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Isolation of a Series of Fatty Acid Components of Ongokea gore Seed (Isano) Oil and their Detailed Structural Analysis

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Lipids

Abstract

The total oil production capacity of isano oil is estimated at about 10,000 tons annually. Previous studies of this oil revealed that it is rich in fatty acids including a conjugated diyne moiety. This makes isano oil an excellent candidate for sustainable applications development. However, only a few of its fatty acids have been isolated and identified so far. In this study, we have reinvestigated this oil by characterizing its physicochemical properties and isolating several of its fatty acids as ethyl esters for their detailed structural analysis and identification. Six ethyl esters of fatty acids constituting isanic oil were isolated by flash column chromatography and semipreparative HPLC. The detailed structural analysis of these fatty acid esters by infrared, high resolution, mass spectroscopy, and nuclear magnetic resonance (1-D and 2-D) allowed determining unequivocally their chemical structure. The main fatty acid component of the oil (35.7 %) was identified as isanic acid. Four minor acids were found to possess also two conjugated triple bonds, while the sixth fatty acid does not contain carbon–carbon triple bonds nor double bonds but possessed a cis epoxide function. Results obtained in this study are currently being used to explore potential applications of isano oil.

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Abbreviations

APCI:

Atmospheric pressure chemical ionization

COSY:

Correlation spectroscopy

FTIR:

Fourier transform infrared spectroscopy

HMBC:

Heteronuclear multiple-bond correlation spectroscopy

HMQC:

Heteronuclear multiple-quantum correlation spectroscopy

HPLC:

High performance liquid chromatography

HRMS:

High resolution mass spectrometry

IR:

Infrared

MS:

Mass spectrometry

NMR:

Nuclear magnetic resonance

SV:

Saponification value

TMS:

Tetramethylsilane

UV:

Ultraviolet

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Acknowledgments

We thank the Commission Universitaire pour le Développement (CUD) for financial support. We are grateful to Cécile Le Duff for her help in NMR analysis, Stéphanie Wautier, Tran Trieu-Van, Fabio Luccacioni, and Raoul Rozenberg for technical assistance, as well as Lisette Simonis who helped us with viscosity determination. We also acknowledge Muntinsumu for providing us with Ongokea gore seeds. RR is a Chercheur Qualifié of the Fonds de la Recherche Scientifique—FNRS.

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Authors and Affiliations

  1. Institute of Condensed Matter and Nanosciences, Université catholique de Louvain, Place Louis Pasteur 1 Box L4.01.02, 1348, Louvain-la-Neuve, Belgium

    Joséphine K. Ntumba, Laurent Collard & Raphaël Robiette

  2. Chemistry Department, University of Kinshasa, P. O. Box 190, Kinshasa XI, Democratic Republic of the Congo

    Joséphine K. Ntumba & Kalulu M. Taba

Authors
  1. Joséphine K. Ntumba
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  2. Laurent Collard
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  3. Kalulu M. Taba
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  4. Raphaël Robiette
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Corresponding author

Correspondence to Raphaël Robiette.

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Ntumba, J.K., Collard, L., Taba, K.M. et al. Isolation of a Series of Fatty Acid Components of Ongokea gore Seed (Isano) Oil and their Detailed Structural Analysis. Lipids 50, 313–322 (2015). https://doi.org/10.1007/s11745-014-3984-6

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  • DOI: https://doi.org/10.1007/s11745-014-3984-6

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