvents with log P values between 3.5 and 4.5 supported the acidolysis reaction better than those with log P values between −0.33 and 3.0. 相似文献
5.
Production of triglycerides enriched in long-chain n-3 polyunsaturated fatty acids from fish oil 总被引:1,自引:0,他引:1
Stephen R. Moore Gerald P. McNeill 《Journal of the American Oil Chemists' Society》1996,73(11):1409-1414
Processes that combine enzymic and physical techniques have been studied for concentrating and separating eicosapentaenoic
acid (EPA) and docosahexaenoic acid (DHA) from fish oil.Candida rugosa lipase was used in hydrolysis reactions to concentrate these acids in the glyceride fraction. By controlling the degree of
hydrolysis, two products have been obtained, one enriched in total n-3(∼50%), the other enriched in DHA and depleted in EPA
(DHA∼40%, EPA∼7%). The glyceride fraction from these reactions was recovered by evaporation and converted back to triglycerides
by partial enzymic hydrolysis, followed by enzymic esterification. Both reactions were carried out withRhizomucor miehei lipase. DHA-depleted free fatty acids from aC. rugosa hydrolysis were fractionated to increase the EPA level (∼30%) and re-esterified to triglycerides by reaction with glycerol
andR. miehei. 相似文献
6.
Yi-Hsu Ju Fang-Cheng Huang Chia-Hui Fang 《Journal of the American Oil Chemists' Society》1998,75(8):961-965
The purpose of this work was to add n-3 polyunsaturated fatty acids (PUFA) into the acylglycerols of borage oil. The acidolysis
reaction between borage oil and n-3 PUFA was carried out with lipase (Lipozyme IM-60) in organic solvent. The effects of temperature,
solvent, and water content on the reaction product were investigated. For the acidolysis reaction between acylglycerols (product
of the selective hydrolysis of borage oil, catalyzed by immobilized Candida rugosa lipase) and n-3 PUFA, the total content of n-3 and n-6 PUFA in acylglycerols was 72.8% after a reaction time of 18 h. The
contents of γ-linolenic acid, eicosapentaenoic acid, and docosahexaenoic acid were 26.5, 19.8, and 18.1%, respectively. By
properly controlling the reaction time, acylglycerols with ca. 70–72% PUFA and a ratio of n-3 PUFA to n-6 PUFA from 0–1.09 can be obtained. 相似文献
7.
Lipase-catalyzed transesterification of trilinolein or trilinolenin with selected phenolic acids 总被引:1,自引:0,他引:1
Kebba Sabally Salwa Karboune Richard St-Louis Selim Kermasha 《Journal of the American Oil Chemists' Society》2006,83(2):101-107
The enzymatic transesterification of selected phenolic acids with TAG, including trilinolein (TLA) and trillinolenin (TLNA),
was investigated in an organic solvent medium. Maximal bioconversion of 66% was obtained with a dihydrocaffeic acid (DHCA)
to TLA ratio of 1∶2 after 5 d of reaction. Similarly, the highest bioconversion of 62% was obtained with a DHCA to TLNA ratio
of 1∶2, but after 12 d of reaction. However, a ratio of 1∶4 DHCA/TLA decreased the bioconversion to 53%. Transesterification
reactions of ferulic acid with both TAG, using a ratio of 1∶2, resulted in low bioconversion of 16 and 14% with TLA and TLNA,
respectively. The overall results indicated that bioconversion of phenolic MAG was higher than that of phenolic DAG. The structures
of mono- and dilinoleyl dihydrocaffeate as well as those of mono- and dilinolenyl dihydrocaffeate were confirmed by LC-MS
analyses. The phenolic lipids demonstrated moderate radical-scavenging activity. 相似文献
8.
Structured lipids: Lipase-catalyzed interesterification of tricaproin and trilinolein 总被引:2,自引:0,他引:2
Structured lipids were synthesized by interesterification of trilinolein and tricaproin with sn-1,3-specific (IM 60) and nonspecific (SP 435) lipases. The interesterification reaction was performed by incubating a 1:2
mole ratio of trilinolein and tricaproin in 3 mL hexane at 45°C for the IM 60 lipase from Rhizomucor miehei, and at 55°C for the SP 435 lipase from Candida antarctica. Reaction products were analyzed by reverse-phase high-performance liquid chromatography with an evaporative light-scattering
detector. The fatty acids at the sn-2 position were identified after pancreatic lipase hydrolysis and analysis with a gas chromatograph. IM 60 lipase produced
53,5 mol% dicaproyllinolein (total carbon number = C33) and 22.2% monocaproyldilinolein (C45). SP 435 lipase produced 41%
C33 and 18% C45. When caproic acid was used in place of tricaproin as the acyl donor, the IM 60 lipase produced 62.9% C33.
