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Enzymatic glycerolysis converts vegetable oils into structural fats with the potential to replace palm oil in food products

Abstract

Current trans fat replacement strategies provide food products with acceptable textural and sensory properties on a large scale, and at a reasonable price, but carry health and environmental burdens. Palm oil is used extensively because of its high solidity and functionality; however, increased production has led to deforestation throughout the world’s tropical regions. To reduce dependence on palm oil it is necessary to find a means of structuring a variety of readily available vegetable oils. Using cottonseed and peanut oils, among others, we show that enzymatic glycerolysis can structure liquid oils into solid fats through monoacylglycerol and diacylglycerol production from their native triacylglycerols without the addition of saturated or hydrogenated fat, thus not altering fatty acid composition. Solid fat contents of cottonseed and peanut oils were increased from 8% to 29% and 9% to 30% at 5 °C, respectively, and 21% and 10% at 20 °C, respectively. Additionally, oil-binding capacity was enhanced significantly. These novel oils were used to produce margarine and peanut butter with similar textural properties to commercial products and, importantly, represent a healthy and sustainable means to replace hydrogenated or saturated fats.

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Fig. 1: Partial glycerol contents in glycerolysis reaction products.
Fig. 2: Effects of glycerolysis conditions on crystallization, SFC and oil binding.
Fig. 3: SFC melting profiles of glycerolysis reaction products.
Fig. 4: Implications of glycerolysis reaction product properties on microstructure.
Fig. 5: Optimally structured cottonseed oil glycerolysis product.
Fig. 6: Stabilization of peanut butter with peanut oil glycerolysis product.

Data availability

Data are available upon request from the authors and source data are provided with this paper.

References

  1. 1.

    Wang, F. C., Gravelle, A. J., Blake, A. I. & Marangoni, A. G. Novel trans fat replacement strategies. Curr. Opin. Food Sci. 7, 27–34 (2016).

    Article  Google Scholar 

  2. 2.

    Austin, K. G. et al. Shifting patterns of oil palm driven deforestation in Indonesia and implications for zero-deforestation commitments. Land Use Policy 69, 41–48 (2017).

    Article  Google Scholar 

  3. 3.

    The Recent Development of the Indonesian Palm Oil Industry (Indonesian Palm Oil Association, 2020); https://gapki.id/en/news/18397/the-recent-development-of-the-indonesian-palm-oil-industry

  4. 4.

    Palm Oil (Indonesia Investments, 2020); https://www.indonesia-investments.com/business/commodities/palm-oil/

  5. 5.

    Ramli, U. S. et al. Sustainable palm oil—the role of screening and advanced analytical techniques fro geographical traceability and authenticity verification. Molecules 25, 2927 (2020).

    CAS  Article  PubMed Central  Google Scholar 

  6. 6.

    Global Oil Palm Plantations Have Larger Acreage than Other Vegetable Oil Plantations—Myths and Facts 2-02 (Indonesian Palm Oil Association, 2020); https://gapki.id/en/news/18597/global-oil-palm-plantations-have-larger-acreage-than-other-vegetable-oil-plantations-myths-facts-2-02

  7. 7.

    Coral Medina, J. D., Magalhaes, A. I., Zamora, H. D. & Quijano Melo, J. D. Oil palm cultivation and production in South America: status and perspectives. Biofuel. Bioprod. Biorefin. 13, 1202–1210 (2019).

    Article  Google Scholar 

  8. 8.

    8 Things to Know About Palm Oil (World Wildlife Fund for Nature, 2020); https://www.wwf.org.uk/updates/8-things-know-about-palm-oil

  9. 9.

    Meijaard, E., Abrams, J. F., Juffe-Bignoli, D., Voigt, M. & Shell, D. Coconut oil, conservation and the conscientious consumer. Current Biology 30, R737–R758 (2020).

    Article  Google Scholar 

  10. 10.

    Carlson, K. M. et al. Effect of oil palm sustainability certification on deforestation and fire in Indonesia. Proc. Natl Acad. Sci. USA 115, 121–126 (2018).

    ADS  CAS  Article  PubMed  Google Scholar 

  11. 11.

    Kinsell, L. W. et al. Dietary modification of serum cholesterol and phospholipid levels. J. Clin. Endocrinol. Metab. 12, 909–913 (1952).

    CAS  Article  PubMed  Google Scholar 

  12. 12.

    Ahrens, E. H. Jr., Blankenhorn, D. H. & Tsaltas, T. T. Effect on human serum lipids of substituting plant for animal fat in diet. Proc. Soc. Exp. Biol. Med. 86, 872–878 (1954).

    CAS  Article  PubMed  Google Scholar 

  13. 13.

    Beveridge, J. M. R., Connell, W. F. & Mayer, G. A. Dietary factors affecting the level of plasma cholesterol in humans: the role of fat. Can. J. Biochem. Physiol. 34, 441–455 (1956).

    CAS  Article  PubMed  Google Scholar 

  14. 14.

    Ahrens, E. H. Jr. et al. The influence of dietary fats on serum lipid levels in man. Lancet 1, 943–953 (1957).

    Article  Google Scholar 

  15. 15.

    Keys, A., Anderson, J. T. & Grande, F. Prediction of serum-cholesterol responses of man to changes in fats in the diet. Lancet 2, 959–966 (1957).

    Article  Google Scholar 

  16. 16.

