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1.
The photobiont of the lichen, Dictyonema glabratum (Scytonema sp.), was isolated and cultivated in a soil-extract medium and submitted to chemical analysis. Successive extractions with CHCl3-MeOH, aqueous MeOH, and H2O gave rise to solutions of lipids (25%), low-molecular-weight carbohydrates (22%), and polysaccharides (4%), respectively. TLC of the lipid extract showed the presence of glycolipids, which were further purified and examined by NMR spectroscopy and GC-MS. Monogalactosyldiacylglycerol (1%), digalactosyldiacylglycerol (0.8%), trigalactosyldiacylglycerol (0.4%), and sulfoquinovosyldiacylglycerol (0.5%) were identified. The most abundant fatty acid ester in each fraction was palmitic (C16:0), but a great variation of the ester composition from one to another was found. Others present were those of C12:0, C14:0, C15:0, C16:1, C17:0, C18:0, C18:1, C18:2, C18:3, C22:0, C22:2, and C24:0. The lipid extract was also subjected to acid methanolysis, which gave rise to dodecane, 2-Me-heptadecane, 2,6-Me2-octadecane, and 8-Me-octadecane, methyl esters of C14:0, C15:0, C16:0, C16:1, C17:0, C18:0, C18:1, C18:2, C20:0, and C24:0 fatty acids, and the dimethyl ester of decanedioic acid. The polysaccharide had mainly Glc, Gal, and Man, with small amounts of 3-O-methylrhamnose and 2-O-methylxylose, both found in plants, and unexpectedly, some of the units were beta-galactofuranose, typical of fungal, but not cyanobacterial polysaccharides. The low-molecular-weight carbohydrates showed mannose as the main free reducing sugar, which differs from Nostoc sp. and Trebouxia sp. photobionts.  相似文献   

2.
This investigation was carried out to develop methods for a reverse-phase, high-performance liquid chromatography analysis of the monocarboxylic and dicarboxylic acids produced by permanganate-periodate oxidation of monoenoic fatty acids. Oxidation reactions were performed using [U-14C]oleic acid and [U-14C]oleic acid methyl ester in order to measure reaction yields and product distributions. The 14C-labeled oxidation products consisted of nearly equal amounts of monocarboxylic and dicarboxylic acid (or dicarboxylic acid monomethyl ester), with few side products (yield greater than 98%). Conversion of the carboxylic acids to phenacyl esters proceeded to completion. HPLC of carboxylic acid phenacyl esters was performed using a C18 column with a linear solvent gradient beginning with acetonitrile/water (1/1) and ending with 100% acetonitrile. Excellent resolution was achieved for all components of a mixture of C5 through C12 monocarboxylic acid phenacyl esters and C6 through C11 dicarboxylic acid phenacyl esters. Resolution was also achieved for all components of a mixture of C5 through C12 monocarboxylic acid phenacyl esters and C6 through C11 dicarboxylic acid monomethyl, monophenacyl esters. The resolution obtained by HPLC demonstrates that, for a wide range of monoenoic fatty acids, both products of a permanganate-periodate oxidation can be identified on a single chromatogram. Free fatty acids and fatty acid methyl esters were analyzed with equal success. Neither the oxidation nor the esterification reaction caused detectable hydrolysis of methyl ester. The method is illustrated for free acids and methyl esters of 14:1 (cis-9), 16:1 (cis-9), 18:1 (cis-6), 18:1 (cis-9), and 18:1 (cis-11).  相似文献   

3.
A crude acetone extract and oil of ripe fruits from Melia azedarach L. were evaluated against the 2nd and 4th instar larvae of Spodoptera littoralis (Boisd.) (Lepidoptera: Noctuidae). Both oil and extract exhibited highly significant growth inhibition at all concentrations tested, while the oil of M. azedarach recorded higher insecticidal activity against both instars than the crude extract. GC-MS analysis of the oil revealed the presence of linoleic acid methyl ester, oleic acid methyl ester, and free oleic acid as the main components in addition to hexadecanol, palmitic acid, methyl esters of stearic acid and myristic acid. Fatty acids and their esters were not only the main constituents of essential oil from the ripe fruits of M. azedarach, but also mainly responsible for the insecticidal and growth inhibition activity against S. littoralis.  相似文献   

