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1.
Open tubular gas liquid chromatographic (GLC) analyses of fatty acids from total lipids of 12 species of Echinoidea collected
at several locations along the Pacific coast of Japan showed the same unusualcis-5-olefinic acids in all species, i.e.,cis-5-octadecenoic acid (5–18∶1),cis-5-eicosenoic acid (5–20∶1), all-cis-5,11- and 5,13-eicosadienoic acids (5,11- and 5,13–20∶2), allcis-5,11,14-eicosatrienoic acid (5,11,14–20∶3) and all-cis-5,11,14,17-eicosatetraenoic acid (5,11,14,17–20∶4). The structural analysis of partially purified 5,11,14,17–20∶4 was undertaken
by reductive ozonolysis with GLC and gas chromatographic-mass spectrometric analyses of the products.13C-Nuclear magnetic resonance analyses of the totals and fractions of fatty acid methyl esters from the sea urchin lipids did
not show any occurrence of fatty acids having an isolated olefinic bond in the 2, 3 or 4 positions. The 5-olefinic acids were
concentrated on the polar lipids rather than neutral lipids. The branched and odd chain fatty acid contents of mud-feeding
sea urchins were found to be relatively greater proportions of total fatty acids than in algae feeders. 相似文献
2.
The fatty acid compositions of lipids from two species of Crinoidea and two species of Ophiuroidea have been investigated
with open-tubular gas chromatography. About 5–10% of tetracosahexaenoic acid was found in total fatty acids from all the samples,
and the structure was determined as all-cis-6,9,12,15,18,21-tetracosahexaenoic acid [24∶6(n−3)] by13C-NMR of the methyl esters and mass spectrometric analyses of the methyl esters, the pyrrolidides and the ozonolysis products.
The 24∶6(n−3) was concentrated in the polar lipids rather than neutral lipids. The n−3 hexaenoic structure suggested chain
elongation of 22∶6(n−3) as the source.
The 5-olefinic acids (5−18∶1, 5−20∶1, 5,11- and 5,13−20∶2) were low in Crinoidea (0.2–1.3%) but were present in higher levels
(2.5–5.2%) in Ophiuroidea. Polyunsaturated acids found other than 24∶6(n−3) were 20∶4(n−6), 20∶5(n−3) and 22∶6(n−3) as major
components and 16∶3(n−3), 18∶2(n−6), 18∶3(n−6), 18∶3(n−3), 18∶4(n−3), 20∶2(n−9), 20∶2(n−6), 20∶3(n−6), 20∶3(n−3), 21∶5(n−3)
and 22∶5(n−3) as minor components in all the samples. 相似文献
3.
Liver nuclear incorporation of stearic (18∶0), linoleic (18∶2n−6), and arachidonic (20∶4n−6) acids was studied by incubation
in vitro of the [1-14C] fatty acids with nuclei, with or without the cytosol fraction at different times. The [1-14C] fatty acids were incorporated into the nuclei as free fatty acids in the following order: 18∶0>20∶4n−6≫18∶2n−6, and esterified
into nuclear lipids by an acyl-CoA pathway. All [1-14C] fatty acids were esterified mainly to phospholipids and triacylglycerols and in a minor proportion to diacylglycerols.
Only [1-14C] 18∶2n−6-CoA was incorporated into cholesterol esters. The incorporation was not modified by cytosol addition. The incorporation
of 20∶4n−6 into nuclear phosphatidylcholine (PC) pools was also studied by incubation of liver nuclei in vitro with [1-14C]20∶4n−6-CoA, and nuclear labeled PC molecular species were determined. From the 15 PC nuclear molecular species determined,
five were labeled with [1-14C]20∶4n−6-CoA: 18∶0–20∶4, 16∶0–20∶4, 18∶1–20∶4, 18∶2–20∶4, and 20∶4–20∶4. The highest specific radioactivity was found in
20∶4–20∶4 PC, which is a minor species. In conclusion, liver cell nuclei possess the necessary enzymes to incorporate exogenous
saturated and unsaturated fatty acids into lipids by an acyl-CoA pathway, showing specificity for each fatty acid. Liver cell
nuclei also utilize exogenous 20∶4n−6-CoA to synthesize the major molecular species of PC with 20∶4n−6 at the sn-2 position. However, the most actively synthesized is 20∶4–20∶4 PC, which is a quantitatively minor component. The labeling
pattern of 20∶4–20∶4 PC would indicate that this molecular species is synthesized mainly by the de novo pathway. 相似文献
4.
