bluuebunny/crossref_metadata_2025_split huggingface dataset:
Dietary sandalwood seed oil modifies fatty acid composition of mouse adipose tissue, brain, and liver
Authors: Liu Yandi , Longmore Robert B. 
Published: November 2006

AbstractSandalwood (Santalum spicatum) seed oil, which occurs to about 50% of the weight of the seed kernels, contains 30–35% of total fatty acids (FA) as ximenynic acid (XMYA). This study was designed to obtain basic information on changes in tissue FA composition and on the metabolic fate of XMYA in mice fed a sandalwood seed oil (SWSO)‐enriched diet. Female mice were randomly divided into three groups, each receiving different semisynthetic diets containing 5.2% (w/w) fat (standard laboratory diet), 15% canola oil, or 15% SWSO for 8 wk. The effects of SWSO as a dietary fat on the FA composition of adipose tissue, brain, and liver lipids were determined by analyses of FA methyl ester derivatives of extracted total lipid. The FA compositions of the liver and adipose tissue were markedly altered by the dietary fats, and mice fed on a SWSO‐enriched diet were found to contain XMYA but only in low concentration (0.3 3%) in these tissues; XMYA was not detected in brain. Oleic acid was suggested to be a principal XMYA biotransformation product. The results were interpreted to suggest that the metabolism of XMYA may involve both biohydrogenation and oxidation reactions.
The unusual occurrence of 14‐methylhexadecanoic acid in pinaceae seed oils among plants
Authors: Wolff Robert L. , Christie William W. , Coakley David 
Published: November 2006

Abstract14‐Methylhexadecanoic (14‐MHD) acid has been identified in a sample of pine seed oil (Pinus contorta) by gas‐liquid chromatography‐mass spectrometry of its picolinyl ester derivative: Its identification (through its equivalent chain length) and its distribution in four conifer families have been checked. It occurred only in Pinaceae, where it was found in 72 species belonging to the genera Pinus, Abies, Cedrus, Tsuga, Pseudotsuga, Larix, and Picea, in the range 0.02–1.15%. 14‐MHD acid could not be detected in the lipids of Taxaceae (Taxus baccata), Cupressaceae (Juniperus communis), or Taxodiaceae (Sciadopytis verticillata), even after a 10‐fold concentration of the saturated acid fraction isolated by argentation thinlayer chromatography. It is concluded that Pinaceae, along with Ginkgo biloba seed lipids, are major exceptions in the plant kingdom with regard to 14‐MHD acid, which otherwise occurs almost exclusively in lipids of animals and microorganisms. The biosynthesis and metabolic role of 14‐MHD acid, which other‐wise also occur in wood and leaf lipids, remain unknown.
Analysis of oxylipins by high‐performance liquid chromatography with evaporative light‐scattering detection and particle beam‐mass spectrometry
Authors: Rehbock Bettina , Gansser Dietmar , Berger Ralf G. 
Published: November 2006

