Abstracts
Kinetic features of oxidation and cis-trans isomerization of methyl linoleate in the presence of lipophilic thiol in hydrocarbon solution are considered taking 2-mercaptoethanol (RSH), the simplest thiol, as an example. The effects of hydrophilic endogenous thiol glutathione (GSH) on hydrogen peroxide decomposition, thiol-ene reaction of GSH with unsaturated phenol resveratrol (RVT) and the oxidation of sunflower oil and methyl linoleate in the micellar solution in the presence of GSH are discussed as well. Both RSH and GSH were found to reduce hydroperoxides and H2O2, and these reactions are accompanied by free radical formation.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Abedinzadeh Z (2001) Sulfur-centered reactive intermediates derived from the oxidation of sulfur compounds of biological interest. Can J Physiol Pharmacol 79(2):166–170. https://doi.org/10.1139/y00-085
Abedinzadeh Z, Gardes-Albert M, Ferradini C (1989) Kinetic study of the oxidation mechanism of glutathione by hydrogen peroxide in neutral aqueous medium. Can J Chem 67:1247
Afaf K-E, Min DB (eds) (2008) Lipid oxidation pathways. AOCS Press, Champain
Aitken CE, Marshall RA, Puglisi JD (2008) An oxygen scavenging system for improvement of dye stability in single-molecule fluorescence experiments. Biophys J 94(5):1826–1835. https://doi.org/10.1529/biophysj.107.117689
Aldini G, Altomare A, Baron G, Vistoli G, Carini M, Borsani L, Sergio F (2018) N-Acetylcysteine as an antioxidant and disulphide breaking agent: the reasons why. Free Radical Res 52(7):751–762. https://doi.org/10.1080/10715762.2018.1468564
Chatgilialoglu C, Bowry VW (2018) Why not trans? Inhibited radical isomerization cycles and coupling chains of lipids and alkenes with alkane-thiols. J Org Chem 83(16):9178–9189. https://doi.org/10.1021/acs.joc.8b01216
Chatgilialoglu C, Ferreri C (2005) Trans lipids: the free radical path. Acc Chem Res 36:441. https://doi.org/10.1021/ar0400847
Chatgilialoglu C, Altieri A, Fischer H (2002) The kinetics of Thiyl radical-induced reactions of monounsaturated fatty acid esters. J Am Chem Soc 124:12816–12823
Conway JG, Neptun DA, Garvey LK, Popp JA (1987) Carcinogen treatment increases glutathione hydrolysis by gamma-glutamyltranspeptidase. Carcinogenesis 8:999–1004
Denisov ET, Afanas’ev IF (2005) Oxidation and antioxidants in organic chemistry and biology. CRC Press Taylor & Francis Group
Emanuel NM, Gal D (1978) Oxidation of ethylbenzene. A model reaction. Nauka, Moscow
Emanuel NM, Denisov ET, Maizus ZN (1965) Chain reactions of hydrocarbons oxidation in liquid phase. Nauka, Moscow
Estrela JM, Ortega A, Obrador E (2006) Glutathione critical reviews. Clin Lab Sci 43(2):143–181. https://doi.org/10.1080/10408360500523878
Ferreri C, Chatgilialoglu C (2012) Lipid isomerization in Encyclope-dia of radicals in chemistry. In: Chatgilialoglu C, Studer A (eds) Biology and materials. John Wiley & Sons Ltd, Chichester, UK, pp 1599–1622
Frankel EN (2005) Lipid oxidation. The Oily Press, Glasgow
Guo RW, Yang G, Feng ZJ, Zhu YJ et al (2018) Glutathione-induced amino-activatable micellar photosensitization platform for synergistic redox modulation and photodynamic therapy. Biomater Sci 6(5):1238–1249. https://doi.org/10.1039/c8bm00094h
Halliwell B (2007) Gutteridge, free radicals in biology and medicine, 4th edn. University Press, Oxford
Hawkiks WL, Worthikgston MA (1963) Synergistic antioxidant combinations. Carbon black substitutes. J Polymer Sci Part A 1:3489–3497
