The pharmacology of the antioxidant: Lipoic acid

General Pharmacology

Volumn 29, Issue 3, 1997, Pages 315-331

  Biewenga, Gerreke Ph ^a   Haenen, Guido R M M ^a   Bast, Aalt ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Antioxidant pharmacology; Dihydrolipoic acid; Glutathione; Lipoic acid; Metabolism; Metal chelation; Peptide methionine sulfoxide reductase; Reactive oxygen species; Scavenging; Vitamin C; Vitamin E

Indexed keywords

ALPHA 1 ANTITRYPSIN; ALPHA TOCOPHEROL; ASCORBIC ACID; CADMIUM; COPPER; DIHYDROLIPOAMIDE DEHYDROGENASE; DIHYDROLIPOATE; GLUTATHIONE; IRON; OXIDOREDUCTASE; REACTIVE OXYGEN METABOLITE; THIOCTIC ACID;

ANTIOXIDANT ACTIVITY; BIOAVAILABILITY; DOSE RESPONSE; HUMAN; IN VITRO STUDY; METAL BINDING; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; REVIEW; SCAVENGING SYSTEM;

ANIMALS; ANTIOXIDANTS; HUMANS; OXIDATIVE STRESS; THIOCTIC ACID;

EID: 0030768236     PISSN: 03063623     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0306-3623(96)00474-0     Document Type: Review

References (109)

