Kwas α-liponowy – antyutleniacz antyutleniaczy : właściwości i metody oznaczania

• Autorzy: Skorupa A. , Michałkiewicz S.

Warianty tytułu

EN

α -lipoic acid – antioxidant of antioxidants : properties and determination metods

• Języki publikacji: PL

Abstrakty

EN

Attention has been paid to healthy lifestyle in recent years. This is possible through increased physical activity and proper nutrition. This involves a significant increase in the interest in natural ingredients in a human daily diet. They come from both vegetable and animal products. This group of substances includes, for example, ascorbic acid (vitamin C), tocopherol (vitamin E), vitamin D, coenzyme Q10 and others. The important role of many compounds provided with food is their antioxidant action, which protects the body against the harmful effects of reactive oxygen species. They also exhibit therapeutic effects in diseases caused by oxidative stress. α-Lipoic acid (LA) also fits well into this group of substances and even gains the title of an “universal antioxidant” and an “antioxidant of antioxidants”. LA is produced in the human body in small amounts, and its biosynthesis occurs in the mitochondria. It is a compound with a very broad spectrum of therapeutic and biological activity. The amounts produced in the body are not sufficient and should therefore be supplied to the body from external sources. Food is the second, except de novo synthesis, the source of this compound. LA is a great antioxidant that can counteract the effects of aging. It is used mainly in the treatment of diabetic neuropathy and cardiovascular diseases, multiple sclerosis and Alzheimer’s disease. Such a wide action and occurrence causes the development of determination methods. Literature data indicate that free LA is primarily determined by liquid and gas chromatography, capillary electrophoresis, spectrophotometric and electrochemical techniques. In plant and animal cells it is mainly in the form of lipoyllysine. Determination of such a bound LA requires the proper preparation of the sample. This is usually acid, alkaline or enzymatic hydrolysis. This review summarizes the basic physicochemical and biochemical properties of α-lipoic acid and the methods of its determination.

Słowa kluczowe

PL

kwas α-liponowy; kwas dihydroliponowy; lipolizyna; przeciwutleniacz; oznaczanie

EN

α-lipoic acid; dihydrolipoic acid; lipoyllysine; antioxidant; determination

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2017
• Tom: [Z] 71, 11-12
• Strony: 817--842
• Opis fizyczny: Bibliogr. 69 poz., schem., tab., wykr.

Twórcy

autor

Skorupa A.

• Uniwersytet Jana Kochanowskiego, Instytut Chemii, ul. Świętokrzyska 15G, 25-408 Kielce

autor

Michałkiewicz S.

• Uniwersytet Jana Kochanowskiego, Instytut Chemii, ul. Świętokrzyska 15G, 25-408 Kielce

