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CONJUGATED LINOLEIC ACID AND FATTY ACID ISOMERS IN SELECTED COLD PRESSED OILS: ANALYSIS BY GC/FID TECHNIQUE

Year 2023, Volume: 24 Issue: 4 - Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering, 289 - 299, 27.12.2023

Fatma Nur Arslan

https://doi.org/10.18038/estubtda.1315013

Abstract

The conjugated linoleic acid (CLA) isomers in cold pressed oils [pomegranate seed oil (PGSO), linseed oil (LSO), black cumin seed oil (BCSO), nettle seed oil (NSO),grape seed oil (GSO), sesame seed oil (SSO),safflower oil (SFO), pumpkin seed oil (PSO), wheat germ oil (WGO), fig seed oil (FSO), coriander oil (CO), walnut oil (WO) and coconut oil (CNO)] extracted with lab–scale screw press machine were further subjected to gas chromatography/flame ionization detection (GC/FID) analysis. The composition of polyunsaturated fatty acids (PUFAs), monounsaturated fatty acids (MUFA) and saturated fatty acids (SFAs) of the samples was also determined. The five different positional and geometric isomers of CLA [cis–9, cis–11 CLA, cis–9, trans–11 CLA, trans–9, cis–11 CLA, trans–9, trans–11 CLA and trans–10, cis–12 CLA] were also well separated by a highly polar column (100m×0.2μm×0.25mm i.d; HP–88 cyanopropyl) and an applied GC temperature program. It was concluded that the samples were all rich in total CLA (∑CLA) and they were found between 0.14% for PSO and 2.11% for SSO. The most abundant CLA isomer was in general to be cis–9, trans–11 CLA form, which represented the content of isomer between 3.15% and 72.08% of ∑CLA. Besides, the ∑SFA values were detected between 2.43% and 93.14%, ∑MUFA values were between 4.60% and 71.11% and ∑PUFA values were between 1.79% and 87.59%. Therefore, this study might offer valuable information for the introduction of new food sources, as well as incorporation into medicinal purposes and food formulations which have the potential to be commercially valuable.