The effects of variation in mole ratio, temperature, added water, solvent polarity, and time course on the interesterification
reaction were also investigated. In the absence of organic solvent, IM 60 lipase produced 52.3% C33. 相似文献
9.
Preparation of phospholipids highly enriched with n-3 polyunsaturated fatty acids by lipase 总被引:3,自引:0,他引:3
Gudmundur G. Haraldsson Atli Thorarensen 《Journal of the American Oil Chemists' Society》1999,76(10):1143-1149
The immobilized 1,3-regiospecific Rhizomucor miehei lipase (Lipozyme™) was employed to catalyze the transesterification reaction (acidolysis) of 1,2-diacyl-sn-glycero-3-phosphatidylcholine with n-3 polyunsaturated fatty acids under nonaqueous solvent-free conditions. With a concentrate
of 55% eicosapentaenoic acid (EPA) and 30% docosahexaenoic acid (DHA) and pure phosphatidylcholine from egg yolk, phospholipids
of 32% EPA and 16% DHA content were obtained, presumably as a mixture of phosphatidylcholine and lysophosphatidylcholine.
31P nuclear magnetic resonance (NMR) analysis turned out to be a valuable technique to study the details of the reactions involved.
It revealed that when 1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine was transesterified with 98% pure EPA, a substantial amount of hydrolysis side reaction took
place (39%), leading to a product mixture of 39% phosphatidylcholine, 44% lysophosphatidylcholine, and 17% sn-glycerol-3-phosphatidylcholine. The lysophosphatidylcholine constituent comprised 70% EPA, whereas the phosphatidylcholine
component contained 58% EPA. The 31P NMR technique provided valid information about the mechanism of the reaction. It became evident that a high dosage of lipase
containing 5% water afforded optimal conditions for the optimal extent of EPA incorporation into the phospholipids, under
which the extent of hydrolysis side reaction remained relatively high. 相似文献
10.
Casimir C. Akoh 《Journal of the American Oil Chemists' Society》1994,71(3):319-323
Two immobilized lipases fromCandida antarctica (SP 382) andC. cylindraceae, nowrugosa (2001), catalyzed the synthesis of novel acetylated glucose fatty acid esters with glucose pentaacetate (GP) and Trisun 80
(80% oleic) vegetable oil or methyl oleate as substrates in organic solvents. The relative yield was between 6.4–52%, and
the incorporation of oleic acid onto the glucose was between 31–100%. In addition, these enzymes were able to catalyze the
synthesis of glucose fatty acid esters with free glucose as the sugar substrate. The highest oleic acid incorporation (100%)
was obtained in benzene with SP 382 lipase and Trisun 80 as the acyl donor. With methyl oleate as the acyl donor, greater
incorporation was obtained in benzene (90.5%) compared to 75% in isooctane. The 2001 lipase was better in benzene/pyridine
(2∶1 vol/vol) 74%) and chloroform (61%) compared to benzene and isooctane. However, with free glucose and Trisun 80 as substrates,
both enzymes gave acceptable levels of oleic acid incorporation (82–100%) in benzene, benzene/pyridine and pyridine. The best
conditions for the ester interchange reaction reported are: lipase (10% by weight of substrate); incubation time 48 h; molar
ratio of Trisun/GP 1∶2; 3 mL solvent and 3% added water. These glucose esters have potential applications as emulsifiers in
food, cosmetics and pharmaceutical formulations. 相似文献
11.
Enzymatic modification of triolein: Incorporation of caproic and butyric acids to produce reduced-calorie structured lipids 总被引:3,自引:0,他引:3
Lipase-catalyzed acidolysis of triolein with caproic and butyric acids was performed to produce reduced-calorie structured
lipids (SL). The SL were obtained by incubating a 1:4:4 mole ratio of triolein, caproic acid, and butyric acid, respectively,
with 10% of lipase (w/w of total substrates) in 1.5 mL hexane at 55°C for 24 h. Of nine commercially avaialble lipases screened,
IM60, which contains the lipase from Rhizomucor miehei, was the most effective and produced 13 mol% unreacted triolein, 49% disubstituted, and 38% monosubstituted triacylglycerols
that contained short-chain fatty acids. The products were analyzed by reverse-phase high performance liquid chromatography
with an evaporative light-scattering detector. Reaction parameters studied included time course, temperature, enzyme load,
and substrate mole ratio. The yields obtained demonstrate that a structured lipid with long-chain and short-chain fatty acids
can be synthesized by using IM60 lipase in organic medium. 相似文献
12.
Geranyl acetate is an important flavor and fragrance compound. Two immobilizedCandida antarctica lipases, SP382 and SP435, were investigated for their use in the synthesis of geranyl acetate by direct esterification. Yields
between 95 and 99% molar conversion were obtained with 2 and 15% (w/w reactants) of SP435 and SP382 lipases, respectively.