AbstractThe metabolism of 13 S‐hydroperoxy‐9Z,11E,15Z‐octadecatrienoic acid was investigated in a crude enzyme extract from mung bean seedlings (Phaseolus radiatus L.). Hydroperoxide‐metabolizing activity was mainly due to a hydroperoxide lyase and, to a lesser extent, to an allene oxide synthase and a peroxygenase. Oxylipins originating from hydrolysis and cyclization of the allene oxide synthase product 12,13‐epoxy‐9Z,11,15Z‐octadecatrienoic acid and from peroxygenase catalysis were identified by high‐performance liquid chromatography (HPLC) particle beam‐mass spectrometry (PB‐MS) and quantified by normal‐phase HPLC with an evaporative light‐scattering detector (ELSD). An advantage of this methodology was the possibility to avoid extensive derivatization procedures commonly used for the gas chromatographic analysis of oxylipins. Owing to a comparable sample inlet system, the ELSD served an important analytical pilot function for the PB‐MS: Qualitatively identical chromatographic patterns were obtained with both detection systems. The HPLC system enabled the separation of methyl 12‐oxo‐phytodienoate, methyl 11‐hydroxy‐12‐oxo‐9Z,15Z‐octadecadienoate, methyl 12‐oxo‐13‐hydroxy‐9Z,15Z‐octadecadienoate, methyl 9‐hydroxy‐12‐oxo‐10E,15Z‐octadecadienoate, methyl 13‐hydroxy‐9Z,11E,15Z‐octadecatrienoate, methyl 15,16‐epoxy‐13‐hydroxy‐9Z,11E,15Z‐octadecatrienoate, and methyl 13‐hydroperoxy‐9Z,11E,15Z‐octadecatrienoate on a Lichrospher DIOL column within 33 min. Compared with a diode array detector, the ELSD proved to be more sensitive, in the case of methyl 12‐oxo‐13‐hydroxy‐9Z, 15Z‐octadecadienoate by a factor of about 15. In addition, volatile metabolites were analyzed by capillary gas chromatography. The yield of the hydroperoxide lyase product 2E‐hexenal was 49%, whereas the sum of oxylipins reached about 15%.
Use of an improved internal‐standard method in the quantitative sterol analyses of phytoplankton and oysters
Authors: Ghosh Parthasarathi , Patterson Glenn W. , Wikfors Gary H. 
Published: November 2006

AbstractMost work reporting the sterol composition of living organisms has not been done quantitatively, although good quantitative data are available for fatty acids and many other cellular components using an internal‐standard method that compensates for errors during gas chromatographic analysis. In this paper, we report on the use of 7‐stigmastenyl acetate as an internal standard for sterol analysis in two species of phytoplankton and oysters produced with two different diets. This internal‐standard method provides an internal standard for this entire process of analysis, not just the gas chromatographic analysis. When analyzing 50‐μg samples of cholesterol acetate after hydrolysis and acetylation, about 30% of the sample was lost, resulting in a 30% error using the older external‐standard method. Using the internal‐standard method, the analysis error was less than 2%. Losses of sterol during analysis apparently are greater with plant and animal samples than with pure sterol standards. This internal‐standard method was shown to be extremely useful, especially for samples with less than 500 μg of sterol. Finally, the standard error in sterol analysis is much lower when the internal‐standard, method is used, allowing statistical distinctions that are not possible otherwise. Use of 7‐stigmastenyl acetate as an internal standard offers several advantages over the use of cholestane.
High‐resolution nuclear magnetic resonance spectroscopy —Applications to fatty acids and triacylglycerols
Authors: Lie Ken Jie Marcel S. F. , Mustafa J. 
Published: November 2006

AbstractDuring the past two decades, nuclear magnetic resonance spectroscopy (NMR) has played an ever‐increasing role in the structural determination of fatty acids, fatty acid derivatives and analogues, and in the analysis of the structures of triacylglycerols including the quantitative analysis of lipid mixtures. This article discusses some of the results obtained through the application of the NMR technique to lipid molecules and reviews the literature. To maintain brevity, this article does not cover the underlying theory of NMR spectroscopy as numerous books devoted to modern NMR spectroscopy have been published.
Synthesis and nuclear magnetic resonance properties of all geometrical isomers of conjugated linoleic acids
Authors: Lie Ken Jie Marcel S. F. , Pasha Mohammed Khysar , Alam Mohammad Shahin 
Published: November 2006

