Abstract
This study evaluated contribution of minor compounds naturally present in peppermint (Mentha piperita) to the iron-catalyzed lipid oxidation of oil-in-water emulsion. Emulsions consisted of tocopherol-stripped soybean oil and pH 4.0 citrate buffer (4:6, w/w) with iron. Minor compounds included α-tocopherol, rosmarinic acid, caffeic acid, β-carotene, and chlorophyll b at natural concentration in 400 ppm of the peppermint extract. The emulsions were oxidized in the dark, and headspace oxygen contents, hydroperoxide contents, and p-anisidine values were determined. Addition of phenolic compounds decreased headspace oxygen consumption and hydroperoxide and p-anisidine values of emulsions, however, β-carotene or chlorophyll b tended to increase them. The results suggest that tocopherols at low concentration were the most important to reduce lipid oxidation of emulsions via radical scavenging, followed by high contents of polyphenols via radical scavenging and iron-chelation. Carotenoids and chlorophylls should be precisely controlled even in the dark, possibly due to their oxidation products.
Similar content being viewed by others
References
Adomako-Bonsu AG, Chan SLF, Pratten M, Fry JR. Antioxidant activity of rosmarinic acid and its principal metabolites in chemical and cellular systems: Importance of physico-chemical characteristics. Toxicol. In Vitro 40: 248–255 (2017)
AOAC. Official Method of Analysis of AOAC Intl. 18th ed. Method 970.64. Association of Official Analytical Chemists, Gaithersburg, MD, USA (2005)
AOCS. Official Methods and Recommended Practices of the American Oil Chemists’ Society. 4th ed. Method Cd 18-90. AOCS Press, Champaign, IL, USA (2006)
Banerjee A, Kunwar A, Mishra B, Priyadarsini KI. Concentration dependent antioxidant/pro-oxidant activity of curcumin, Studies from AAPH induced hemolysis of RBCs. Chem. Biol. Interact. 174: 134–139 (2008)
Burton GW, Ingold KU. β-carotene: an unusual type of lipid antioxidant. Science 224: 569–573 (1984)
Cheng Z, Li Y, Chang W. Kinetic deoxyribose degradation assay and its application in assessing the antioxidant activities of phenolic compounds in a Fenton-type reaction system. Anal. Chim. Acta 478: 129–137 (2003)
Choe E, Min DB. Mechanisms and factors for edible oil oxidation. Comp. Rev. Food Sci. Food Saf. 5: 169–186 (2006)
Choe E. Min DB. Mechanisms of antioxidants in the oxidation of foods. Comp. Rev. Food Sci. Food Saf. 8: 345–358 (2009)
Choe J, Choe E. Effect of soy-derived phospholipid on the autoxidation of canola oil in a water/oil emulsion. J. Am. Oil Chem. Soc. 93: 1085–1094 (2016)
de Arruda GR, Canniatti-Brazaca SG. Iron availability in the presence of β-carotene in different mixtures. Ciênc. Tecnol. Aliment. Campinas. 31: 327–333 (2011)
Fukumoto LR, Mazza G. Assessing antioxidant and prooxidant activities of phenolic compounds. J. Agric. Food Chem. 48: 3597–3604 (2000)
Guedon DJ, Pasquier BP. Analysis and distribution of flavonoid glycosides and rosmarinic acid in 40 Mentha piperita clones. J. Agric. Food Chem. 42: 679–684 (1994)
Gulcin I, Buyukokuroglu ME, Kufrevioglu OI. Metal chelating and hydrogen peroxide scavenging effects of melatonin. J. Pineal Res. 34: 278–281 (2003)
Hadjmohammadi M, Karimiyan H, Sharifi V. Hollow fibre-based liquid phase microextraction combined with high-performance liquid chromatography for the analysis of flavonoids in Echinophora platyloba DC and Mentha piperita. Food Chem. 141: 731–735 (2013)
Hahm TS. Effects of initial peroxide contents on the oxidative stability of soybean oil to prevent environmental pollution. J. Environ. Research 1:112–120 (1988)
Hernández-Marin E, Barbosa A, Martínez A. The metal cation chelating capacity of astaxanthin. Does this have any influence on antiradical activity? Molecules 17: 1039–1054 (2012)