Lih-Ling Wang Andrew C. Peng Andrew Proctor 《Journal of the American Oil Chemists' Society》1990,67(8):499-502
Lipids from five cultivars of highbush blueberries (Vaccinium corymbosum L.) were extracted and fractionated into neutral lipids (60–66%), glycolipids (20–22%) and phospholipids (14–18%). The major
fatty acids in all fractions were palmitic (16∶0), oleic (18∶1), linoleic (18∶2), and linolenic (18∶3) acids. All lipid classes
had a large concentration of C18 polyunsaturated acids (84–92%), indicating that blueberries are a rich source of linoleic and linolenic acids. Changes in
the fatty acid composition of neutral lipids and phospholipids were not significantly different among the five cultivars,
but significant differences were noted in the ratios of linoleic and linolenic acids in the glycolipids fraction. 相似文献
5.
Robert L. Wolff William W. Christie Frédérique Pédrono Anne M. Marpeau Nanzad Tsevegsüren Kurt Aitzetmüller Frank D. Gunstone 《Lipids》1999,34(8):855-864
The fatty acid compositions of the seed lipids from four Ephedra species, E. nevadensis, E. viridis, E. przewalskii, and E. gerardiana (four gymnosperm species belonging to the Cycadophytes), have been established with an emphasis on Δ5-unsaturated polymethylene-interrupted
fatty acids (Δ5-UPIFA). Mass spectrometry of the picolinyl ester derivatives allowed characterization of 5,9- and 5,11–18∶2;
5,9,12–18∶3; 5,9,12,15–18∶4; 5,11–20∶2; 5,11,14–20∶3; and 5,11,14,17–20∶4 acids. Δ5-UPIFA with a Δ11-ethylenic bond (mostly
C20 acids) were in higher proportions than δ5-UPIFA with a δ9 double bond (exclusively C18 acids) in all species. The total δ5-UPIFA content was 17–31% of the total fatty acids, with 5, 11, 14–20∶3 and 5, 11, 14,
17–20∶4 acids being the principal δ5-UPFIA isomers. The relatively high level of cis-vaccenic (11–18∶1) acid found in Ephedra spp. seeds, the presence of its δ5-desaturation product, 5, 11–18∶2 acid (proposed trivial name: ephedrenic acid), and of
its elongation product, 13–20∶1 acid, were previously shown to occur in a single other species, Ginkgo biloba, among the approximately 170 gymnosperm species analyzed so far. Consequently, Ephedraceae and Coniferophytes (including
Ginkgoatae), which have evolved separately since the Devonian period (≈300 million yr ago), have kept in common the ability
to synthesize C18 and C20 δ5-UPIFA. We postulate the existence of two δ5-desaturases in gymnosperm seeds, one possibly specific for unsaturated acids
with a δ9-ethylenic bond, and the other possibly specific for unsaturated acids with a δ11-ethylenic bond. Alternatively,
the δ5-desaturases might be specific for the chain length with C18 unsaturated acids on the one hand and C20 unsaturated acids on the other hand. The resulting hypothetical pathways for the biosynthesis of δ5-UPIFA in gymnosperm seeds
are only distinguished by the position of 11–18∶1 acid. Moreover, 13C nuclear magnetic resonance spectroscopy of the seed oil from two Ephedra species has shown that δ5-UPIFA are essentially excluded from the internal position of triacylglycerols, a characteristic
common to all of the Coniferophytes analyzed so far (more than 30 species), with the possibility of an exclusive esterification
at the sn-3 position. This structural feature would also date back to the Devonian period, but might have been lost in those rare angiosperm
species containing δ5-UPIFA. 相似文献
6.