AbstractPure geometric isomers of conjugated linoleic acid were prepared from castor oil as the primary starting material. Methyl octadeca‐9Z, 11E‐dienoate (2) and methyl octadeca‐9Z, 11Z‐dienoate (4) were obtained by zinc reduction of methyl santalbate (1, methyl octadec‐11E‐en‐9‐ynoate) and methyl octadec‐11 Z‐en‐9‐ynoate (3), respectively, as the key intermediates. Methyl octadeca‐9E, 11E‐dienoate (8) and methyl octadeca‐9E, 11Z‐dienoate (9) were prepared by demesylation of the mesyloxy derivative of methyl ricinelaidate (6, methyl 12‐hydroxy‐octadec‐9 E‐enoate). A study of the nuclear magnetic resonance spectral properties was carried out and the shifts of the olefinic carbon atoms of 18:2(9Z, 11E) (2) and 18:2(9E, 11Z) (9) were readily identified by a combination of incredible natural abundance double quantum transfer experiment, heteronuclear multiple bond correlation, and 1H−13C correlation spectroscopy correlation techniques. Doubts remain in the absolute identification of the individual olefinic carbon atoms of the 18:2(9Z, 11Z) (4) and 18:2(9E, 11E) (8), except the fact that the shifts of the “inner” (C‐10 and C‐11) and “outer” (C‐9 and C‐12) positioned olefinic carbon atoms of the conjugated diene system are distinguishable.
Breast milk fatty acid composition: A comparative study between Hong Kong and Chongqing Chinese
Authors: Chen Z. Y. , Kwan K. Y. , Tong K. K. , Ratnayake W. M. N. , Li H. Q. , Leung S. S. F. 
Published: November 2006

AbstractThe fatty acids of milk samples obtained from 51 Hong Kong Chinese and 33 Chongqing Chinese (Si Chuan Province, China) were analyzed by gas‐liquid chromatography. Compared with those of published data for Canadian and other Western countries, the Chinese milk from both Hong Kong and Chongqing contained higher levels of longer‐chain polyunsaturated fatty acids, particularly docosahexaenoic acid (22:6n‐3) and arachidonic acid (20:4n‐6). In contrast, the content of trans fatty acids in the Chinese milk was lower compared with those for Canadian and other Western countries. Longitudinally, the concentrations of 22:6n‐3 and 20:4n‐6 gradually decreased when lactation progressed from colostrum (week 1) to mature (week 6). Over the same interval, linoleic acid (18:2n‐6) remained unchanged in Chongqing Chinese but significantly increased in Hong Kong Chinese. Unlike 18:2n‐6, linolenic acid (18:3n‐3) increased in Chongqing Chinese but remained unchanged in Hong Kong Chinese throughout the study. The total milk fat also increased with the duration of lactation. In addition, the milk of Chongqing Chinese had higher total milk fat than that of Hong Kong Chinese and Canadians. The content of erucic acid (22:1n‐9) increased with the progression of lactation in Chongqing Chinese, indicating that there was a switch in dietary consumption from fats of animal origin to rapeseed oil when lactation reached week 6. The present study showed that Hong Kong and Chongqing Chinese had a different fatty acid profile in many ways, which largely reflected a different dietary habit and life‐style in these two places.
Low‐dose eicosapentaenoic or docosahexaenoic acid administration modifies fatty acid composition and does not affect susceptibility to oxidative stress in rat erythrocytes and tissues
Authors: Calviello Gabriella , Palozza Paola , Franceschelli Piergiorgio , Bartoli Gianna Maria 
Published: November 2006

AbstractIn view of the promising future for use of n‐3 polyunsaturated fatty acids (PUFA) in the prevention of cancer and cardiovascular diseases, it is necessary to ensure that their consumption does not result in detrimental oxidative effects. The aim of the present work was to test a hypothesis that low doses of eicosapentaenoic acid (EPA) or docosahexaenoic acid (DHA) do not induce harmful modifications of oxidative cell metabolism, as modifications of membrane fatty acid composition occur. Wistar rats received by gavage oleic acid, EPA, or DHA (360 mg/kg body weight/day) for a period of 1 or 4 wk. Fatty acid composition and α‐tocopherol content were determined for plasma, red blood cell (RBC) membranes, and liver, kidney, lung, and heart microsomal membranes. Susceptibility to oxidative stress induced by tert‐butylhydroperoxide was measured in RBC. EPA treatment increased EPA and docosapentaenoic acid (DPA) content in plasma and in all the membranes studied. DHA treatment mainly increased DHA content. Both treatments decreased arachidonic acid content and n‐6/n‐3 PUFA ratio in the membranes, without modifying the Unsaturation Index. No changes in tissue α‐tocopherol content and in RBC susceptibility to oxidative stress were induced by either EPA or DHA treatment. The data suggest that EPA and DHA treatments can substantially modify membrane fatty acids, with‐out increasing susceptibility to oxidative stress, when administered at low doses. This opens the possibility for use of low doses of n‐3 PUFA for chemoprevention without risk of detrimental secondary effects.
Oxidation reactions of acetylenic fatty esters with selenium dioxide/tert‐butyl hydroperoxide
Authors: Lie Ken Jie Marcel S. F. , Khysar Pasha Mohammed , Shahin Alam Mohammad 
Published: November 2006

