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1.
The cyclopropane fatty acids 17-methyl-trans-4,5-methyleneoctadecanoic acid, 18-methyl-trans-4,5-methylenenonadecanoic acid, and 17-methyl-trans-4,5-methylenenonadecanoic acid were characterized for the first time in nature in the phospholipids (mainly PE, PG and PS)
of the hermit-crab sponge Pseudospongosorites suberitoides. Pyrrolidine derivatization was the key in identifying the position of the cyclopropyl and methyl groups in the acyl chains
and 1H NMR was used to determine the trans stereochemistry of the cyclopropane ring. The phospholipids from the sponge also contained an interesting series of iso-anteiso Δ5,9 fatty acids with chain-lengths between 17 and 21 carbons, with the fatty acids (5Z,9Z)-18-methyl-5,9-nonadecadienoic acid and the (5Z,9Z)-17-methyl-5,9-nonadecadienoic acid being described for the first time in sponges. The anteiso α-methoxylated fatty acid 2-methoxy-12-methyltetradecanoic acid was also identified for the first time in nature in the phospholipids
of this interesting marine sponge. The novel cyclopropyl fatty acids could have originated from the phospholipids of a cyanobacterium
living in symbiosis with the sponge. 相似文献
2.
The phospholipid FA composition of the Carbbean sponge Agelas dispar was revisited and 40 different FA were identified. Among these a novel 2-methoxylated FA, namely, the anteiso methyl-branched
2-methoxy-14-methylhexadecanoic acid, was identified together with the recently discovered iso methyl-branched 2-methoxy-14-methylpentadecanoic
acid and the normal-chain 2-methoxytetradecanoic acid. The structures of the iso and anteiso methyl-branched 2-methoxylated
FA were confirmed by total syntheses, which were accomplished in seven steps and in 45–48% overall yields. Other phospholipid
FA identified in A. dispar include the unusual methyl-branched 10, 130dimethyltetradecanoic acid, 3,7,11,15-tetramethylhexadecanoic (phytanic) acid,
and the 11-methyloctadecanoic acid. In addition, the Δ5,9 FA (5Z, 9Z)-15-methyl-5,9-hexadecadienoic acid and (5Z, 9Z)-5,9-octadecadienoic acid were characterized. These findings establish alternative FA biosynthetic possibilities for these
marine organisms. 相似文献
3.
The hydrocarbons (3Z,6Z,9Z)-3,6,9-octadecatriene (3Z,6Z,9Z-18:H) and (3Z,6Z,9Z)-3,6,9-nonadecatriene (3Z,6Z,9Z-19:H) constitute the pheromone of the winter moth, Erannis bajaria. These compounds belong to a large group of lepidopteran pheromones which consist of unsaturated hydrocarbons and their corresponding
oxygenated derivatives. The biosynthesis of such hydrocarbons with an odd number of carbons in the chain is well understood.
In contrast, knowledge about the biosynthesis of even numbered derivatives is lacking. We investigated the biosynthesis of
3Z,6Z,9Z-18:H by applying deuterium-labeled precursors to females of E. bajaria followed by gas chromatography–mass spectrometry analysis of extracts of the pheromone gland. A mixture of deuterium-labeled
[17,17,18,18-2H4]-3Z,6Z,9Z-18:H and the unlabeled 3Z,6Z,9Z-18:H was obtained after topical application and injection of (10Z,13Z,16Z)-[2,2,3,3-2H4]-10,13,16-nonadecatrienoic acid ([2,2,3,3-2H4]-10Z,13Z,16Z-19:acid) or (11Z,14Z,17Z)-[3,3,4,4-2H4]-11,14,17-icosatrienoic acid ([3,3,4,4-2H4]-11Z,14Z,17Z-20:acid). These results are consistent with a biosynthetic pathway that starts with α-linolenic acid (9Z,12Z,15Z-18:acid). Chain elongation leads to 11Z,14Z,17Z-20:acid, which is shortened by α-oxidation as the key step to yield 10Z,13Z,16Z-19:acid. This acid can be finally reduced to an aldehyde and decarbonylated or decarboxylated to furnish the pheromone component
3Z,6Z,9Z-18:H. A similar transformation of 11Z,14Z,17Z-20:acid yields the second pheromone component, 3Z,6Z,9Z-19:H. 相似文献
4.