Lipids of some thermophilic fungi 总被引:1,自引:0,他引:1
Total lipid content in the thermophilic fungi—Thermoascus aurantiacus, Humicola lanuginosa, Malbranchea pulchella var.sulfurea, andAbsidia ramosa—varied from 5.3 to 19.1% of mycelial dry weight. The neutral and polar lipid fractions accounted for 56.4 to 80.2% and 19.8
to 43.6%, respectively. All the fungi contained monoglycerides, diglycerides, triglycerides, free fatty acids, and sterols
in variable amounts. Sterol ester was detected only inA. ramosa. Phosphatide composition was: phosphatidyl choline (15.9–47%), phosphatidyl ethanolamine (23.4–67%), phosphatidyl serine
(9.3–17.6%), and phosphatidyl inositol (1.9–11.9%). Diphosphatidyl glycerol occurred in considerable quantity only inH. lanuginosa andM. pulchella var.sulfurea. Phosphatidic acid, detected as a minor component only inM. pulchella var.sulfurea andA. ramosa, does not appear to be a characteristic phosphatide of thermophilic fungi as suggested earlier. The 16∶0, 16∶1, 18∶0, 18∶1,
and 18∶2 acids were the main fatty acid components. In addition,A. ramosa contained 18∶3 acid. Total lipids contained an average of 0.93 double bonds per mole of fatty acids, and neutral lipids tend
to be more unsaturated than phospholipids. 相似文献
7.
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
8.
Satyesh C. Pakrashi Pradeep K. Duffa Basudeb Achari Suniti Misra Amalesh Choudhury Subhashis Chattopadhyay Amitabha Ghosh 《Lipids》1989,24(5):443-447
Total lipids from hepatopancreas of the horseshoe crabs,Tachypleus gigas andCarcinoscorpius rotundicauda, obtained in 7.6 and 3.3% wet weight respective yields, were fractionated by various chromatographic techniques and identified
by gas-liquid chromatography and spectroscopic methods. Fatty acid-containing lipids were rich in 16∶0 (8.0–25%), 18∶1ω9 (6.9–22%)
and 18∶2ω6 (6.8–18.5%); appreciable amounts of 16∶1ω7, 18∶3ω3, 20∶5ω3 and 22∶6ω3 were also present. The level of 26∶0 in the
hydrocarbon fractions was unusually high (64 and 68%). Carbon chain lengths of major wax esters were 44, 46 and 48 forT. gigas and 38, 40 and 42 forC. rotundicauda. 1-O-Alkyl diglycerides were 7.2 and 9.1% of the total lipids in the two species and contained 14∶0(20%), 16∶0(60%) and 18∶0(20%)
alkyl chains along with a relatively higher percentage (32–35%) of saturated fatty acids. High levels of cholesterol (>50%
of total sterol) in the free and combined state were encountered in both samples, phospholipid contents being 40 and 35%,
respectively, and contained highest levels of unsaturated fatty acids. 相似文献
9.
The effect of a diet containingtrans-fatty acids (tFA) on the fatty acid composition and fat accumulation in adipose tissue was investigated in mice. Male C57BI/6J mice were
fed Control or Trans Diets that were similar, except that 50% of the 18∶1, which was allcis in the Control Diet, was replaced bytFA in the Trans Diet. At selected ages, body weight, epididymal fat pad weight, perirenal fat yield, adipose tissue cellularity
and fatty acid composition were examined. Over the time period studied (2–24 mon), the proportion of 18∶0 and 16∶0 tended
to decrease whilecis-18∶1 levels increased. Compared to the Control Diet, the Trans Diet resulted in adipose tissue lipids with higher percentages
of 14∶0 and 18∶2n−6 and lower percentages ofcis-18∶1 and 20∶4n−6. In polar lipids,tFA replaced saturated fatty acids, whereastFA replacedcis-18∶1 in the nonpolar lipids. Body weights at 16 and 24 mon of age and epididymal fat pad weights at 8–24 mon of age were
lower in mice fed the Trans Diet as compared to those fed the Control Diet. At the ages studied, the Trans Diet also resulted
in lower values for perirenal fat weights, triacylglycerol to polar lipid ratios, and adipose cell size. The data suggest
that chronic consumption oftFA affects lipid metabolism and results in decreased fat accumulation in murine adipose tissue. 相似文献
10.
The unsaponifiable lipids and total fatty acids of a nonphotosynthetic diatom,Nitzschia alba, have been examined. The major fatty acids were found to be 14∶0, 16∶0, 18∶1, and 20∶5; small amounts of 15∶0, 16∶1, 18∶0,
18∶2, 18∶3, and 20∶4 acids also were present. The unsaponifiable lipids consisted mostly of sterols, with only traces (<0.1%)
of hydrocarbons (chiefly C16, C18, and C28 normal olefins). The sterols contained brassicasterol (major) and clionasterol (minor), as well as traces of an unidentified
sterol; clionasterol was present only in glycosidically bound form. 相似文献
11.