AbstractReaction of methyl undec‐10‐ynoate (1) with selenium dioxide/tert‐butyl hydroperoxide (TBHP) in aqueous dioxane gave methyl 9‐oxo‐undec‐10‐ynoate (2, 9%) and 9‐hydroxy‐undec‐10‐ynoate (3, 60%), while methyl octadec‐9‐ynoate (4) yielded mixtures of positional isomers of mono‐keto (viz. methyl 8‐oxo‐ and 11‐oxo‐octadec‐9‐ynoate, 5, 5%), hydroxy‐keto (viz. methyl 8‐hydroxy‐11‐oxo‐and 11‐hydroxy‐8‐oxo‐octadec‐9‐ynoate, 6, 10%), and dihydroxy (viz. methyl 8,11‐dihydroxy‐octadec‐9‐ynoate, 7, 24%) derivatives. Similar treatment of a conjugated diacetylenic fatty ester (methyl octadeca‐6,8‐diynoate, 8) furnished a mixture of methyl 5‐oxo‐and 10‐oxo‐octadeca‐6,8‐diynoate (9, 12%) and a complex mixture of very polar products. Reaction of methyl octadec‐11E‐en‐9‐ynoate (methyl santalbate) (10) with selenium dioxide/TBHP in aqueous dioxane gave exclusively a mixture of regiospecific products, viz. methyl 8‐oxo‐octadec‐11(E) Z‐en‐9‐ynoate (11, 6%) and methyl 8‐hydroxy‐octadec‐11 E‐en‐9‐ynoate (12, 70%). The structures of the various products were determined by a combination of spectroscopic and mass spectral analyses.
The effect of dietary docosahexaenoic acid on plasma lipoproteins and tissue fatty acid composition in humans
Authors: Nelson G. J. , Schmidt P. C. , Bartolini G. L. , Kelley D. S. , Kyle David 
Published: November 2006