The very long-chain fatty acids, (5E,9Z)-6-bromo-5,9-tetracosadienoic, (5E,9Z)-6-bromo-23-methyl-5,9-tetracosadienoic, (5E,9Z)-6-bromo-5,9-pentacosadienoic and (5E,9Z)-6-bromo-24-methyl-5,9-pentacosadienoic acids, were identified in the phospholipids (mainly phosphatidylethanolamine) of
the spongeAgelas sp. Structure elucidation was accomplished by means of mass spectrometry and chemical transformations, including deuteration
with Wilkinson's catalyst. All of the sterols from the sponge had the Δ5,7 nucleus, with 24-methylcholesta-5,7,22-trien-3β-ol
(ergosterol) and 24-ethylcholesta-5,7,22-trien-3β-ol being the most abundant. 相似文献
5.
Our objective was to identify the sex pheromone of Lymantria bantaizana (Lepidoptera: Lymantriidae) whose larvae feed exclusively on walnut, Juglans spp., in China, and Japan. Coupled gas chromatographic–electroantennographic detection (GC-EAD) analyses of pheromone gland extracts revealed a single EAD-active component. Retention index calculations of this compound on four GC columns suggested that it was a methyl-branched octadecadiene with conjugated double bonds. In GC-EAD analyses of 2-methyloctadecenes, (Z)-2-methyl-7-octadecene and (E)-2-methyl-7-octadecene elicited the strongest antennal responses, suggesting that the double bond positions were at C7 and C9. In comparative GC-EAD analyses of pheromone gland extract and stereoselectively synthesized isomers (E,E; E,Z; Z,E; Z,Z) of 2-methyl-7,9-octadecadiene, the (E,Z)- and (Z,E)-isomer had retention times identical to that of the candidate pheromone, but only the latter isomer elicited strong EAD activity. Results of field experiments in Japan substantiated that (7Z,9E)-2-methyl-7,9-octadecadiene is the L. bantaizana sex pheromone, a compound previously unknown in the Lepidoptera. Detection surveys in North America for exotic Eurasian forest defoliators could include traps baited with the L. bantaizana pheromone. 相似文献
6.
Reinvestigation of the current FA composition of the regional freshwater sponge Baicalospongia bacillifera showed that the main measured isomer of EPA (14% of the total FA now detected) is, in fact, an unusual 5Z,8Z,11Z,14Z,18E-EPA. Two other isomers of this acid also present were identified as a novel 5Z,8Z,11Z,15Z,18E-EPA and the common methylene-interrupted 5Z,8Z,11Z,14Z,17Z-EPA (usually written simply as EPA). Isolation of these acids as their methyl ester derivatives was accomplished with the
use of a combination of silver-ion column chromatography and HPLC. The structure of the two new compounds was deduced from
GC-MS and detailed NMR data. Partial hydrazine reduction of all three isolated EPA esters followed by separation of cis/trans isomers of the resulting monoenoic acids and GC-MS analysis of their dimethyl disulfide adducts were used for determination
of the configuration and position of the double bonds. We may assume that the sponge B. bacillifera cannot receive these unusual EPA isomers directly from food sources (e.g., algal diatoms), and accordingly restructuring
of ordinary EPA to novel acids may take place in the sponge tissue. 相似文献
7.
