In the present study, we investigated the effect of long-acyl chain SFA, namely palmitic acid (16:0) and stearic acid (18:0), at sn-1, 3 positions of TAG on obesity. Throughout the 15 weeks of the experimental period, C57BL/6 mice were fed diets fortified with cocoa butter, sal stearin (SAL), palm mid fraction (PMF) and high-oleic sunflower oil (HOS). The sn-1, 3 positions were varied by 16:0, 18:0 and 18:1, whilst the sn-2 position was preserved with 18:1. The HOS-enriched diet was found to lead to the highest fat deposition. This was in accordance with our previous postulation. Upon normalisation of total fat deposited with food intake to obtain the fat:feed ratio, interestingly, mice fed the SAL-enriched diet exhibited significantly lower visceral fat/feed and total fat/feed compared with those fed the PMF-enriched diet, despite their similarity in SFA-unsaturated fatty acid-SFA profile. That long-chain SFA at sn-1, 3 positions concomitantly with an unsaturated FA at the sn-2 position exert an obesity-reducing effect was further validated. The present study is the first of its kind to demonstrate that SFA of different chain lengths at sn-1, 3 positions exert profound effects on fat accretion.
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http://dx.doi.org/10.1017/S0007114513003668 | DOI Listing |
Molecules
December 2024
Institute of Environmental Engineering, Wrocław University of Environmental and Life Sciences, Grunwaldzki Square 24, 50-363 Wrocław, Poland.
The aim of this research was to design and synthesize new lipid conjugates of 7-DHC that could serve as a new storage form of esterified provitamin D, increasing the reservoir of this biomolecule in the epidermis and enabling controlled production of vitamin D even during periods of sunlight deficiency. Acylglycerol and glycerophospholipid containing succinate-linked provitamin D at the -2 position of the glycerol backbone were synthesized from dihydroxyacetone (DHA) and -glycerophosphocholine (GPC), respectively. The three-step synthesis of 1,3-dipalmitoyl-2-(7-dehydrocholesterylsuccinoyl)glycerol involved the esterification of DHA with palmitic acid, reduction of the carbonyl group, and conjugation of the resulting 1,3-dipalmitoylglycerol with 7-dehydrocholesterol hemisuccinate (7-DHC HS).
View Article and Find Full Text PDFMolecules
December 2024
Science Institute, Chemistry Department, University of Iceland, Dunhaga 3, 107 Reykjavik, Iceland.
This report describes the asymmetric synthesis of a focused library of enantiopure structured triacylglycerols (TAGs) comprised of a single saturated fatty acid (C6, C8, C10, C12, C14 or C16), a pure bioactive n-3 polyunsaturated fatty acid (EPA or DHA) and a potent drug (ibuprofen or naproxen) intended as a novel type of prodrug. One of the terminal -1 or -3 positions of the glycerol backbone is occupied with a saturated fatty, the remaining one with a PUFA, and the drug entity is present in the -2 position. This was accomplished by a six-step chemoenzymatic approach starting from enantiopure ()- and ()-solketals.
View Article and Find Full Text PDFFEBS Lett
December 2024
Membrane Biochemistry & Biophysics, Department of Chemistry, Utrecht University, The Netherlands.
Yeast is a poikilothermic organism and adapts its lipid composition to the environmental temperature to maintain membrane physical properties. Studies addressing temperature-dependent adaptation of the lipidome have described changes in the phospholipid composition at the level of sum composition (e.g.
View Article and Find Full Text PDFJ Agric Food Chem
December 2024
State Key Laboratory of Food Science and Resources, School of Food Science and Technology, National Engineering Research Center for Functional Food, International Joint Research Laboratory for Lipid Nutrition and Safety, Collaborative Innovation Center of Food Safety and Quality Control in Jiangsu Province, Jiangnan University, Jiangsu 214126, China.
Glycerol core aldehydes (GCAs) are significant nonvolatile aldehyde compounds generated in heated edible oils, which may pose potential health risks. Utilizing the complementary CID and EAD mass spectrometry data, this study introduced a predict-to-hit strategy, identifying 42 types of GCAs from oxidized OOO, LLL, and LnLnLn. Structural analysis revealed that oxidation occurred at both the sn-2 and sn-1/3 positions of triglyceride (TG), with the Sn-1/3 position exhibiting greater susceptibility as the degree of TG unsaturation increased.
View Article and Find Full Text PDFRapid Commun Mass Spectrom
February 2025
Université Paris-Saclay, CNRS, ICSN, UPR 2301, Gif-sur-Yvette, France.
Rationale: The emergence of new mass spectrometry (MS) dissociation methods has highlighted lipid isomers as new biomarkers. Only a few commercial methods without derivatization are available to characterize phosphatidylcholines (PCs) at the isomeric level. We propose to use electron transfer dissociation (ETD) as a method to determine the position of both double bonds and stereo numbering (sn) on glycerol for PC species.
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