Skip to main content
Log in

Assessment of the triacylglycerol fraction of olive oil by 1D-NMR spectroscopy: exploring the usefulness of DEPT tool on the peak assignments of 13C NMR spectra

  • Original Paper
  • Published:
European Food Research and Technology Aims and scope Submit manuscript

Abstract

Nuclear magnetic resonance (NMR) spectroscopy has been extensively used to date for the analysis of olive oil samples and constitutes a valuable tool particularly for the study of the triacylglycerol fraction, which is the major fraction of olive oils. In this report, we demonstrate the usefulness of one-dimensional NMR spectroscopy (1H and 13C NMR) for the non-destructive analysis of the triacylglycerol fraction of olive oils. To achieve this goal, 13C spectral editing technique known as distortionless enhancement by polarization transfer (DEPT), namely 13C NMR DEPT 45, 13C NMR DEPT 90, 13C NMR DEPT 135 was used for the analysis of the triacylglycerol fraction of the olive oil sample owing to the simplification on peak assignments of 13C spectra. The suitability and usefulness of those DEPT experiments using different angle values in only one pulse sequence will be explored on the interpretation of 13C NMR spectra. In overall, DEPT tool improves the sensitivity of the analysis due to the enhancement in the signal-to-noise ratio, which is important for this type of analysis contributing to the characterization of olive oils.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Vlahov G, Schiavone C, Simone N (2001) Quantitative 13C NMR method using the DEPT pulse sequence for the determination of the geographical origin (DOP) of olive oils. Magn Reson Chem 39(11):689–695. https://doi.org/10.1002/mrc.929

    Article  CAS  Google Scholar 

  2. Dais P, Hatzakis E (2013) Quality assessment and authentication of virgin olive oil by NMR spectroscopy: a critical review. Anal Chim Acta 765:1–27. https://doi.org/10.1016/j.aca.2012.12.003

    Article  CAS  PubMed  Google Scholar 

  3. Gunstone F (2011) Vegetable oils in food technology: composition, properties and uses. Wiley, New York

    Book  Google Scholar 

  4. Regulation C (1992) Council Regulation (EEC) No. 2081/92 of 14 July 1992 on the protection of geographical indications and designations of origin for agricultural products and foodstuffs. Off. J. Eur. Union 208, pp 1–8

  5. Rongai D, Sabatini N, Del Coco L, Perri E, Del Re P, Simone N, Marchegiani D, Fanizzi FP (2017) 1H NMR and multivariate analysis for geographic characterization of commercial extra virgin olive oil: a possible correlation with climate data. Foods 6(11):96–105. https://doi.org/10.3390/foods6110096

    Article  CAS  PubMed Central  Google Scholar 

  6. Knothe G, Kenar JA (2004) Determination of the fatty acid profile by 1H-NMR spectroscopy. Eur J Lipid Sci Technol 106(2):88–96. https://doi.org/10.1002/ejlt.200300880

    Article  CAS  Google Scholar 

  7. Miyake Y, Yokomizo K, Matsuzaki N (1998) Determination of unsaturated fatty acid composition by high-resolution nuclear magnetic resonance spectroscopy. J Am Oil Chem Soc 75(12):1091–1094. https://doi.org/10.1007/s11746-998-0118-4

    Article  CAS  Google Scholar 

  8. Yang Y, Ferro MD, Cavaco I, Liang Y (2013) Detection and identification of extra virgin olive oil adulteration by GC-MS combined with chemometrics. J Agric Food Chem 61(15):3693–3702. https://doi.org/10.1021/jf4000538

    Article  CAS  PubMed  Google Scholar 

  9. Ur Rahman I, Qureshi MN, Ahmad S (2012) Comparative study of fatty acid components in oils of different olive varieties grown in different regions of pakistan by gas chromatography-mass spectrometry. J Chin Chem Soc 59(1):46–50. https://doi.org/10.1002/jccs.201000397

    Article  CAS  Google Scholar 

  10. Mannina L, Sobolev AP (2011) High resolution NMR characterization of olive oils in terms of quality, authenticity and geographical origin. Magn Reson Chem 49(S1):S3–S11. https://doi.org/10.1002/mrc.2856