Keywords

CLA Cold press oil Fatty acid Gas chromatography

Project Number

05–M–20

References

  • [1] Kramer JKG, Hernandez M, Cruz-hernandez C, et al. Combining Results of Two GC Separations Partly Achieves Except CLA Isomers of Milk Fat as Demonstrated Using Ag-Ion SPE Fractionation. Lipids 2008;43:259–73.
  • [2] Cossignani L, Giua L, Lombardi G, et al. Analysis of CLA Isomer Distribution in Nutritional Supplements by Single Column Silver-Ion HPLC. J Am Oil Chem Soc 2013;90:327–35.
  • [3] Lehmann L, Yurawecz MP. Synthesis and Isolation of trans -7 , cis -9 Octadecadienoic Acid and Other CLA Isomers by Base Conjugation of Partially Hydrogenated γ -Linolenic Acid. Lipids 2003;38:579–83.
  • [4] Delmonte P, Roach JAG, Mossoba MM, et al. Synthesis , Isolation , and GC Analysis of All the 6 , 8- to 13 , 15- cis / trans Conjugated Linoleic Acid Isomers. Lipids 2004;39:185–91.
  • [5] Bertschi I, Collomb M, Rist L, et al. Maternal Dietary Alpine Butter Intake Affects Human Milk : Fatty Acids and Conjugated Linoleic Acid Isomers. Lipids 2005;40:581–7.
  • [6] Miroslav L, Rumen D, Michal H. Retention behavior of isomeric triacylglycerols in silver-ion HPLC : Effects of mobile phase composition and temperature. J Sep Sci 2013;36:2888–900.
  • [7] Kuhnt K, Degen C, Jahreis G. 2-Propanol in the mobile phase reduces the time of analysis of CLA isomers by silver ion-HPLC. J Chromatogr B 2010;878:88–91.
  • [8] Angel M, Fuente D, Luna P, et al. Chromatographic techniques to determine conjugated linoleic acid isomers. Trends Anal Chem 2006;25:917–26.
  • [9] Rodrıguez-Castanedas JL, Pena-Egido MJ, Garcıa-Marino M, et al. Quantitative determination of conjugated linoleic acid isomers by silver ion HPLC in ewe milk fat. J Food Compos Anal 2011;24:1004–8.
  • [10] Katarzyna T, Wszołek M. Comparative study of walnut and Camelina sativa oil as a functional components for the unsaturated fatty acids and conjugated linoleic acid enrichment of kefir. LWT - Food Sci Technol 2021;147:111681.
  • [11] Martín-González MZ, Palacios H, Rodríguez MA, et al. Beneficial Effects of a Low-dose of Conjugated Linoleic Acid on Body Weight Gain and other Cardiometabolic Risk Factors in Cafeteria. Nutrients 2020;12:1–20.
  • [12] Bruen R, Fitzsimons S, Belton O. Atheroprotective effects of conjugated linoleic acid. Br J Clin Pharmacol 2017;83:46–53.
  • [13] Ramadan MF. Healthy blends of high linoleic sunflower oil with selected cold pressed oils : Functionality , stability and antioxidative characteristics. Ind Crop Prod 2013;43:65–72.
  • [14] Lutterodt H, Slavin M, Whent M, et al. Fatty acid composition , oxidative stability , antioxidant and antiproliferative properties of selected cold-pressed grape seed oils and flours. Food Chem 2011;128:391–9.
  • [15] Michotte D, Rogez H, Chirinos R, et al. Linseed oil stabilisation with pure natural phenolic compounds. Food Chem 2011;129:1228–31.
  • [16] Emin M, Mustafa S. Recovery of valuable compounds from orange processing wastes using supercritical carbon dioxide extraction. J Clean Prod 2022;375:134169.
  • [17] Argun ME, Arslan FN, Ates H, et al. A pioneering study on the recovery of valuable functional compounds from olive pomace by using supercritical carbon dioxide extraction : Comparison of perlite addition and drying. Sep Purif Technol 2023;306:122593.
  • [18] Arslan FN, Çağlar F. Attenuated Total Reflectance – Fourier Transform Infrared (ATR – FTIR) Spectroscopy Combined with Chemometrics for Rapid Determination of Cold-Pressed Wheat Germ Oil Adulteration. Food Anal Methods 2019;12:355–70.
  • [19] Kenar A, Çiçek B, Arslan FN, et al. Electron Impact – Mass Spectrometry Fingerprinting and Chemometrics for Rapid Assessment of Authenticity of Edible Oils Based on Fatty Acid Profiling. Food Anal Methods 2019;12:1369–81.
  • [20] Arslan FN. ATR–FTIRspectroscopy combined with chemometrics for rapid classification of extra virgin olive oils and edible oils from different cultivars available on the Turkish markets. Eskişehir Tech Univ J Sci Technol A- Appl Sci Eng 2018;19:926–47.
  • [21] Dedebas T, Ekici L, Sagdic O. Chemical characteristics and storage stabilities of different cold-pressed seed oils. J Food Process Preserv 2021;45.
  • [22] Sanja Kostadinovic-Velickovska* SM. Journal of Food Chemistry and Nutrition antıoxıdant actıvıty of cold pressed and refıned edıble oıls from. j Food Chemstry Nutr 2013.
  • [23] Arslan FN, Çağlar F. Attenuated Total Reflectance–Fourier Transform Infrared (ATR–FTIR) Spectroscopy Combined with Chemometrics for Rapid Determination of Cold-Pressed Wheat Germ Oil Adulteration. Food Anal Methods 2019;12:355–70.
  • [24] Gharibzahedi SMT, Mousavi SM, Hamedi M, et al. Response surface modeling for optimization of formulation variables and physical stability assessment of walnut oil-in-water beverage emulsions. Food Hydrocoll 2012;26:293–301.
  • [25] Şirinyildiz DD, Vardin AY, Yorulmaz A. The influence of microwave roasting on bioactive components and chemical parameters of cold pressed fig seed oil. Grasas y Aceites 2023;74:1–9.
  • [26] Jing P, Ye T, Shi H, et al. Antioxidant properties and phytochemical composition of China-grown pomegranate seeds. Food Chem 2012;132:1457–64.
  • [27] Marina AM, Che Man YB, Nazimah SAH, et al. Chemical properties of virgin coconut oil. JAOCS, J Am Oil Chem Soc 2009;86:301–7.