John K. G. Kramer Najibullah Sehat Michael E. R. Dugan Magdi M. Mossoba Martin P. Yurawecz John A. G. Roach Klaus Eulitz Jennifer L. Aalhus Allan L. Schaefer Youh Ku 《Lipids》1998,33(6):549-558
Pigs were fed a commercial conjugated linoleic acid (CLA) mixture, prepared by alkali isomerization of sunflower oil, at 2%
of the basal diet, from 61.5 to 106 kg live weight, and were compared to pigs fed the same basal diet with 2% added sunflower
oil. The total lipids from liver, heart, inner back fat, and omental fat of pigs fed the CLA diet were analyzed for the incorporation
of CLA isomers into all the tissue lipid classes. A total of 10 lipid classes were isolated by three-directional thin-layer
chromatography and analyzed by gas chromatography (GC) on long capillary columns and by silver-ion high-performance liquid
chromatography (Ag+-HPLC); cholesterol was determined spectrophotometrically. Only trace amounts (<0.1%; by GC) of the 9,11–18∶2 cis/trans and trans, trans isomers were observed in pigs fed the control diet. Ten and twelve CLA isomers in the diet and in pig tissue lipids were
sepatated by GC and Ag+-HPLC, respectively. The relative concentration of all the CLA isomers in the different lipid classes ranged from 1 to 6%
of the total fatty acids. The four major cis/trans isomers (18.9% 11 cis, 13 trans-18∶2; 26.3% 10 trans, 12 cis-18∶2; 20.4% 9 cis, 11 trans-18∶2; and 16.1% 8 trans, 10 cis-18∶2) constituted 82% of the total CLA isomers in the dietary CLA mixture, and smaller amounts of the corresponding cis,cis (7.4%) and trans,trans (10.1%) isomers were present. The distribution of CLA isomers in inner back fat and in omental fat of the pigs was similar
to that found in the diet. The liver triacylglycerols (TAG), free fatty acids (FFA), and cholesteryl esters showed a similar
patterns to that found in the diet. The major liver phospholipids showed a marked increase of 9 cis,11 trans-18∶2, ranging from 36 to 54%, compared to that present in the diet. However, liver diphosphatidylglycerol (DPG) showed a
high incorporation of the 11 cis,13 trans-18∶2 isomer (43%). All heart lipid classes, except TAG, showed a high content of 11 cis,13 trans-18∶2, which was in marked contrast to results in the liver. The relative proportion of 11 cis,13 trans-18∶2 ranged from 30% in the FFA to 77% in DPG. The second major isomer in all heart lipids was 9 cis,11 trans-18∶2. In both liver and heart lipids the relative proportions of both 10 trans,12 cis-18∶2 and 8 trans,10 cis-18∶2 were significantly lower compared to that found in the diet. The FFA in liver and heart showed the highest content of
trans,trans isomers (31 to 36%) among all the lipid classes. The preferential accumulation of the 11 cis,13 trans-18∶2 into cardiac lipids, and in particular the major phospholipid in the inner mitochondrial membrane, DPG, in both heart
and liver, appears unique and may be of concern. The levels of 11 cis,13 trans-18∶2 naturally found in foods have not been established. 相似文献
12.
Olivier Berdeaux Robert L. Wolff 《Journal of the American Oil Chemists' Society》1996,73(10):1323-1326
The fatty acids from the seed oils of three Conifer species (one Pinaceae,Pinus pinaster, and two Cupressaceae,Chamaecyparis lawsoniana andBiota orientalis) have been analyzed as their 4,4-dimethyloxazoline (DMOX) derivatives by gas-liquid chromatography coupled with mass spectrometry.
The structures of six Δ5-unsaturated polymethylene-interrupted fatty acids (Δ5-UPIFA) were established, confirming previous
studies in which they were identified by their equivalent chainlengths (ECL) and by comparison with related authentic standards.
These acids were:cis-5,cis-9 18∶2,cis-5,cis-9,cis-12 18∶3 (P. pinaster),cis-5,cis-9,cis-12,cis-15 18∶4 (C.lawsoniana),cis-5,cis-11 20∶2,cis-5,cis-11,cis-14 20∶3 (all species),cis-5,cis-11,cis-14,cis-17 20∶4 (B. orientalis) acids. In addition,cis-9 18∶1,cis-9,cis-12 18∶2 (all species) andcis-9,cis-12,cis-15 18∶3 (Cupressaceae) acids, together with their elongation products [cis-11 20∶1,cis-11,cis-14 20∶2 (all species) andcis-11,cis-14,cis-17 20∶3 (B. orientalis) acids] were also identified. In the mass spectra, DMOX derivatives of all Δ5-UPIFA showed an intense peak atm/z 153, which is a diagnostic ion of fatty acid derivatives with a Δ5-ethylenic bond. Other double bonds were localized by ion
pairs that differed by 12 atomic mass units. The present study fully justifies the use of ECL to identify Δ5-UPIFA in Conifer
seed oils, in which they are ordinary components. 相似文献
13.