    Article  CAS  PubMed  Google Scholar 

  11. Girelli CR, Del Coco L, Fanizzi FP (2017) Tunisian extra virgin olive oil traceability in the EEC market: Tunisian/Italian (Coratina) EVOOs blend as a case study. Sustainability 9(8):1471–1481. https://doi.org/10.3390/su9081471

    Article  CAS  Google Scholar 

  12. Malz F, Jancke H (2005) Validation of quantitative NMR. J Pharm Biomed Anal 38(5):813–823. https://doi.org/10.1016/j.jpba.2005.01.043

    Article  CAS  PubMed  Google Scholar 

  13. Sun S, Jin M, Zhou X, Ni J, Jin X, Liu H, Wang Y (2017) The application of quantitative 1H-NMR for the determination of Orlistat in tablets. Molecules 22(9):1517–1526. https://doi.org/10.3390/molecules22091517

    Article  CAS  PubMed Central  Google Scholar 

  14. Dugo G, Rotondo A, Mallamace D, Cicero N, Salvo A, Rotondo E, Corsaro C (2015) Enhanced detection of aldehydes in extra-virgin olive oil by means of band selective NMR spectroscopy. Phys A 420:258–264. https://doi.org/10.1016/j.physa.2014.11.010

    Article  CAS  Google Scholar 

  15. Vlahov G, Del Re P, Simone N (2003) Determination of geographical origin of olive oils using 13C nuclear magnetic resonance spectroscopy. I—classification of olive oils of the Puglia region with denomination of protected origin. J Agric Food Chem 51(19):5612–5615. https://doi.org/10.1021/jf0207124

    Article  CAS  PubMed  Google Scholar 

  16. Vlahov G (2005) 13C nuclear magnetic resonance spectroscopy to check 1, 3-random, 2-random pattern of fatty acid distribution in olive oil triacylglycerols. J Spectrosc 19(2):109–117. https://doi.org/10.1155/2005/765236

    Article  CAS  Google Scholar 

  17. Sanders JK, Hunter BK (1988) Modern NMR spectroscopy: a guide for chemists, 2nd edn. Oxford University Press, Oxford

    Google Scholar 

  18. D’Imperio M, Mannina L, Capitani D, Bidet O, Rossi E, Bucarelli FM, Quaglia GB, Segre A (2007) NMR and statistical study of olive oils from Lazio: a geographical, ecological and agronomic characterization. Food Chem 105(3):1256–1267. https://doi.org/10.1016/j.foodchem.2007.02.045

    Article  CAS  Google Scholar 

  19. Mannina L, Dugo G, Salvo F, Cicero L, Ansanelli G, Calcagni C, Segre A (2003) Study of the cultivar- composition relationship in Sicilian olive oils by GC, NMR, and statistical methods. J Agric Food Chem 51(1):120–127. https://doi.org/10.1021/jf025656l

    Article  CAS  PubMed  Google Scholar 

  20. Nam AM, Bighelli A, Tomi F, Casanova J, Paoli M (2017) Quantification of squalene in olive oil using 13C nuclear magnetic resonance spectroscopy. Magnetochemistry 3(4):34–43. https://doi.org/10.3390/magnetochemistry3040034

    Article  CAS  Google Scholar 

  21. Gao L, Sedman J, García-González DL, Ehsan S, Sprules T, Van de Voort FR (2009) 13C NMR as a primary method for determining saturates, cis-and trans-monounsaturates and polyunsaturates in fats and oils for nutritional labeling purposes. Eur J Lipid Sci Technol 111(6):612–622. https://doi.org/10.1002/ejlt.200800242

    Article  CAS  Google Scholar 

  22. Del Coco L, Schena FP, Fanizzi FP (2012) 1H nuclear magnetic resonance study of olive oils commercially available as italian products in the United States of America. Nutrients 4(5):343–355. https://doi.org/10.3390/nu4050343

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Merchak N, El Bacha E, Khouzam RB, Rizk T, Akoka S, Bejjani J (2017) Geoclimatic, morphological, and temporal effects on Lebanese olive oils composition and classification: a 1H NMR metabolomic study. Food Chem 217:379–388. https://doi.org/10.1016/j.foodchem.2016.08.110

