Skip to main content
SpringerLink
Log in

Determination of Unsaturated Fatty Acids Composition in Walnut (Juglans regia L.) Oil Using NMR Spectroscopy

  • Published:
Food Analytical Methods Aims and scope Submit manuscript

Abstract

Walnut is a precious marketed nut characterised by kernels containing more than 60% of oil. Gas chromatography (GC) is the most used method to analyse oils; nonetheless, polyunsaturated (PUFA)s and monounsaturated fatty acids (MUFA)s were not separated sufficiently. Therefore, our study is based on the employment of two GC systems with different columns. However, for determination of PUFAs and MUFAs composition, 13C nuclear magnetic resonance (NMR) seems to be a promising technique by showing the resonance for each unsaturated fatty acids (UFA)s in olefinic region, and also for saturated fatty acids (SFA) in the aliphatic region. 13C NMR was able to distinguish between fatty acid isomers such as oleic (C18:1 Δ9) and vaccenic (C18:1 Δ11) acid. In addition, different fatty acid length with same position of unsaturated carbon were distinguished and determined by 13C NMR, for instance between vaccenic (C18:1 Δ11) and eicosenoic (C20:1 Δ11) acid. NMR quantification takes the advantages of chemical shifts to accurately calculate fatty acid contents for both saturated and unsaturated one. Besides providing the full profile of fatty acids, this study adds information regarding quantitative and qualitative composition of walnut oil. This can expand the analytical methods used to improve the knowledge of nutritional values of oil and food products.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

Data availability

All data generated or analysed during this study are included in this published article [and its supplementary information files].

References

  • Amaral JS, Casal S, Pereira JA, Seabra RM, Oliveira BPP (2003) Determination of sterol and fatty acid compositions, oxidative stability, and nutritional value of six walnut (Juglans regia L.) cultivars grown in Portugal. J Agric Food Chem 51(26):7698–7702

    Article  CAS  PubMed  Google Scholar 

  • Amaral JS, Cunha SC, Alves MR, Pereira JA, Seabra RM, Oliveira BPP (2004) Triacylglycerol composition of walnut (Juglans regia L.) cultivars: characterization by HPLC-ELSD and chemometrics. J Agric Food Chem 52(26):7964–7969

    Article  CAS  PubMed  Google Scholar 

  • Aziz DM, Hama JR, Alam SM (2015) Synthesising a novel derivatives of piperine from black pepper (Piper nigrum L.). J Food Meas Charact 9(3):324–331

    Article  Google Scholar 

  • Bada JC, León-Camacho M, Prieto M, Copovi P, Alonso L (2010) Characterization of walnut oils (Juglans regia L.) from Asturias, Spain. J Am Oil Chem Soc 87(12):1469–1474

    Article  CAS  Google Scholar 

  • Bail S, Stuebiger G, Unterweger H, Buchbauer G, Krist S (2009) Characterization of volatile compounds and triacylglycerol profiles of nut oils using SPME-GC-MS and MALDI-TOF-MS. Eur J Lipid Sci Technol 111(2):170–182

    Article  CAS  Google Scholar 

  • Bella G, Rotondo A (2020) Theoretical prediction of 13C NMR spectrum of mixed triglycerides by mean of GIAO calculations to improve vegetable oils analysis. Chem Phys Lipids 232:104973

    Article  CAS  PubMed  Google Scholar 

  • Chauhan A, Chauhan V (2020) Beneficial effects of walnuts on cognition and brain health. Nutrients 12(2):550

    Article  CAS  PubMed Central  Google Scholar 

  • Christopoulos MV, Tsantili E (2015) Oil composition in stored walnut cultivars—quality and nutritional value. Eur J Lipid Sci Technol 117(3):338–348

    Article  CAS  Google Scholar 

  • Delmonte P, Fardin Kia A-R, Kramer JKG, Mossoba MM, Sidisky L, Rader JI (2011) Separation characteristics of fatty acid methyl esters using SLB-IL111, a new ionic liquid coated capillary gas chromatographic column. J Chromatogr A 1218(3):545–554

    Article  CAS  PubMed  Google Scholar 

  • Delmonte P, Hu Q, Kia A-RF, Rader JI (2008) Preparation, chromatographic separation and relative retention times of cis/trans heptadecaenoic (17:1) fatty acids. J Chromatogr A 1214(1):30–36

    Article  CAS  PubMed  Google Scholar 

  • Diehl BWK (2001) High resolution NMR spectroscopy. Eur J Lipid Sci Technol 103(12):830–834

    Article  CAS  Google Scholar 

  • Elyashberg M (2015) Identification and structure elucidation by NMR spectroscopy. TrAC Trends Anal Chem 69:88–97