AbstractNormal, healthy male volunteers (n=6) were fed diets [high docosahexaenoic acid‐DHA] containing 6 g/d of DHA for 90 d. The stabilization (low‐DHA) diet contained less than 50 mg/d of DHA. A control group (n=4) remained on the low‐DHA diet for the duration of the study (120 d). Blood samples were drawn on study days 30 (end of the stabilization period), 75 (midpoint of the intervention period), and 120 (end of the intervention period). Adipose tissue (AT) samples were taken on days 30 and 120. The plasma cholesterol (C), low density lipoprotein (LDL)‐C and apolipoproteins (apo) [Al, B, and lipoprotein (a)] were unchanged after 90 d, but the triglycerides (TAG) were reduced from a mean value of 76.67±24.32 to 63.83±16.99 mg/dL (n=6, P<0.007 using a paired t‐test) and the high density lipoprotein (HDL)‐C increased from 34.83±4.38 mg/dL to 37.83±3.32 mg/dL (n=6, P<0.017 using a paired t‐test). The control group showed no significant reduction in plasma TAG levels. Apo‐E, however, showed a marked increase in the volunteers’ plasma after 90 d on the high‐DHA diet, from 7.06±4.47 mg/dL on study day 30 to 12.01±4.96 mg/dL on study day 120 (P<0.002 using a paired t‐test). The control subjects showed no significant change in the apo‐E in their plasma (8.46±2.90 on day 30 vs. 8.59±2.97 on day 120). The weight percentage of plasma DHA rose from 1.83±0.22 to 8.12±0.76 after 90 d on the high‐DHA diet. Although these volunteers were eating a diet free of eicosapentaenoic acid (EPA), plasma EPA levels rose from 0.38±0.05 to 3.39±0.52 (wt%) after consuming the high‐DHA diet. The fatty acid composition of plasma lipid fractions—cholesterol esters, TAG, and phospholipid—showed marked similarity in the enrichment of DHA, about 10%, after the subjects consumed the high‐DHA diet. The DHA content of these plasma lipid fractions varied from less than 1% (TAG) to 3.5% (phospholipids) at baseline, study day 30. EPA also increased in all plasma lipid fractions after the subjects consumed the high‐DHA diet. There were no changes in the plasma DHA or EPA levels in the control group. Consumption of DHA also caused an increase in AT levels of DHA, from 0.10±0.02 to 0.31±0.07 (wt%) (n=6, P<0.001 using a paired t‐test), but the amount of EPA in their AT did not change. Thus, dietary DHA will lower plasma TAG without EPA, and DHA is retroconverted to EPA in significant amounts. Dietary DHA appears to enhance apo‐E synthesis in the liver. It appears that DHA can be a safe and perhaps beneficial supplement to human diets.
Epicoprostanol found in adipocere from five human autopsies
Authors: Adachi Junko , Ueno Yasuhiro , Miwa Atsuko , Asano Migiwa , Nishimura Akiyoshi , Tatsuno Yoshitsugu 
Published: November 2006

AbstractAdipocere formation is well known as a later postmortem change. We collected adipocere from five male victims which had been submerged under the sea or fresh water for 1 mon to 4 yr. Fresh subcutaneous fat of a male victim who died from a cerebral contusion was used as the control. The samples were homogenized, and the lipids were extracted with chloroform and methanol followed by injection into a gas chromatograph and a gas chromatograph‐mass spectrometer. We detected hydroxy fatty acids (10‐hydroxyocatadecanoic and 10‐hydroxyhexadecanoic acid) as well as 10‐ketooctadecanoic acid in adipocere, but not in the control. In addition, we found for the first time a cholesterol‐related peak with a molecular ion of 388 in adipocere and identified it as epicoprostanol, suggesting not only oxidation but also reduction had occurred during the formation of adipocere. In addition, we showed the time‐course of epicoprostanol accumulation. The relationship between the time of adipocere formation and the characteristic lipid composition is discussed.
Generation and remodeling of highly polyunsaturated molecular species of rat hepatocyte phospholipids
Authors: Schmid Patricia C. , Spimrova Ilona , Schmid Harald H. O. 
Published: November 2006

AbstractFreshly isolated rat hepatocytes were incubated for 20 min with [U‐14C]glycerol in the presence or absence of unlabeled linoleic (18∶2n‐6), arachidonic (20∶4n‐6), or docosahexaenoic (22∶6n‐3) acid, added as albumin complex in 10% ethanol. Most of the radioactivity (≈95%) recovered in hepatocyte lipids was present in phosphatidylcholine (PC), phosphatidylethanolamine (PF), and triacylglycerol (TAG). The presence of exogenous fatty acids resulted in (i) higher incorporation of [U‐14C]glycerol, (ii) higher percentage of label in TAG, and (iii) enhanced formation of PC and PE molecular species bearing the exogenous fatty acid at both the sn‐1 and sn‐2 positions of glycerol. In each case, these molecular species contained 60 to 70% of the label in that lipid class. Further incubation of the cells for 40 and 80 min in the absence of labeled substrate and exogenous fatty acids resulted in a redistribution of label among PC and PE molecular species due to deacylation‐reacylation at the sn‐1 position of glycerol.
Analysis of the seed oil of Heisteria silvanii (Olacaceae)—A rich source of a novel C18 acetylenic fatty acid
Authors: Spitzer Volker , Tomberg Werner , Hartmann Rudolf , Aichholz Reiner 
Published: November 2006