4.
Two glycolipids were isolated from pig brain and were shown to be the fatty acid esters of kerasin and cerebron in which the second fatty acid moiety is attached to the 6-position of the galactose. The point of attachment was shown in two ways: by permethylation and by cleavage with periodate. Methanolysis of the permethylated cerebroside esters yielded O-methyl sphingosines, methyl esters of nonhydroxy or 2-methoxy acids, and methyl 2,3,4-trimethyl galactoside. Cleavage of the cerebron ester with periodate, followed by treatment with sodium borohydride and dilute HCl, yielded ceramide plus 1-monoglyceride. The ester-linked fatty acids were primarily 16:0, 18:0, and 18:1, while the amide-linked fatty acids showed the wide assortment of chain lengths typical of brain cerebrosides. The methylation step, with silver oxide and methyl iodide, yielded two derivatives with the cerebroside esters, but the structural explanation for the difference was not elucidated. The galactose in the cerebron ester was shown to exist in the beta-pyranoside form.  相似文献   

5.
Nannochloropsis salina was cultured batch-wise to evaluate the potential of the alga to produce biodiesel. The cells were harvested at the end of the exponential growth phase when the concentration was 18 x 10(6) cells/mL culture. The growth estimated as dry weight from this cell number was (3.8 +/- 0.7) mg/L. The lipid and triglyceride contents were 40% and 12% on a dry weight basis, respectively. The amount of the ratio triglycerides/total lipids was approximately 0.3. The composition of triglyceride fatty acid methyl esters (biodiesel) was analysed by gas-liquid chromatography and identified as: C14:0, C16:0, C16:1, C18:0, C18:1, C18:2, C18:3, C20:1, and C20:5. The ratio of unsaturated to saturated fatty acid contents was approximately 4.4. Additionally, the characterization of each individual fatty acid ester was discussed with regard to the fuel properties of biodiesel produced by the alga.  相似文献   

6.
In recent years seaweeds increasingly attracted interest in the search for new drugs and have been shown to be a primary source of bioactive natural products including antibiotics. In the present investigation the antimicrobial activity of Gracilariopsis longissima lipidic extract was assayed and its chemical characterization was carried out by means of advanced analytical techniques such as gas-chromatography and multinuclear and multidimensional NMR spectroscopy. G. longissima lipidic extract showed an antibacterial activity against several Vibrio species. These results are interesting considering both the resistance against antibiotics developed by vibrios and the need to control fish and shellfish diseases due to vibriosis. Analysis of fatty acid methyl esters performed by gas-chromatography showed that palmitic acid methyl ester (16:0) was the predominant saturated fatty acid (42%), while, among monounsaturated fatty acids, oleic acid methyl ester (18:1) prevailed (8.5%). Because the palmitic acid represents the main component of fatty acids we hypothesized its involvement in the antibacterial activity observed. However, a pure sample of palmitic acid did not show an antibacterial activity. The fatty acid profile of G. longissima revealed also an interesting composition in polyunsaturated fatty acids and in particular the ratio of ω-3 to ω-6 fatty acids was >1 thus suggesting that this macroalga may be used as a natural source of ω3. Moreover, the (1)H NMR spectrum in CDCl(3) of algal lipid fraction shows the characteristic signals of saturated and unsaturated fatty acids as well as other metabolites. Interestingly, in the lipid extract the presence of polyhydroxybutyrate, a linear biodegradable and biocompatible polyester, was clearly identified by NMR spectroscopy. In conclusion, the lipidic extract of G. longissima on account of its antimicrobial activity, nutritional value and content in biodegradable and biocompatible polyester represents an interesting potential biotechnological resource.  相似文献   