Optimum yields were obtained at 0.1M acetic acid and 0.12M geraniol after 16-h incubation. No inhibitory effect was observed
at increasing concentrations of geraniol. Addition of 60% (w/w reactants) water led to 50 and 60% reduction in the esterification
activity of SP382 and SP435 lipases, respectively. The best yields were obtained at added water contents between 0–5% (w/w
reactants). Solvents with a logP value of 0.85 or more gave reaction yields of more than 80% molar conversion. Higher logP values did not necessarily lead to higher conversion yields. The immobilized lipase SP382 was still active after reusing
ten times in the direct esterification reaction. 相似文献
13.
Yuji Shimada Yoshinori Hirota Takashi Baba Akio Sugihara Shigeru Moriyama Yoshio Tominaga Tadamasa Terai 《Journal of the American Oil Chemists' Society》1999,76(6):713-716
Steryl esters of long-chain fatty acids have water-holding properties, and polyunsaturated fatty acids (PUFA) have various physiological functions. Because steryl ester of PUFA can be expected to have both features, we attempted to synthesize steryl esters of PUFA by enzymatic methods. Among lipases used, Pseudomonas lipase was the most effective for the synthesis of cholesteryl docosahexaenoate. When a mixture of cholesterol/docosahexaenoic acid (3:1, mol/mol), 30% water, and 3000 units/g of lipase was stirred at 40°C for 24 h, the esterification extent attained 89.5%. Under the same reaction conditions, cholesterol, cholestanol, and sitosterol were also esterified efficiently with docosahexaenoic, eicosapentaenoic, arachidonic, and γ-linolenic acids. 相似文献
14.
Lipase-assisted concentration of n-3 polyunsaturated fatty acids in acylglycerols from marine oils 总被引:1,自引:0,他引:1
Udaya N. Wanasundara Fereidoon Shahidi 《Journal of the American Oil Chemists' Society》1998,75(8):945-951
Preparation of n-3 polyunsaturated fatty acid (PUFA) concentrates from seal blubber oil (SBO) and menhaden oil (MHO) in the
form of acylglycerols was carried out by hydrolysis with a number of commercial microbial lipases. The lipases tested were
Aspergillus niger, Candida cylindracea (CC), Chromobacterium viscosum, Geotrichum candidum, Mucor miehei, Pseudomonas sp., Rhizopus oryzae, and Rhizopus niveus. After lipase-assisted hydrolysis of oils, free fatty acids were removed, and fatty acid composition of the mixture containing
mono-, di-, and triacylglycerols was determined. All lipases were effective in increasing the n-3 PUFA content of the remaining
acylglycerols of both SBO and MHO. The highest concentration of n-3 PUFA was provided by CC lipase; 43.5% in SBO [9.75% eicosapentaenoic
acid (EPA), 8.61% docosapentaenoic acid (DPA), and 24.0% docosahexaenoic acid (DHA)] and 44.1% in MHO (18.5% EPA, 3.62% DPA,
and 17.3% DHA) after 40 h of hydrolysis. Thus, CC lipase appears to be most suitable for preparation of n-3 PUFA in the acylglycerol
form from marine oils. 相似文献
15.
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
16.
Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) were incorporated into groundnut oil by interesterification with
a 1,3-specific lipase fromMucor miehei. The resultant EPA and DHA concentrations of the groundnut oil were 9.5 and 8.0%, respectively. 相似文献
17.
Enzymatic synthesis of high-purity structured lipids with caprylic acid at 1,3-positions and polyunsaturated fatty acid at 2-position 总被引:2,自引:0,他引:2
Akiko Kawashima Yuji Shimada Miwa Yamamoto Akio Sugihara Toshihiro Nagao Sadao Komemushi Yoshio Tominaga 《Journal of the American Oil Chemists' Society》2001,78(6):611-616
We attempted to synthesize high-purity structured triacylglycerols (TAG) with caprylic acid (CA) at the 1,3-positions and
a polyunsaturated fatty acid (PUFA) at the 2-position by a two-step enzymatic method. The first step was synthesis of TAG
of PUFA (TriP), and the second step was acidolysis of TriP with CA. Candida antarctica lipase was effective for the first reaction. When a reaction medium of PUFA/glycerol (3∶1, mol/mol) and 5% immobilized Candida lipase was mixed for 24 h at 40°C and 15 mm Hg, syntheses of TAG of γ-linolenic, arachidonic, eicosapentaenoic, and docosahexaenoic
acids reached 89, 89, 88, and 83%, respectively. In these reactions, the lipase could be used for at least 10 cycles without
significant loss of activity. In the second step, the resulting trieicosapentaenoin was acidolyzed at 30°C for 48h with 15
mol parts CA using 7% of immobilized Rhizopus delemar lipase. The CA content in the acylglycerol fraction reached 40 mol%. To increase the content further, the acylglycerols were
extracted from the reaction mixture with n-hexane and were allowed to react again with CA under conditions similar to those of the first acidolysis. After three successive
acidolysis reactions, the CA content reached 66 mol%. The content of dicapryloyl-eicosapentaenoyl-glycerol reached 86 wt%
of acylglycerols, and the ratio of 1,3-dicapryloyl-2-eicosapentaenoyl-glycerol to 1(3),2-dicapryloyl-3(1)-eicosapentaenoyl-glycerol
was 98∶2 (w/w). In this reaction, the lipase could be used for at least 20 cycles without significant loss of activity. Repeated
acidolysis of the other TriP with CA under similar conditions synthesized 1,3-dicapryloyl-2-γ-linolenoyl-glycerol, 1,3-dicapryloyl-2-arachidonoyl-glycerol,
and 1,3-dicapryloyl-2-docosahexaenoyl-glycerol in yields of 58, 87, and 19 wt%, respectively. 相似文献
18.
