anteiso-Fatty Acids in Brussels Sprouts (Brassica oleracea var. gemmifera L.): Quantities, Enantioselectivities, and Stable Carbon Isotope Ratios

Eibler, Dorothee; Seyfried, Carolin; Kaffarnik, Stefanie; Vetter, Walter

doi:10.1021/acs.jafc.5b03877

Cited by 22 publications

(43 citation statements)

References 45 publications

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“…About 50 g saponifiable matter was methylated with 300 mL 1% sulfuric acid in methanol by refluxing for 4 h at 80 °C in a 1-L round-bottom flask [5,6]. After cooling to room temperature, 100 mL of a saturated NaCl solution and 100 mL demin.…”

Section: Preparation Of Fatty Acid Methyl Esters (Fame)mentioning

confidence: 99%

“…SHFA methyl esters were enriched by hydrogenation and urea complexation using the method of Eibler et al with modifications [6]. For hydrogenation, FAME were divided into four equal portions (~12-13 g) and hydrogenated as described previously but over the course of three days [6]. Hydrogenation process was controlled by measurement of an aliquot (c ~0.1 mg in 1 mL n-hexane) and continued until no further unsaturated fatty acids were detectable by GC/MS.…”

Section: Enrichment Of Sulfur-heterocyclic Fatty Acid (Shfa) Methyl Ementioning

confidence: 99%

“…An aliquot of ~0.1 mg/mL was removed for GC/MS analysis. Hydrogenated FAME were combined to batches of ~25 g and urea complexation was carried out for three days using the protocol of Eibler et al [6]. Afterwards, the solutions were filtrated through a fluted filter paper.…”

Section: Enrichment Of Sulfur-heterocyclic Fatty Acid (Shfa) Methyl Ementioning

confidence: 99%

“…Analysis of FAME prior and after different enrichment steps was carried out with an HP 5890/5971A GC/ MS system (system I, Hewlett-Packard/Agilent, Waldbronn, Germany) as described earlier by Eibler et al [6]. In brief, the GC/MS system was equipped with a 60 m length, 0.25 mm internal diameter, 0.1 µm film thickness Rtx-2330 column (Restek, Bellefonte, USA).…”

Section: Gas Chromatography With Electron Ionization Mass Spectrometrmentioning

confidence: 99%

“…Simultaneously, the share of saturated FAME (initially <10%) increased to >98%, mainly in form of 18:0, 20:0 and 22:0 ( Table 1). Saturated fatty acid methyl esters with more than fourteen carbons are known to precipitate with urea [6,11]. After the first urea complexation procedure ("Materials and Methods"), most of the long chain fatty acids (>C 18 ) could be removed, while the relative share of 16:0 and 18:0 in the filtrate mostly increased (Table 1).…”

Section: Enrichment Of the Potential Sulfur-heterocyclic Fatty Acids mentioning

confidence: 99%

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Up to 21 Different Sulfur‐Heterocyclic Fatty Acids in Rapeseed and Mustard Oil

Eibler

Hammerschick

Buck

et al. 2017

J Americ Oil Chem Soc

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Abbreviations FAME Fatty acid methyl ester(s) FAPEFatty acid picolinyl ester(s) GC/MS Gas chromatography with electron ionization mass spectrometry SHFA Sulfur-heterocyclic fatty acid(s) SIM Selected ion monitoring mode Abstract Three sulfur-heterocyclic fatty acids (SHFA) had been tentatively identified in rapeseed oil in the late 1980s. In this study we aimed to enrich and verify the presence of potential SHFA in one sample of native rapeseed oil, refined rapeseed oil and mustard seed oil. Fifty-gram samples of the three oils were individually saponified and converted into methyl esters. The resulting samples were hydrogenated and subjected three times to urea complexation. The resulting extracts of native rapeseed oil and mustard oil contained 21 different SHFA with 18, 20, 22 or 24 carbons. The refined rapeseed oil contained only nine C 18 -SHFA. Structure investigation of the SHFA was performed by gas chromatography with mass spectrometry (GC/MS) using methyl esters and also 3-pyridylcarbinol esters. A direct screening of non-enriched samples by GC/ MS in the selected ion monitoring mode and by GC with flame photometric detector (sulfur-selective) verified that the SHFA were native compounds of the oils and no artefacts of the sample preparation. Similar abundances of the four isomer groups of SHFA with monoenoic fatty acids of the same carbon number in these and five further rapeseed and mustard samples indicated that these could be the precursors of the SHFA.Keywords Sulfur containing fatty acids · GC/MS · GC-flame photometric detector · Rapeseed oil · Mustard oil Electronic supplementary material The online version of this article (