Conjugated linoleic acid (CLA) is a collective term that describes different isomers of linoleic acid with conjugated double
bonds. Although the main dietary isomer is 9cis,11trans-18∶2, which is present in dairy products and ruminant fat, the biological effects of CLA generally have been studied using
mixtures in which the 9cis,11trans- and the 10trans,12cis-18∶2 were present at similar levels. In the present work, we have studied the impact of each isomer (9cis,11trans- and 10trans,12cis-18∶2) given separately in the diet of rats for 6 wk. The 10trans,12cis-18∶2 decreased the triacylglycerol content of the liver (−32%) and increased the 18∶0 content at the expense of 18∶1n−9,
suggesting an alteration of the Δ9 desaturase activity, as was already demonstrated in vitro. This was not observed when the 9cis,11trans-18∶2 was given in the diet. Moreover, the 10trans,12cis-18∶2 induced an increase in the C22 polyunsaturated fatty acids in the liver lipids. The 10trans,12cis-18∶2 was mainly metabolized into conjugated 16∶2 and 18∶3, which have been identified. The 9cis,11trans isomer was preferentially metabolized into a conjugated 20∶3 isomer. Thus, the 9cis,11trans- and the 10trans,12cis-CLA isomers are metabolized differently and have distinct effects on the metabolism of polyunsaturated fatty acids in rat
liver while altering liver triglyceride levels differentially. 相似文献
14.
The fatty acid composition of the seeds from Agathis robusta, an Australian gymnosperm (Araucariaceae), was determined by a combination of chromatographic and spectrometric techniques.
These enabled the identification of small amounts of arachidonic (5,8,11,14–20∶4) and eicosapentaenoic (5,8,11,14,17–20∶5)
acid for the first time in the seed oil of a higher plant. They were apparently derived from γ-linolenic (6,9,12–18∶3) and
stearidonic (6,9,12,15–18∶4) acids, which were also present, via chain elongation and desaturation, together with other expected biosynthetic intermediates [bis-homo-γ-linolenic (8,11,14–20∶3)
and bishomo-stearidonic (8,11,14,17–20∶4) acids]. Also present were a number of C20 fatty acids, known to occur in most gymnosperm families, i.e., 5,11–20∶2, 11,14–20∶2 (bishomo-linoleic), 5,11,14–20∶3 (sciadonic),
11,14,17–20∶3 (bishomo-α-linolenic), and 5,11,14,17–20∶4 (juniperonic) acids. In contrast to most other gymnosperm seed lipids
analyzed so far, A. robusta seed lipids did not contain C18 Δ5-desaturated acids [i.e., 5,9–18∶2 (taxoleic), 5,9,12–18∶3 (pinolenic), or 5,9,12,15–18∶4 (coniferonic)]. These structures
support the simultaneous existence of Δ6- and Δ5-desaturase activities in A. robusta seeds. The Δ6-ethylenic bond is apparently introduced into C18 polyunsaturated acids, whereas the Δ5-ethylenic bond is introduced into C20 polyunsaturated acids. A general metabolic pathway for the biosynthesis of unsaturated fatty acids in gymnosperm seeds is
proposed. When compared to Bryophytes, Pteridophytes (known to contain arachidonic and eicosapentaenoic acids), and species
from other gymnosperm families (without such acids), A. robusta appears as an “intermediate,” with the C18 Δ6-desaturase/C18→C20 elongase/C20 Δ5-desaturase system in common with the former subphyla, and the unsaturated C18→C20 elongase/C20 Δ5-desaturase system specific to gymnosperms. The following hypothetical evolutionary sequence for the C18 Δ6/Δ5-desaturase class in gymnosperm seeds is suggested: Δ6 (initial)→Δ6/Δ5 (intermediate)→Δ5 (final). 相似文献
15.