Hoyle CE, Bowman CN (2010) Thiol–ene click chemistry. Angew Chem Int Ed 49:1540. https://doi.org/10.1002/anie.200903924
Kade MJ, Burke DJ, Hawker CJ (2010) The power of thiol-ene chemistry. J Polym Sci A Polym Chem 48:743–750. https://doi.org/10.1002/pola.23824
Kamal-Eldin A (2003) Lipid oxidation pathway. AOCS Press, Champaign, IL
Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 40(11):2004–2021. https://doi.org/10.1002/1521-3773(20010601)40:11<2004::aid-anie2004>3.3.co;2-x
Koo SPS, Stamenović MM, Prasath RA, Inglis AJ et al (2010) Limitations of radical thiol-ene reactions for polymer-polymer conjugation. J Polym Sci A Polym Chem 48:1699–1171
Loshadkin DV, Pliss EM, Kasaikina OT (2020) Features of methyl linoleate oxidation in triton X-100 micellar buffer solutions. Russ J Appl Chem 93(7):1083–1088. https://doi.org/10.1134/S1070427220070216
Mengele EA, Krugovov DA, Kasaikina OT (2015) Effect of mercaptoethanol on the hydrocarbon oxidation and cis—trans-isomerization of unsaturated lipid. Russ Chem Bull 64:846. https://doi.org/10.1007/s11172-015-0943-1
Niki E (2012) Lipid peroxidation in encyclopedia of radicals in chemistry. In: Chatgilialoglu C, Studer A (eds) Biology and materials. John Wiley & Sons Ltd, Chichester, UK, pp 1577–1597
Penninck MJ (2000) A short review on the role of glutathione in the response of yeasts to nutritional, environmental, and oxidative stresses. Enzym Microb Technol 26:737–742
Roy K-M (2005) Thiols and organic sulphides. In: Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim. https://doi.org/10.1002/14356007.a26_767
Saito S, Kawabata J (2004) Synergistic effects of thiols and amines on antiradical efficiency of protocatechuic acid. J Agric Food Chem 52:8163–8168
Sajewicz W, Zalewska M, Milnerowicz H (2015) Comparative study on thiol drugs’ effect on tert-butyl hydroperoxide induced luminol chemiluminescence in human erythrocyte lysate and hemoglobin oxidation. Toxicol In Vitro 29:149
Salehi B, Mishra AP, Nigam M, Sener B, Kilic M, Sharifi-Rad M, Fokou PVT, Martins N, Sharifi-Rad J (2018) Resveratrol: a double-edged sword in health benefits. Biomedicines 6(3):91. https://doi.org/10.3390/biomedicines6030091
Scott G (1965) Atmospheric oxidation and Antioxidation. Elsevier, Amsterdam
Sebedio JL, Christie WW (1998) Trans fatty acids in human nutrition. The Oily Press, Dundee
Sies H, Jones DP (2007) Oxidative stress. In: Fink G (ed) Encyclopedia of stress, vol 3. Elsevier, San Diego, CA, pp 45–48
Stavrovskaya AA (2000) Cellular mechanisms of multidrug resistance of tumor cells. Biochemistry (Mosc) 65:95–106
Takashima M, Shichiri M, Hagihara Y, Yoshida Y, Niki E (2012) Reactivity toward oxygen radicals and antioxidant action of thiol compounds. Biofactors 38(3):240. https://doi.org/10.1002/biof.1014
Townsend DM, Tew KD, Tapiero H (2003) The importance of glutathione in human disease. Biomed Pharmacother 57:145–155
Toyokuni S (2014) Iron and thiols as two major players in carcinogenesis: friends or foes? Front Pharmacol 5:200
Turunc O, Meier AR (2012) The thiol-ene (click) reaction for the synthesis of plant oil derived polymers. Eur J Lipid Sci Technol 115:41–54. https://doi.org/10.1002/ejlt.201200148
Ulrich K, Jakob U (2019) The role of thiols in antioxidant systems. Free Radic Biol Med 140:14–27
Vanslambrouck S, Riva R, Ucakar B, Préat V, Gagliardi M, Molin DGB, Lecomte H, Jérôme C (2021) Thiol-ene reaction: an efficient tool to design lipophilic Polyphosphoesters for drug delivery systems. Molecules 26(6):1750. https://doi.org/10.3390/molecules26061750