    Article  CAS  PubMed  Google Scholar 

  24. Alonso-Salces R, Héberger K, Holland M, Moreno-Rojas J, Mariani C, Bellan G, Reniero F, Guillou C (2010) Multivariate analysis of NMR fingerprint of the unsaponifiable fraction of virgin olive oils for authentication purposes. Food Chem 118(4):956–965. https://doi.org/10.1016/j.foodchem.2008.09.061

    Article  CAS  Google Scholar 

  25. Alonso-Salces RM, Holland MV, Guillou C (2011) 1H-NMR fingerprinting to evaluate the stability of olive oil. Food Control 22(12):2041–2046. https://doi.org/10.1016/j.foodcont.2011.05.026

    Article  CAS  Google Scholar 

  26. Ruiz-Aracama A, Goicoechea E, Guillén MD (2017) Direct study of minor extra-virgin olive oil components without any sample modification. 1H NMR multisupression experiment: a powerful tool. Food Chem 228:301–314. https://doi.org/10.1016/j.foodchem.2017.02.009

    Article  CAS  PubMed  Google Scholar 

  27. Zhang Y, Zhao Y, Shen G, Zhong S, Feng J (2018) NMR spectroscopy in conjugation with multivariate statistical analysis for distinguishing plant origin of edible oils. J Food Compos Anal 69:140–148. https://doi.org/10.1016/j.jfca.2018.03.006

    Article  CAS  Google Scholar 

  28. Vlahov G (1999) Application of NMR to the study of olive oils. Prog Nucl Magn Reson Spectrosc 35(4):341–357

    Article  CAS  Google Scholar 

  29. Vlahov G, Angelo CS (1996) the structure of triglycerides of monovarietal olive oils: a 13C-NMR comparative study. Eur J Lipid Sci Technol 98(6):203–205. https://doi.org/10.1002/lipi.19960980605

    Article  CAS  Google Scholar 

  30. Vlahov G (2006) 13C nuclear magnetic resonance spectroscopy to determine olive oil grades. Anal Chim Acta 577(2):281–287. https://doi.org/10.1016/j.aca.2006.06.044

    Article  CAS  PubMed  Google Scholar 

  31. Popescu R, Costinel D, Dinca OR, Marinescu A, Stefanescu I, Ionete RE (2015) Discrimination of vegetable oils using NMR spectroscopy and chemometrics. Food Control 48:84–90. https://doi.org/10.1016/j.foodcont.2014.04.046

    Article  CAS  Google Scholar 

  32. Sacchi R, Addeo F, Paolillo L (1997) 1H and 13C NMR of virgin olive oil. An overview. Magn Reson Chem 35(13):S133–S145

    Article  CAS  Google Scholar 

  33. Zamora R, Alba V, Hidalgo FJ (2001) Use of high-resolution 13C nuclear magnetic resonance spectroscopy for the screening of virgin olive oils. J Am Oil Chem Soc 78(1):89–94. https://doi.org/10.1007/s11746-001-0225-z

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors thank Project “Por3O—Portuguese Olive Oil Omics for traceability and authenticity—PTDC/AGRPRO/2003/2014, funding by European Regional Development Fund (FEDER) and National Funds through Fundação para a Ciência e a Tecnologia (FCT); Project “MedOOmics—Mediterranean Extra Virgin Olive Oil Omics: profiling and fingerprinting- Arimnet2/0001/2015” funding by the National Funds through Fundação para a Ciência e a Tecnologia (FCT); and FEDER funds through the Operational Program for Competitive Factors (COMPETE) for funding the FCT Projects UID/AGR/00115/2019 and UID/QUI/0619/2016, respectively. Nuno Martins acknowledges French National Agency for Research (ANR-15-ARM2-0002-04) supported by the European Union’s Seventh Framework Programme for research, technological development and demonstration under Grant Agreement Number 618127 (ARIMNet2).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Maria João Cabrita.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Compliance with ethics requirements

This article does not contain any studies with human or animal subjects.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Garcia, R., Pires, A., Martins, N. et al. Assessment of the triacylglycerol fraction of olive oil by 1D-NMR spectroscopy: exploring the usefulness of DEPT tool on the peak assignments of 13C NMR spectra. Eur Food Res Technol 245, 2479–2488 (2019). https://doi.org/10.1007/s00217-019-03359-0

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00217-019-03359-0

Keywords

Navigation