Néstor M. Carballeira Anastacio Emiliano Anthony Sostre José A. Restituyo Ileana M. González Gretchen M. Colon Carmen G. Tosteson Thomas R. Tosteson 《Lipids》1998,33(6):627-632
The fatty acid composition of a Pseudomonas sp. (Alteromonas) and its host, the dinoflagellate Ostreopsis lenticularis, vectors in ciguatera fish poisoning, has been studied. The major fatty acids in O. lenticularis were 16∶0, 20∶5n-3, and 22∶6n-3, but 18∶2n-6, 18∶3n-3, and 18∶n-3 were also identified. In contrast to other dinoflagellates,
18∶5n-3 was not detected in O. lenticularis. Even-chain fatty acids such as 9–16∶1, 11–18∶1, and 13–20∶1 predominated in the Pseudomonas sp. from O. lenticularis, but 16–20% of (E)-11-methyl-12-octadecenoic acid was also identified. The chirality of the latter was confirmed by total synthesis (28% overall
yield) starting from oxacyclotridecan-2-one. The fatty acid compositions of two other Pseudomonas species, from the palytoxin-producing zoanthids Palythoa mamillosa and P. caribdea, were also studied and were similar to that of the Pseudomonas sp. from O. lenticularis. The possibility of using some of these fatty acids as chemotaxonomic lipids in identifying marine animals that consume toxic
dinoflagellates or zoanthids is discussed. 相似文献
16.
Mixtures of triglycerides containing deuterium-labeled hexadecanoic acid (16∶0), octadecanoic acid (18∶0),cis-9-octadecenoic acid (9c–18∶1),cis-9,cis-12-octadecadienoic acid (9c, 12c–18∶2) andcis-12,trans-15-octadecadienoic acid (12c,15t–18∶2) were fed to two young-adult males. Plasma lipid classes were isolated from samples
collected periodically over 48 hr. Incorporation and turnover of the deuterium-labeled fats in plasma lipids were followed
by gas chromatography-mass spectrometry (GC-MS) analysis of the methyl ester derivatives. Absorption of the deuterated fats
was followed by GC-MS analysis of chylomicron triglycerides isolated by ultracentrifugation.
Results were the following: (i) endogenous fat contributed about 40% of the total fat incorporated into chylomicron triglycerides;
(ii) elongation, desaturation and chain-shortened products from the deuterated fats were not detected; (iii) the polyunsaturated
isomer 12c,15t–18∶2 was metabolically more similar to saturated and 9c–18∶1 fatty acids than to 9c,12c–18∶2 (iv) relative
incorporation of 9c,12c–18∶2 into phospholipids did not increase proportionally with an increase of 9c,12c–18∶2 in the mixture
of deuterated fats fed; (v) absorption of 16∶0, 18∶0, 9c–18∶1, 9c,12c–18∶2 and 12c,15t–18∶2 were similar; and (vi) data for
the 1- and 2-acyl positions of phosphatidylcholine and for cholesteryl ester fractions reflected the known high specificity
of phosphatidylcholine acyltransferase and lecithin:cholesteryl acyltransferase for 9c,12c–18∶2.
These results illustrate that incorporation of dietary fatty acids into human plasma lipid classes is selectively controlled
and that incorporation of dietary 9c,12c–18∶2 is limited. These results suggest that nutritional benefits of diets high in
9c,12c–18∶2 may be of little value to normal subjects and that the 12c,15t–18∶2 isomer in hydrogenated fat is not a nutritional
liability at the present dietary level. 相似文献
17.
Gary J. Blomquist Charles L. Soliday Barbara A. Byers Joyce W. Brakke Larry L. Jackson 《Lipids》1972,7(5):356-362
Wax esters of secondary alcohols constitute 18–20% of the cuticular lipid extract ofMelanoplus packardii and 26–31% of the cuticular lipids ofMelanoplus sanguinipes. The total number of carbons in the wax esters range from 37–54 with 41 predominating in both species. The fatty acids ofM. packardii wax esters are 16∶0, 18∶0, 14∶0, 20∶0 and 12∶0 in decreasing quantity. The fatty acids ofM. sanguinipes wax esters are 18∶0, 20∶0, 16∶0 22∶0, 14∶0, 19∶0 and 17∶0 in decreasing quantity. The secondary alcohols from the wax esters
ofM. packardii are C25, C23 and C27 in decreasing quantity, and the secondary alcohols of theM. sanguinipes are C23, C25, C21, C27, C24, C22 and C26 in decreasing quantity. Each secondary alcohol consists of two to four isomers with the hydroxyl group located near the center
of the chain.