Quévrain E Barnathan G Meziane T Domart-Coulon I Rabesaotra V Bourguet-Kondracki ML 《Lipids》2012,47(4):345-353
The fatty acid composition of the temperate calcareous marine sponge Leuconia johnstoni Carter 1871 (Calcaronea, Calcarea) was characterized for the first time in specimens collected off the Brittany coast of
France over four years from October 2005 to September 2008. Forty-one fatty acids (FA) with chain lengths ranging from C14 to C22 were identified as fatty methyl esters (FAME) and N-acyl pyrrolidide (NAP) derivatives by gas chromatography–mass spectrometry (GC–MS). Twenty-two saturated fatty acids (SFA)
were identified accounting for 52.1–59.0% of the total FA and dimethylacetals (DMA). In addition, among the SFA, we noticed
the presence of numerous methyl-branched iso and anteiso FA, suggesting a large number of associated bacteria within L. johnstoni. Thirteen monounsaturated fatty acids (MUFA, 28.0–36.0% of total FA + DMA) were also identified as well as six polyunsaturated
fatty acids (PUFA, 4.0–8.2%). A noticeable DMA was detected at a high level, particularly in September 2008 (11.8%), indicating
the presence of plasmalogens in this sponge species. This calcareous sponge lacked the non-methylene-interrupted FA (NMI FA)
with a Δ5,9 system typical of siliceous Demosponges and Hexactinellids. The occurrence of the unusual 8,13-octadecadienoic
acid was reported for the first time as a minor PUFA in a calcareous sponge. The major FA, representing 20–25% of this sponge
FA, was identified as the new 2-methyl-13-icosenoic acid from mass spectra of its methyl ester and its corresponding N-acyl pyrrolidide derivatives as well as a dimethyl disulfide adduct. 相似文献
8.
Two new monogalactosyl diacylglycerols (MGDGs) along with two known glycolipids were isolated from the moderate polar fraction
of the methanolic extract of the brown alga Sargassum thunbergii by using reversed silica flash chromatography. Two new MGDGs were identified as (2S)-1-O-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-2-O-(9Z,12Z,15Z-octadecatrienoyl)-3-O-β-d-galactopyranosyl-sn-glycerol (1) and (2S)-1-O-(9Z,12Z,15Z-octadecatrienoyl)-2-O-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-3-O-β-d-galactopyranosyl-sn-glycerol (2) by FAB tandem mass spectrometry, NMR techniques, and specific enzyme-catalyzed hydrolysis of the sn-1 fatty acyl linkage. The regiochemical attachment of the acyl chains in the glycerol moiety was established by 2D NMR correlations
and confirmed by enzymatic hydrolysis. 相似文献
9.
Claire Denis Gaëtane Wielgosz-Collin Anne Bretéché Nicolas Ruiz Vony Rabesaotra Nicole Boury-Esnault Jean-Michel Kornprobst Gilles Barnathan 《Lipids》2009,44(7):655-663
The phospholipid fatty acid composition of the North-East Atlantic sponge Polymastia
penicillus (South Brittany, France) was investigated. Sixty fatty acids (FA) were identified as methyl esters (FAME) and N-acyl pyrrolidides (NAP) by gas chromatography–mass spectrometry (GC/MS), including eight Δ5,9 unsaturated FA and three long-chain
2-hydroxylated FA. The major phospholipid FA were palmitic (14.3% of the total FA mixture), vaccenic (12.7%), 15(Z)-docosenoic (13.4%) and 5(Z),9(Z)-hexacosadienoic (13.3%) acids. In addition to the iso- and anteiso-branched saturated FA, several unusual short-chain branched saturated FA were identified. In addition to the known Δ5,9 FA,
and interestingly regarding their identification by GC–MS as N-acyl pyrrolidides, was the co-occurrence of unusual FA possessing a Δ3, Δ4 and Δ5 double bond such as iso-4-pentadecenoic, iso-5-heptadecenoic, anteiso-5-heptadecenoic and two new compounds, not hitherto found in nature, namely 17-methyl-13-octadecenoic (0.8%) and 3,16-docosadienoic
(1.1%) acids. 相似文献
10.