CONJUGATED LINOLEIC ACID AND FATTY ACID ISOMERS IN SELECTED COLD PRESSED OILS: ANALYSIS BY GC/FID TECHNIQUE

Year 2023, Volume: 24 Issue: 4 - Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering, 289 - 299, 27.12.2023

Fatma Nur Arslan

https://doi.org/10.18038/estubtda.1315013

Abstract

The conjugated linoleic acid (CLA) isomers in cold pressed oils [pomegranate seed oil (PGSO), linseed oil (LSO), black cumin seed oil (BCSO), nettle seed oil (NSO),grape seed oil (GSO), sesame seed oil (SSO),safflower oil (SFO), pumpkin seed oil (PSO), wheat germ oil (WGO), fig seed oil (FSO), coriander oil (CO), walnut oil (WO) and coconut oil (CNO)] extracted with lab–scale screw press machine were further subjected to gas chromatography/flame ionization detection (GC/FID) analysis. The composition of polyunsaturated fatty acids (PUFAs), monounsaturated fatty acids (MUFA) and saturated fatty acids (SFAs) of the samples was also determined. The five different positional and geometric isomers of CLA [cis–9, cis–11 CLA, cis–9, trans–11 CLA, trans–9, cis–11 CLA, trans–9, trans–11 CLA and trans–10, cis–12 CLA] were also well separated by a highly polar column (100m×0.2μm×0.25mm i.d; HP–88 cyanopropyl) and an applied GC temperature program. It was concluded that the samples were all rich in total CLA (∑CLA) and they were found between 0.14% for PSO and 2.11% for SSO. The most abundant CLA isomer was in general to be cis–9, trans–11 CLA form, which represented the content of isomer between 3.15% and 72.08% of ∑CLA. Besides, the ∑SFA values were detected between 2.43% and 93.14%, ∑MUFA values were between 4.60% and 71.11% and ∑PUFA values were between 1.79% and 87.59%. Therefore, this study might offer valuable information for the introduction of new food sources, as well as incorporation into medicinal purposes and food formulations which have the potential to be commercially valuable.

Keywords

CLA Cold press oil Fatty acid Gas chromatography

Supporting Institution

Karamanoğlu Mehmetbey University

Project Number

05–M–20

Thanks

The study was financed by the project of Karamanoğlu Mehmetbey University (project grant 05–M–20).