AbstractBesides some usual fatty acids (FA), two conjugated ene‐yne acetylenic FA [trans‐10‐heptadecen‐8‐ynoic acid (pyrulic acid) (7.4%), and trans‐11‐octadecen‐9‐ynoic acid (ximenynic acid) (3.5%)], a novel ene‐yne‐ene acetylenic FA [cis‐7, trans‐11‐octadecadiene‐9‐ynoic acid (heisteric acid) (22.6%)], and 9,10‐epoxystearic acid (0.6%) could be identified in the seed oil of Heisteria silvanii (Olacaceae). Two further conjugated acetylenic FA [9,11‐octadecadiynoic acid (0.1%) and 13‐octadecene‐9,11‐diynoic acid (0.4%)] were identified tentatively by their mass spectra. The FA mixture has been analyzed by gas chromatography/mass spectrometry (GC/MS) of their methyl ester and 4,4‐dimethyloxazoline derivatives. The structure of heisteric acid was elucidated after isolation via preparative silver ion thin‐layer chromatography and by various spectroscopic methods [ultraviolet; infrared; 1H, 13C nuclear magnetic resonance (NMR); 1H−1H and 1H−13C correlation spectroscopy]. To determine the position of the conjugated ene‐yne‐ene system, the NMR spectra were also measured after addition of the lanthanide shift reagent Resolve‐Al EuFODTM. Furthermore, the triyglyceride mixture was analyzed by high‐temperature GC and high‐temperature GC coupled with negative chemical ionization MS. A glass capillary column coated with a methoxy‐terminated 50%‐diphenyl‐50%‐dimethylpolysiloxane was used for the separation of the triacylglycerol (TAG) species. No evidence of decomposition of the TAG species containing conjugated ene‐yne‐ene FA was observed. Twenty‐six species of the separated TAG were identified by means of their abundant quasi molecular ion [M−H]− and their corresponding carboxylate anions [RCOO]− of the fatty acids, respectively. The major molecular species of the TAG were found to be 16:0/18:1/18:1, 16:0/18:1/18:3 (heisteric acid), 17:2 (pyrulic acid)/18:1/18:1, 18:1/18:1/18:3 (heisteric acid). The TAG containing acetylenic FA showed an unexpected increase of the retention time in comparison to the TAG containing usual FA, thus making the prediction of the elution order of lipid samples containing acetylenic FA difficult.
Elution factors of synthetic oxotriacylglycerols as an aid in identification of peroxidized natural triacylglycerols by reverse‐phase high‐performance liquid chromatography with electrospray mass spectrometry
Authors: Sjövall Olli , Kuksis Arnis , Marai Lajos , Myher John J. 
Published: November 2006

AbstractSelected elution factors were determined for model oxotriacylglycerols as an aid in identification of the peroxidation products of natural triacylglycerols by reverse‐phase high‐performance liquid chromatography (HPLC) with electrospray mass spectrometry (LC/ES/MS). For this purpose synthetic triacylglycerols of known structure were converted to hydroperoxides, hydroxides, epoxides, and core aldehydes and their dinitrophenylhydrazones by published procedures. The oxotriacylglycerols were resolved by normal‐phase thin‐layer chromatography and reverse‐phase HPLC, and the identities of the oxotriacylglycerols confirmed by LC/ES/MS. Elution factors of oxotriacylglycerols were determined in relation to a homologous series of saturated triacylglycerols, ranging from 24 to 54 acylcarbons, and analyzed by reverse‐phase HPLC, using a gradient of 20–80% isopropanol in methanol as eluting solvent and an evaporative light‐scattering detector. It was shown that the elution times varied with the nature of the functional group and its regiolocation in the triacylglycerol molecule. A total of 31 incremental elution factors were calculated from chromatography of 33 oxygenated and nonoxygenated triacylglycerol species, ranging in carbon number from 36 to 54 and in double‐bond number from 0 to 6.