    Hegsted, D. M., McGandy, R. B., Myers, M. L. & Stare, F. J. Quantitative effects of dietary fat on serum cholesterol in man. Am. J. Clin. Nutr. 17, 281–295 (1965).

    CAS  Article  PubMed  Google Scholar 

  17. 17.

    Keys, A., Anderson, J. T. & Grande, F. Serum cholesterol response to changes in the diet. IV. Particular fatty acids in the diet. Metabolism 14, 776–787 (1965).

    CAS  Article  PubMed  Google Scholar 

  18. 18.

    Mensink, R. P., Zock, P. L., Kester, A. D. M. & Katan, M. B. Effects of dietary fatty acids and carbohydrates on the ratio of serum total to HDL cholesterol and on serum lipids and apolipoproteins: a meta-analysis of 60 controlled trials. Am. J. Clin. Nutr. 77, 1146–1155 (2003).

    CAS  Article  Google Scholar 

  19. 19.

    Micha, R. & Mozaffarian, D. Saturated fat and cardiometabolic risk factors, coronary heart disease, stroke, and diabetes: a fresh look at the evidence. Lipids 45, 893–905 (2010).

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  20. 20.

    Mensink, R. P. Effects of Saturated Fatty acids on Serum Lipids and Lipoproteins: A Systematic Review and Regression Analysis (World Health Organization, 2016).

  21. 21.

    Nettleton, J. A., Brouwer, I. A., Geleijnse, J. M. & Hornstra, G. Saturated fat consumption and risk of coronary heart disease and ischemic stroke: a science update. Ann. Nutr. Metab. 70, 26–33 (2017).

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  22. 22.

    Rogers, M. A. Novel structuring strategies for unsaturated fats—meeting the zero-trans, zero-saturated fat challenge: a review. Food Res. Int. 42, 747–753 (2009).

    ADS  CAS  Article  Google Scholar 

  23. 23.

    Co, E. & Marangoni, A. G. Organogels:an alternative edible oil-structuring method. J. Am. Oil Chem. Soc. 89, 749–780 (2012).

    Article  Google Scholar 

  24. 24.

    Patel, A. R. & Dewettinck, K. Edible oil structuring: an overview and recent updates. Food Funct. 7, 20–29 (2016).

    CAS  Article  PubMed  Google Scholar 

  25. 25.

    Belitz, H. D., Grosch, W. & Schieberle, P. Food Chemistry (Springer, 2009).

  26. 26.

    Yanai, H. et al. Diacylglycerol oil for the metabolic syndrome. Nutr. J. 6, 1–6 (2007).

    Article  Google Scholar 

  27. 27.

    Flickinger, B. D. & Matsuo, N. Nutritional characteristics of DAG oil. Lipids 38, 129–132 (2003).

    CAS  Article  PubMed  Google Scholar 

  28. 28.

    Matsuo, N. Nutritional characteristics and health benefits of diacylglycerol in foods. Food Sci. Technol. Res. 10, 103–110 (2004).

    CAS  Article  Google Scholar 

  29. 29.

    Teramoto, T. et al. Significant effects of diacylglycerol on body fat and lipid metabolism in patients on hemodialysis. Clin. Nutr. 23, 1122–1126 (2004).

    CAS  Article  PubMed  Google Scholar 

  30. 30.

    Lo, S. K., Tan, C. P., Long, K., Yusoff, M. S. A. & Lai, O. M. Diacylglycerol oil—properties, processes, and products: a review. Food Bioproc. Tech. 1, 223–233 (2008).

    Article  Google Scholar 

  31. 31.

    Code of Practice for the Reduction of 3-Monochloropropane-1,2-Diol Esters (3-MCPDEs) and Glycidyl Esters (GEs) in Refined Oils and Food Products Made with Refined Oils CXC 79-2019 (Food and Agriculture Organization of the United Nations, 2019).

  32. 32.

    Chen, C. H. & Terentjev, E. M. Aging and metastability of monoglycerides in hydrophobic solutions. Langmuir 25, 6717–6724 (2009).

    CAS  Article  PubMed  Google Scholar 

  33. 33.

    Malkin, T. & Riad el Shurbagy, M. An X-ray and thermal examination of the glycerides. Part II. The α-monoglycerides. J. Chem. Soc., 1628–1634 (1936).

  34. 34.

    Barret, R. Medicinal Chemistry: Fundamentals (Elsevier, 2018).

  35. 35.

    Firestone, D. Physical and Chemical Characteristics of Oils, Fats, and Waxes (AOCS Press, 2013).

Download references

Acknowledgements

We acknowledge the financial support of the Natural Sciences and Engineering Research Council of Canada (NSERC), the Canada Research Chairs (CRC) Program, the Government of Ontario and the Barrett Foundation.

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R.A.N. contributed to the planning and execution of all experimental procedures and the writing of the manuscript. A.G.M. contributed to the experimental planning and the writing of the manuscript.

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Correspondence to Alejandro G. Marangoni.

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Supplementary Information

Supplementary Figs. 1–6, Tables 1–3.

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Supplementary Data

Raw experimental data used to generate Supplementary Figs. 1–6 and Tables 1–3.

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Nicholson, R.A., Marangoni, A.G. Enzymatic glycerolysis converts vegetable oils into structural fats with the potential to replace palm oil in food products. Nat Food 1, 684–692 (2020). https://doi.org/10.1038/s43016-020-00160-1

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