ACS Publications. Most Trusted. Most Cited. Most Read
Effects of Riboflavin and Fatty Acid Methyl Esters on Cholesterol Oxidation during Illumination
My Activity

Figure 1Loading Img
    Article

    Effects of Riboflavin and Fatty Acid Methyl Esters on Cholesterol Oxidation during Illumination
    Click to copy article linkArticle link copied!

    View Author Information
    Department of Nutrition and Food Science, Fu Jen University, Taipei, Taiwan 242
    Other Access Options

    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2002, 50, 12, 3572–3578
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jf020003q
    Published May 10, 2002
    Copyright © 2002 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!

    The effect of riboflavin or fatty acid methyl esters on cholesterol photooxidation was studied. Samples containing cholesterol, either alone or in combination with riboflavin or fatty acid methyl esters, were illuminated at 25 °C in an incubator for 28 days. The various cholesterol oxidation products (COPs) and cholesterol were analyzed by gas chromatography−mass spectrometry (GC−MS), and riboflavin was determined by HPLC. Results showed that the presence of riboflavin or fatty acid methyl esters facilitated production of COPs and degradation of cholesterol, and the degradation fits a first-order model. The COPs formed during light storage included 7α-OH, 7β-OH, 7-keto, 3,5-cholestadien-7-one, 5,6α-EP, and 5,6β-EP. The addition of riboflavin caused formation of 3,5-cholestadien-7-one through dehydration of 7-keto, whereas in the presence of docosahexaenoic acid methyl ester, the formation of 5,6α-EP or 5,6β-EP was favored. Riboflavin was more effective for generation of COPs than fatty acid methyl esters.

    Keywords: Riboflavin; fatty acid methyl ester; cholesterol photooxidation; GC−MS

    Copyright © 2002 American Chemical Society

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    *

     To whom correspondence should be addressed. Phone:  886-2-29031111-3626. Fax:  886-2-29021215. E-mail:  [email protected].

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai

    This article is cited by 25 publications.

