Optimization of Triacylglycerol‐estolide Analysis by Matrix‐Assisted Laser Desorption/Ionization‐Mass Spectrometry

Zhang, Haixia; Smith, Mark A.; Purves, Randy W.

doi:10.1007/s11746-014-2437-y

Cited by 5 publications

(3 citation statements)

References 37 publications

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“…Triacylglycerol estolides (TG-ESTs) are a minor class of lipids consisting of a glycerol backbone to which a combination of fatty acids (FA) and estolides is esterified (also reported as fatty acid esters of hydroxy fatty acid, FAHFA, and ( O -acyl)-hydroxy fatty acid [ 1 , 2 , 3 ]) as a structural subunit [ 4 ]. TG-ESTs are biologically active molecules known from mammals [ 5 , 6 , 7 , 8 , 9 , 10 , 11 ], plants [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ], and fungi [ 29 , 33 , 39 , 40 , 41 ]. In mammalian TG-ESTs, a hydroxy fatty acid (HFA) is usually esterified with a non-hydroxy FA (“capped” estolide), while in plants and fungi, another HFA may be attached (“uncapped” estolide).…”

Section: Introductionmentioning

confidence: 99%

“…The estolide regioisomers branched in the ω-position (terminal carbon atom of the HFA chain) are found in some plants [ 12 , 14 , 19 , 20 , 21 , 24 , 31 ]. The FAHFA subunit is, however, more often branched on an “inner” carbon of the HFA chain; such TG-ESTs exist in plants, fungi, and mammals [ 6 , 7 , 8 , 9 , 11 , 15 , 16 , 17 , 18 , 22 , 25 , 26 , 27 , 28 , 29 , 30 , 32 , 33 , 34 , 35 , 36 , 39 , 40 , 41 ]. To our knowledge, TG-ESTs with the FAHFA branched in the α-position (carbon number 2 of HFA) have not been reported yet.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of Triacylglycerol Estolide Isomers Using High-Resolution Tandem Mass Spectrometry with Nanoelectrospray Ionization

et al. 2023

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Triacylglycerol estolides (TG-EST) are biologically active lipids extensively studied for their anti-inflammatory and anti-diabetic properties. In this work, eight standards of TG-EST were synthesized and systematically investigated by nanoelectrospray tandem mass spectrometry. Mass spectra of synthetic TG-EST were studied with the purpose of enabling the unambiguous identification of these lipids in biological samples. TG-EST glycerol sn-regioisomers and isomers with the fatty acid ester of hydroxy fatty acid (FAHFA) subunit branched in the ω-, α-, or 10-position were used. Ammonium, lithium, and sodium adducts of TG-EST formed by nanoelectrospray ionization were subjected to collision-induced dissociation (CID) and higher-energy collisional dissociation (HCD). Product ion spectra allowed for identification of fatty acid (FA) and FAHFA subunits originally linked to the glycerol backbone and distinguished the α-branching site of the FAHFA from other estolide-branching isomers. The ω- and 10-branching sites were determined by combining CID with ozone-induced dissociation (OzID). Lithium adducts provided the most informative product ions, enabling characterization of FA, hydroxy fatty acid (HFA), and FAHFA subunits. Glycerol sn-regioisomers were distinguished based on the relative abundance of product ions and unambiguously identified using CID/OzID of lithium and sodium adducts.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Characterization of Triacylglycerol Estolide Isomers Using High-Resolution Tandem Mass Spectrometry with Nanoelectrospray Ionization

et al. 2023

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“…Estolides (Fig. 1 ) result from secondary acylation reactions, where additional fatty acids are esterified to the hydroxyl moieties of ricinoleic acid, leading to the formation of high molecular weight species 12 . The use of high resolution tandem mass spectrometry allowed us to perform a structural characterization of these species, as reported in Fig.…”

Section: Introductionmentioning

confidence: 99%

Long-lasting ergot lipids as new biomarkers for assessing the presence of cereals and cereal products in archaeological vessels

Łucejko

Nasa

Porta

et al. 2018

Sci Rep

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Cereals were very important in ancient diets, however evidence from archaeological sites of the vessels used for processing or storing cereals is comparatively rare. Micro-organisms, as well as chemical-physical effects can easily degrade cereals during the burial period. This can lead to a complete cereal decay and to serious difficulties in estimating the intensity of use of the cereals by ancient populations. Here, we present a novel biomarker approach entailing the detection of secondary lipid metabolites produced by ergot fungi (genus Claviceps), which are common cereal pests. The aim was to identify the original presence of Gramineae and to indirectly establish if vessels were used for cereal storage/processing. The fatty acid and TAG-estolide profiles of the remains from more than 30 archaeological vessels were investigated by gas chromatography/mass spectrometry (GC/MS) and high performance liquid chromatography/high resolution mass spectrometry (HPLC/ESI-Q-ToF). The detection of lipids derived from ergot in archaeological and historic contexts rests on its complex chemistry, providing a unique and relatively recalcitrant chemical signature for cereals. This research demonstrated that the combination of our innovative biomarker approach along with environmental and archaeological evidence can provide unprecedented insights into the incidence of cereals and related processing activities in ancient societies.

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Seeds as oil factories

Baud

2018

Plant Reprod

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Studying seed oil metabolism. The seeds of higher plants represent valuable factories capable of converting photosynthetically derived sugars into a variety of storage compounds, including oils. Oils are the most energy-dense plant reserves and fatty acids composing these oils represent an excellent nutritional source. They supply humans with much of the calories and essential fatty acids required in their diet. These oils are then increasingly being utilized as renewable alternatives to petroleum for the chemical industry and for biofuels. Plant oils therefore represent a highly valuable agricultural commodity, the demand for which is increasing rapidly. Knowledge regarding seed oil production is extensively exploited in the frame of breeding programs and approaches of metabolic engineering for oilseed crop improvement. Complementary aspects of this research include (1) the study of carbon metabolism responsible for the conversion of photosynthetically derived sugars into precursors for fatty acid biosynthesis, (2) the identification and characterization of the enzymatic actors allowing the production of the wide set of fatty acid structures found in seed oils, and (3) the investigation of the complex biosynthetic pathways leading to the production of storage lipids (waxes, triacylglycerols). In this review, we outline the most recent developments in our understanding of the underlying biochemical and molecular mechanisms of seed oil production, focusing on fatty acids and oils that can have a significant impact on the emerging bioeconomy.

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Optimization of Triacylglycerol‐estolide Analysis by Matrix‐Assisted Laser Desorption/Ionization‐Mass Spectrometry

Cited by 5 publications

References 37 publications

Characterization of Triacylglycerol Estolide Isomers Using High-Resolution Tandem Mass Spectrometry with Nanoelectrospray Ionization

Characterization of Triacylglycerol Estolide Isomers Using High-Resolution Tandem Mass Spectrometry with Nanoelectrospray Ionization

Long-lasting ergot lipids as new biomarkers for assessing the presence of cereals and cereal products in archaeological vessels

Seeds as oil factories

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