Dataset Information

Cholesteryl esters of ?-(O-acyl)-hydroxy fatty acids in vernix caseosa.

ABSTRACT: Cholesteryl esters of ?-(O-acyl)-hydroxy FAs (Chl-?OAHFAs) were identified for the first time in vernix caseosa and characterized using chromatography and MS. Chl-?OAHFAs were isolated using adsorption chromatography on silica gel and magnesium hydroxide. Their general structure was established using high-resolution and tandem MS of intact lipids, and products of their transesterification and derivatizations. Individual molecular species were characterized using nonaqueous reversed-phase HPLC coupled to atmospheric pressure chemical ionization. The analytes were detected as protonated molecules, and their structures were elucidated in the negative ion mode using controlled thermal decomposition and data-dependent fragmentation. About three hundred molecular species of Chl-?OAHFAs were identified in this way. The most abundant Chl-?OAHFAs contained 32:1 ?-hydroxy FA (?-HFA) and 14:0, 15:0, 16:0, 16:1, and 18:1 FAs. The double bond in the 32:1 ?-HFA was in the n-7 and n-9 positions. Chl-?OAHFAs are estimated to account for approximately 1-2% of vernix caseosa lipids.

SUBMITTER: Kaluzikova A

PROVIDER: S-EPMC5538280 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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Cholesteryl esters of ω-(<i>O</i>-acyl)-hydroxy fatty acids in vernix caseosa.

Kalužíková Aneta A Vrkoslav Vladimír V Harazim Eva E Hoskovec Michal M Plavka Richard R Buděšínský Miloš M Bosáková Zuzana Z Cvačka Josef J

Journal of lipid research 20170602 8

Cholesteryl esters of ω-(<i>O</i>-acyl)-hydroxy FAs (Chl-ωOAHFAs) were identified for the first time in vernix caseosa and characterized using chromatography and MS. Chl-ωOAHFAs were isolated using adsorption chromatography on silica gel and magnesium hydroxide. Their general structure was established using high-resolution and tandem MS of intact lipids, and products of their transesterification and derivatizations. Individual molecular species were characterized using nonaqueous reversed-phase ...[more]

PMID: 28576934

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Project description:Background: Fatty acid esters of hydroxy fatty acids (FAHFAs) are a group of fatty acids with potential anti-inflammatory and anti-diabetic effects. The blood levels of FAHFAs and their regulation in humans have hardly been studied. Objective: We aimed to investigate serum FAHFA levels in well-characterized human cohorts, to evaluate associations with age, sex, BMI, weight loss, diabetic status, and diet. Methods: We analyzed levels of stearic-acid-9-hydroxy-stearic-acid (9-SAHSA), oleic-acid-9-hydroxy-stearic-acid (9-OAHSA) and palmitic-acid-9-hydroxy-palmitic-acid (9-PAHPA) as well as different palmitic acid-hydroxy-stearic-acids (PAHSAs) by HPLC-MS/MS with the use of an internal standard in various cohorts: A cohort of different age groups (18-25y; 40-65y; 75-85y; Σ n = 60); severely obese patients undergoing bariatric surgery and non-obese controls (Σ n = 36); obese patients with and without diabetes (Σ n = 20); vegetarians/vegans (n = 10) and omnivores (n = 9); and young men before and after acute overfeeding with saturated fatty acids (SFA) (n = 15). Results: Omnivores had substantially higher FAHFA levels than vegetarians/vegans [median (25th percentile; 75th percentile) tFAHFAs = 12.82 (7.57; 14.86) vs. 5.86 (5.10; 6.71) nmol/L; P < 0.05]. Dietary overfeeding by supplementation of SFAs caused a significant increase within 1 week [median tFAHFAs = 4.31 (3.31; 5.27) vs. 6.96 (6.50; 7.76) nmol/L; P < 0.001]. Moreover, obese patients had lower FAHFA levels than non-obese controls [median tFAHFAs = 3.24 (2.80; 4.30) vs. 5.22 (4.18; 7.46) nmol/L; P < 0.01] and surgery-induced weight loss increased 9-OAHSA level while other FAHFAs were not affected. Furthermore, significant differences in some FAHFA levels were found between adolescents and adults or elderly, while no differences between sexes and between diabetic and non-diabetic individuals were detected. Conclusions: FAHFA serum levels are strongly affected by high SFA intake and reduced in severe obesity. Age also may influence FAHFA levels, whereas there was no detectable relation with sex and diabetic status. The physiological role of FAHFAs in humans remains to be better elucidated. Trial Registration: All studies referring to these analyses were registered in the German Clinical Trial Register (https://www.drks.de/drks_web/) with the numbers DRKS00009008, DRKS00010133, DRKS00006211, and DRKS00009797.

Dataset Information

Cholesteryl esters of ?-(O-acyl)-hydroxy fatty acids in vernix caseosa.

Publications

Cholesteryl esters of ω-(<i>O</i>-acyl)-hydroxy fatty acids in vernix caseosa.

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