Direct glycerolysis of novel edible Sacha Inchi (Plukenetia volubilis L.) seed oil (PvLO) into diacylglycerols (DAG) and monoacylglycerols (MAG) was studied over solid Na2SiO3 with or without microwave assistance. The glycerolysis yield was calculated by qualitative and semiquantitative analyses of 1H NMR, 13C NMR, and FT-IR spectra. The yields of ~33% 1, 3-DAG, ~16% 1, 2-DAG, ~40% 1-MAG, and ~2.3% 2-MAG were achieved after 16 hours at 120 °C in three consecutive cycles using acetone, with an interesterification rate of 92%. The modified oil showed enhanced gelation ability at low temperatures. The yield of 1, 2-DAG can be increased by adding acetone as solvent. The fatty acid compositions and unsaturated structure of lipids were less destroyed after alkaline glycerolysis. However, more α-linolenic and linoleic acids were transferred to the sn-2 position of glyceryl skeleton. The oxidative stability of the modified oil was still controllable. In summary, this work provides a feasible method to convert polyunsaturated plant oils into oils rich in DAG and MAG with less destructive impact on the olefinic structure of oil. Also, it provides a useful example of how to quickly evaluate the influence of chemical modification on the chemical structure of plant oils by using various spectral technologies.
Conflict of Interest
The authors declare that they have no conflict of interest.
|aocs12354-sup-0001-Supinfo.pdfPDF document, 995.2 KB||
Appendix S1. Supporting Information
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
- 2010) Multivariate analysis of NMR fingerprint of the unsaponifiable fraction of virgin olive oils for authentication purposes. Food Chemistry, 118: 956–965. https://doi.org/10.1016/j.foodchem.2008.09.061
- 2016) Metabolism and functional effects of plant-derived omega-3 fatty acids in humans. Progress in Lipid Research, 64: 30–56. https://doi.org/10.1016/j.plipres.2016.07.002
- 2018) A comprehensive review of chemistry, sources and bioavailability of omega-3 fatty acids. Nutrients, 10: 1662. https://doi.org/10.3390/nu10111662
- 2014) Chemical composition, oxidative stability and antioxidant capacity of oil extracted from roasted seeds of Sacha-Inchi (Plukenetia volubilis L.). Journal of Agricultural and Food Chemistry, 62: 5191–5197. https://doi.org/10.1021/jf500936j
- 2006) Hydrogenation and interesterification effects on the oxidative stability and melting point of soybean oil. Journal of Agricultural and Food Chemistry, 54: 6011–6015. https://doi.org/10.1021/jf053263r
- 2005) The base-catalyzed, low-temperature interesterification mechanism revisited. European Journal of Lipid Science and Technology, 107: 912–921. https://doi.org/10.1002/ejlt.200501199
- 2011) Chemical characterization of sacha inchi (Plukenetia volubilis L.) oil. Journal of Agricultural and Food Chemistry, 59: 13043–13049. https://doi.org/10.1021/jf203184y
- 2018) Diglyceride-rich oils from glycerolysis of edible vegetable oils. Catalysis Today, 302: 233–241. https://doi.org/10.1016/j.cattod.2017.04.008
- 2012) The influence of traditional and minimal refining on the minor constituents of canola oil. Ontario, Canada: University of Guelph.
- 2003) Characterization of sacha inchi (Plukenetia volubilis L.) oil by FTIR spectroscopy and 1H NMR. Comparison with linseed oil. Journal of the American Oil Chemists'Society, 80: 755–762. https://doi.org/10.1007/s11746-003-0768-z
- 2018) Quality of sacha inchi oil prepared by different methods. China Oils and Fats, 43: 84–88.
- 2011) High-resolution NMR spectroscopy: An alternative fast tool for qualitative and quantitative analysis of diacylglycerol (DAG) oil. Journal of the American Oil Chemists'Society, 88: 1695–1708. https://doi.org/10.1007/s11746-011-1848-2
- 2014) A randomized clinical trial to determine the efficacy of manufacturers' recommended doses of omega-3 fatty acids from different sources in facilitating cardiovascular disease risk reduction. Lipids in Health and Disease, 13: 99. https://doi.org/10.1186/1476-511X-13-99
- 2017) Applications of nuclear magnetic resonance in lipid analyses: An emerging powerful tool for lipidomics studies. Progress in Lipid Research, 68: 37–56. https://doi.org/10.1016/j.plipres.2017.09.003
- 2014) Chemical composition and oxidative evolution of sacha inchi (Plukentia volubilis L.) oil from Xishuangbanna (China). Grasas y Aceites, 65:e012. https://doi.org/10.3989/gya.075713
- 2016) The effects of intermolecular interactions on the physical properties of organogels in edible oils. Journal of Colloid and Interface Science, 483: 154–164. https://doi.org/10.1016/j.jcis.2016.08.009
- 2014) A review of thermo-oxidative degradation of food lipids studied by 1H NMR spectroscopy: Influence of degradative conditions and food lipid nature. Comprehensive Reviews in Food Science and Food Safety, 13: 838–859. https://doi.org/10.1111/1541-4337.12090
- 2007) Structuring of edible oils by alternatives to crystalline fat. Current Opinion in Colloid & Interface Science, 12: 221–231. https://doi.org/10.1016/j.cocis.2007.07.002
- 2016) Diacylglycerol-enriched oil production using chemical glycerolysis. European Journal of Lipid Science and Technology, 118: 1880–1890. https://doi.org/10.1002/ejlt.201500489
- 2012) Chemical interesterification of blends of palm stearin, coconut oil, and canola oil: Physicochemical properties. Journal of Agricultural and Food Chemistry, 60: 1461–1469. https://doi.org/10.1021/jf204111t
- 1999) Application of NMR to the study of olive oils. Progress in Nuclear Magnetic Resonance Spectroscopy, 35: 341–357. https://doi.org/10.1016/s0079-6565(99)00015-1
- 2014) Degree of oxidation depending on the positional distribution of linolenic acid in perilla oil and interesterified products. Food Science and Biotechnology, 23: 1733–1740. https://doi.org/10.1007/s10068-014-0237-7
- 2014) Heterogeneous interesterification of triacylglycerols catalyzed by using potassium-doped alumina as a solid catalyst. Journal of Agricultural and Food Chemistry, 62: 10414–10421. https://doi.org/10.1021/jf503726a
- 2013) Interesterification of soybean oil and lard blends catalyzed by SBA-15-pr-NR3OH as a heterogeneous base catalyst. Journal of Agricultural and Food Chemistry, 61: 3373–3381. https://doi.org/10.1021/jf400216z
- 2018) Catalytic transesterification to biodiesel at room temperature over several solid bases. Energy Conversion and Management, 164: 112–121. https://doi.org/10.1016/j.enconman.2018.02.085
- 2014) Low-temperature chemical glycerolysis to produce diacylglycerols by heterogeneous base catalyst. European Journal of Lipid Science and Technology, 116: 470–476. https://doi.org/10.1002/ejlt.201300438
- 2010) Production of diacylglycerols through low-temperature chemical glycerolysis. Food Chemistry, 122: 228–232. https://doi.org/10.1016/j.foodchem.2010.02.067