The phospholipid fatty acid composition of the Caribbean sponge Erylus goffrilleri is described for the first time. A total of 70 fatty acids with chain lengths between 13 and 29 carbons were identified in
the sponge. Methyl-branched fatty acids predominated in E. goffrilleri suggesting the presence of a considerable number of bacterial symbionts. The novel fatty acids (5Z,9Z)-2-methoxy-5,9-hexadecadienoic acid, (5Z,9Z)-2-methoxy-5,9-octadecadienoic acid, (5Z,9Z)-2-methoxy-5,9-nonadecadienoic acid, and (5Z,9Z)-2-methoxy-5,9-eicosadienoic acid are described for the first time in the literature. In addition, the iso-methyl-branched fatty acids (9Z)-2-methoxy-15-methyl-9-hexadecenoic acid and (5Z,9Z)-2-methoxy-15-methyl-5,9-hexadecadienoic acid, also identified in E. goffrilleri, were identified for the first time in nature. Based on the identified metabolites it is proposed that the unprecedented
biosynthetic sequence: i-17:1Δ9 → 2-OMe-i-17:1Δ9 → 2-OMe-i-17:2Δ5,9 might be responsible for the biosynthesis of the novel iso-α-methoxylated fatty acids in E. goffrilleri. 相似文献
11.
Mary J. Garson Mary P. Zimmermann Max Hoberg Rundi M. Larsen Christopher N. Battershill Peter T. Murphy 《Lipids》1993,28(11):1011-1014
Preliminary investigation of the phospholipid fatty acid composition of the tropical marine spongeAmphimedon terpenensis by gas chromatography/mass spectrometry revealed the presence of some novel brominated fatty acids. Two new brominated fatty
acids, (5E, 9Z)-6-bromo-5,9-tetracosadienoic acid (2a) and (5E, 9Z)-6-bromo-5,9-pentacosadienoic acid (3a) were subsequently isolated from a chloroform/methanol (3∶1, vol/vol) extract of the
sponge and characterized as their methyl esters 2b and 3b. The known brominated fatty acid (5E, 9Z)-6-bromo-5,9-hexacosadienoic acid (4a) was also isolated. The new fatty acid methyl esters were confirmed as brominated δ5,9
acid derivatives by chemical ionization mass spectrometry. The position of the bromine substituent was determined to be C-6
by nuclear magnetic resonance techniques while the stereochemistry of the two double bonds was deduced by nuclear Overhauser
enhancement difference spectroscopy. The biosynthetic implications of the co-occurrence of the three brominated acids are
discussed. 相似文献
12.
Burger BV Viviers MZ Bekker JP le Roux M Fish N Fourie WB Weibchen G 《Journal of chemical ecology》2008,34(5):659-671
The territorial marking fluid of the male Bengal tiger, Panthera tigris, consists of a mixture of urine and a small quantity of lipid material that may act as a controlled-release carrier for the
volatile constituents of the fluid. Using gas chromatography and gas chromatography–mass spectrometry, 98 volatile compounds
and elemental sulfur were identified in the marking fluid. Another 16 volatiles were tentatively identified. The majority
of these compounds were alkanols, alkanals, 2-alkanones, branched and unbranched alkanoic acids, dimethyl esters of dicarboxylic
acids, γ- and δ-lactones, and compounds containing nitrogen or sulfur. Several samples of the marking fluid contained pure
(R)-3-methyl-2-octanone, (R)-3-methyl-2-nonanone, and (R)-3-methyl-2-decanone, but these ketones were partly or completely racemized in other samples. The γ-lactone (S)-(+)-(Z)-6-dodecen-4-olide and the C8 to C16 saturated (R)-γ-lactones and (S)-δ-lactones were present in high enantiomeric purities. The chiral carboxylic acids, 2-methylnonanoic acid, 2-methyldecanoic
acid, 2-methylundecanoic acid, and 2-ethylhexanoic acid were racemates. Cadaverine, putrescine, and 2-acetylpyrroline, previously
reported as constituents of tiger urine, were not detected. The dominant contribution of some ketones, fatty acids, and lactones
to the composition of the headspace of the marking fluid suggests that these compounds may be important constituents of the
pheromone. Although it constitutes only a small proportion, the lipid fraction of the fluid contained larger quantities of
the volatile organic compounds than the aqueous fraction (urine). The lipid derives its role as controlled-release carrier
of the chemical message left by the tiger, from its affinity for the volatiles of the marking fluid. Six proteins with masses
ranging from 16 to 69 kDa, inter alia, the carboxylesterase-like urinary protein known as cauxin, previously identified in the urine of the domestic cat and other
felid species, were identified in the urine fraction of the marking fluid.
Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. 相似文献
13.
Five cerebrosides (1–5), including three new ones named cortenuamide A (1), cortenuamide B (2), and cortenuamide C (3), were isolated from the fruiting bodies of the basid-iomycete Cortinarius tenuipes. The structures of those compounds were elucidated as (4E,8E)-N-d-2′-hydroxytetracosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (1), (4E,8E)-N-d-2′-hydroxytricosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8 sphingadienine (2), (4E, 8E)-N-d-2′-hydroxydocosanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (3), (4E, 8E)-N-d-2′-hydroxyoctadecanoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (4), and (4E, 8E)-N-d-2′-hydroxypalmitoyl-1-O-β-d-glycopyranosyl-9-methyl-4,8-sphingadienine (5) by spectral and chemical methods. 相似文献
14.
Mary J. Garson Mary P. Zimmermann Christopher N. Battershill Janet L. Holden Peter T. Murphy 《Lipids》1994,29(7):509-516
The tropical marine spongeAmphimedon terpenensis (family Niphatidae, order Haplosclerida) has previously been shown to possess unusual lipids, including unusual fatty acids.
The biosynthetic origin of these fatty acids is of interest as the sponge supports a significant population of eubacterial
and cyanobacterial symbionts. The total fatty acid composition of the sponge was analyzed by gas chromatography/mass spectrometry
of the methyl esters. Among the most abundant of the fatty acids in intact tissue were 16∶0, 18∶0 and 3,7,11,15-tetramethylhexadecanoic
(phytanic) acid. In addition, three brominated fatty acids, (5E,9Z)-6-bromo-5,9-tetracosadienoic acid (24∶2Br), (5E,9Z)-6-bromo-5,9-pentacosadienoic acid (25∶2Br) and (5E,9Z)-6-bromo-5,9-hexacosadienoic acid (26∶2Br) were also present. The three brominated fatty acids, together with phytanic acid,
were isolated from both ectosomoal (superficial) and choanosomal (internal) regions of the sponge. Analysis of extracts prepared
from sponge/symbiont cells, partitioned by density gradient centrifugation on Ficoll, indicated that phytanic acid and the
three brominated fatty acids were associated with sponge cells only. Further, a fatty acid methyl ester sample from intact
tissue ofA. terpenensis was partitioned according to phospholipid class, and the brominated fatty acids were shown to be associated with the phosphatidylserine
and phosphatidylethanolamine fractions that are commonly present in marine sponge lipids. The phosphatidylcholine and phosphatidylglycerol
fractions were rich in the relatively shorter chain fatty acids (16∶0 and 18∶0). The association of brominated long-chain
fatty acids (LCFA) with sponge cells has been confirmed. The findings allow comment on the use of fatty acid profiles in chemotaxonomy
and permit further interpretation of LCFA biosynthetic pathways in sponges. The assignment of the sponge studied, which is
currently placed asA. terpenensis, is being supported to some extent, but the species is unusual in having C25 fatty acids as the major constituent in this group. Other factors, such as season or microenvironmental conditions, may influence
observed fatty acid composition which tends to reduce the usefulness of fatty acid profiles as markers in sponge chemotaxonomy. 相似文献
15.