    Article  CAS  Google Scholar 

  • Gao P, Liu R, Jin Q, Wang X (2019) Comparison of solvents for extraction of walnut oils: lipid yield, lipid compositions, minor-component content, and antioxidant capacity. LWT 110:346–352

    Article  CAS  Google Scholar 

  • Hama JR (2017) Comparison of fatty acid profile changes between unroasted and roasted brown sesame (Sesamum indicum L.) seeds oil. Int J Food Prop 20(5):957–967

    Article  CAS  Google Scholar 

  • Hama JR, Omer RA, Rashid RSM, Mohammad N-EA, Thoss V (2016) The diversity of phenolic compounds along defatted kernel, green husk and leaves of walnut (Juglans regia L.). Anal Chem Lett 6(1):35–46

    Article  CAS  Google Scholar 

  • Hardman WE (2014) Walnuts Have potential for cancer prevention and treatment in mice. J Nutr 144(4):555S-560S

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Lavedrine F, Ravel A, Villet A, Ducros V, Alary J (2000) Mineral composition of two walnut cultivars originating in France and California. Food Chem 68(3):347–351

    Article  CAS  Google Scholar 

  • Li R Tsao, Yang R, Kramer JKG, Hernandez M (2007) Fatty acid profiles, tocopherol contents, and antioxidant activities of heartnut (Juglans ailanthifolia Var. cordiformis) and Persian walnut (Juglans regia L.). J Agric Food Chem 55(4):1164–1169

    Article  CAS  PubMed  Google Scholar 

  • Li B, Wang H, Zhao Q, Ouyang J, Wu Y (2015) Rapid detection of authenticity and adulteration of walnut oil by FTIR and fluorescence spectroscopy: a comparative study. Food Chem 181:25–30

    Article  CAS  PubMed  Google Scholar 

  • Lie Ken Jie MSF (2001) Analysis of conjugated linoleic acid esters by nuclear magnetic resonance spectroscopy. Eur J Lipid Sci Technol 103(9):628–632

    Article  Google Scholar 

  • Martínez ML, Labuckas DO, Lamarque AL, Maestri DM (2010) Walnut (Juglans regia L.): genetic resources, chemistry, by-products. J Sci Food Agric 90(12):1959–1967

    PubMed  Google Scholar 

  • Martínez ML, Mattea MA, Maestri DM (2006) Varietal and crop year effects on lipid composition of walnut (Juglans regia) genotypes. J Am Oil Chem Soc 83(9):791–796

    Article  Google Scholar 

  • Mattes RD, Kris-Etherton PM, Foster GD (2008) Impact of peanuts and tree nuts on body weight and healthy weight loss in adults. J Nutr 138(9):1741S-1745S

    Article  CAS  PubMed  Google Scholar 

  • 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(9):1091–1094

    Article  CAS  Google Scholar 

  • Pereira JA, Oliveira I, Sousa A, Ferreira ICFR, Bento A, Estevinho L (2008) Bioactive properties and chemical composition of six walnut (Juglans regia L.) cultivars. Food Chem Toxicol 46(6):2103–2111

    Article  CAS  PubMed  Google Scholar 

  • Poggetti L, Ferfuia C, Chiabà C, Testolin R, Baldini M (2018) Kernel oil content and oil composition in walnut (Juglans regia L) accessions from north-eastern Italy. J Sci Food Agric 98(3):955–962

    Article  CAS  PubMed  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Qian J, Zhao C, Zhu H, Tong J, Zhao X, Yang H, Guo H (2021) NMR detection of fatty acids content in walnut oil and compared with liquid chromatography. J Food Meas Charact 15(3):2716–2726

    Article  Google Scholar 

  • Rotondo A, La Torre GL, Dugo G, Cicero N, Santini A, Salvo A (2020) Oleic acid is not the only relevant mono-unsaturated fatty ester in olive oil. Foods 9(4):384

    Article  CAS  PubMed Central  Google Scholar 

  • Rotondo A, Mannina L, Salvo A (2019) Multiple assignment recovered analysis (MARA) NMR for a Direct Food labeling: the case study of olive oils. Food Anal Methods 12(5):1238–1245

    Article  Google Scholar 

  • Sabaté J (2003) Nut consumption and body weight. Am J Clin Nutr 78(3):647S-650S

    Article  PubMed  Google Scholar 

  • 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 

  • Safar M, Bertrand D, Robert P, Devaux MF, Genot C (1994) Characterization of edible oils, butters and margarines by Fourier transform infrared spectroscopy with attenuated total reflectance. J Am Oil Chem Soc 71(4):371

