Estolide triglycerides of<i>Trewia nudiflora</i> seed oil

Madrigal, R. V.; Smith, C. R.

doi:10.1007/bf02535373

Cited by 19 publications

(17 citation statements)

References 20 publications

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“…The fatty acid compositions are given in Table 1. Results confirmed that both species contained kamlolenic acid (K) as the predominant fatty acid at levels similar to those reported previously [2,4]. As no mass spectra for this fatty acid are available we have presented the mass spectrum of the trimethyl-silyl derivative of kamlolenic FAME (K-TMS FAME) in Fig.…”

Section: Identification Of Fatty Acidssupporting

confidence: 88%

“…Characterization of M. philippensis oil by lipase hydrolysis and thin layer chromatography suggested that TAG-estolides were symmetrical in structure with FA-estolides of up to three fatty acids in the sn-1 and sn-3 positions and either kamlolenic acid or a di-kamlolenic acid FA-estolide at the sn-2 position [3]. Examination of oil from T. nudiflora suggested that the FA-estolide components of this species contained predominantly two fatty acids, only one of which was kamlolenic acid [4].…”

Section: Introductionmentioning

confidence: 96%

“…The majority of plant seed oils are composed of triacylglycerols, where three fatty acids are esterified to a single glycerol ''backbone''. Acylglycerols (AG) containing more than three fatty acids have been reported for a number of plant species and are generally associated with the synthesis of fatty acids containing a hydroxyl group [1][2][3][4][5][6]. The hydroxyl moiety enables the attachment, by ester linkage, of additional fatty acids secondary to the glycerol backbone.…”

Section: Introductionmentioning

confidence: 99%

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Characterization of Novel Triacylglycerol Estolides from the Seed Oil of Mallotus philippensis and Trewia nudiflora

Smith

Zhang

Forseille

et al. 2012

Lipids

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Triacylglycerol estolides have been reported as components of the seed oil of a number of plant species and are generally associated with the presence of fatty acids containing hydroxyl groups. We have used MALDI-TOF MS to examine the intact acylglycerol species present in the seed oils of two plants that produce kamlolenic acid (18-hydroxy-Δ9cis,11trans,13trans-octadecatrienoic acid). Mallotus philippensis and Trewia nudiflora were both shown to produce seed oil rich in TAG-estolides. Analysis by MALDI-TOF MS/MS demonstrated that the TAG-estolides had a structure different to that previously proposed after enzymatic digestion of the oil. Acylglycerols containing up to 14 fatty acids were detected but fatty acid estolides were only present in a single position on the glycerol backbone, with predominantly non-hydroxyl fatty acids in the remaining two positions. Increased numbers of fatty acids per glycerol backbone were accounted for by the presence of fatty acid estolides containing a correspondingly greater number of fatty acids. For example, acylglycerols containing seven fatty acids had a fatty acid estolide of five fatty acids at one position on the glycerol backbone. Both capped and uncapped fatty acid estolides, with a free hydroxyl group, were present, with capped fatty acid estolides being more abundant in T. nudiflora and uncapped fatty acid estolides in M. philippensis.

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Section: Identification Of Fatty Acidssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Characterization of Novel Triacylglycerol Estolides from the Seed Oil of Mallotus philippensis and Trewia nudiflora

Smith

Zhang

Forseille

et al. 2012

Lipids

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“…For instance, toxic cyanolipids and wax esters were reported only for Sapindaceae [48] and Jojoba seed oils [47], respectively. Acetoglycerides were found in the seed oils of species from the Celastraceae, Lardizabalaceae, Ranunculaceae, Rosaceae [49,50], and Balsaminaceae [51], and tetra-and pentaacylglycerides appeared in Euphorbiaceae, Cruciferae, Polygalaceae and Compositae [45].…”

Section: Fatty Acids and Lipids Vs Chemotaxonomymentioning

confidence: 99%

Screening analysis of unknown seed oils

Spitzer¹

1999

Fett/Lipid

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In the present paper, modern tools for the screening analysis of unknown seed oils have been reviewed. The known plant fatty acid structures have been divided into three groups (usual, unusual nonoxygenated, unusual oxygenated fatty acids) and examples for each class are presented. Moreover, the importance of chemotaxonomy for the screening analysis of some lipid components is discussed. The main part of the work is focussed on various aspects of preliminary seed oil analyses for the detection of unusual fatty acids and lipid classes and the analysis of fatty acid derivatives by gas chromatography and gas chromatography/mass spectrometry. Furthermore, some useful methods to obtain rapid information on the configuration of double bonds are cited. The paper concludes with a scheme for the detection of unusual fatty acids and lipid classes in seed oils.

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“…The kernel oil of Chinese tallow (Sapium sebiferum) seed contains tetraester triglycerides composed of trans-2,cis-4-decadienoic acid joined in an estolide linkage to 8-hydroxy-5,6-octadienoic acid [137]. Trewia nudifl ora (false white teak) seed oil contains glycerides of α-kamlolenic (18-hydroxy-9,11,13-octadecatrienoic) acid, largely as estolide triglycerides [138].…”

Section: Estolide Ester Base Stocksmentioning

confidence: 99%