Grasas y Aceites, Vol 70, No 4 (2019)

Characterization of different ozonized sunflower oils I. Chemical changes during ozonization


https://doi.org/10.3989/gya.1166182

O. E. Ledea-Lozano
CNIC Ave 25 y 158 N0 15202, Cuba
orcid http://orcid.org/0000-0001-8521-2747

L. A. Fernández-García
CNIC Ave 25 y 158 N0 15202, Cuba
orcid http://orcid.org/0000-0002-1043-5505

D. Gil-Ibarra
CNIC Ave 25 y 158 N0 15202, Cuba
orcid http://orcid.org/0000-0002-1561-6495

N. Tena
Instituto de la Grasa, CSIC, Spain
orcid http://orcid.org/0000-0003-0933-5192

R. Garcés
Instituto de la Grasa, CSIC, Spain
orcid http://orcid.org/0000-0003-2571-8644

E. Martínez-Force
Instituto de la Grasa, CSIC, Spain
orcid http://orcid.org/0000-0001-5324-9537

J. J. Salas
Instituto de la Grasa, CSIC, Spain
orcid http://orcid.org/0000-0002-3259-2587

Abstract


Vegetable oils are usually rich in unsaturated fatty acids which are susceptible to oxidation. The oxidation of vegetable oils has been one of the most widely studied fields within lipid chemistry, because it alters their properties and nutritive value, inducing the formation of harmful compounds and off-flavors. Moreover, oxidized vegetable oils display altered physical and chemical properties which are conferred by the newer oxygenated compounds they contain. This is the case of ozonized oils. Ozone is a powerful oxidizing agent that mainly acts on olefinic compounds which generate ozonides and other peroxidic species that can decompose into carbonilic fragments. The action of the oxidant and the later reactions depend on the chemical environment of the reaction as well as the carbonyl termination products resulting from peroxide cleavage. In recent years, sunflower oils with different fatty acid compositions have been developed by breeding and mutagenesis. They displayed higher contents of oleic, stearic or palmitic acids, which mainly alters their triacylglycerol composition. Therefore, four different sunflower oils, common, high oleic, high stearic-high oleic and high palmitic-high oleic, were oxidized with ozone and the progress of the reaction was monitored by measuring the level of oil peroxygenation and the changes in the oils’ fatty acid compositions. The peroxidated species formed during ozonation were studied by FT-IR spectroscopy. The main conclusions of this work were that ozonation caused linear oxidation rates that were similar in all the oils assayed. The addition of water accelerated oxidation, which tended to occur in linoleic polyunsaturated fatty acid The FT-IR pointed to the presence of ozonide-derived peroxides as the major oxygenated species.

Keywords


Carbonyls; Fatty acids; FT-IR; Kinetics; Mutant sunflower oil; Oxidation; Ozone; Peroxides

Full Text:


HTML PDF XML

References


Bailey PS. Ozonation in organic chemistry. Volume I. Olefinic compounds. (New York, Academic press, 1978). ISBN: 9780323157483.

Bradley DG, Min DB. 1992. Singlet oxygen oxidation of foods. Critical Rev. Food Sci. Nutrition 31, 211–236.

Choe E, Min DB. 2006. Mechanisms and factors for edible oil oxidation. Comprehensive Rev. Food Sci. Food safety 5, 169–186.

Crapiste, GH, Brevedan MI, Carelli AA. 1999. Oxidation of sunflower oil during storage. J. Am. Oil Chem. Soc.76, 1437–1444.

Devlin RB, McKinnon KP, Noah T, Becker S, Koren HS. 1994. Ozone-induced release of cytokines and fibronectin by alveolar macrophages and airway epithelial cells. Am. J. Physiol.-Lung Cellular Mol. Physiol. 266, L612-L619.

Díaz MF, Gavín-Sazatornil JA, Ledea OE, Hernández F, Alaiz M, Garcés R. 2005. Spectroscopic characterization of ozonated sunflower oil. Ozone Sci. Eng. 27, 247–253.

