Abstract
4-Vinylsyringol was produced by decarboxylation from sinapic acid. To evaluate the antioxidant activity of 4-vinylsyringol, 500 ppm of 4-vinylsyringol, sinapic acid, or α-tocopherol was added to soybean oil and the oxidation processes were monitored by the peroxide value (PV), the thiobarbituric acid reactive substances value (TBARS) assay, and 1H-NMR spectroscopy. The results obtained by PV and TBARS indicated that soybean oil containing 4-vinylsyringol (SBO-VS) showed the highest oxidative stability. 1H-NMR analysis also showed concurring results. After 19 days of oxidation, the degradation rates of linoleic acid (4.2 %) and linolenic acid (4.4 %) in SBO-VS were significantly lower than those in other oils. Secondary oxidation products (i.e. aldehydes) were undetectable in SBO-VS by 1H NMR, whereas concentrations of such compounds in soybean oils containing α-tocopherol or sinapic acid were 38.0 ± 0.4 and 2.75 ± 0.2 mM oil, respectively. In addition, synergistic antioxidant effect between any two antioxidants was not observed.
Similar content being viewed by others
References
Zarkovic N (2003) 4-Hydroxynonenal as a bioactive marker of pathophysiological processes. Mol Aspects Med 24:281–291
Uchida K, Shiraishi M, Naito Y, Torii Y, Nakamura Y, Osawa T (1999) Activation of stress signaling pathways by the end product of lipid peroxidation 4-hydroxy-2-nonenal is a potential inducer of intracellular peroxide production. J Biol Chem 274:2234–2242
Baldioli M, Servili M, Perretti G, Montedoro G (1996) Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil. J Am Oil Chem Soc 73:1589–1593
Pekkarinen S, Hopia A, Heinonen M (1999) Rapeseed oil antioxidative compounds. Bioproducts for the next millennium. Yliopistopaino, Helsinki, p 82
Pekkarinen S, Hopia A, Heinonen M (1998) Effect of processing on the oxidative stability of low erucic acid turnip rapeseed (Brassica rapa) oil. Lipid/Fett 100:69–74
Rice-Evans C, Miller N, Paganga G (1997) Antioxidant properties of phenolic compounds. Trends Plant Sci 2:152–159
Rice-Evans C, Miller N (1996) Antioxidant activities of flavonoids as bioactive components of food. Biochem Soc Trans 24:790–794
Fujioka K, Shibamoto T (2006) Quantitation of volatiles and nonvolatile acids in an extract from coffee beverages: correlation with antioxidant activity. J Agric Food Chem 54:6054–6058
Vuorela S, Salminen H, Mäkelä M, Kivikari R, Karonen M, Heinonen M (2005) Effect of plant phenolics on protein and lipid oxidation in cooked pork meat patties. J Agric Food Chem 53:8492–8497
Koski A, Pekkarinen S, Hopia A, Wähälä K, Heinonen M (2003) Processing of rapeseed oil: effects on sinapic acid derivative content and oxidative stability. Eur Food Res Technol 217:110–114
Terpinc P, Polak T, Šegatin N, Hanzlowsky A, Ulrih NP, Abramovič H (2011) Antioxidant properties of 4-vinyl derivatives of hydroxycinnamic acids. Food Chem 128:62–69
Boon CS, Xu Z, Yue X, McClements DJ, Weiss J, Decke EA (2008) Factors affecting lycopene oxidation in oil-in-water emulsions. J Agric Food Chem 56:1408–1414
Lee JH, Lee KT, Akoh CC, Chung SK, Kim MR (2006) Antioxidant evaluation and oxidative stability of structured lipids from extra virgin olive oil and conjugated linoleic acid. J Agric Food Chem 54:5416–5421
Shantha NC, Decker EA (1994) Rapid, sensitive, iron-based spectrophotometric methods for determination of peroxide values of food lipids. J AOAC Int 77:421–424
Pegg RB (2005) Spectrophotometric measurement of secondary lipid oxidation products. In: Wrolstad RE, Decker EA, Schwartz SJ, Sporns P (eds) Handbook of food analytical chemistry, water, proteins, enzymes, lipids, and carbohydrates. Wiley-Interscience, Hoboken, pp 547–564
SPSS Statistics, Release 16.01 (2007) SPSS Inc., Chicago
Spielmeyer A, Wagner A, Jahreis G (2009) Influence of thermal treatment of rapeseed on the canolol content. Food Chem 112:944–948
Bernini R, Mincione E, Barontini M, Provenzano G, Setti L (2007) Obtaining 4-vinylphenols by decarboxylation of natural 4-hydroxycinnamic acids under microwave irradiation. Tetrahedron 63:9663–9667
Park EY, Murakami H, Mori T, Matsumura Y (2005) Effects of protein and peptide addition on lipid oxidation in powder model system. J Agric Food Chem 53:137–144
Knothe G, Kenar JA (2004) Determination of the fatty acid profile by 1H-NMR spectroscopy. Eur J Lipid Sci Technol 106:88–96
Halliwell B, Chirico S (1993) Lipid peroxidation: its mechanism, measurement, and significance. Am J Clin Nutr 57:715S–724S
Haywood RM, Claxson AWD, Hawkes GE, Richardson DP, Naughton DP, Coumbarides G, Hawkes J, Lynch EJ, Grootveld MC (1995) Detection of aldehydes and their conjugated hydroperoxydiene precursors in thermally stressed culinary oils and fats: investigations using high resolution proton NMR spectroscopy. Free Radic Res 22:441–482
Goicoechea E, Guillen MD (2010) Analysis of hydroperoxides, aldehydes and epoxides by 1H nuclear magnetic resonance in sunflower oil oxidized at 70 and 100 C. J Agric Food Chem 58:6234–6245
Juntachote T, Berghofer E, Siebenhandl S, Bauer F (2006) The antioxidative properties of Holy basil and Galangal in cooked ground pork. Meat Sci 72:446–456
Janero DR (1990) Malondialdehyde and thiobarbituric acid-reactivity as diagnostic indices of lipid peroxidation and peroxidative tissue injury. Free Radic Biol Med 9:515–540
Guillen MD, Goicoechea E (2009) Oxidation of corn oil at room temperature: primary and secondary oxidation products and determination of their concentration in the oil liquid matrix from 1H nuclear magnetic resonance data. Food Chem 116:183–192
Hideo K, Ayako K, Daisuke W, Shigeru M, Kenji K, Takaaki A, Hiroshi M (2004) Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil. J Agric Food Chem 52:4380–4387
Aleksandra SC, Iwona BB, Igor K, György K, Edward S (2011) Antioxidant capacity, total phenolics, glucosinolates and colour parameters of rapeseed cultivars. Food Chem 127:556–563
Acknowledgments
This work was carried out with the support of “The Cooperative Research Program for Agriculture Science & Technology Development (Project No.PJ 009164)” Rural Development Administration, Republic of Korea.
Author information
Authors and Affiliations
Corresponding author
About this article
Cite this article
Wang, XY., Yang, D., Zhang, H. et al. Antioxidant Activity of Soybean Oil Containing 4-Vinylsyringol Obtained from Decarboxylated Sinapic Acid. J Am Oil Chem Soc 91, 1543–1550 (2014). https://doi.org/10.1007/s11746-014-2492-4
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11746-014-2492-4