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Section: Preparation Of Fatty Acid Methyl Esters (Fame)mentioning

confidence: 99%

Section: Enrichment Of Sulfur-heterocyclic Fatty Acid (Shfa) Methyl Ementioning

confidence: 99%

Section: Enrichment Of Sulfur-heterocyclic Fatty Acid (Shfa) Methyl Ementioning

confidence: 99%

Section: Gas Chromatography With Electron Ionization Mass Spectrometrmentioning

confidence: 99%

Section: Enrichment Of the Potential Sulfur-heterocyclic Fatty Acids mentioning

confidence: 99%

See 3 more Smart Citations

Up to 21 Different Sulfur‐Heterocyclic Fatty Acids in Rapeseed and Mustard Oil

Eibler

Hammerschick

Buck

et al. 2017

J Americ Oil Chem Soc

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Skin derived branched‐chain fatty acids in fetal horse gut

Wang,

Qi,

Yang

et al. 2024

Euro J Lipid Sci & Tech

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Branched‐chain fatty acids (BCFAs) are mostly saturated fatty acids with a methyl branch at the penultimate or antepenultimate position to the CH3 end. Very‐long‐chain BCFAs (C ≥ 20) are uniquely found in surface lipids. Human and California sea lion (Zalophus californianus) are the only two species that possess vernix at birth, and vernix particles carry loads of BCFA to the gut, potentially influencing the establishment of the first microbiota. Horse (Equus caballus) contains high levels of BCFA in its surface lipids, and the current study aims to investigate if BCFA are components of a neonatal foal's gut. Electron ionization tandem mass spectrometry was used to distinguish iso‐ and anteiso‐form of BCFA from straight‐chain fatty acids. Abundant very‐long‐chain iso‐BCFA, mainly even‐numbered iso‐20:0, iso‐22:0, iso‐24:0, and iso‐26:0 were found in horse meconium but not in their manure collected a few months later. There are little differences in BCFA types and concentrations between foal manure and adult manure. Moderate to high levels of very‐long‐chain anteiso‐BCFA were also found. Comparisons of horse meconium BCFA to horse skin cholesterol ester BCFA content and to meconium from human and sea lion suggest its skin derived origin. The study expands our knowledge on the gut nutritional environment of a newborn horse, and further study is needed to establish the relationship between gut BCFA and microbiota composition in the first few hours of life.Practical Applications: Branched‐chain fatty acids (BCFA) are bioactive compounds found in vernix caseosa, the lipid‐laden material covering the surface of a newborn baby. BCFA also reaches high concentrations from the third trimester of gestation until birth. However, the exact functionality and mechanisms of BCFA in the surface and gut of a fetus remain unclear. The current study aims to clarify the lipid conditions in the gut of newborn foals and to identify the associations between BCFA in the gut and on the skin at a critical point when the horse's microbiota establishes itself. The findings of the current study lay a path for studying the physiological functions of BCFA in horse models, potentially accelerating research related to BCFA.

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Synthesis, liquid chromatographic fractionation and partial characterization of polybrominated dibenzofuran congeners

Gallistl

Vetter

2016

Journal of Chromatography A

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anteiso-Fatty Acids in Brussels Sprouts (Brassica oleracea var. gemmifera L.): Quantities, Enantioselectivities, and Stable Carbon Isotope Ratios

Cited by 22 publications

References 45 publications

Up to 21 Different Sulfur‐Heterocyclic Fatty Acids in Rapeseed and Mustard Oil

Up to 21 Different Sulfur‐Heterocyclic Fatty Acids in Rapeseed and Mustard Oil

Skin derived branched‐chain fatty acids in fetal horse gut

Synthesis, liquid chromatographic fractionation and partial characterization of polybrominated dibenzofuran congeners

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