Montana Agriculture Experiment Station, Journal Series No. 332. 相似文献
18.
Mixtures of deuterium-labeledtrans-8-,cis-8- andcis-9-octadecenoic acids (8t–18∶1, 8c–18∶1, 9c–18∶1) were fed as triglycerides (TG) to two adult male subjects. Blood samples
were collected sequentially over a 48-hour period. Plasma and lipoprotein lipids were separated by thin layer chromatography
and analyzed by gas chromatography-mass spectroscopy. Results indicate (i) absorption of the 8t- and 8c–18∶1 isomers were
similar to 9c–18∶1; (ii) the 8t–18∶1 isomer was cleared approximately 30% faster than 9c–18∶1 from plasma TG; (iii) cholesterol
ester samples contained 8.4 times less 8t–18∶1 than 9c–18∶1; (iv) incorporation at the 1-acyl phosphatidylcholine (PC) position
was higher for 8t–18∶1 and 8c–18∶1 (2.2 and 1.7 times) than for 9c–18∶1; and (v) discrimination at the 2-acyl PC position
was 4.6-fold against 8t–18∶1 and 1.3-fold against 8c–18∶1 compared with 9c–18∶1. Discrimination against uptake of the Δ-8
isomers in both neutral and phospholipid classes suggests that both 8t- and 8c–18∶1 may be preferentially oxidized relative
to 9c–18∶1. Except for triglycerides, data for each of the lipid classes from total plasma and individual lipoprotein samples
were similar. These data indicate that differences for incorporation and turnover of the 8t- and 8c–18∶1 isomers relative
to 9c–18∶1 are not substantially influenced by the lipoprotein classes. The maximum isotopic enrichment detected in the chylomicron
triglycerides fractions was 60%, which indicates that a substantial amount of endogenous triglycerides was mobilized during
absorption of the deuterated fats. 相似文献
19.
The carbon and energy source for aerobically grown cultures ofCandida guilliermondii profoundly influenced the neutral lipid content and the fatty acid composition of the individual lipid components. Methanol
(0.80%, w/v) grown cells cultivated at 30 C in presence of 0.025% ammonium sulfate contained 12% total lipids, 67% of which
was neutral lipids. Glucose (0.74%, w/v) or ethanol (0.53%, w/v) grown cells contained 21–22% total lipids, 80% of which was
neutral lipids, under the same conditions. Methanol-grown cells contained a decreased 18∶1 acid (52–54% of total fatty acids)
and an increased 18∶2 acid (23–25%), as compared with glucose- or ethanol-grown cells which contained 57–66% 18∶1 acid and
8–14% 18∶2 acid, in both neutral and polar lipid fractions. The relationship between methanol metabolism and desaturation
of fatty acid in yeast was discussed. 相似文献
20.
Jean-Michel Chardigny Jean-Paul Blond Lionel Bretillon Estelle Mager Didier Poullain Lucy Martine Jean-Michel Vatèle Jean-Pierre Noël Jean-Louis Sébédio 《Lipids》1997,32(7):731-735
Several years ago, it was established that the Δ15 trans isomer of α-linolenic acid is converted in vivo into fatty acids containing 20 and 22 carbons (geometrical isomers of eicosapentaenoic and docosahexaenoic acids). The present
study focused on the in vitro Δ6 desaturation, the first step of the biosynthesis of the n-3 long-chain polyunsaturated fatty acids from 18:3n-3. For that
purpose, rat liver microsomes were prepared and incubated with radiolabeled 18∶3 Δ9cis, 12cis, 15cis (18∶3 c,c,c) or 18∶3 Δ9cis, 12cis, 15trans (18∶3c,c,t) under desaturation conditions. The data show that 18∶3c,c,t is converted at a lower rate compared with α-linolenic acid. The product of conversion of 18∶3 c,c,t may be 18∶4 Δ6cis, 9cis, 12cis, 15trans resulting from a Δ6 desaturation of the trans substrate. Moreover, the conversion of radiolabeled 18∶3c,c,t was strongly decreased by the presence of 18∶3c,c,c (up to 48%) while the 18∶3c,c,t only slightly decreased the conversion of radiolabeled 18∶3c,c,c. Thus, the desaturation enzyme presented a higher affinity for the native all-cis n-3 substrate. 相似文献