7.
The synthesis of fatty acid methyl esters (FAME) as a substitute to petroleum diesel was investigated in this study from crude jatropha oil (CJO), a non-edible, low-cost alternative feedstock, using aluminium modified heterogeneous basic oxide (Mg-Zn) catalyst. The transesterification reaction with methanol to methyl esters yielded 94% in 6 h with methanol-oil ratio of 11:1, catalyst loading of 8.68 wt.% at 182 °C and the properties of CJO fuel produced were determine and found to be comparable to the standards according to ASTM. In the range of experimental parameters investigated, it showed that the catalyst is selective to production of methyl esters from oil with high free fatty acid (FFA) and water content of 7.23% and 3.28%, respectively in a single stage process. Thus, jatropha oil is a promising feedstock for methyl ester production and large scale cultivation will help to reduce the product cost.  相似文献   

8.
Structural determination of polyunsaturated fatty acids by gas chromatography-mass spectrometry (GC-MS) requires currently the use of nitrogen containing derivatives such as picolinyl esters, 4,4-dimethyloxazoline or pyrrolidides derivatives. The derivatization is required in most cases to obtain low energy fragmentation that allows accurate location of the double bonds. In the present work, the following metabolites of rumelenic (cis-9,trans-11,cis-15 18:3) acid, from rat livers, were identified: cis-8,cis-11,trans-13,cis-17 20:4, cis-5,cis-8,cis-11,trans-13,cis-17 20:5, cis-7,cis-10,cis-13,trans-15,cis-19 22:5, and cis-4,cis-7,cis-10,cis-13,trans-15,cis-19 22:6 acids by GC-MS as their 4,4-dimethyloxazoline and methyl esters derivatives. Specific fragmentation of the methyl ester derivatives revealed some similarity with their corresponding DMOX derivatives. Indeed, intense ion fragments at m/z=M+-69, corresponding to a cleavage at the center of a bis-methylene interrupted double bond system were observed for all identified metabolites. Moreover, intense ion fragments at m/z=M+-136, corresponding to allylic cleavage of the n-12 double bonds were observed for the C20:5, C22:5, C22:6 acid metabolites. For the long chain polyunsaturated fatty acids from the rumelenic metabolism, we showed that single methyl esters derivatives might be used for both usual quantification by GC-FID and identification by GC-MS.  相似文献   

9.
The fatty acids obtained from extractable lipids of the anaerobic sulfate bacterium Desulfovibrio desulfuricans were identified. Saturated and monoenoic iso (C15-C19) and anteiso (C15, C17) fatty acids and saturated normal (C14-C18) and monoenoic normal (C16, C18) fatty acids were shown to be shown to be present by capillary gas chromatography-mass spectrometry. Iso and anteiso beta-hydroxy fatty acids were analyzed as trimethylsilyl ethers in the same way. The position of methyl branches in the monoenoic fatty acids was determined from characteristic fragment ions in the mass spectra of their methyl esters. Disilyloxy methyl esters, prepared by derivatization of the mono unsaturated methyl esters and analyzed by capillary gas chromatography-mass spectrometry, provided the position of double bonds. The monoenoic fatty acids identified in this way were normal (delta7-C16:1, delta9-C16:1, delta9-C18:1, delta11-C18:1), iso (delta7-C15:1, delta9-C16:1, delta9-C17:1, delta11-C18:1, delta11-C19:1), and anteiso (delta7-C15:1, delta9-C17:1). Iso delta9-C17:1 fatty acid is present as the major component. The occurrence of these monoenoic fatty acids in this bacterium is of taxonomical importance.  相似文献   

10.
Characteristics of acyl-coenzyme A (acyl-CoA):steroid acyltransferase from the digestive gland of the oyster Crassostrea virginica were determined by using estradiol (E2) and dehydroepiandrosterone (DHEA) as substrates. The apparent Km and Vmax values for esterification of E2 with the six fatty acid acyl-CoAs tested (C20:4, C18:2, C18:1, C16:1, C18:0, and C16:0) were in the range of 9-17 microM E2 and 35-74 pmol/min/mg protein, respectively. Kinetic parameters for esterification of DHEA (Km: 45-120 microM; Vmax: 30-182 pmol/min/mg protein) showed a lower affinity of the enzyme for this steroid. Formation of endogenous fatty acid esters of steroids by microsomes of digestive gland and gonads incubated in the presence of ATP and CoA was assessed, and at least seven E2 fatty acid esters and five DHEA fatty acid esters were observed. Some peaks eluted at the same retention times as palmitoleoyl-, linoleoyl-, oleoyl/palmitoyl-, and stearoyl-E2; and palmitoleoyl-, oleoyl/palmitoyl-, and stearoyl-DHEA. The same endogenous esters, although in different proportions, were produced by gonadal microsomes. The kinetic parameters for both E2 (Km: 10 microM; Vmax: 38 pmol/min/mg protein) and DHEA (Km: 61 microM; Vmax: 60 pmol/min/mg protein) were similar to those obtained in the digestive gland. Kinetic parameters obtained are similar to those observed in mammals; thus, fatty acid esterification of sex steroids appears to be a well-conserved conjugation pathway during evolution.  相似文献   