J.-F. Butaud P. Raharivelomanana J.-P. Bianchini E. M. Gaydou 《Journal of the American Oil Chemists' Society》2008,85(4):353-356
The sandalwood kernels of Santalum insulare (Santalaceae) collected in French Polynesia give seed oils containing significant amounts of ximenynic acid, E-11-octadecen-9-oic acid (64–86%). Fatty acid (FA) identifications were performed by gas chromatography/mass spectrometry
(GC/MS) of FA methyl esters. Among the other main eight identified fatty acids, oleic acid was found at a 7–28% level. The
content in stearolic acid, octadec-9-ynoic acid, was low (0.7–3.0%). An inverse relationship was demonstrated between ximenynic
acid and oleic acid using 20 seed oils. Results obtained have been compared to other previously published data on species
belonging to the Santalum genus, using multivariate statistical analysis. The relative FA S. insulare composition, rich in ximenynic acid is in the same order of those given for S. album or S. obtusifolium. The other compared species (S. acuminatum, S. lanceolatum, S. spicatum and S. murrayanum) are richer in oleic acid (40–59%) with some little differences in linolenic content. 相似文献
16.
Elena Pastor-Cavada Rocio Juan Julio E. Pastor Manuel Alaiz Javier Vioque 《Journal of the American Oil Chemists' Society》2009,86(4):329-335
The fatty acid composition of the seed oil of 19 wild legume species from southern Spain was analyzed by gas chromatography.
The main seed oil fatty acids ranged from C14:0 to C20:0. Among unsaturated fatty acids, the most abundant were linoleic, oleic and linolenic acids, except for Lathyrus angulatus, L. aphaca, L. clymenum, L. sphaericus and L. nigricans where C18:3 contents were higher than C18:1 contents. Palmitic acid was the most abundant saturated acid in studied species, ranging from 11.6% in Lathyrus sativus to 19.3% in Lens nigricans. All studied species showed higher amounts of total unsaturated fatty acids than saturated ones. Among studied species, the
ω6/ω3 ratio was variable, ranging from 2.0% in L. nigricans to 13.8% in L. sativus, there being eight species in which the ω6/ω3 ratio was below 5. The fatty acids observed in these plants supports the use
of these plants as a source of important dietary lipids. 相似文献
17.
New glyceroglycolipid and ceramide from <Emphasis Type="Italic">Premna microphylla</Emphasis> 总被引:1,自引:0,他引:1
Iwo new compounds (1,2) were isolated from the ethanolic extract of the leaves of Premna microphylla, together with five known compounds. The structures of compounds 1 and 2 were elucidated as (2S,3S,4R,11E)-2-[(2R)-2-hydroxytetracosanoylamino]-11-octadecene-1,3,4-triol (1) and 1-O(9Z,12Z, 15Z-octadecatrienoyl)-3-O-[β-d-galactopyranosyl-(1→6)-O-β-d-galactopyranosyl-(1→6)-α-d-galactopyranosyl] glycerol (2) by means of spectroscopic and chemical methods. 相似文献
18.
Trail pheromones mediate communication among western subterranean termites, Reticulitermes hesperus Banks. Repetitive passages of ≥28 termites were required to establish a pheromone trail and trails needed to be reinforced
because they lasted <48 hr. The minimal threshold concentration for inducing responses from termite workers and secondary
reproductives was between 0.01 and 0.1 fg/cm of (3Z,6Z,8E)-dodecatrien-1-ol (henceforth, dodecatrienol). Workers showed optimal trail-following behavior to dodecatrienol at a concentration
of 10 fg/cm. Trails with concentrations >10 pg/cm were repellent to workers. Workers did not detect pheromone gradients, responding
equally to increasing or decreasing gradients of dodecatrienol, and termite workers were not able to differentiate between
different concentrations of dodecatrienol. Termites preferred dodecatrienol trails to 2-phenoxyethanol trails. Antennae played
a key role in trail pheromone perception. Dodecatrienol acted as an arrestant for worker termites (10 fg/cm2) and male alates (5 ng/cm2), whereas sternal gland extracts from females attracted male alates. Workers and alates, upon contact with filter paper disks
treated with higher doses (10 fg/cm2 and 5 ng/cm2, respectively) of dodecatrienol, were highly excited (increased antennation and palpation) and repeatedly returned to the
treated disks. Dodecatrienol did not act as a phagostimulant when offered on a paper towel disk. Reticulitermes hesperus is highly responsive to dodecatrienol, and it may play an important role in orientation of workers and alates. 相似文献
19.
