with the collaboration of Iranian Food Science and Technology Association (IFSTA)

Document Type : Research Article

Authors

Department of Food Science and Technology, Faculty of Agriculture, Ferdowsi University of Mashhad, Mashhad, Iran.

Abstract

Introduction: Hydroxybenzoic acids are a large family of phenolic acids capable of inhibiting one of the most destructive reactions called lipid oxidation. Their antioxidant activities are markedly influenced by the number and position of phenolic OH groups. Increasing the number of electron-donating groups in the molecule and their placement at the ortho and/or para positions of the phenolic ring, could lead to the increased ability of H atom abstraction or electron donating capacity. Gentisic (3,5-dihydroxybenzoic acid) and Alpha-resoecylic (2,5-dihydroxybenzoic acid) acids are dihydroxybenzoic acids wildly dispersed in the plant tissues with some valuable biological and pharmacological properties for human health. These compounds are different in structure and position of hydroxyl groups in phenolic ring, that may had a strong in‌fluence on their antioxidant properties. In addition of structural property, environmental interference can play an important role in the antioxidant potency. Antioxidants are found to behave differently when used in different media.

Materials and methods: Partition coefficient (log P) of Gentisic acid and Alpha-resorcylic acid was measured between 1-octanol and acetate buffers. Antiradical and antioxidant activity of compounds was investigated in different medium (solvent system, purified bulk olive and soybean oils and their O/W emulsions). DPPH radical scavenging activity of gentisic acid and alpha-resorcylic acid was measured in the methanolic solvent. Progress of lipid oxidation in olive oil and soybean oil containing 200 ppm of the antioxidants at 80 oC was followed by monitoring the changes in peroxide value (PV). PV was measured spectrophotometrically at 500 nm using a UV– Vis instrument. Oxygen depletion in emulsion systems in the absence and present of the antioxidant (200 ppm) was measured using a YSI Model 5300A biological oxygen monitor at 37oC. The effectiveness of the antioxidants in bulk oils and emulsions was estimated on the basis of the induction period (IP).

Results and discussion: The obtained results indicated that the effectiveness of the Gentisic and - resorcylic acids in free radicals scavenging, was greatly affected by molecular structure of these antioxidants and environmental conditions.
Ortho position of hydroxyl group with respect to the carboxyl group in Gentisic acid, caused higher antiradical potency of Gentisic acid than α-resorcylic acid, with meta-structure, in different used mediums.
In addition, it was found that the environment plays an important role in the free radical scavenging activity of phenolic compounds. Gentisic acid with more hydrophilic structure showed better antioxidant activity in bulk oil hydrophobic systems, than emulsion systems, while -resorcylic acid with less hydrophilic structure showed better activity in O/W emulsions. Both antioxidants showed low antioxidant performance in solvent system. The polar medium of the methanol used in DPPH assay, with enhanced intermolecular hydrogen bonds, decreased the radical scavenging potency of antioxidants.