    Article  CAS  Google Scholar 

  • Salvo A, Rotondo A, La Torre GL, Cicero N, Dugo G (2017) Determination of 1,2/1,3-diglycerides in Sicilian extra-virgin olive oils by 1H-NMR over a one-year storage period. Nat Prod Res 31(7):822–828

    Article  CAS  PubMed  Google Scholar 

  • Savage GP, Dutta PC, McNeil DL (1999) Fatty acid and tocopherol contents and oxidative stability of walnut oils. J Am Oil Chem Soc 76(9):1059–1063

    Article  CAS  Google Scholar 

  • Tapsell LC, Batterham MJ, Teuss G, Tan SY, Dalton S, Quick CJ, Gillen LJ, Charlton KE (2009) Long-term effects of increased dietary polyunsaturated fat from walnuts on metabolic parameters in type II diabetes. Eur J Clin Nutr 63(8):1008–1015

    Article  CAS  PubMed  Google Scholar 

  • Thoss V, Murphy PJ, Marriott R, Wilson T (2012) Triacylglycerol composition of British bluebell (Hyacinthoides non-scripta) seed oil. RSC Adv 2(12):5314–5322

    Article  CAS  Google Scholar 

  • Tindall AM, McLimans CJ, Petersen KS, Kris-Etherton PM, Lamendella R (2019) Walnuts and vegetable oils containing oleic acid differentially affect the gut microbiota and associations with cardiovascular risk factors: follow-up of a randomized, controlled, feeding trial in adults at risk for cardiovascular disease. J Nutr 150(4):806–817

    Article  PubMed Central  Google Scholar 

  • Torres MM, Martínez ML, Maestri DM (2005) A multivariate study of the relationship between fatty acids and volatile flavor components in olive and walnut oils. J Am Oil Chem Soc 82(2):105–110

    Article  CAS  Google Scholar 

  • Vlahov G (2006) 13C nuclear magnetic resonance spectroscopy to determine olive oil grades. Anal Chim Acta 577(2):281–287

    Article  CAS  PubMed  Google Scholar 

  • Vlahov G, Shaw AD, Kell DB (1999) Use of 13C nuclear magnetic resonance distortionless enhancement by polarization transfer pulse sequence and multivariate analysis to discriminate olive oil cultivars. J Am Oil Chem Soc 76(10):1223–1231

    Article  CAS  Google Scholar 

  • Wollenberg KF (1990) Quantitative high resolution13C nuclear magnetic resonance of the olefinic and carbonyl carbons of edible vegetable oils. J Am Oil Chem Soc 67(8):487–494

    Article  CAS  Google Scholar 

  • 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

    Article  CAS  Google Scholar 

  • Zibaeenezhad MJ, Farhadi P, Attar A, Mosleh A, Amirmoezi F, Azimi A (2017) Effects of walnut oil on lipid profiles in hyperlipidemic type 2 diabetic patients: a randomized, double-blind, placebo-controlled trial. Nutr Diabetes 7(4):e259–e259

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Funding

This study was funded by HCDP program in the Ministry of Higher Education and Scientific Research of Kurdistan Regional Government—Iraq (Grand Number: JUOR15).

Author information

Authors and Affiliations

  1. Chemistry School, Bangor University, Bangor, LL57 2UW, Gwynedd, UK

    Jawameer R. Hama & Vera Fitzsimmons-Thoss

  2. Department of Chemistry, College of Science, University of Raparin, Rania, Kurdistan Region, Iraq

    Jawameer R. Hama

Authors
  1. Jawameer R. Hama
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vera Fitzsimmons-Thoss
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Conceptualization, methodology, formal analysis and investigation, writing—original draft preparation, writing—review and editing, funding acquisition: Jawameer Hama. Conceptualization, methodology, formal analysis and investigation, writing—original draft preparation, writing—review and editing, funding acquisition, resources, supervision: Vera Fitzsimmons-Thoss. All authors read and approved the final manuscript.

Corresponding author

Correspondence to Jawameer R. Hama.

Ethics declarations

Conflict of interest

Jawameer Hama declares that there is no conflict of interest. Vera Fitzsimmons-Thoss declares that there is no conflict of interest.

Ethics approval

This article does not contain any studies with human participants or animals.

Additional information

Publisher's Note

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

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 6785 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hama, J.R., Fitzsimmons-Thoss, V. Determination of Unsaturated Fatty Acids Composition in Walnut (Juglans regia L.) Oil Using NMR Spectroscopy. Food Anal. Methods 15, 1226–1236 (2022). https://doi.org/10.1007/s12161-021-02203-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12161-021-02203-0

Keywords

Search

Navigation