Research Article | | Peer-Reviewed

L-proline Interaction with Methyl Linoleate Oxidation Products Formation in Dry System and at Temperatures: For Understanding in Low-Moisture Foods

Received: 20 March 2024    Accepted: 7 April 2024    Published: 29 April 2024
Views:       Downloads:
Abstract

Dry and low-moisture foods could experience a significant loss in nutritional value due to the process of methyl linoleate oxidation. L-proline could interact with lipid oxidation products, potentially modifying their formation and reaction path. However, there was a lack of research on the interaction between L-proline and methyl linoleate oxidation products in dry and low-moisture food matrices, which was a concern given the potential impact on food safety and nutrition. To address this knowledge gap, a study investigated the interaction between L-proline and the oxidation products of methyl linoleate in a dry system. The study examined the formation of methyl linoleate oxidation products such as conjugated dienes, hydroperoxide, and hexanal in the absence and presence of varying moles of L-proline at different temperatures. The formation of conjugated diene, hydroperoxide, and hexanal was analyzed using UV spectrometer analysis, xylenol orange, and DNPH derivatization HPLC-UV analysis. The results showed that adding proline to methyl linoleate samples stabilized conjugated diene and decreased hydroperoxide and hexanal levels as temperature increased, compared to the control sample. This suggests that L-proline effectively interacted with methyl linoleate oxidation products and altered their formation and oxidation path in the dry system. Overall, this study provided a basis for significantly enhancing understanding of the reactions between L-proline and methyl linoleate oxidation products in dry and low-moisture foods, offered practical implications for the food industry, and paved the way for future research.

Published in International Journal of Nutrition and Food Sciences (Volume 13, Issue 2)
DOI 10.11648/j.ijnfs.20241302.15
Page(s) 38-55
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Oxidized Lipids, Amino Acid, Interaction, Co-oxidation, Arid System, High Oxidation, Autoxidation, Lipid Oxidation Markers