    1. L. J. Chen, Y. F. Lu, J. T. Chien, and B. H. Chen . Formation and Inhibition of Cholesterol Oxidation Products in Tea-Leaf Eggs during Marinating. Journal of Agricultural and Food Chemistry 2010, 58 (19) , 10467-10474. https://doi.org/10.1021/jf102487j
    2. Hsien-Wei Lee,, John-Tung Chien, and, Bing-Huei Chen. Formation of Cholesterol Oxidation Products in Marinated Foods during Heating. Journal of Agricultural and Food Chemistry 2006, 54 (13) , 4873-4879. https://doi.org/10.1021/jf060461p
    3. Eleonora Laura De Paola, Giuseppe Montevecchi, Milena Marega, Francesca Masino, Davide Garbini, Sonia Scaramagli, Andrea Antonelli. Determination of cholesterol oxidation products in cheese under photo-oxidative stress using QuEChERS and LC–MS. European Food Research and Technology 2024, 250 (2) , 483-493. https://doi.org/10.1007/s00217-023-04404-9
    4. Magdalena Rudzińska. Phytosterols as Functional Compounds and Their Oxidized Derivatives. 2022, 361-380. https://doi.org/10.1007/978-3-030-87222-9_16
    5. Yan Liu, Xuan Yang, Fan Xiao, Fan Jie, Qinjun Zhang, Yuqi Liu, Hang Xiao, Baiyi Lu. Dietary cholesterol oxidation products: Perspectives linking food processing and storage with health implications. Comprehensive Reviews in Food Science and Food Safety 2022, 21 (1) , 738-779. https://doi.org/10.1111/1541-4337.12880
    6. Jingnan Chen, Dami Li, Guiyun Tang, Jinfen Zhou, Wei Liu, Yanlan Bi. Thermal-Oxidation Stability of Soybean Germ Phytosterols in Different Lipid Matrixes. Molecules 2020, 25 (18) , 4079. https://doi.org/10.3390/molecules25184079
    7. Yajing Zhao, Bowen Yang, Tao Xu, Mengmeng Wang, Baiyi Lu. Photooxidation of phytosterols in oil matrix: Effects of the light, photosensitizers and unsaturation degree of the lipids. Food Chemistry 2019, 288 , 162-169. https://doi.org/10.1016/j.foodchem.2019.02.105
    8. Blanca Barriuso, Diana Ansorena, Iciar Astiasarán. Oxysterols formation: A review of a multifactorial process. The Journal of Steroid Biochemistry and Molecular Biology 2017, 169 , 39-45. https://doi.org/10.1016/j.jsbmb.2016.02.027
    9. Carlo Barnaba, Maria Teresa Rodríguez-Estrada, Giovanni Lercker, Hugo Sergio García, Ilce Gabriela Medina-Meza. Cholesterol photo-oxidation: A chemical reaction network for kinetic modeling. Steroids 2016, 116 , 52-59. https://doi.org/10.1016/j.steroids.2016.10.004
    10. Blanca Barriuso, Iciar Astiasarán, Diana Ansorena. Unsaturated lipid matrices protect plant sterols from degradation during heating treatment. Food Chemistry 2016, 196 , 451-458. https://doi.org/10.1016/j.foodchem.2015.09.074
    11. Ilce Gabriela Medina‐Meza, Maria Teresa Rodriguez‐Estrada, Giovanni Lercker, Carlo Barnaba, Hugo Sergio García. Kinetics of 25‐hydroperoxycholesterol formation during photo‐oxidation of crystalline cholesterol. Journal of the Science of Food and Agriculture 2014, 94 (8) , 1543-1551. https://doi.org/10.1002/jsfa.6455
    12. Diana Ansorena, Blanca Barriuso, Vladimiro Cardenia, Iciar Astiasarán, Giovanni Lercker, Maria Teresa Rodriguez-Estrada. Thermo-oxidation of cholesterol: Effect of the unsaturation degree of the lipid matrix. Food Chemistry 2013, 141 (3) , 2757-2764. https://doi.org/10.1016/j.foodchem.2013.04.129
    13. Ilce Gabriela Medina-Meza, Carlo Barnaba. Kinetics of Cholesterol Oxidation in Model Systems and Foods: Current Status. Food Engineering Reviews 2013, 5 (3) , 171-184. https://doi.org/10.1007/s12393-013-9069-0
    14. Marc Poirot, Sandrine Silvente-Poirot. Cholesterol-5,6-epoxides: Chemistry, biochemistry, metabolic fate and cancer. Biochimie 2013, 95 (3) , 622-631. https://doi.org/10.1016/j.biochi.2012.05.006
    15. Ilce Gabriela Medina-Meza, María Teresa Rodríguez-Estrada, Hugo Sergio García, Giovanni Lercker. Oxidative Pattern from Fluorescent Light Exposition of Crystalline Cholesterol. Food Biophysics 2012, 7 (3) , 209-219. https://doi.org/10.1007/s11483-012-9259-y
    16. Emanuele Boselli, Vladimiro Cardenia, Maria Teresa Rodriguez‐Estrada. Cholesterol photosensitized oxidation in muscle foods. European Journal of Lipid Science and Technology 2012, 114 (6) , 644-655. https://doi.org/10.1002/ejlt.201100352
    17. Ting‐Yang Yen, Yi‐Fa Lu, Baskaran Stephen Inbaraj, Bing‐Huei Chen. Cholesterol oxidation in lard as affected by CLA during heating – A kinetic approach. European Journal of Lipid Science and Technology 2011, 113 (2) , 214-223. https://doi.org/10.1002/ejlt.201000405
    18. Guihua Xu, Junliang Sun, Yintong Liang, Chao Yang, Zhen-Yu Chen. Interaction of fatty acids with oxidation of cholesterol and β-sitosterol. Food Chemistry 2011, 124 (1) , 162-170. https://doi.org/10.1016/j.foodchem.2010.06.003
    19. T.Y. Yen, B. Stephen Inbaraj, J.T. Chien, B.H. Chen. Gas chromatography–mass spectrometry determination of conjugated linoleic acids and cholesterol oxides and their stability in a model system. Analytical Biochemistry 2010, 400 (1) , 130-138. https://doi.org/10.1016/j.ab.2010.01.031
    20. Tomasz Wielkoszyński, Katarzyna Gawron, Joanna Strzelczyk, Piotr Bodzek, Marzena Zalewska‐Ziob, Gizela Trapp, Małgorzata Srebniak, Andrzej Wiczkowski. Cellular toxicity of oxycholesterols. BioEssays 2006, 28 (4) , 387-398. https://doi.org/10.1002/bies.20383
    21. P. A. Morrissey, M. Kiely. Oxysterols: Formation and Biological Function. 2006, 641-674. https://doi.org/10.1007/0-387-28813-9_18
    22. Eunok Choe, David B. Min. Chemistry and Reactions of Reactive Oxygen Species in Foods. Critical Reviews in Food Science and Nutrition 2006, 46 (1) , 1-22. https://doi.org/10.1080/10408390500455474
    23. Eunok Choe, David B. Min. Chemistry and Reactions of Reactive Oxygen Species in Foods. Journal of Food Science 2005, 70 (9) , R142-R159. https://doi.org/10.1111/j.1365-2621.2005.tb08329.x
    24. Robert Sieber. Oxidised cholesterol in milk and dairy products. International Dairy Journal 2005, 15 (3) , 191-206. https://doi.org/10.1016/j.idairyj.2004.07.013
    25. J.-T. Chien, Y.F. Lu, P.C. Hu, B.H. Chen. Cholesterol photooxidation as affected by combination of riboflavin and fatty acid methyl esters. Food Chemistry 2003, 81 (3) , 421-431. https://doi.org/10.1016/S0308-8146(02)00472-7

    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2002, 50, 12, 3572–3578
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jf020003q
    Published May 10, 2002
    Copyright © 2002 American Chemical Society

    Article Views

    356

    Altmetric

    -

    Citations

    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.