Lipase-produced hydroxytyrosyl eicosapentaenoate is an excellent antioxidant for the stabilization of omega-3 bulk oils, emulsions and microcapsules

Molecules

Volumn 23, Issue 2, 2018, Pages

  Akanbi, Taiwo Olusesan ^a   Barrow, Colin James ^a  

^a DEAKIN UNIVERSITY   (Australia)

Author keywords

Antioxidant; Candida antarctica B; Conjugation; Eicosapentaenoic acid; Enzyme; Hydroxytyrosol; Lipase; Microencapsulation

Indexed keywords

ANTIOXIDANT; FUNGAL PROTEIN; ICOSAPENTAENOIC ACID; LIPASE B, CANDIDA ANTARCTICA; TRIACYLGLYCEROL LIPASE;

ANALOGS AND DERIVATIVES; CANDIDA; CHEMISTRY; EMULSION; ENZYMOLOGY; MICROCAPSULE;

ANTIOXIDANTS; CANDIDA; CAPSULES; EICOSAPENTAENOIC ACID; EMULSIONS; FUNGAL PROTEINS; LIPASE;

EID: 85041130320     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules23020275     Document Type: Article

References (37)

1. Pazos, M.; Alonso, A.; Sánchez, I.; Medina, I. Hydroxytyrosol prevents oxidative deterioration in foodstuffs rich in fish lipids. J. Agric. Food Chem. 2008, 56, 3334–3340. [CrossRef] [PubMed]
2. Morton, L.W.; Caccetta, R.A.A.; Puddey, I.B.; Croft, K.D. Chemistry and biological effects of dietary phenolic compounds: Relevance to cardiovascular disease. Clin. Exp. Pharmacol. Physiol. 2000, 27, 152–159. [CrossRef] [PubMed]
3. Richard, N.; Arnold, S.; Hoeller, U.; Kilpert, C.; Wertz, K.; Schwager, J. Hydroxytyrosol is the major anti-inflammatory compound in aqueous olive extracts and impairs cytokine and chemokine production in macrophages. Planta Med. 2011, 77, 1890–1897. [CrossRef] [PubMed]
4. Turck, D.; Bresson, J.L.; Burlingame, B.; Dean, T.; Fairweather-Tait, S.; Heinonen, M.; Hirsch-Ernst, K.I.; Mangelsdorf, I.; McArdle, H.J.; Naska, A. Safety of hydroxytyrosol as a novel food pursuant to Regulation (EC) No. 258/97. EFSA J. 2017, 15, 4728. [CrossRef]
5. Bouallagui, Z.; Bouaziz, M.; Lassoued, S.; Engasser, J.M.; Ghoul, M.; Sayadi, S. Hydroxytyrosol acyl esters: Biosynthesis and activities. Appl. Biochem. Biotechnol. 2011, 163, 592–599. [CrossRef] [PubMed]
6. Pereira-Caro, G.; Madrona, A.; Bravo, L.; Espartero, J.L.; Alcudia, F.; Cert, A.; Mateos, R. Antioxidant activity evaluation of alkyl hydroxytyrosyl ethers, a new class of hydroxytyrosol derivatives. Food Chem. 2009, 115, 86–91. [CrossRef]
7. Trujillo, M.; Mateos, R.; Collantes de Teran, L.; Espartero, J.L.; Cert, R.; Jover, M.; Alcudia, F.; Bautista, J.; Cert, A.; Parrado, J. Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems. J. Agric. Food Chem. 2006, 54, 3779–3785. [CrossRef] [PubMed]
8. Akanbi, T.O.; Barrow, C.J. Lipase-catalysed incorporation of EPA into emu oil: Formation and characterisation of new structured lipids. J. Funct. Foods 2015, 19, 801–809. [CrossRef]
9. Akanbi, T.O.; Barrow, C.J. Candida antarctica lipase a effectively concentrates DHA from fish and thraustochytrid oils. Food Chem. 2017, 229, 509–516. [CrossRef] [PubMed]
10. Lucas, R.; Comelles, F.; Alcántara, D.; Maldonado, O.S.; Curcuroze, M.; Parra, J.L.; Morales, J.C. Surface-active properties of lipophilic antioxidants tyrosol and hydroxytyrosol fatty acid esters: A potential explanation for the nonlinear hypothesis of the antioxidant activity in oil-in-water emulsions. J. Agric. Food Chem. 2010, 58, 8021–8026. [CrossRef] [PubMed]
11. Medina, I.; Lois, S.; Alcántara, D.; Lucas, R.; Morales, J.C. Effect of lipophilization of hydroxytyrosol on its antioxidant activity in fish oils and fish oil-in-water emulsions. J. Agric. Food Chem. 2009, 57, 9773–9779. [CrossRef] [PubMed]
12. Pande, G.; Akoh, C.C. Enzymatic synthesis of tyrosol-based phenolipids: Characterization and effect of alkyl chain unsaturation on the antioxidant activities in bulk oil and oil-in-water emulsion. J. Am. Oil Chem. Soc. 2016, 93, 329–337. [CrossRef]
13. Warnakulasuriya, S.N.; Rupasinghe, H. Long chain fatty acid acylated derivatives of quercetin-3-O-glucoside as antioxidants to prevent lipid oxidation. Biomolecules 2014, 4, 980–993. [CrossRef] [PubMed]
14. de Pinedo, A.T.; Penalver, P.; Rondon, D.; Morales, J. Efficient lipase-catalyzed synthesis of new lipid antioxidants based on a catechol structure. Tetrahedron 2005, 61, 7654–7660. [CrossRef]
15. Zhou, D.-Y.; Sun, Y.-X.; Shahidi, F. Preparation and antioxidant activity of tyrosol and hydroxytyrosol esters. J. Funct. Foods 2017, 37, 66–73. [CrossRef]