References
[1] Partanen, R., Raula, J., Seppänen, R., Buchert, J., Kauppinen, E., and Forssell, P., Effect of relative humidity on oxidation of flaxseed oil in spray dried whey protein emulsions. J Agric Food Chem. 2008; 56(14), 5717-5722.
[2] Kim, J., Kim, M., and Lee, J. Role of moisture on the lipid oxidation determined by D(2)O in a linoleic acid model system. Food Chem. 2014, 146, 134-140.
[3] Vieira, S., Zhang, G., and Decker, E. Biological Implications of Lipid Oxidation Products. J Am Oil Chem Soc, 2017, 94, 339-351.
[4] Feussner, I., and Wasternack, C. The lipoxygenase pathway. Annu Rev Plant Biol. 2002, 53, 275-297.
[5] Schaich, K., Shahidi, F., Zhong, Y., and Eskin, N. A. M. Lipid Oxidation. In: Biochemistry of Foods, Third Edition, Ed. Eskin, N. A. M., Elsevier, 2013, pp. 419-478.
[6] Gumus, C., and Decker, E. Oxidation in Low Moisture Foods as a Function of Surface Lipids and Fat Content. Foods. 2021, 10(4), 860.
[7] Hardas, N., Danvirivakul, S., Foley, J. L., Nawar, W. W. and Chinachoti, P. Effect of relative humidity on the oxidative and physical stability of encapsulated milk fat. J Amer Oil Chem Soc, 2002, 79, 151-158.
[8] Decker, E., & Bayram, I., Why does lipid oxidation in foods continue to be such a challenge? INFORM - International News on Fats. 2021, 32(5) 18-23.
[9] Signorelli, S., Coitiño, E. L., and Borsani. O., Monza, J., Molecular mechanisms for the reaction between (˙)OH radicals and proline: insights on the role as reactive oxygen species scavenger in plant stress. J Phys Chem B., 2014, 118(1), 37-47.
[10] Spiteller, G., Peroxyl radicals: inductors of neurodegenerative and other inflammatory diseases. Their origin and how they transform cholesterol, phospholipids, plasmalogens, polyunsaturated fatty acids, sugars, and proteins into deleterious products. Free Radic Biol Med. 2006, 41(3), 362-387.
[11] Hidalgo, F., and Zamora, R., Amino Acid Degradations Produced by Lipid Oxidation Products. Critical reviews in food science and nutrition. 2016, 56(8), 1242-1252.
[12] Schaich, K., Co-oxidations of oxidizing lipids: Reactions with proteins, in Lipid Oxidation Pathways, Chapter 8, Vol 2, ed. Kamal-Eldin, A. and Min, D., AOCS Press, 2008, pp. 183-274.
[13] American Oil Chemistry Society, Official Method Ti 1a-64, “Spectrophotometric Determination of Conjugated Dienoic Acid in Dehydrated Castor Oils and Acids”
[14] Xiong, Y., and Guo, A. Animal and Plant Protein Oxidation: Chemical and Functional Property Significance. Foods. 2020, 10(1), 40.
[15] Kleinveld HA, Hak-Lemmers HL, Stalenhoef AF, Demacker PN. Improved measurement of low-density-lipoprotein susceptibility to copper-induced oxidation: application of a short procedure for isolating low-density lipoprotein. Clin Chem. 1992 Oct; 38(10): 2066-72. PMID: 1394991.
[16] Yildiz, G., Wehling, R., and Cuppett, S. Comparison of four analytical methods for the determination of peroxide value in oxidized soybean oils. J Amer Oil Chem Soc. 2003, 80, 103–107.
[17] Sigma-Aldrich, “PeroxiDetect™ Kit”
[18] Steltzer, E., Evaluation of chemical assays for determining hydroperoxides levels in oxidized lipids. M. S. Thesis, Rutgers, The State University of New Jersey, May 2012.
[19] DeLong, J., Prange, R., Hodges, D., Forney, C., Bishop, M., and Quilliam, M., Using a Modified Ferrous Oxidation−Xylenol Orange (FOX) Assay for Detection of Lipid Hydroperoxides in Plant Tissue. Journal of agricultural and food chemistry. 2002, 50, 248-54.
