Stability and volatile oxidation compounds of grape seed, flax seed and black cumin seed cold-pressed oils as affected by thermal oxidation

M. Kiralan; G. Çalik; S. Kiralan; A. Özaydin; G. Özkan; M. F. Ramadan

doi:10.3989/gya.0570181

Authors

M. Kiralan Department of Food Engineering, Faculty of Engineering, University of Balikesir https://orcid.org/0000-0001-7401-8025
G. Çalik Faculty of Engineering and Architecture, Department of Food Engineering, Abant Izzet Baysal University https://orcid.org/0000-0002-9031-2344
S. Kiralan Department of Food Engineering, Faculty of Engineering, University of Balikesir https://orcid.org/0000-0003-1522-064X
A. Özaydin Suleyman Demirel University, Experimental and Observational Student Research and Practice Center https://orcid.org/0000-0001-7860-8356
G. Özkan Faculty of Engineering, Department of Food Engineering, Suleyman Demirel University https://orcid.org/0000-0002-3333-7537
M. F. Ramadan Faculty of Agriculture, Biochemistry Department, Zagazig University - Deanship of Scientific Research, Umm Al-Qura University https://orcid.org/0000-0002-5431-8503

DOI:

https://doi.org/10.3989/gya.0570181

Keywords:

Linum usitatissimum, Nigella sativa, Quality control, SPME–GC/MS, Vegetable oils, Vitis vinifera, Volatile oxidation compounds

Abstract

The old-pressed oils (CPO) from grape seeds (GSO), flax seeds (FSO) and black cumin seeds (BSO) were analyzed for their fatty acid profiles, tocopherols, total phenolics, bioactives and phenolic compositions. The stability of CPO under thermal oxidation conditions was evaluated. The main fatty acid in FSO was linolenic acid (56.5% of total fatty acids); while GSO and BSO were rich in linoleic acid, which accounted for 66.8 and 56.8%, respectively. GSO was rich in ?-tocopherol (123.0 mg/kg), while ?-tocopherol was a prevalent isomer in FSO and BSO (137.9 and 128.9 mg/kg, respectively). The total phenolic contents in the oils ranged from 554 mg GAE/kg oil (FSO) to 1140 mg GAE/kg oil (BSO). Luteolin, dihydroquercetin and benzoic acids were the dominant bioactives and phenolics in FSO, GSO and BSO, respectively. Based on the oxidative stability index (OSI) value, BSO showed the highest value (6.14 h) among the other oils. The oxidative stability of FSO and BSO were higher than GSO according to peroxide value (PV) and conjugated diene (CD) values of the oils during storage at 60 °C. Hexanal, 2,4-heptadienal and (E,E)-2,4-heptadienal were the major volatile oxidation compounds (VOC) in FSO. Hexanal and (E)-2-heptanal were the main identified VOC in the GSO and BSO under the same oxidation conditions.

Downloads

Download data is not yet available.

References

Abuzaytoun R, Shahidi F. 2006. Oxidative stability of flax and hemp oils. J. Am. Oil Chem. Soc. 83, 855-861. https://doi.org/10.1007/s11746-006-5037-7

AOCS. 1997. In: Firestone D (ed) Official Methods and Recommended Practices of the American Oil Chemists' Society, 4th edn. American Oil Chemists' Society, Champaign. The Society.

AOCS. 2003. Official Methods and Recommended Practices of the American Oil Chemist's Society (5th ed.). Champaign, Illinois, U.S.A.

Apaydin D, Demirci AS, Gecgel U. 2017. Effect of gamma irradiation on biochemical properties of grape seeds. J. Am. Oil Chem. Soc. 94, 57–67. https://doi.org/10.1007/s11746-016-2917-3

Bail S, Stuebiger G, Krist S, Unterweger H, Buchbauer G. 2008. Characterisation of various grape seed oils by volatile compounds, triacylglycerol composition, total phenols and antioxidant capacity. Food Chem. 108, 1122-1132. https://doi.org/10.1016/j.foodchem.2007.11.063 PMid:26065780

Bozan B, Temelli F. 2008. Chemical composition and oxidative stability of flax, safflower and poppy seed and seed oils. Biores. Technol. 99, 6354-6359. https://doi.org/10.1016/j.biortech.2007.12.009 PMid:18198133

Brühl L, Matthäus B, Scheipers A, Hofmann T. 2008. Bitter off-taste in stored cold-pressed linseed oil obtained from different varieties. E. J. Lipid Sci. Technol. 110, 625-631. https://doi.org/10.1002/ejlt.200700314

Caponio F, Gomes T, Pasqualone A. 2001. Phenolic compounds in virgin olive oils: influence of the degree of olive ripeness on organoleptic characteristics and shelf-life. E. Food Res. Technol. 212, 329-333. https://doi.org/10.1007/s002170000268

Cheikh-Rouhou S, Besbes S, Hentati B, Blecker C, Deroanne C, Attia H. 2007. Nigella sativa L.: Chemical composition and physicochemical characteristics of lipid fraction. Food Chem. 101, 673-681. https://doi.org/10.1016/j.foodchem.2006.02.022

Choe E, Min DB. 2006. Mechanisms and factors for edible oil oxidation. Com. Rev. in Food Sci. Food Saf. 5, 169-186.