16. Porter, W.L.; Black, E.D.; Drolet, A.M. Use of polyamide oxidative fluorescence test on lipid emulsions: Contrast in relative effectiveness of antioxidants in bulk versus dispersed systems. J. Agric. Food Chem. 1989, 37, 615–624. [CrossRef]
17. Shahidi, F.; Zhong, Y. Revisiting the polar paradox theory: A critical overview. J. Agric. Food Chem. 2011, 59, 3499–3504. [CrossRef] [PubMed]
18. Wang, J.; Shahidi, F. Acidolysis of p-coumaric acid with omega-3 oils and antioxidant activity of phenolipid products in in vitro and biological model systems. J. Agric. Food Chem. 2013, 62, 454–461. [CrossRef] [PubMed]
19. Mateos, R.; Trujillo, M.; Pereira-Caro, G.; Madrona, A.; Cert, A.; Espartero, J.L. New lipophilic tyrosyl esters. Comparative antioxidant evaluation with hydroxytyrosyl esters. J. Agric. Food Chem. 2008, 56, 10960–10966. [CrossRef] [PubMed]
20. Lu, Y.; Foo, L.Y. Antioxidant and radical scavenging activities of polyphenols from apple pomace. Food Chem. 2000, 68, 81–85. [CrossRef]
21. Antolovich, M.; Prenzler, P.D.; Patsalides, E.; McDonald, S.; Robards, K. Methods for testing antioxidant activity. Analyst 2002, 127, 183–198. [CrossRef] [PubMed]
22. Tan, Z.; Shahidi, F. Chemoenzymatic synthesis of phytosteryl ferulates and evaluation of their antioxidant activity. J. Agric. Food Chem. 2011, 59, 12375–12383. [CrossRef] [PubMed]
23. Zhong, Y.; Shahidi, F. Lipophilized epigallocatechin gallate (EGCG) derivatives as novel antioxidants. J. Agric. Food Chem. 2011, 59, 6526–6533. [CrossRef] [PubMed]
24. Williams, G.; Iatropoulos, M.; Whysner, J. Safety assessment of butylated hydroxyanisole and butylated hydroxytoluene as antioxidant food additives. Food Chem. Toxicol. 1999, 37, 1027–1038. [CrossRef]
25. Martin-Rubio, A.; Sopelana, P.; Ibargoitia, M.; Guillén, M.D. Prooxidant effect of α-tocopherol on soybean oil. Global monitoring of its oxidation process under accelerated storage conditions by 1h nuclear magnetic resonance. Food Chem. 2018, 245, 312–323. [CrossRef] [PubMed]
26. Khan, M.A.; Shahidi, F. Oxidative stability of stripped and nonstripped borage and evening primrose oils and their emulsions in water. J. Am. Oil Chem. Soc. 2000, 77, 963–969. [CrossRef]
27. Frankel, E.N.; Huang, S.W.; Prior, E.; Aeschbach, R. Evaluation of antioxidant activity of rosemary extracts, carnosol and carnosic acid in bulk vegetable oils and fish oil and their emulsions. J. Sci. Food Agric. 1996, 72, 201–208. [CrossRef]
28. Hamam, F.; Shahidi, F. Synthesis of structured lipids via acidolysis of docosahexaenoic acid single cell oil (DHASCO) with capric acid. J. Agric. Food Chem. 2004, 52, 2900–2906. [CrossRef] [PubMed]
29. Maqsood, S.; Benjakul, S. Comparative studies of four different phenolic compounds on in vitro antioxidative activity and the preventive effect on lipid oxidation of fish oil emulsion and fish mince. Food Chem. 2010, 119, 123–132. [CrossRef]
30. Wang, B.; Adhikari, B.; Barrow, C.J. Optimisation of the microencapsulation of tuna oil in gelatin–sodium hexametaphosphate using complex coacervation. Food Chem. 2014, 158, 358–365. [CrossRef] [PubMed]
31. Wang, B.; Vongsvivut, J.; Adhikari, B.; Barrow, C.J. Microencapsulation of tuna oil fortified with the multiple lipophilic ingredients vitamins A, D3, E, K2, curcumin and coenzyme Q10. J. Funct. Foods 2015, 19, 893–901. [CrossRef]
32. Mazza, M.; Pomponi, M.; Janiri, L.; Bria, P.; Mazza, S. Omega-3 fatty acids and antioxidants in neurological and psychiatric diseases: An overview. Prog. Neuropsychopharmacol. Biol. Psychiatry 2007, 31, 12–26. [CrossRef] [PubMed]
33. Akanbi, T.O.; Adcock, J.L.; Barrow, C.J. Selective concentration of EPA and DHA using thermomyces lanuginosus lipase is due to fatty acid selectivity and not regioselectivity. Food Chem. 2013, 138, 615–620. [CrossRef] [PubMed]
34. Akanbi, T.O.; Barrow, C.J. Compositional information useful for authentication of krill oil and the detection of adulterants. Food Anal. Methods 2018, 11, 178–187. [CrossRef]
35. Nenadis, N.; Tsimidou, M. Observations on the estimation of scavenging activity of phenolic compounds using rapid 1, 1-diphenyl-2-picrylhydrazyl (DPPH•) tests. J. Am. Oil Chem. Soc. 2002, 79, 1191–1195. [CrossRef]
36. Rice-Evans, C.; Miller, N.; Paganga, G. Antioxidant properties of phenolic compounds. Trends Plant Sci. 1997, 2, 152–159. [CrossRef]
37. Madhujith, T.; Shahidi, F. Optimization of the extraction of antioxidative constituents of six barley cultivars and their antioxidant properties. J. Agric. Food Chem. 2006, 54, 8048–8057. [CrossRef] [PubMed]