Lipase-catalyzed esterification of glycerol and n-3 polyunsaturated fatty acid concentrate in organic solvent 总被引:5,自引:0,他引:5
Enzymatic synthesis of glycerides from glycerol and n-3 polyunsaturated fatty acid in organic solvent was studied. Optimal
conditions for glyceride synthesis by lipases were established. Of the commercially available lipases that were investigated,
lipase PS-30 fromPseudomonas sp. and lipase IM-60 fromMucor miehei resulted in the highest extent of esterification. Isooctane and hexane were particularly useful organic solvents in glyceride
synthesis. The water content in the reaction mixture was of primary importance. For lipase PS-30 and lipase IM-60, optimal
water contents were 5 and 1%, respectively. Lipases PS-30 and IM-60 manifested contrasting positional specificities in glyceride
synthesis. Glycerides containing predominantly eicosapentaenoic acid and docosahexaenoic acid can be easily synthesized. 相似文献
19.
Production of n-3 polyunsaturated fatty acid-enriched fish oil by lipase-catalyzed acidolysis without solvent 总被引:1,自引:0,他引:1
Tsuneo Yamane Tomomasa Suzuki Youko Sahashi Line Vikersveen Tamotsu Hoshino 《Journal of the American Oil Chemists' Society》1992,69(11):1104-1107
Fish oil rich in n-3 polyunsaturated fatty acid (n-3 PUFA) was prepared by nonsolvent enzymic acidolysis. n-3 PUFA-enriched
fish oil contained 25% eicosapentaenoic acid (EPA) and 40% docosahexaenoic acid (DHA). In acidolysis of cod liver oil, EPA
content of the original fish oil was reduced at 5 h, but DHA content of the fish oil increased. It was assumed that EPA in
the fish oil was replaced by DHA to reach a new chemical equilibrium. Two-stage acidolysis, which was carried out under CO2 replacement early (about 3 h) and also in vacuum at 5–24 h, was effective for reduction in the content of diacylglycerol,
which was formed by reverse reaction, hydrolysis. This method has industrial significance because PUFA-enriched triacylglycerol
is easily separated from the reaction mixture by molecular distillation.
Bioreactors for fats and their derivatives, Part XIV. 相似文献
20.
Multiple sclerosis (MS) is a neurologic autoimmune disease, which is the leading cause of nontraumatic neurologic disability in young adults in United States and Europe. n-3 polyunsaturated fatty acids (PUFA) are reported to mitigate severity of this disease. Recent studies suggest that phospholipid (PL) form of dietary n-3 PUFA may lead to their higher tissue accretion than triacylglycerol (TAG) form. We compared efficacy of PL-docosahexaenoic acid (22:6n-3) (DHA) and TAG-DHA on onset and severity of experimental autoimmune encephalomyelitis (EAE) in a mouse model of MS. Female mice were fed low alpha-linolenic acid (18:3n-3) (ALA) diet (control) for 2 weeks and then fed either control, 0.3%, or 1.0% DHA (PL or TAG) for 4 weeks pre-EAE induction and 4 weeks post-EAE induction. The brain and spinal cord n-6:n-3 ratio was significantly lower in all mice fed DHA compared to control. EAE onset was delayed in mice fed both DHA forms and concentrations, except for 1% TAG-DHA. The inverse association between the EAE score and the brain DHA concentration was nonsignificant at the end of the study (p = 0.08). Daily EAE scores of mice fed different DHA diets did not differ from control, however, the score of all DHA groups combined during days 9–16 was lower (p = 0.028) compared to the control. During days 17–22, the EAE score trended lower in 0.3% TAG-DHA and during days 23–28, the EAE score trended lower in both PL-DHA groups than those in all other groups. These findings suggest that TAG-DHA may be more effective than PL-DHA in the early phases of EAE, and in the final outcome, PL-DHA may be more effective than TAG-DHA. 相似文献