References

  • [1] Kramer JKG, Hernandez M, Cruz-hernandez C, et al. Combining Results of Two GC Separations Partly Achieves Except CLA Isomers of Milk Fat as Demonstrated Using Ag-Ion SPE Fractionation. Lipids 2008;43:259–73.
  • [2] Cossignani L, Giua L, Lombardi G, et al. Analysis of CLA Isomer Distribution in Nutritional Supplements by Single Column Silver-Ion HPLC. J Am Oil Chem Soc 2013;90:327–35.
  • [3] Lehmann L, Yurawecz MP. Synthesis and Isolation of trans -7 , cis -9 Octadecadienoic Acid and Other CLA Isomers by Base Conjugation of Partially Hydrogenated γ -Linolenic Acid. Lipids 2003;38:579–83.
  • [4] Delmonte P, Roach JAG, Mossoba MM, et al. Synthesis , Isolation , and GC Analysis of All the 6 , 8- to 13 , 15- cis / trans Conjugated Linoleic Acid Isomers. Lipids 2004;39:185–91.
  • [5] Bertschi I, Collomb M, Rist L, et al. Maternal Dietary Alpine Butter Intake Affects Human Milk : Fatty Acids and Conjugated Linoleic Acid Isomers. Lipids 2005;40:581–7.
  • [6] Miroslav L, Rumen D, Michal H. Retention behavior of isomeric triacylglycerols in silver-ion HPLC : Effects of mobile phase composition and temperature. J Sep Sci 2013;36:2888–900.
  • [7] Kuhnt K, Degen C, Jahreis G. 2-Propanol in the mobile phase reduces the time of analysis of CLA isomers by silver ion-HPLC. J Chromatogr B 2010;878:88–91.
  • [8] Angel M, Fuente D, Luna P, et al. Chromatographic techniques to determine conjugated linoleic acid isomers. Trends Anal Chem 2006;25:917–26.
  • [9] Rodrıguez-Castanedas JL, Pena-Egido MJ, Garcıa-Marino M, et al. Quantitative determination of conjugated linoleic acid isomers by silver ion HPLC in ewe milk fat. J Food Compos Anal 2011;24:1004–8.
  • [10] Katarzyna T, Wszołek M. Comparative study of walnut and Camelina sativa oil as a functional components for the unsaturated fatty acids and conjugated linoleic acid enrichment of kefir. LWT - Food Sci Technol 2021;147:111681.
  • [11] Martín-González MZ, Palacios H, Rodríguez MA, et al. Beneficial Effects of a Low-dose of Conjugated Linoleic Acid on Body Weight Gain and other Cardiometabolic Risk Factors in Cafeteria. Nutrients 2020;12:1–20.
  • [12] Bruen R, Fitzsimons S, Belton O. Atheroprotective effects of conjugated linoleic acid. Br J Clin Pharmacol 2017;83:46–53.
  • [13] Ramadan MF. Healthy blends of high linoleic sunflower oil with selected cold pressed oils : Functionality , stability and antioxidative characteristics. Ind Crop Prod 2013;43:65–72.
  • [14] Lutterodt H, Slavin M, Whent M, et al. Fatty acid composition , oxidative stability , antioxidant and antiproliferative properties of selected cold-pressed grape seed oils and flours. Food Chem 2011;128:391–9.
  • [15] Michotte D, Rogez H, Chirinos R, et al. Linseed oil stabilisation with pure natural phenolic compounds. Food Chem 2011;129:1228–31.
  • [16] Emin M, Mustafa S. Recovery of valuable compounds from orange processing wastes using supercritical carbon dioxide extraction. J Clean Prod 2022;375:134169.
  • [17] Argun ME, Arslan FN, Ates H, et al. A pioneering study on the recovery of valuable functional compounds from olive pomace by using supercritical carbon dioxide extraction : Comparison of perlite addition and drying. Sep Purif Technol 2023;306:122593.
  • [18] Arslan FN, Çağlar F. Attenuated Total Reflectance – Fourier Transform Infrared (ATR – FTIR) Spectroscopy Combined with Chemometrics for Rapid Determination of Cold-Pressed Wheat Germ Oil Adulteration. Food Anal Methods 2019;12:355–70.
  • [19] Kenar A, Çiçek B, Arslan FN, et al. Electron Impact – Mass Spectrometry Fingerprinting and Chemometrics for Rapid Assessment of Authenticity of Edible Oils Based on Fatty Acid Profiling. Food Anal Methods 2019;12:1369–81.
  • [20] Arslan FN. ATR–FTIRspectroscopy combined with chemometrics for rapid classification of extra virgin olive oils and edible oils from different cultivars available on the Turkish markets. Eskişehir Tech Univ J Sci Technol A- Appl Sci Eng 2018;19:926–47.
  • [21] Dedebas T, Ekici L, Sagdic O. Chemical characteristics and storage stabilities of different cold-pressed seed oils. J Food Process Preserv 2021;45.
  • [22] Sanja Kostadinovic-Velickovska* SM. Journal of Food Chemistry and Nutrition antıoxıdant actıvıty of cold pressed and refıned edıble oıls from. j Food Chemstry Nutr 2013.
  • [23] Arslan FN, Çağlar F. Attenuated Total Reflectance–Fourier Transform Infrared (ATR–FTIR) Spectroscopy Combined with Chemometrics for Rapid Determination of Cold-Pressed Wheat Germ Oil Adulteration. Food Anal Methods 2019;12:355–70.
  • [24] Gharibzahedi SMT, Mousavi SM, Hamedi M, et al. Response surface modeling for optimization of formulation variables and physical stability assessment of walnut oil-in-water beverage emulsions. Food Hydrocoll 2012;26:293–301.
  • [25] Şirinyildiz DD, Vardin AY, Yorulmaz A. The influence of microwave roasting on bioactive components and chemical parameters of cold pressed fig seed oil. Grasas y Aceites 2023;74:1–9.
  • [26] Jing P, Ye T, Shi H, et al. Antioxidant properties and phytochemical composition of China-grown pomegranate seeds. Food Chem 2012;132:1457–64.
  • [27] Marina AM, Che Man YB, Nazimah SAH, et al. Chemical properties of virgin coconut oil. JAOCS, J Am Oil Chem Soc 2009;86:301–7.
There are 27 citations in total.

Details

Primary Language English
Subjects Analytical Chemistry (Other)
Journal Section Articles
Authors

Fatma Nur Arslan 0000-0002-5748-8268

Project Number 05–M–20
Publication Date December 27, 2023
Published in Issue Year 2023 Volume: 24 Issue: 4 - Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering

Cite

AMA Arslan FN. CONJUGATED LINOLEIC ACID AND FATTY ACID ISOMERS IN SELECTED COLD PRESSED OILS: ANALYSIS BY GC/FID TECHNIQUE. Eskişehir Technical University Journal of Science and Technology A - Applied Sciences and Engineering. December 2023;24(4):289-299. doi:10.18038/estubtda.1315013