Advertisement

Analytical and Bioanalytical Chemistry

, Volume 411, Issue 7, pp 1479–1489 | Cite as

Gas chromatography–mass spectrometry of sapucainha oil (Carpotroche brasiliensis) triacylglycerols comprising straight chain and cyclic fatty acids

  • Habtewold D. Waktola
  • Chadin Kulsing
  • Yada Nolvachai
  • Claudia M. Rezende
  • Humberto R. Bizzo
  • Philip J. MarriottEmail author
Research Paper

Abstract

Sapucainha oil, which may be used to treat leprosy, comprises straight chain and cyclic fatty acids (FA), and triacylglycerols (TAG). The FA and TAG content of the oil sample was analysed using gas chromatography–electron ionisation mass spectrometry (GC–EIMS). FA analysis was performed after derivatisation to fatty acid methyl esters (FAME). For free FA and TAG analysis, the oil sample was dissolved in hexane and injected into a short, high-temperature column, for GC with MS analysis. Free FA and FAME were tentatively identified based on mass spectrum information of their molecular and fragment ions, as well as library matching. Overlapping TAG peaks were deconvoluted based on mass fingerprint data. The FA composition was utilised to predict possible TAG identities. FA residues of TAG were identified based on characteristic fragment ions, such as [M–RCO2]+, [RCO+128]+, [RCO+74]+ and RCO+ where R is the aliphatic hydrocarbon chain. FAME analysis showed that the cyclic FA hydnocarpic (36.1%), chaulmoogric (26.5%) and gorlic (23.6%) acids were the major components. In addition, straight chain FA such as palmitic, palmitoleic, stearic, oleic and linoleic acids were detected. Palmitic, oleic, hydnocarpic, chaulmoogric and gorlic acids were also detected as free FA in the oil sample. Six groups of TAG peaks were eluted from GC at temperatures ≥330 °C. After deconvolution and mass spectrum analysis, each TAG peak group was revealed to comprise 2 to 5 co-eluted TAG molecules; >18 TAG were identified. These TAG consisted of a mix of both cyclic and straight chain FA, but were mostly derived from cyclic FA.

Keywords

Sapucainha oil Triacylglycerols Cyclic fatty acids High-temperature GC Mass spectrometry 

Notes

Acknowledgements

HDW acknowledges provision of MGS and DIPRS Scholarships from Monash University. This work was conducted under support from the Australian Research Council and PerkinElmer through ARC Linkage Grant LP150100465. We are grateful for the support from the Brazil funding agencies Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ).

Compliance with ethical standards

Conflict of interest

The authors declare no conflict of interest.

Supplementary material

216_2019_1579_MOESM1_ESM.pdf (4.2 mb)
ESM 1 (PDF 4254 kb)

References

  1. 1.
    Sebedio JL, Grandgirard A. Cyclic fatty acids: natural sources, formation during heat treatment, synthesis and biological properties. Prog Lipid Res. 1989;28(4):303–36.CrossRefGoogle Scholar
  2. 2.
    Cole HI, Cardoso HT. Analysis of chaulmoogra oils. I. Carpotroche brasiliensis (Sapucainha) oil. J Am Chem Soc. 1938;60(3):614–7.CrossRefGoogle Scholar
  3. 3.
    Sengupta A, Gupta JK, Dutta J, Ghosh A. The component fatty acids of chaulmoogra oil. J Sci Food Agric. 1973;24(6):669–74.CrossRefGoogle Scholar
  4. 4.
    Oliveira AS, Lima JA, Rezende CM, Pinto AC. Cyclopentenyl acids from sapucainha oil (Carpotroche brasiliensis Endl, Flacourtiaceae): the first antileprotic used in Brazil. Quim Nova. 2009;32(1):139–45.Google Scholar
  5. 5.
    Shukla VKS, Spener F. High-performance liquid chromatography of triglycerides of Flacourtiaceae seed oils containing cyclopentenyl fatty acids (chaulmoogric oils). J Chromatogr A. 1985;348:441–6.Google Scholar
  6. 6.
    Ruiz-Samblás C, González-Casado A, Cuadros-Rodríguez L. Triacylglycerols determination by high-temperature gas chromatography in the analysis of vegetable oils and foods: a review of the past 10 years. Crit Rev Food Sci Nutr. 2015;55(11):1618–31.CrossRefGoogle Scholar
  7. 7.
    Novaes FJM, Kulsing C, Bizzo HR, de Aquino Neto FR, Rezende CM, Marriott PJ. Analysis of underivatised low volatility compounds by comprehensive two-dimensional gas chromatography with a short primary column. J Chromatogr A. 2018;1536:75–81.CrossRefGoogle Scholar
  8. 8.
    Waktola HD, Kulsing C, Nolvachai Y, Marriott PJ. High temperature multidimensional gas chromatographic approach for improved separation of triacylglycerols in olive oil. J Chromatogr A. 2018;1549:77–84.CrossRefGoogle Scholar
  9. 9.
    Moldoveanu SC, Chang Y. Dual analysis of triglycerides from certain common lipids and seed extracts. J Agric Food Chem. 2011;59(6):2137–47.CrossRefGoogle Scholar
  10. 10.
    Kalo P, Kemppinen A. Mass spectrometric identification of triacylglycerols of enzymatically modified butterfat separated on a polarizable phenylmethylsilicone column. J Am Oil Chem Soc. 1993;70(12):1209–17.CrossRefGoogle Scholar
  11. 11.
    Laakso P. Mass spectrometry of triacylglycerols. Eur J Lipid Sci Technol. 2002;104(1):43–9.CrossRefGoogle Scholar
  12. 12.
    Kemppinen A, Kalo P. Quantification of triacylglycerols in butterfat by gas chromatography-electron impact mass spectrometry using molar correction factors for [M-RCOO]+ ions. J Chromatogr A. 2006;1134(1–2):260–83.CrossRefGoogle Scholar
  13. 13.
    Ballus CA, Meinhart AD, de Souza Campos FA Jr, da Silva LFO, de Oliveira AF, Godoy HT. A quantitative study on the phenolic compound, tocopherol and fatty acid contents of monovarietal virgin olive oils produced in the southeast region of Brazil. Food Res Int. 2014;62:74–83.CrossRefGoogle Scholar
  14. 14.
    Christie WW, Rebello D, Holman RT. Mass spectrometry of derivatives of cyclopentenyl fatty acids. Lipids. 1969;4(3):229–31.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  • Habtewold D. Waktola
    • 1
  • Chadin Kulsing
    • 1
    • 2
  • Yada Nolvachai
    • 1
  • Claudia M. Rezende
    • 3
  • Humberto R. Bizzo
    • 4
  • Philip J. Marriott
    • 1
    Email author
  1. 1.Australian Centre for Research on Separation Science, School of ChemistryMonash UniversityClaytonAustralia
  2. 2.Chromatographic Separation and Flavor Chemistry Research Unit and Center of Molecular Sensory Science, Department of Chemistry, Faculty of ScienceChulalongkorn UniversityBangkokThailand
  3. 3.Instituto de QuímicaUniversidade Federal do Rio de JaneiroRio de JaneiroBrazil
  4. 4.Embrapa Agroindústria de AlimentosRio de JaneiroBrazil

Personalised recommendations