Choo W-S, Birch J, Dufour J-P. 2007. Physicochemical and quality characteristics of cold-pressed flaxseed oils. J. Food Comp. Anal. 20, 202-211. https://doi.org/10.1016/j.jfca.2006.12.002

Emir DD, Güne?er O, Yilmaz E. 2014. Cold pressed poppy seed oils: Sensory properties, aromatic profiles and consumer preferences. Grasas Aceites 65, e029. https://doi.org/10.3989/gya.109213

Fernandes L, Casal S, Cruz R, Pereira JA, Ramalhosa E. 2013. Seed oils of ten traditional Portuguese grape varieties with interesting chemical and antioxidant properties. Food Res. Int. 50, 161-166. https://doi.org/10.1016/j.foodres.2012.09.039

Frankel EN, Neff WE, Selke E. 1981. Analysis of autoxidized fats by gas chromatography-mass spectrometry: VII. Volatile thermal decomposition products of pure hydroperoxides from autoxidized and photosensitized oxidized methyl oleate, linoleate and linolenate. Lipids 16, 279-285. https://doi.org/10.1007/BF02534950

Gromadzka J, Wardencki W, Lores M, LLompart M, Fernandez- Alvarez M, Lipinska K. 2008. Investigation of edible oils oxidation stability using photooxidation and SPME-GC method for determination of volatile compounds-preliminary investigation. Pol. J. Food Nut. Sci. 58, 321-324.

Hamed SF, Abo-Elwafa GA. 2012. Enhancement of oxidation stability of flax seed oil by blending with stable vegetable oils. J. App. Sci. Res. 8, 5039-5048.

Hassanien MMM, Abdel-Razek AG, Rudzi?ska M, Siger A, Ratusz K, Przybylski R. 2014. Phytochemical contents and oxidative stability of oils from non-traditional sources. Eur. J. Lipid Sci. Technol. 116, 1563-1571. https://doi.org/10.1002/ejlt.201300475

Hidalgo FJ, Gómez G, Navarro JL, Zamora R. 2002. Oil stability prediction by high-resolution 13C nuclear magnetic resonance spectroscopy. J. Agric. Food Chem. 50, 5825-5831. https://doi.org/10.1021/jf0256539 PMid:12358445

IUPAC. 1987. Standard methods for the analysis of oils, fats and derivatives: International Union of Pure and Applied Chemistry (IUPAC) Method 2.301, Report of IUPAC Working Group WG 2/87 Blackwell Scientific Publications, Palo Alto, CA, USA.

Ivanova-Petropulos V, Mitrev S, Stafilov T, Markova N, Leitner E, Lankmayr E, Siegmund B. 2015. Characterisation of traditional Macedonian edible oils by their fatty acid composition and their volatile compounds. Food Res. Int. 77, 506-514. https://doi.org/10.1016/j.foodres.2015.08.014

Jang S, Lee J, Choi WS. 2015. Oxidative stability of grape seed oil by addition of grape seed extract. J. Korean Soc. Food Sci. Nut. 44, 1813-1818. https://doi.org/10.3746/jkfn.2015.44.12.1813

Jele? HH, Obuchowska M, Zawirska-Wojtasiak R, Wa?sowicz E. 2000. Headspace solid-phase microextraction use for the characterization of volatile compounds in vegetable oils of different sensory quality. J. Agric. Food Chem. 48, 2360- 2367.

Kasote DM, Badhe YS, Hegde MV. 2013. Effect of mechanical press oil extraction processing on quality of linseed oil. Ind. Crops Prod. 42, 10-13. https://doi.org/10.1016/j.indcrop.2012.05.015

Kiralan M, Özkan G, Bayrak A, Ramadan MF. 2014. Physicochemical properties and stability of black cumin (Nigella sativa) seed oil as affected by different extraction methods. Ind. Crops Prod. 57, 52–58. https://doi.org/10.1016/j.indcrop.2014.03.026

Kiralan M, Ramadan MF. 2016. Volatile oxidation compounds and stability of safflower, sesame and canola cold-pressed oils as affected by thermal and microwave treatments. J. Oleo Sci. 65, 825-833. https://doi.org/10.5650/jos.ess16075