11.
Identification of the thiol ester linked lipids in apolipoprotein B   总被引:4,自引:0,他引:4  
G Huang  D M Lee  S Singh 《Biochemistry》1988,27(5):1395-1400
Human plasma low-density lipoproteins of 1.032-1.043 g/mL density were totally delipidized. The reduced and carboxymethylated apolipoprotein B was incubated with 50 mM [14C]methylamine at pH 8.5 at 30 degrees C. Covalent incorporation of [14C]methylamine was observed with concomitant generation of new sulfhydryl groups, which could be blocked with [3H]- or [14C]iodoacetic acid. One type of the [14C]methylamine-modified products was separated from the protein and was found to be lipid in nature. Its Rf on thin-layer chromatography (TLC) was similar to that of the synthetic N-methyl fatty acyl amides. After purification with TLC and transesterification in 3 N methanolic HCl, methyl esters of C16 and C18 fatty acids at 1:1 ratio were identified by gas-liquid chromatography. The transesterification method was verified with the known N-methyl fatty acyl amides. These results suggest the presence of labile thiol ester linked palmitate and stearate in apolipoprotein B. Under mild alkaline conditions, the thiol ester bonds are broken by methylamine and form N-methyl fatty acyl amides and release new-SH groups. Intramolecular thiol ester bonds linked between cysteine side chains and acidic amino acid residues were also found present, which will be reported separately.  相似文献   

12.
Diet and postnatal age effect the fatty acid composition of plasma and tissue lipids. This work was designed as a transversal study to evaluate the changes in the fatty acid composition of plasma phospholipids, cholesteryl esters, triglycerides and free fatty acids in preterm infants (28-35 weeks gestational age), fed human milk (HM) and milk formula (MF) from birth to 1 month of life. Sixteen blood samples were obtained from cord, and 19 at 6-8 h after birth, 14 at 1 week and 9 at 4 weeks from HM-fed infants and 18 at 1 week and 14 at 4 weeks from MF-fed ones. Groups had similar mean birth weight, gestational age and sex ratio. The MF provided 69 kcal/dl and contained 16% of linoleic acid and 1.3% of alpha-linolenic acid on the total fat. Plasma lipid fractions were extracted and separated by thin-layer chromatography and fatty acid methyl esters were quantitated by gas liquid chromatography. In plasma phospholipids, linoleic acid (18:2 omega 6) continuously increased from birth to 1 month of age, but no changes were seen as related to type of diet; polyunsaturated fatty acids greater than 18 carbon atoms of both the omega 6 and omega 3 series (PUFA omega 6 greater than 18 C and omega 3 greater than 18 C) dropped from birth to 1 week and continued to decrease in MF-fed infants until 1 month; eicosatrienoic (20:3 omega 6), arachidonic (20:4 omega 6) and docosahexaenoic (22:6 omega 3) were the fatty acids implicated. In cholesteryl esters palmitoleic (16:1 omega 7) and oleic (18:1 omega 9) acids decreased from birth to 1 month and linoleic acid increased and arachidonic acid dropped, especially in MF fed infants. In triglycerides, palmitic, palmitoleic and stearic acid (18:0) decreased during the first month of life; oleic acid remained constant and linoleic acid increased in all infants, but arachidonic acid decreased only in those fed formula. Free fatty acids showed a similar behavior in fatty acids and in plasma triglycerides. Preterm neonates seem to have special requirements of long-chain PUFA and adapted MF should contain these fatty acids in similar amounts to those of HM to allow the maintenance of an adequate tissue structure and physiology.  相似文献   