Bibliografia

• [1] V.E. Kagan, A. Shvedova, E. Serbinova, S. Khan, C. Swanson, R. Powell, L. Packer, Biochem. Pharmacol., 1992, 44, 1637.
• [2] C.V. Krishnan, M. Garnett, Int. J. Electrochem. Sci., 2011, 6, 3607.
• [3] F. Navari-Izzo, M.F. Quartacci, C. Sgherri, Plant Physiol. Biochem., 2002, 40, 463.
• [4] A. Bilska, L. Włodek, Pharm. Rep., 2005, 27, 570.
• [5] A. Gorąca, H. Huk-Kolega, A. Piechota, P. Kleniewska, E. Ciejka, B. Skibska, Pharm. Rep., 2011, 63, 849.
• [6] A. Bilska, Kwas liponowy. Udział w metabolizmie oraz możliwości farmakologicznego działania [w:] Biotiole w warunkach fizjologicznych, patologicznych i w terapii, red. L. Włodek, Wyd. Uniwersytetu Jagiellońskiego, Krakow 2003.
• [7] D. Malińska, K. Winiarska, Postepy Hig. Med. Dosw., 2005, 59, 535.
• [8] A. Azimi, M. Khalili, Lipoic Acid Function and Its Safety in Multiple Sclerosis [w:] Probiotics, Prebiotics, and Synbiotics. Bioactive Foods in Health Promotion, R.R. Watson, V.R. Preedy (Red.), Elsevier, 2016.
• [9] https://pubchem.ncbi.nlm.nih.gov/compound/864#section=2D-Structure, [dostęp 11.11.2017].
• [10] https://www.drugbank.ca/drugs/DB00166, [dostęp 11.11.2017].
• [11] Karta charakterystyki substancji chemicznej, zgodnie z Rozporządzeniem WE 1907/2006, Aktualizacja 11.01.2015, Sigma Aldrich.
• [12] www.chemicalize.com, [dostęp 11.11.2017].
• [13] M. Marin, C. Lete, B.N. Manolescu, S. Lupu, J. Electroanal. Chem., 2014, 729, 128.
• [14] A.I. Durrani, H. Schwartz, W. Schmid, G. Sontag, J. Pharm. Biomed. Anal., 2007, 45, 694.
• [15] H.Y. Aboul-Enein, H. Hoenen, J. Liq. Chromatogr. Related Technol., 2004, 27, 3029.
• [16] M. Koike, K. Koike, Lipoic acid [w:] Metabolism of Sulfur Compounds, D.M. Greenberg (Red.), Academic Press, Londyn, 1975.
• [17] K. Izutsu, Electrochemistry in Nonaqueous Solutions, WILEY-VCH Verlag GmbH, Weinheim 2002.
• [18] L. Packer, E.H. Witt, H.J. Tritschler, Free Rad. Biol. Med., 1995, 19, 227.
• [19] G. Bartosz, Druga twarz tlenu. Wolne rodniki w przyrodzie, Wyd. Naukowe PWN, Warszawa 2006.
• [20] R. Moreau, W.-J. Zhang, T.M. Hagen, Cellular Effects of Lipoic Acid and Its Role in Aging [w:] Handbook of Antioxidants, E. Cadenas, L. Packer (Red.), Marcel Dekker, 2002.
• [21] H. Moini, L. Packer, N.-E.L. Saris, Toxicol. Appl. Pharmacol., 2002, 182, 84.
• [22] J. Bustamante, J.K. Lodge, L. Marcocci, H.J. Tritschler, L. Packer, B.H. Rihn, Free Rad. Biol. Med., 1998, 24, 1023.
• [23] J.K. Lodge, L. Packer, Natural Sources of Lipoic Acid in Plant and Animal Tissues [w:] Antioxidant Food Supplements in Human Health, L. Packer, M. Hiramatsu, T. Yoshikawa (Red.), ACADEMIC PRESS, San Diego 1999.
• [24] M. Valko, C.J. Rhodes, J. Moncol, M. Izakovic, M. Mazur, Chem-Biol. Interact., 2006, 160, 1.
• [25] G. Atmaca, Yonsei Med. J., 2004, 45, 776.
• [26] O. Tirosh, S. Roy, L. Packer, Lipoic acid: Cellular Metabolism, Antioxidant Activity, and Clinical Relevance [w:] Handbook of Antioxidants, E. Cadenas, L. Packer (Red.), Marcel Dekker, 2002.
• [27] L. Patrick, Altern. Med. Rev., 2002, 7, 456.
• [28] L. Patrick, Altern. Med. Rev., 2003, 8, 106.
• [29] H. Gurer, H. Ozgunes, S. Oztezcan, N. Ercal. Free Rad. Biol. Med., 1999, 27, 75.
• [30] P. Ou, H.J. Tritschlert, S.P. Wolff, Biochem. Pharmacol., 1995, 50, 123.
• [31] B. Carrier, T.C. Rideout, J. Hum. Nutr. Food Sci., 2013, 1, 1002.
• [32] M. Jasik, N. Chojnowska, T. Stasiak, E. Wojcik-Sosnowska, W. Karnafel, Med. Metab., 2013, 4, 75.
• [33] B. Skibska, A. Goraca, Oxid. Med. Cell. Longev., 2015, doi: 10.1155/2015/313021
• [34] V. Yadav, G. Marracci, J. Lovera, W. Woodward, K. Bogardus, W. Marquardt, L. Shinto, C. Morris, D. Bourdette, Mult. Scler., 2005, 11, 159.