Kiralan M. 2014. Changes in volatile compounds of black cumin (Nigella Sativa L.) seed oil during thermal oxidation. International J. Food Prop. 17, 1482-1489. https://doi.org/10.1080/10942912.2012.723231

Kiralan M, Çalik G, Kiralan S, Ramadan MF. 2018. Monitoring stability and volatile oxidation compounds of coldpressedflax seed, grape seed and black cumin seed oils upon photo-oxidation. J. Food Measur. Charact. 12, 616- 621. https://doi.org/10.1007/s11694-017-9674-3

Kiralan M, Ula? M, Özaydin AG, Özdemir N, Özkan G, Bayrak A, Ramadan MF. 2017. Blends of cold pressed black cumin oil and sunflower oil with improved stability: A study based on changes in the levels of volatiles, tocopherols and thymoquinone during accelerated oxidation conditions. J. Food Biochem. 41, e12272. https://doi.org/10.1111/jfbc.12272

Koski A, Psomiadou E, Tsimidou M, Hopia A, Kefalas P, Wähälä K, Heinonen M. 2002. Oxidative stability and minor constituents of virgin olive oil and cold-pressed rapeseed oil. Eur. Food Res. Tech. 214, 294-298. https://doi.org/10.1007/s00217-001-0479-5

Krist S, Stuebiger G, Bail S, Unterweger H. 2006. Analysis of volatile compounds and triacylglycerol composition of fatty seed oil gained from flax and false flax. Eur. J. Lipid Sci. Tech. 108, 48-60. https://doi.org/10.1002/ejlt.200500267

Lutterodt H, Luther M, Slavin M, Yin J-J, Parry J, Gao J-M, Yu L. 2010. Fatty acid profile, thymoquinone content, oxidative stability, and antioxidant properties of cold-pressed black cumin seed oils. LWT-Food Sci. Tech. 43, 1409-1413.

Lutterodt H, Slavin M, Whent M, Turner E, Yu L. 2011. Fatty acid composition, oxidative stability, antioxidant and antiproliferative properties of selected cold-pressed grape seed oils and flours. Food Chem. 128, 391-399. https://doi.org/10.1016/j.foodchem.2011.03.040 PMid:25212146

Matthäus B, Brühl L. 2003. Quality of cold-pressed edible rapeseed oil in Germany. Food/Nahrung 47, 413-419.

Parker TD, Adams DA, Zhou K, Harris M, Yu L. 2003. Fatty acid composition and oxidative stability of cold-pressed edible seed oils. J. Food Sci. 68, 1240-1243. https://doi.org/10.1111/j.1365-2621.2003.tb09632.x

Parry J, Su L, Luther M, Zhou K, Yurawecz MP, Whittaker P, Yu L. 2005. Fatty acid composition and antioxidant properties of cold-pressed marionberry, boysenberry, ted raspberry, and blueberry seed oils. J. Agric. Food Chem. 53, 566-573. https://doi.org/10.1021/jf048615t PMid:15686403

Porto Cda, Porretto E, Decorti D. 2013. Comparison of ultrasound-assisted extraction with conventional extraction methods of oil and polyphenols from grape (Vitis vinifera L.) seeds. Ultrasonics Sonochem. 20, 1076–1080. https://doi.org/10.1016/j.ultsonch.2012.12.002 PMid:23305938

Prescha A, Grajzer M, Dedyk M, Grajeta H. 2014. The antioxidant activity and oxidative stability of cold-pressed oils. J. Am. Oil Chem. Soc. 91, 1291-1301. https://doi.org/10.1007/s11746-014-2479-1 PMid:25076788 PMCid:PMC4110403

Raczyk M, Popis E, Kruszewski B, Ratusz K, Rudzi?ska M. 2016. Physicochemical quality and oxidative stability of linseed (Linum usitatissimum) and camelina (Camelinasativa) cold-pressed oils from retail outlets. Eur. J. Lipid Sci. Technol. 118, 834-839. https://doi.org/10.1002/ejlt.201500064

Ramadan MF. 2007. Nutritional value, functional properties and nutraceutical applications of black cumin (Nigella sativa L.) oilseeds: An overview. Int. J. Food Sci. Tech. 42, 1208- 1218. https://doi.org/10.1111/j.1365-2621.2006.01417.x

Ramadan MF. 2013. Healthy blends of high linoleic sunflower oil with selected cold pressed oils: Functionality, stability and antioxidative characteristics. Ind. Crops Prod. 43, 65-72. https://doi.org/10.1016/j.indcrop.2012.07.013

Ramadan MF, Mörsel J-T. 2004. Oxidative stability of black cumin (Nigella sativa L.), coriander (Coriandrum sativum L.) and niger (Guizotia abyssinica Cass.) crude seed oils upon stripping. Eur. J. Lipid Sci. Tech. 106, 35-43. https://doi.org/10.1002/ejlt.200300895

Ramadan MF, Asker MMS, Tadros M. 2012. Antiradical and antimicrobial properties of cold-pressed black cumin and cumin oils. Eur. Food Res. Tech. 234, 833–844. https://doi.org/10.1007/s00217-012-1696-9

Rudzi?ska M, Hassanein MMM, Abdel–Razek AG, Ratusz K, Siger A. 2016. Blends of rapeseed oil with black cumin and rice bran oils for increasing the oxidative stability. J. Food Sci. Tech. 53, 1055-1062.