[20] Xie, Jia. Evidence for multiple oxidation pathways from non-volatile products of methyl linoleate. Ph. D. Thesis, Rutgers, The State University of New Jersey, May 2015. Retrieved from
[21] Gunstone, F. D., Harwood, J. L., & Harwood, J. L. The Lipid Handbook with CD-ROM (3rd ed.). CRC Press; 2007, pp. 470-534.
[22] Walstra, P. Aspects of Thermodynamics. Physical Chemistry of Foods (1st ed.). CRC Press; 2001, pp. 9-41.
[23] Hartel, R. Advances in food crystallization. Annu Rev Food Sci Technol. 2013, 4, 277-292.
[24] Frankel, E. Chapter 1- Free radical Oxidation, Lipid Oxidation (Second Edition) Woodhead Publishing, 2012, pp. 15-24.
[25] Kaul, S., Sharma, S., Mehta. I. Free radical scavenging potential of L-proline: evidence from in vitro assays. Amino Acids. 2008, 34(2), 315-320.
[26] Yunping, Y., Tianliang, W., Zhiyuan, Q., Wenqi, D., & Changmo, L. Mechanisms of the Formation of Nonvolatile and Volatile Oxidation Products from Methyl Linoleic Acid at High Temperatures. Journal of Agricultural and Food Chemistry, 2024, 72(1), 704-714.
[27] Frankel, E. N., Huang, S., Prior, E. M., & Aeschbach, R. Evaluation of Antioxidant Activity of Rosemary Extracts, Carnosol and Carnosic Acid in Bulk Vegetable Oils and Fish Oil and Their Emulsions. Journal of the Science of Food and Agriculture, 1996, 72, 201-208.
[28] Pignoli, G., Bou, R., Rodriguez-Estrada, M. T., & Decker, E. A. Suitability of saturated aldehydes as lipid oxidation markers in washed turkey meat. Meat science, 2009, 83(3), 412–416.
[29] McWEENY, D.J. Reactions in food systems: negative temperature coefficients and other abnormal temperature effects. International Journal of Food Science & Technology, 1968, 3: 15-30.
[30] Dix, T. A., & Marnett, L. J.. Hematin-catalyzed rearrangement of hydroperoxylinoleic acid to epoxy alcohols via an oxygen rebound. Journal of the American Chemical Society, 1983, 105(23), 7001-7002.
[31] Girotti AW. Lipid hydroperoxide generation, turnover, and effector action in biological systems. J Lipid Res. 1998, 39(8), 1529-1542. (PMID: 9717713)
[32] Decker, E. A., and McClements, D. J. Transition metal and hydroperoxide interactions: An important determinant in the oxidative stability of lipid dispersions. Inform, 2001, 12, 251-255.
[33] Musakhanian, J., Rodier, J. D., & Dave, M. Oxidative Stability in Lipid Formulations: a Review of the Mechanisms, Drivers, and Inhibitors of Oxidation. AAPS PharmSciTech, 2022, 23(5), 151.
[34] Halliwell, B., & Gutteridge, J. M. Role of free radicals and catalytic metal ions in human disease: an overview. Methods in enzymology, 1990, 186, 1–85.
[35] Karel, M. Lipid Oxidation, Secondary Reactions, and Water Activity of Foods. In: Simic, M. G., Karel, M. (eds) Autoxidation in Food and Biological Systems. Springer, Boston, MA, 1980, pp. 191-206.
[36] Truong, D. H., Lan Nguyen, T., H., and Dao, Q., Revisiting the HO-initiated oxidation of L-proline amino acid in the aqueous phase: influence of transition metal ions Royal Society Open Science., 2023, 10(6) http://doi.org/10.1098/rsos.230114
[37] Damodaran, S., and Parkin, K. L. (Eds.). Lipids. Fennema's Food Chemistry (5th ed.). Boca Raton, CRC Press., 2017, pp. 171-233.
[38] Barden, L., Vollmer, D., Johnson, D., and Decker, E. Impact of iron, chelators, and free fatty acids on lipid oxidation in low-moisture crackers. J Agric Food Chem. 2015, 63(6), 1812-1818.
[39] Harris, A. L., and Henry S. O. Reaction of aliphatic tertiary amines with hydroperoxides., Journal of the American Oil Chemists Society, 1966, 43, 11-14.
Cite This Article
  • APA Style

