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

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Lipids

Abstract

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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Abbreviations

FA:

Fatty acid(s)

FAME:

Fatty acid methyl ester(s)

HFA:

Hydroxy fatty acid(s)

AG:

Acylglycerol(s)

TAG:

Triacylglycerol(s)

MALDI-TOF MS:

Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry

X:Y∆z :

X is the chain length, Y is the number of double bonds and ∆z is the double bond position relative to the carboxyl end of the molecule

TAG (A:B):

A is the total number of carbon atoms in the acyl chains and B is the total number of double bonds

OH TAG (A:B:C):

A is the total number of carbon atoms in the acyl chains, B is the total number of double bonds and C is the number of free hydroxyl groups

TAG-estolides (A:B:C:D):

A is the total number of carbon atoms in the acyl chains, B is the total number of double bonds, C is the number of free hydroxyl groups and D is the number of FA–FA ester bonds (estolide linkage)

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Acknowledgments

The authors acknowledge the financial support of the National Research Council Canada National Bioproducts Program, and would like to thank Dr. Elizabeth Marillia and Dr. Irina Zaharia for critical review of the manuscript. NRC publication number 54660.

Conflict of interest

The authors declare no conflict of interest.

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Authors and Affiliations

  1. National Research Council Canada, 110 Gymnasium Place, Saskatoon, SK, S7N 0W9, Canada

    Mark A. Smith, Haixia Zhang, Li Forseille & Randy W. Purves

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  1. Mark A. Smith
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  2. Haixia Zhang
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  3. Li Forseille
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  4. Randy W. Purves
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Correspondence to Mark A. Smith.

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Smith, M.A., Zhang, H., Forseille, L. et al. Characterization of Novel Triacylglycerol Estolides from the Seed Oil of Mallotus philippensis and Trewia nudiflora . Lipids 48, 75–85 (2013). https://doi.org/10.1007/s11745-012-3721-y

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  • DOI: https://doi.org/10.1007/s11745-012-3721-y

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