Díaz MF, Gavín JA, Gómez M, Curtielles V, Hernández F. 2006. Study of ozonated sunflower oil using 1H NMR and microbiological analysis. Ozone Sci. Eng. 28, 59–63.

Fernández-Martínez JM, Mancha M, Osorio J, Garcés R. 1997. Sunflower mutant containing high levels of palmitic acid in high oleic background. Euphytica 97, 113–116.

Fernández-Moya V, Martínez-Force E, Garcés R. 2005. Oils from improved high stearic acid sunflower seeds. J. Agric. Food Chem. 53, 5326–5330.

Frankel EN. 1980. Lipid oxidation. Prog. Lipid Res. 19, 1–22.

Garcés R, García JM, Mancha M. 1989. Lipid characterization in seeds of a high oleic acid sunflower mutant. Phytochem. 28, 2597–2600.

Gunstone FD. 2011. Vegetable Oils in Food Technology: Composition, Properties and Uses. Blackwell Publishing, Oxford, UK. ISBN 1-84127-331-7

Guzel-Seydim ZB, Greene AK, Seydim AC. 2004. Use of ozone in the food industry. LWT-Food Sci. Technol. 37, 453–460.

Kim JG, Yousef AE, Dave S. 1999. Application of ozone for enhancing the microbiological safety and quality of foods: a review. J. Food Protection 62, 1071–1087.

Kubow S. 1992. Routes of formation and toxic consequences of lipid oxidation products in foods. Free Radical Biol. Med. 12, 63–81.

Márquez-Ruiz G, Garcés R, León-Camacho M, Mancha M. 1999. Thermoxidative stability of triacylglycerols from mutant sunflower seeds. J. Am. Oil Chem. Soc. 76, 1169–1174.

Martínez-Téllez G, Ledea Lozano O, Díaz-Gómez MF. 2006. Measurement of peroxidic species in ozonized sunflower oil. Ozone Sci. Eng. 28, 181–185.

Pietsch GJ, Gibalov VI. 1998. Dielectric barrier discharges and ozone synthesis. Pure Applied Chem. 70, 1169–1174.

Salas JJ, Bootello MA, Garcés R. 2015. Food Uses of Sunflower Oils. In: Sunflower Chemistry, Production, Processing, and Utilization. Salas JJ, Enrique MF and Dunford NT (Eds.) AOCS Press, Champaign, IL (pp. 441–464).

Santrock J, Gorski RA, O’Gara JF. 1992. Products and mechanism of the reaction of ozone with phospholipids in unilamellar phospholipid vesicles. Chem. Res. Toxicol. 5, 134–141.

Sechi LA, Lezcano I, Nunez N, Espim M, Duprè I, Pinna A, Molicotti P, Fadda G, Zanetti S. 2001. Antibacterial activity of ozonized sunflower oil (Oleozon). J. Appl. Microbiol. 90, 279–284.

Serio F, Pizzolante G, Cozzolino G, D’Alba M, Bagordo F, De Giorgi M, Grassi T, Idolo A, Guido M, De Donno A. 2017. A new formulation based on ozonated sunflower seed oil: in vitro antibacterial and safety evaluation. Ozone Sci. Eng. 39, 139–147.

Skalska K, Ledakowicz S, Perkowski J, Sencio B. 2009. Germicidal properties of ozonated sunflower oil. Ozone Sci. Eng. 31, 232–237.

Thomas MC, Mitchell TW, Harman DG, Deeley JM, Murphy RC, Blanksby SJ. 2007. Elucidation of double bond position in unsaturated lipids by ozone electrospray ionization mass spectrometry. Anal. Chem. 79, 5013–5022.

Valacchi G, Zanardi I, Lim Y, Belmonte G, Miracco C, Sticozzi C, Bocci V, Travagli V. 2013. Ozonated oils as functional dermatological matrices: Effects on the wound healing process using SKH1 mice. Int. J. Pharmaceutics 458, 65–73.




Copyright (c) 2019 Consejo Superior de Investigaciones Científicas (CSIC)

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.


Contact us grasasyaceites@ig.csic.es

Technical support soporte.tecnico.revistas@csic.es