    Shah, V., Buonopane, G., Fleck, L. (2024). L-proline Interaction with Methyl Linoleate Oxidation Products Formation in Dry System and at Temperatures: For Understanding in Low-Moisture Foods. International Journal of Nutrition and Food Sciences, 13(2), 38-55. https://doi.org/10.11648/j.ijnfs.20241302.15

    Copy | Download

    ACS Style

    Shah, V.; Buonopane, G.; Fleck, L. L-proline Interaction with Methyl Linoleate Oxidation Products Formation in Dry System and at Temperatures: For Understanding in Low-Moisture Foods. Int. J. Nutr. Food Sci. 2024, 13(2), 38-55. doi: 10.11648/j.ijnfs.20241302.15

    Copy | Download

    AMA Style

    Shah V, Buonopane G, Fleck L. L-proline Interaction with Methyl Linoleate Oxidation Products Formation in Dry System and at Temperatures: For Understanding in Low-Moisture Foods. Int J Nutr Food Sci. 2024;13(2):38-55. doi: 10.11648/j.ijnfs.20241302.15

    Copy | Download

  • @article{10.11648/j.ijnfs.20241302.15,
      author = {Viral Shah and Gerald Buonopane and Louis Fleck},
      title = {L-proline Interaction with Methyl Linoleate Oxidation Products Formation in Dry System and at Temperatures: For Understanding in Low-Moisture Foods
    },
      journal = {International Journal of Nutrition and Food Sciences},
      volume = {13},
      number = {2},
      pages = {38-55},
      doi = {10.11648/j.ijnfs.20241302.15},
      url = {https://doi.org/10.11648/j.ijnfs.20241302.15},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ijnfs.20241302.15},
      abstract = {Dry and low-moisture foods could experience a significant loss in nutritional value due to the process of methyl linoleate oxidation. L-proline could interact with lipid oxidation products, potentially modifying their formation and reaction path. However, there was a lack of research on the interaction between L-proline and methyl linoleate oxidation products in dry and low-moisture food matrices, which was a concern given the potential impact on food safety and nutrition. To address this knowledge gap, a study investigated the interaction between L-proline and the oxidation products of methyl linoleate in a dry system. The study examined the formation of methyl linoleate oxidation products such as conjugated dienes, hydroperoxide, and hexanal in the absence and presence of varying moles of L-proline at different temperatures. The formation of conjugated diene, hydroperoxide, and hexanal was analyzed using UV spectrometer analysis, xylenol orange, and DNPH derivatization HPLC-UV analysis. The results showed that adding proline to methyl linoleate samples stabilized conjugated diene and decreased hydroperoxide and hexanal levels as temperature increased, compared to the control sample. This suggests that L-proline effectively interacted with methyl linoleate oxidation products and altered their formation and oxidation path in the dry system. Overall, this study provided a basis for significantly enhancing understanding of the reactions between L-proline and methyl linoleate oxidation products in dry and low-moisture foods, offered practical implications for the food industry, and paved the way for future research.
    },
     year = {2024}
    }
    

    Copy | Download

  • TY  - JOUR
    T1  - L-proline Interaction with Methyl Linoleate Oxidation Products Formation in Dry System and at Temperatures: For Understanding in Low-Moisture Foods
    
    AU  - Viral Shah
    AU  - Gerald Buonopane
    AU  - Louis Fleck
    Y1  - 2024/04/29
    PY  - 2024
    N1  - https://doi.org/10.11648/j.ijnfs.20241302.15
    DO  - 10.11648/j.ijnfs.20241302.15
    T2  - International Journal of Nutrition and Food Sciences
    JF  - International Journal of Nutrition and Food Sciences
    JO  - International Journal of Nutrition and Food Sciences
    SP  - 38
    EP  - 55
    PB  - Science Publishing Group
    SN  - 2327-2716
    UR  - https://doi.org/10.11648/j.ijnfs.20241302.15
    AB  - Dry and low-moisture foods could experience a significant loss in nutritional value due to the process of methyl linoleate oxidation. L-proline could interact with lipid oxidation products, potentially modifying their formation and reaction path. However, there was a lack of research on the interaction between L-proline and methyl linoleate oxidation products in dry and low-moisture food matrices, which was a concern given the potential impact on food safety and nutrition. To address this knowledge gap, a study investigated the interaction between L-proline and the oxidation products of methyl linoleate in a dry system. The study examined the formation of methyl linoleate oxidation products such as conjugated dienes, hydroperoxide, and hexanal in the absence and presence of varying moles of L-proline at different temperatures. The formation of conjugated diene, hydroperoxide, and hexanal was analyzed using UV spectrometer analysis, xylenol orange, and DNPH derivatization HPLC-UV analysis. The results showed that adding proline to methyl linoleate samples stabilized conjugated diene and decreased hydroperoxide and hexanal levels as temperature increased, compared to the control sample. This suggests that L-proline effectively interacted with methyl linoleate oxidation products and altered their formation and oxidation path in the dry system. Overall, this study provided a basis for significantly enhancing understanding of the reactions between L-proline and methyl linoleate oxidation products in dry and low-moisture foods, offered practical implications for the food industry, and paved the way for future research.
    
    VL  - 13
    IS  - 2
    ER  - 

    Copy | Download

Author Information
  • Sections