Winterbourn CC (2015) Are free radicals involved in thiol-based redox signaling? Free Rad Biol Med 80:164–170
Winterbourn CC (2016) Revisiting the reactions of superoxide with glutathione and other thiols. Arch Biochemistry Biophysics 595:68
Winterbourn CC (2018 Aug 20) Biological production, detection and fate of hydrogen peroxide. Antioxid Redox Signal. 29(6):541–551. https://doi.org/10.1089/ars.2017.7425. Epub 2017 Dec 14
Winterbourn CC, Hampton MB (2008) Thiol chemistry and specificity in redox signaling. Free Radic Biol Med 45(5):549–461. https://doi.org/10.1016/j.freeradbiomed.2008.05.004
Winterbourn CC, Metodieva D (1995) Reaction of superoxide with glutathione and other thiols. Methods Enzymol 252:81–86
Wu G, Fang YZ, Yang S, Lupton JR, Turner ND (2004) Glutathione metabolism and its implications for health. J Nutr 134:489–492
Yu W, Fu Y-C, Wang W (2012) Cellular and molecular effects of resveratrol in health and disease. J Cell Biochem 11(3):752–759. https://doi.org/10.1002/jcb.23431
Zinatullina KM, Kasaikina OT, Kuzmin VA, Khrameeva NP, Shapiro BI (2016) Interaction of polymethine dyes with hydroperoxides and free radicals. Russ Chem Bull 65(12):2825. https://doi.org/10.1007/s11172-016-1663-x
Zinatullina KM, Kasaikina OT, Kuz’min VA, Khrameeva NP, Shapiro BI (2017a) Kinetic characteristics of the interaction of natural thiols with peroxyl radicals and hydrogen peroxide. Russ Chem Bull 66(7):1300. https://doi.org/10.1134/S0023158417050093
Zinatullina KM, Khrameeva NP, Kasaikina OT, Kuzmin VA, Shapiro BI (2017b) Kinetic characteristics of the interaction of resveratrol with peroxyl radicals and natural thiols in an aqueous medium. Russ Chem Bull 66(11):2145. https://doi.org/10.1007/s11172-017-1995-1
Zinatullina KM, Khrameeva NP, Kasaikina OT (2018) Interaction of natural thiols and catecholamines with reactive oxygen species. Bulg Chem Commun 50:25
Zinatullina KM, Kasaikina OT, Kuz’min VA, Khrameeva NP (2019) Interaction of glutathione with hydrogen peroxide. Kinetic Model Kinet Catal 60(3):266. https://doi.org/10.1134/S0023158419030169
Zinatullina KM, Kasaikina OT, Motyakin MV, Ionova IS, Degtyarev EN, Khrameeva NP (2020) Features of radical formation in the reactions of thiols with hydrogen peroxide. Russ Chem Bull 69(10):1865. https://doi.org/10.1007/s11172-020-2971-8
Zinatullina KM, Kasaikina OT, Khrameeva NP, Indeykina MI, Kononikhin AS (2021) Interaction between glutathione and resveratrol in the presence of hydrogen peroxide: a kinetic model. Kinet Catal 62(2):255. https://doi.org/10.1134/S0023158421020130
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Ethics declarations
This work was supported by the Russian Foundation for Basic Research (project no. 20-03-00753) and performed under a state task (project no. 0082-2018-0006, registration no. АААА-А18-118020890097-1).
Conflict of Interest
The authors declare that there is no conflict of interest regarding the publication of this manuscript.
Rights and permissions
Copyright information
© 2022 The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
Kasaikina, O.T., Zinatullina, K.M., Kancheva, V.D., Slavova-Kasakova, A.K., Loshadkin, D.V. (2022). Effect of Lipophilic and Hydrophilic Thiols on the Lipid Oxidation. In: Bravo-Diaz, C. (eds) Lipid Oxidation in Food and Biological Systems. Springer, Cham. https://doi.org/10.1007/978-3-030-87222-9_8
Download citation
DOI: https://doi.org/10.1007/978-3-030-87222-9_8
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-87221-2
Online ISBN: 978-3-030-87222-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)