Cvacka J Kofronová E Vasícková S Stránský K Jiros P Hovorka O Kindl J Valterová I 《Lipids》2008,43(5):441-450
Unusual fatty acids with 24, 26, and 28 carbon atoms were found in triacylglycerols (TAGs) isolated from fat body tissue of
bumblebee Bombus pratorum. The most abundant one was (Z,Z)-9,19-hexacosadienoic acid. Its structure was determined by mass spectrometry after derivatization with dimethyl disulfide
and by infrared spectroscopy. ECL (equivalent chain length) values of its methyl ester were determined on both DB-1 and DB-WAX
capillary columns. (Z,Z)-9,19-Hexacosadienoic acid is quite rare in nature. So far it has been identified only in marine sponges, and this work is
the first evidence of its occurrence in a terrestrial organism. HPLC/MS analysis of the bumblebee TAGs showed that (Z,Z)-9,19-hexacosadienoic acid is present in one third of all TAG molecular species. As it was found in all sn-TAG positions,
it is likely that (Z,Z)-9,19-hexacosadienoic acid is transported to tissues. Interestingly, labial gland secretion of B. pratorum was found to contain (Z,Z)-7,17-pentacosadiene, a hydrocarbon with markedly similar double bond positions and geometry. Possible biosynthetic relationships
between these two compounds are discussed. 相似文献
20.
Effect of <Emphasis Type="Italic">Fabp1/Scp</Emphasis>-<Emphasis Type="Italic">2/Scp</Emphasis>-<Emphasis Type="Italic">x</Emphasis> Ablation on Whole Body and Hepatic Phenotype of Phytol-Fed Male Mice
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Danilo?Landrock Sherrelle?Milligan Gregory?G.?Martin Avery?L.?McIntosh Kerstin?K.?Landrock Friedhelm?Schroeder Ann?B.?Kier
Liver fatty acid binding protein (Fabp1) and sterol carrier protein‐2/sterol carrier protein‐x (SCP‐2/SCP‐x) genes encode proteins that enhance hepatic uptake, cytosolic transport, and peroxisomal oxidation of toxic branched‐chain fatty acids derived from dietary phytol. Since male wild‐type (WT) mice express markedly higher levels of these proteins than females, the impact of ablating both genes (TKO) was examined in phytol‐fed males. In WT males, high phytol diet alone had little impact on whole body weight and did not alter the proportion of lean tissue mass (LTM) versus fat tissue mass (FTM). TKO conferred on dietary phytol the ability to induce weight loss as well as reduce liver weight, FTM, and even more so LTM. Concomitantly TKO induced hepatic lipid accumulation, preferentially threefold increased phospholipid (PL) at the expense of decreased triacylglycerol (TG) and total cholesterol. Increased PL was associated with upregulation of membrane fatty acid transport/translocase proteins (FATP 2,4), cytosolic fatty acid/fatty acyl‐CoA binding proteins (FABP2, ACBP), and the rate limiting enzyme in PL synthesis (Gpam). Decreased TG and cholesterol levels were not attributable to altered levels in respective synthetic enzymes or nuclear receptors. These data suggest that the higher level of Fabp1 and Scp2/Scpx gene products in WT males was protective against deleterious effects of dietary phytol, but TKO significantly exacerbated phytol effects in males. 相似文献