13.
The inhibitory effects of various fatty acids on topoisomerases were examined, and their structure activity relationships and mechanism of action were studied. Saturated fatty acids (C6:0 to C22:0) did not inhibit topoisomerase I, but cis-unsaturated fatty acids (C16:1 to C22:1) with one double bond showed strong inhibition of the enzyme. The inhibitory potency depended on the carbon chain length and the position of the double bond in the fatty acid molecule. The trans-isomer, methyl ester and hydroxyl derivative of oleic acid had no or little inhibitory effect on topoisomerases I and II. Among the compounds studied petroselinic acid and vaccenic acid (C18:1) with a cis-double bond were the potent inhibitors. Petroselinic acid was a topoisomerase inhibitor of the cleavable complex-nonforming type and acted directly on the enzyme molecule in a noncompetitive manner without DNA intercalation.  相似文献   

14.
The yield of trehalose dimycolate (TDM), the major glycolipid species elaborated by Rhodococcus rhodochrous, a producer of approx. C40-mycolic acid, was not constant in cells cultured for different periods of time. From cells collected at 24, 36, 72, 144 and 172 h of cultivation the following percentages of TDM in diethyl ether soluble lipids (DESL) were found: 10.8%, 23.4%, 10.0%, 9.0% and 5.0%, respectively. In turn, the cellular content accounted for approx. 0.6%, 1.2%, 0.9%, 0.6% and 0.2%, respectively. On the other hand, the yield of galactose monomycolate (GalMM), a minor glycolipid species maintained at approx. 3.4% in DESL during the different periods of time examined; this value represented about 0.3% of the cellular content. The melting temperatures of TDMs fell between 37 degrees C to approximately 97 degrees C with the lowest value from cells grown for 36 h, whereas the melting temperatures of the GalMMs were in a narrow range between 56 degrees C and 64 degrees C. The methyl ester derivatives of the constituent fatty acid moieties of DTMs and GalMMs migrated on thin layer chromatography like methyl esters of C40-C46 mycolic acids, therefore faster than methyl esters of C28-C34 mycolic acids but slower than methyl esters of C50-C56 mycolic acids. Further analysis of the products of pyrolysis of the methyl ester derivatives of the fatty acid moiety released from TDM after alkaline hydrolysis was carried out using gas chromatography combined mass spectrometry.(ABSTRACT TRUNCATED AT 250 WORDS)  相似文献   

15.
Changes in fatty acid composition, cholesterol and fat‐soluble vitamins were studied during development (fertilized eggs, yolk‐sac larvae, and after yolk resorption of shabbout, Barbus grypus). Significant differences were found in the monounsaturated fatty acids (MUFAs), polyunsaturated fatty acids (PUFA), PUFA/saturated fatty acids (SFA), ∑n‐3 and eicosapentaenoic acid (EPA)/docosahexaenoic acid (DHA) ratios between eggs and larvae (P < 0.05). Significant differences were also observed in the C14:0, C16:1n‐7, C18:1n‐9, C18:3n‐6, C20:0, C20:4n‐6, C24:0, C24:1, C22:6n‐3 fatty acids between eggs and larvae after yolk‐sac resorption (P < 0.05). Vitamin α‐ Tocopherol and retinol content increased during embryogenesis, but changes were insignificant in retinol acetate, δ‐Tocopherol, K1, K2 and cholesterol content between eggs and larvae after yolk resorption (P > 0.05).  相似文献   

16.
The effects on growth and mortality of larvae of pink bollworm (Pectinophora gossypiella, Saunders), bollworm (Heliothis zea, Boddie) and tobacco budworm (Heliothis virescens, F.) of adding selected C10–C12 fatty acid methyl esters to a standard diet were determined. The antibiotic activity of straight chain saturated esters was compared to the activity of esters with an olefinic bond either at C-2 or terminally or with a terminal acetylenic or cyclopropyl group. The ester with the greatest activity was the naturally occurring compound methyl (Z,Z)-deca-2,8-diene-4,6-diynoate (matricaria ester) which was lethal to all pink bollworm larvae at 0.01% in the diet and lethal to all bollworm and tobacco budworm larvae at 0.05%.  相似文献   