Hsu C-Y, Chao P-Y, Hu S-P, Yang C-M. The antioxidant and free radical scavenging activities of chlorophylls and pheophytins. Food Nutr. Sci. 4: 1–8 (2013)
Iannone A, Rota C, Bergamini S, Tomasi A, Canfield LM. Antioxidant activity of carotenoids: an electron-spin resonance study on β-carotene and lutein interaction with free radicals generated in a chemical system. J. Biochem. Mol. Toxicol. 12: 299–304 (1998)
Kim J, Choe E. Effect of the pH on the lipid oxidation and polyphenols of soybean oil-in-water emulsion with added peppermint (Mentha piperita) extract in the presence and absence of iron. Food Sci. Biotechnol. 27: In press (2018)
Kim J, Choe E. Effects of selected herb extracts on iron-catalyzed lipid oxidation in soybean oil-in-water emulsion. Food Sci. Biotechnol. 25: 1017–1022 (2016)
Kim J, Choe E. Improvement of the lipid oxidative stability of soybean oil-in water emulsion by addition of daraesoon (shoot of Actinidia arguta) and samnamul (shoot of Aruncus dioicus) extract. Food Sci. Biotechnol. 26: 113–119 (2017)
Kovacheva E, Georgiev M, Pashova S, Angelova M, Ilieva M. Radical quenching by rosmarinic acid from Lavandula vera MM cell culture. Z. Naturforsch C. 61: 517–520 (2006)
Kumarappan CT, Thilagam E, Mandal SC. Antioxidant activity of polyphenolic extracts of Ichnocarpus frutescens. Saudi J. Biol. Sci. 19: 349–355 (2012)
Lambert JD, Elias RJ. The antioxidant and pro-oxidant activities of green tea polyphenols: a role in cancer prevention. Arch. Biochem. Biophys. 501: 65–72 (2010)
Lee E, Ahn H, Choe E. Effects of light and lipids on chlorophyll degradation. Food Sci. Biotechnol. 23: 1061–1065 (2014)
Mochizuki M, Yamazaki S, Kano K, Ikeda T. Kinetic analysis and mechanistic aspects of autoxidation of catehins. Biochim. Biophys. Acta 1569: 35–44 (2002)
Reische DW, Lillard DA, Eitenmiller RR. Antioxidants. pp. 489–516. In: Food Lipids. Akoh CC, Min DB (eds). Marcel Dekker Inc., New York, NY, USA (2002)
Rontani J-F, Aubert C. Characterization of isomeric allylic diols resulting from chlorophyll phytyl side-chain photo- and autoxidation by electron ionization gas chromatography/mass spectrometry. Rapid Commun. Mass Sp. 19: 637–646 (2005)
Rontani J-F, Aubert C. Effect of oxy-free radicals upon the phytyl chain during chlorophyll-a photodegradation. J. Photochem. Photobiol. A 79: 167–172 (1994)
Simić A, Manojlović D, Šegan D, Todorović M. Electrochemical behavior and antioxidant and prooxidant activity of natural phenolics. Molecules 12: 2327–2340 (2007)
Song A, Choe E. Effect of sannamul and herb extract addition on the photooxidation of soybean oil emulsion. Korean J. Food Cook. Sci. 33: 275–284 (2017)
Tsuchihashi H, Kigoshi M, Iwatsuki M, Niki E. Action of beta-carotene as an antioxidant against lipid peroxidation. Arch. Biochem. Biophys. 323:137–147 (1995)
Yüksek H, Alkan M, Cakmak I, Ocak Z, Bahçeci Ş Calapoğlu M, Elmastaş M, Kolomuç A, Aksu H. Preparation, GIAO NMR calculations and acidic properties of some novel 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives with their antioxidant activities. Int. J. Mol. Sci. 9: 12–32 (2008)
Zvezdanovic J, Markovic D. Copper, iron, and zinc interactions with chlorophyll in extracts of photosynthetic pigments studied by Vis spectroscopy. Russ. J. Phys. Chem. A. 83: 1542–1546 (2009)
Acknowledgements
This research was supported by the Inha University (55832-01), for which the authors are grateful.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare no conflict of interest.
Rights and permissions
About this article
Cite this article
Lee, H., Choe, E. Contribution of minor compounds present in the peppermint (Mentha piperita) to the iron-catalyzed lipid oxidation of soybean oil-in-water emulsion. Food Sci Biotechnol 27, 1319–1325 (2018). https://doi.org/10.1007/s10068-018-0386-1
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10068-018-0386-1