Siger A, Nogala-Kalucka M, Lampart-Szczapa E. 2008. The content and antioxidant activity of phenolic compounds in cold-pressed plant oils. J. Food Lipids 15, 137-149. https://doi.org/10.1111/j.1745-4522.2007.00107.x

Snyder JM, Frankel EN, Selke E. 1985. Capillary gas chromatographic analyses of headspace volatiles from vegetable oils. J. Am. Oil Chem. Soc. 62, 1675. https://doi.org/10.1007/BF02541664

Snyder JM, Frankel EN, Selke E, Warner K. 1988. Comparison of gas chromatographic methods for volatile lipid oxidation compounds in soybean oil. J. Am. Oil Chem. Soc. 65, 1617-1620. https://doi.org/10.1007/BF02912565

Takeyama E, Fukushima M. 2013. Physicochemical properties of Plukenetia volubilis L. seeds and oxidative stability of cold-pressed oil (green nut oil). Food Sci. Tech. Res. 19, 875-882. https://doi.org/10.3136/fstr.19.875

Ta?ska M, Roszkowska B, Skrajda M, D?browski G. 2016. Commercial cold pressed flaxseed oils quality and oxidative stability at the beginning and the end of their shelf life. J. Oleo Sci. 65, 111-121.

Teh SS, Birch J. 2013. Physicochemical and quality characteristics of cold-pressed hemp, flax and canola seed oils. J. Food Comp. Anal. 30, 26-31. https://doi.org/10.1016/j.jfca.2013.01.004

Tuberoso CIG, Kowalczyk A, Sarritzu E, Cabras P. 2007. Determination of antioxidant compounds and antioxidant activity in commercial oilseeds for food use. Food Chem. 103, 1494-1501. https://doi.org/10.1016/j.foodchem.2006.08.014

Van Hoed V, Depaemelaere G, Ayala JV, Santiwattana P, Verhe R, De Greyt W. 2006. Influence of chemical refining on the major and minor components of rice brain oil. J. Am. Oil Chem. Soc. 83, 315–321. https://doi.org/10.1007/s11746-006-1206-y

Vujasinovic V, Djilas S, Dimic E, Romanic R, Takaci A. 2010. Shelf Life of Cold-Pressed Pumpkin (Cucurbita pepo L.) Seed Oil Obtained with a Screw Press. J. Am. Oil Chem. Soc. 87, 1497-1505. https://doi.org/10.1007/s11746-010-1630-x

Wei CQ, Liu WY, Xi WP, Cao D, Zhang HJ, Ding M, Chen L, Xu YY, Huang KX. 2015. Comparison of volatile compounds of hot-pressed, cold-pressed and solvent-extracted flaxseed oils analyzed by SPME-GC/MS combined with electronic nose: Major volatiles can be used as markers to distinguish differently processed oils. Eur. J. Lipid Sci. Tech. 117, 320–330. https://doi.org/10.1002/ejlt.201400244

Wei C, Xi W, Nie X, Liu W, Wang Q, Yang B, Cao D. 2013. Aroma characterization of flaxseed oils using headspace solid-phase micro extraction and gas chromatography-olfactometry. Eur. J. Lipid Sci. Tech. 115, 1032-1042. https://doi.org/10.1002/ejlt.201200397

Wen X, Zhu M, Hu R, Zhao J, Chen Z, Li J, Ni Y. 2016. Characterisation of seed oils from different grape cultivars grown in China. J. Food Sci. Tech. 53, 3129-3136. https://doi.org/10.1007/s13197-016-2286-9 PMid:27765984 PMCid:PMC5052182

Wroniak M, Florowska A, Rekas A. 2016. Effect of oil flushing with nitrogen on the quality and oxidative stability of cold-pressed rapeseed and sunflower oils. Acta Sci. Polo. Tech. Alim. 15, 79-87. https://doi.org/10.17306/J.AFS.2016.1.8 PMid:28071041

Yu LL, Zhou KK, Parry J. 2005. Antioxidant properties of cold-pressed black caraway, carrot, cranberry, and hemp seed oils. Food Chem. 91, 723-729. https://doi.org/10.1016/j.foodchem.2004.06.044