17.
Thermally induced isomerisation leading to the formation of conjugated linoleic acids (CLAs) has been observed for the first time during the thermal treatment of 9t12t fatty acid triacylglycerol, and methyl ester. Fifteen microlitre portions of the triacylglycerol sample containing 9t12t fatty acid (trilinoelaidin) were placed in micro glass ampoules and sealed under nitrogen, then subjected to thermal treatment at 250 °C. The glass ampoules were removed at regular time intervals, cut open, and the contents were analysed by infrared spectroscopy using a single reflectance attenuated total internal reflectance crystal accessory. The samples were then subjected to derivatisation into their methyl esters. The methyl esters of the isomerised fatty acids were analysed by gas chromatography. The same procedure was repeated with methyl ester samples containing 9t12t fatty acid (methyl linoelaidate). Each sample was subjected to infrared measurements and gas chromatographic analysis after appropriate dilution in heptane.The results show that the thermally induced isomerisation of 9t12t fatty acids from both triacylglycerol molecules and methyl esters give identical CLA profiles as those found for the thermally induced isomerisation of 9c12c fatty acids. The infrared spectrometry provides additional evidence confirming the formation of CLA acids during thermal treatment. A mechanism for the formation of the CLAs from 9t12t fatty acid molecules is also formulated for the first time. This mechanism complements the pathways of formation of CLAs from 9c12c fatty acids during thermal treatment.  相似文献   

18.
The bactericidal activity of long-chain fatty acids on mycobacteria was examined by exposing the organisms to these acids at 0.04 mM in 0.05 M acetate buffer (pH 5.6). The lethal effect of saturated fatty acids was related to the chain-length of hydrocarbon, C14:0 being the strongest in the activity and longer and shorter fatty acids being less active. Unsaturation, isomerism and the presence of alpha-hydroxy group were found to be other factors governing the activity. The lethal effect was greater in the order of C18:3 greater than C18:2 greater than C18:1(cis) greater than C18:1(trans) greater than alpha-OH C18:0 greater than C18:0. C20:4 was placed between C18:3 and C18:2 in this respect. Esterification of C14:0, C18:1 and C20:4 to methyl esters and cholesteryl esters abolished completely the bactericidal activity of these acids, suggesting the requirement of carboxyl group for the activity. The relationship between the fatty acid structure and the lethal effect was discussed in reference to these observations.  相似文献   

19.
Ilham Z  Saka S 《Bioresource technology》2009,100(5):1793-1796
In this study, the non-catalytic supercritical method has been studied in utilizing dimethyl carbonate. It was demonstrated that, the supercritical dimethyl carbonate process without any catalysts applied, converted triglycerides to fatty acid methyl esters with glycerol carbonate and citramalic acid as by-products, while free fatty acids were converted to fatty acid methyl esters with glyoxal. After 12 min of reaction at 350 degrees C/20 MPa, rapeseed oil treated with supercritical dimethyl carbonate reached 94% (w/w) yield of fatty acid methyl ester. The by-products from this process which are glycerol carbonate and citramalic acid are much higher in value than glycerol produced by the conventional process. In addition, the yield of the fatty acid methyl esters as biodiesel was almost at par with supercritical methanol method. Therefore, supercritical dimethyl carbonate process can be a good candidate as an alternative biodiesel production process.  相似文献   

20.
The present study deals with the concentration and fatty acid composition of cholesterol esters in rat brains infected experimentally with measles virus to induce acute encephalitis. The left side of the cerebrum, as well as other portions of the brain, when inoculated percutaneously contained a large amount of cholesterol esters. The major fatty acids from the esters in the brain were C16:0, C16:1, C18:0, and C18:1; those from the serum were C18:1, C18:2, and C20:4. This result indicates that cholesterol esters may not come from serum but can be synthesized in situ, even in the brain with acute viral infection.  相似文献   

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