Apocynaceae Seed Lipids: Characterization and Occurrence of Isoricinoleic Acid and Triacylglycerol Estolides

Smith, Mark A.; Zhang, Haixia

doi:10.1007/s11746-015-2741-1

Cited by 4 publications

(2 citation statements)

References 33 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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