• [35] V. Yadav, G. Marracci, D.N. Bourdette, US Neurology, 2008, 4, 12.
• [36] A. Maczurek, K. Hager, M. Kenklies, M. Sharman, R. Martins, J. Engel, D.A. Carlson, G. Munch, Adv. Drug Delivery Rev., 2008, 60, 1463.
• [37] L. Patrick, Altern. Med. Rev., 2000, 5, 290.
• [38] H.C. Lukaski, Lipoic Acid [w:] Nutritional ergogenic aids, red. I. Wolinsky, J.A. Driskell, CRC Press LLC, 2004.
• [39] K. Petersen Shay, R.F. Moreau, E.J. Smith, A. R Smith, T.M. Hagen, Biochim. Biophys. Acta, 2009, 1790, 1149.
• [40] L. Rochette, S. Ghibu, A. Muresan, C. Vergely, Can. J. Physiol. Pharmacol., 2015, 93, 1021.
• [41] U. Cakatay, Med. Hypotheses, 2006, 66, 110.
• [42] J.J. Thiele, F. Dreher, L. Packer, Antioxidant Defense Systems in Skin [w:] Cosmeceuticals. Drugs vs. Cosmetics, P. Elsner, H.I. Maibach (Red.), Marcel Dekker, Inc., 2000.
• [43] G. Sontag, H. Schartz, Analytical Methods for Determination of α-Lipoic Acid, Dihydrolipoic Acid, and Lipoyllysine in Dietary Supplements and Foodstuffs [w:] Handbook of Analysis of Active Compounds in Functional Foods, L.M.L. Nollet, F. Toldra (Red.), CRC Press LLC, 2012.
• [44] A.I. Durrani, H. Schwartz, M. Nagl, G. Sontag, Food Chem., 2010, 120, 1143.
• [45] S. Satoh, M. Shindoh, J.Z. Min, T. Toyo’oka, T. Fukushima, S. Inagaki, Anal. Chim. Acta, 2008, 618, 210.
• [46] A. Mattulat, W. Baltes, Z. Labensm. Unters. Forsch., 1992, 194, 326.
• [47] E. Wołyniec, J. Karpińska, S. Łosiewska, M. Turkowicz, J. Klimczuk, A. Kojło, Talanta, 2012, 96, 223.
• [48] L.N. dos Santos Pereira, I.S. da Silva, T.P. Araujo, A.A. Tanaka, L. Angnes, Talanta, 2016, 154, 249.
• [49] B. Rajkumar, T. Bhavya, A.A. Kumar, Int. J. Pharm. Pharm. Sci., 2014, 6, 307.
• [50] S. Satoh, T. Toyo’oka, T. Fukushima, S. Inagaki, J. Chromatogr. B, 2007, 854, 109.
• [51] W. Siangproh, P. Rattanarat, O. Chailapakul, J. Chromatogr. A, 2010, 1217, 7699.
• [52] H. Kataoka, J. Chromatogr. B, 1998, 717, 247.
• [53] H. Kataoka, N. Hirabayashi, M. Makita, J. Chromatogr. B, 1993, 615, 197.
• [54] D.J. Patel, V.C. Jain, H.A. Raj, Research and Reviews: J. Pharm. Anal., 2014, 3, 28.
• [55] P.P. Goti, J.J. Savsani, P.B. Patel, Int. J. Pharm. Pharm. Sci., 2012, 4, 519.
• [56] M.I. Walash, A.M. El-Brashy, M.S. Metwally, A.A. Abdelal, Bull. Korean Chem. Sci., 2004, 25, 517.
• [57] M.I. Walash, M.E.-S. Metwally, A.M. El-Brashy, A.A. Abdelal, Il Farmaco, 2003, 58, 1325.
• [58] Z. Korićanac, M. Čakar, S. Tanasković, T. Jovanović, J. Serb. Chem. Soc., 2007, 72, 29.
• [59] A. Sitton, M.G. Schmid, G. Gubitz, H.Y. Aboul-Enein, J. Biochem. Biophys. Methods, 2004, 61, 119.
• [60] H. Li, Y. Kong, L. Chang, Z. Feng, N. Chang, J. Liu, J. Long, Chromatographia, 2014, 77, 145.
• [61] G.K. Ziyatdinova, G.K. Budnikov, V.I. Pogorel’tsev, J. Anal. Chem., 2004, 59, 288.
• [62] W. Ciesielski, M. Skowron, Chem. Anal., 2005, 50, 47.
• [63] O. Corduneanu, M. Garnett, A.M. Oliveira Brett, Anal. Lett., 2007, 40, 1763.
• [64] D.M. Stanković, E. Mehmeti, K. Kalcher, Anal. Sci., 2016, 32, 847.
• [65] M.P. Miranda, R. del Rio, M.A. del Valle, M. Faundez, F. Armijo, J. Electroanal. Chem., 2012, 668, 1.
• [66] A.P.M.M. Ferreira, L.N. dos Santos Pereira, I.S. da Silva, S.M.C.N. Tanaka, A.A. Tanaka, L. Angnes, Electroanalysis, 2014, 26, 2138.
• [67] N. Ravanić, S. Filipić, K. Nikolić, G. Popović, I. Vovk, B. Simonovska, D. Agbaba, Acta Chromatogr. 2009, 21, 433.
• [68] A. Mrass, E. Bald, Wiad. Chem. 2011, 55, 933.
• [69] J.C.H. Shih, S.C. Steinsberger, Anal. Biochem., 1981, 116, 65.

Uwagi

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).