Keywords

Akoh, C. C. M., D. B. (2002). Food Lipids: Chemistry, Nutrition, and Biotechnology. New York , Basel: Marcel Dekker, Inc.
Ali, H. M., Abo-Shady, A., Sharaf Eldeen, H. A., Soror, H. A., Shousha, W. G., Abdel-Barry, O. A., & Saleh, A. M. (2013). Structural features, kinetics and SAR study of radical scavenging and antioxidant activities of phenolic and anilinic compounds. Chem Cent J, 7(1), 53.
Ashidate, K., Kawamura, M., Mimura, D., Tohda, H., Miyazaki, S., Teramoto, T., Yamamoto, Y., & Hirata, Y. (2005). Gentisic acid, an aspirin metabolite, inhibits oxidation of low-density lipoprotein and the formation of cholesterol ester hydroperoxides in human plasma. Eur J Pharmacol, 513(3), 173-179.
Billaud, C., Lecornu, D., & Nicolas, J. (1996). Substrates and Carboxylic Acid Inhibitors of a Partially Purified Polyphenol Oxidase from Gum Arabic. Journal of Agricultural and Food Chemistry, 44(7), 1668-1675.
Biskup, I., Golonka, I., Gamian, A., & Sroka, Z. (2013). Antioxidant activity of selected phenols estimated by ABTS and FRAP methods. Postepy Hig Med Dosw (Online), 67, 958-963.
Brand-Williams, W., Cuvelier, M. E., & Berset, C. (1995). Use of a free radical method to evaluate antioxidant activity. LWT - Food Science and Technology, 28(1), 25-30.
Cheng, Z., Ren, J., Li, Y., Chang, W., & Chen, Z. (2003). Establishment of a quantitative structure-activity relationship model for evaluating and predicting the protective potentials of phenolic antioxidants on lipid peroxidation. J Pharm Sci, 92(3), 475-484.
Farhoosh, R., & Hoseini-Yazdi, S.-Z. (2013). Shelf-life prediction of olive oils using empirical models developed at low and high temperatures. Food Chemistry, 141(1), 557-565.
Farhoosh, R., Johnny, S., Asnaashari, M., Molaahmadibahraseman, N., & Sharif, A. (2016). Structure-antioxidant activity relationships of o-hydroxyl, o-methoxy, and alkyl ester derivatives of p-hydroxybenzoic acid. Food Chem, 194, 128-134.
Fereidoon Shahidi, M. N. (2003). Phenolics in Food and Nutraceuticals. Boca Raton London New York Washington, D.C.: CRC Press
Gordon, M. H., Paiva-Martins, F., & Almeida, M. (2001). Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols. J Agric Food Chem, 49(5), 2480-2485.
Griffiths, L. A. (1959). On the Distribution of Gentisic Acid in Green Plants. Journal of Experimental Botany, 10(3), 437-442.
Herrmann, K. (1989). Occurrence and content of hydroxycinnamic and hydroxybenzoic acid compounds in foods. Crit Rev Food Sci Nutr, 28(4), 315-347.
Kawabata, J., Okamoto, Y., Kodama, A., Makimoto, T., & Kasai, T. (2002). Oxidative dimers produced from protocatechuic and gallic esters in the DPPH radical scavenging reaction. J Agric Food Chem, 50(19), 5468-5471.
Lima, C. F., Fernandes-Ferreira, M., & Pereira-Wilson, C. (2006). Phenolic compounds protect HepG2 cells from oxidative damage: Relevance of glutathione levels. Life Sciences, 79(21), 2056-2068.
Lingnert, H., Vallentin, K., & Eriksson, C. E. (1979). MEASUREMENT OF ANTIOXIDATIVE EFFECT IN MODEL SYSTEM. Journal of Food Processing and Preservation, 3(2), 87-103.
Marinova, E. M., & Yanishlieva, N. V. (2003). Antioxidant activity and mechanism of action of some phenolic acids at ambient and high temperatures. Food Chemistry, 81(2), 189-197.
Middleton, E., Jr., Kandaswami, C., & Theoharides, T. C. (2000). The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol Rev, 52(4), 673-751.
Perez-Gonzalez, A., Galano, A., & Alvarez-Idaboy, J. R. (2014). Dihydroxybenzoic acids as free radical scavengers: mechanisms, kinetics, and trends in activity. New Journal of Chemistry, 38(6), 2639-2652.
Reblova, Z. (2012). Effect of temperature on the antioxidant activity of phenolic acids. Czech J Food Sci, 30(2), 171-177.
Sakas, M. B., Pericin, D. M., Mandic, A. I., & Kormanjos, s. M. (2004). Antioxidant properties of ethanolic extract of sugar beet pulp. Acta Periodica Technologica.
Schaich, K. M., Shahidi, F., Zhong, Y., & Eskin, N. A. M. (2013). Chapter 11 - Lipid Oxidation. In Biochemistry of Foods (Third Edition), (pp. 419-478). San Diego: Academic Press.
Schwarz, K., Huang, S.-W., German, J. B., Tiersch, B., Hartmann, J., & Frankel, E. N. (2000). Activities of Antioxidants Are Affected by Colloidal Properties of Oil-in-Water and Water-in-Oil Emulsions and Bulk Oils. Journal of Agricultural and Food Chemistry, 48(10), 4874-4882.
Shahidi, F. (2015). 1 - Antioxidants: Principles and applications. In Handbook of Antioxidants for Food Preservation, (pp. 1-14): Woodhead Publishing.
Shahidi, F., & Wanasundara, P. K. (1992). Phenolic antioxidants. Crit Rev Food Sci Nutr, 32(1), 67-103.
Shahidi, F., & Zhong, Y. (2015). Measurement of antioxidant activity. Journal of Functional Foods, 18, Part B, 757-781.
Shantha, N. C., & Decker, E. A. (1994). Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids. J AOAC Int, 77(2), 421-424.
Sroka, Z., & Cisowski, W. (2003). Hydrogen peroxide scavenging, antioxidant and anti-radical activity of some phenolic acids. Food and Chemical Toxicology, 41(6), 753-758.
Verpoorte, R., Contin, A., & Memelink, J. (2002). Biotechnology for the production of plant secondary metabolites. Phytochemistry Reviews, 1(1), 13-25.
Yanishlieva, N., & Marinova, E. M. (1995). Effects of antioxidants on the stability of triacylglycerols and methyl esters of fatty acids of sunflower oil. Food Chemistry, 54(4), 377-382.
Yoshida, H., Kondo, I., & Kajimoto, G. (1992). Participation of free fatty acids in the oxidation of purified soybean oil during microwave heating. Journal of the American Oil Chemists’ Society, 69(11), 1136-1140.
Zhang, J., Wang, S., Guo, Y., Xu, D., Li, X., & Tang, X. (2013). Co-Oxidation Effects of Methanol on Acetic Acid and Phenol in Supercritical Water. Industrial & Engineering Chemistry Research, 52(31), 10609-10618.
Zhong, Y., & Shahidi, F. (2012). Antioxidant Behavior in Bulk Oil: Limitations of Polar Paradox Theory. Journal of Agricultural and Food Chemistry, 60(1), 4-6.
CAPTCHA Image