1. Bast A. (1994) Antioxidant pharmacotherapy. DN&P 7, 465-472.
2. Bast A. and Haenen G. R. M. M. (1988) Interplay between lipoic acid and glutathione in the protection against microsomal lipid peroxidation. Biochim. Biophys. Acta 963, 558-561.
3. Biewenga G. P., de Jong J. and Bast A. (1994) Lipoic acid favors thiolsulfinate formation after hypochlorous acid scavenging: a study with lipoic acid derivatives. Arch. Biochem. Biophys. 312, 114-120.
4. Biewenga G. P., Dorstijn M. A., Verhagen J. V., Haenen G. R. M. M. and Bast A. (1996a) Reduction of lipoic acid by lipoamide dehydrogenase. Biochem. Pharmac. 51, 233-238.
5. Biewenga G. P., Haenen G. R. M. M. and Bast A. (1997b) An overview on lipoate chemistry. In Lipoic Acid in Health and Disease. (Edited by Fuchs J., Packer L. and Zimmer G.) pp. 1-32. Marcel Dekker, New York.
6. Biewenga G. P., Vriesman M. F., Haenen G. R. M. M. and Bast A. (1996c) The metabolism of lipoic acid in man. Submitted.
7. Bisby R. H., Johnson S. A. and Parker A. W. (1996) Quenching of reactive oxidative species by probucol and comparison with other antioxidants. Free Radical Biol. Med. 20, 411-420.
8. Bonomi F. and Pagani S. (1986) Removal of ferritin-bound iron by DL-dihydrolipoate and DL-dihydrolipoamide. Eur. J. Biochem. 155, 295-300.
9. 2- (n=2,4) in aqueous media from iron salts, thiols, and sulfur, sulfide, or thiosulfate plus rhodanese. Inorg. Chem. 24, 4331-4335.
10. 2 to nitric oxide and citrulline. Biochem. Biophys. Res. Commun. 187, 880-886.
11. Brot N., Fliss H., Coleman T. and Weissbach H. (1984) Enzymatic reduction of methionine sulfoxide residues in proteins and peptides. Methods Enzymol. 107, 352-360.
12. Brot N. and Weissbach H. (1988) Methionine sulfoxide: chemistry and biochemistry. In The Chemistry of Functional Groups: The Chemistry of Sulfones and Sulfoxides. (Edited by Patai S., Rappoport Z. and Stirling C. J. M.) pp. 851-872, Wiley, Chichester, UK.
13. Brot N., Weissbach L., Werth J. and Weissbach H. (1981) Enzymatic reduction of protein-bound methionine sulfoxide. Proc. Natl. Acad. Sci. 78, 2155-2158.
14. Brown P. R. and Edwards J. O. (1970) The reactions of 1,3-dimercaptocpropane, lipoic acid, and dihydrolipoic acid with metal ions. J. Inorg. Nucl. Chem. 32, 2671-2675.
15. Burkat V., Koike T., Brenner H.-H., Imai Y. and Kolb H. (1993) Dihydrolipoic acid protects pancreatic islet cells from inflammatory attack. Agents Actions 38, 60-65.
16. Busse E., Zimmer G., Schopohl B. and Kornhuber B. (1992) Influence of α-lipoic acid on intracellular glutathione in vitro and in vivo. Arzneim.-Forsch. Drug Res. 42, 829-831.
17. Cameron N. E., Cotter M. A. and Maxfield E. K. (1993) Anti-oxidant treatment prevents the development of peripheral nerve dysfunction in streptozotocin-diabetic rats. Diabetologia 36, 299-304.
18. Cao X. H. and Phillis J. W. (1995) The free radical scavenger, α-lipoic acid, protects against cerebral ischemia-reperfusion injury in gerbils. Free Radical Res. 23, 365-370.
19. Carp H., Janoff A., Abrams W., Weinbaum G., Drew R. T., Weissbach H. and Brot N. (1983) Human methionine sulfoxide-peptide reductase: an enzyme capable of reactivating oxidized α-1-proteinase inhibitor in vitro. Am. Rev. Respir. Dis. 127, 301-305.
20. Carreau J.-P. (1979) Biosynthesis of lipoic acid via unsaturated fatty acids. Methods Enzymol. 62, 152-158.
21. Ching T.-L., de Jong J. and Bast A. (1994) A method for screening hypochlorous acid scavengers by inhibition of 5-thio-2-nitroberizoic acid. Anal. Biochem. 218, 377-381.
22. Constantinescu A., Pick U., Handelman G. J., Haramaki N., Han D., Podda M., Tritschler H. J. and Packer L. (1995) Reduction and transport of lipoic acid by human erythrocytes. Biochem. Pharmac. 50, 253-261.
23. 3+ salts. Rev. Port. Quim. 27, 273-274.
24. Devasagayam T. P. A., Subramanian M., Pradhan D. S. and Sies H. (1993) Prevention of singlet oxygen-induced DNA damage by lipoate. Chem. Biol. Interact. 86, 79-92.
25. Dikalov S., Khramtsov V. and Zimmer G. (1996) Determination of rate constants of the reactions of thiols with superoxide radical by electron paramagnetic resonance: critical remarks on spectrophotometric approaches. Arch. Biochem. Biophys. 326, 207-218.
26. Folkes L. K., Candeias L. P. and Wardman P. (1995) Kinetics and mechanism of hypochlorous acid reactions. Arch. Biochem. Biophys. 323, 120-126.
27. Fuchs J. and Milbradt R. (1994) Antioxidant inhibition of skin inflammation induced by reactive oxidants: Evaluation of the redox couple dihydrolipoate/lipoate. Skin Pharmac. 7, 278-284.
28. Fuchs J., Schofer H., Milbradt R., Freisteben H. J., Buhl R., Siems W. and Grune T. (1993) Studies on lipoate effects on blood redox state in human immunodeficiency virus infected patients. Arzneim.-Forsch. Drug Res. 43(2), 1359-1362.
29. Fujiwara K., Okamura-Ikeda K. and Motokawa Y. (1995) Assay for protein lipoylation reaction. Methods Enzymol. 251, 333-350.
30. Furr H. C., Chang H.-H. and McCormick D. B. (1978) Lipoate metabolism in pseudomonas putida LP: thiolsulfinates of lipoate and bisnorlipoate. Arch. Biochem. Biophys. 185, 576-583.
31. Glaser C. B., Karic L., Parmelee S., Premachandra B. R., Hinkston D. and Abrams W. R. (1987) Studies on the turnover of methionine oxidized α-1-protease inhibitor in rats. Am. Rev. Respir. Dis. 136, 857-861.
32. Gotz M. E., Dirr A., Burger R., Janetzky B., Weinmuller M., Chan W. W., Chen S. C., Reichmann H., Rausch W. D. and Riederer P. (1994) Effect of lipoic acid on redox state of coenzyme Q in mice treated with l-merhyl-4-phenyl-1,2,3,6-tetrahydropyridine and diethyldithiocarbamate. Eur. J. Pharmac. Mol. Pharm. 266, 291-300.
33. Greenamyre J. T., Garciaosuna M. and Greene J. G. (1994) The endogenous cofactors, thioctic acid and dihydrolipoic acid, are neuroprotective against NMDA and Malonic acid lesions of striatum. Neurosci. Lett. 171, 17-20.
34. Grootveld M. and Halliwell B. (1986) Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Biochem. J. 237, 499-504.
35. Gut J., Christen U., Frey N., Koch V. and Stoffler D. (1995) Molecular mimicry in halothane hepatitis: biochemical and structural characterization of lipoylated autoantigens. Toxicology 97, 199-224.
36. Gutierrez Correa J. G. and Stoppani A. O. M. (1996) Catecholamines enhance dihydrolipoamide dehydrogenase inactivation by the copper Fenton system: enzyme protection by copper chelators. Free Radical Res. 24, 311-322.
37. Haenen G. R. M. M. and Bast A. (1991) Scavenging of hypochlorous acid by lipoic acid. Biochem. Pharmac. 42, 2244-2246.
38. Haenen G. R. M. M. and Bast A. (1989) Modulation of microsomal lipid peroxidation by dihydrolipoate in interplay with vitamin E, vitamin C and glutathione. In Thioctsäure: Neue biochemische, pharmakologische und klinische Erkenntnisse zur Thioctsäure. (Edited by Borbe H. O. and Ulrich H.) pp. 137-153. pmi Verlag, Frankfurt am Main.
39. Haenen G. R. M. M., deRooij B. M., Vermeulen N. P. E. and Bast A. (1990) Mechanism of the reaction of ebselen with endogenous thiols: dihydrolipoate is a better cofactor than glutathione in the peroxidase activity of ebselen. Mol. Pharmac. 37, 412-422.
40. Halliwell B. (1995) Antioxidant characterization: methodology and mechanism. Biochem. Pharmac. 49, 1341-1348.
41. Halliwell B. and Gutteridge J. M. C. (1989) Free Radicals in Biology and Medicine. Clarendon Press, Oxford.
42. Han D., Tritschler H. J. and Packer L. (1995) α-Lipoic acid increases intracellular glutathione in a human T-lymphocyte Jurkat cell line. Biochem. Biophys. Res. Commun. 207, 258-264.
43. Handelman G. J., Han D., Tritschler H. and Packer L. (1994) α-Lipoic acid reduction by mammalian cells to the dithiol form, and release into the culture medium. Biochem. Pharmac. 47, 1725-1730.
44. Haramaki N., Packer L., Assadnazari H. and Zimmer G. (1993) Cardiac recovery during post-ischemic reperfusion is improved by combination of vitamin-E with dihydrolipoic acid. Biochem. Biophys. Res. Commun. 196, 1101-1107.
45. Harrison E. H. and McCormick D. B. (1974) The metabolism of dl-[1,6-14C]-lipoic acid in the rat. Arch. Biochem. Biophys. 160, 514-522.
46. Herbert A. A. and Guest J. R. (1975) Lipoic acid content of Escherichia coli and other microorganisms. Arch. Microbiol. 106, 259-266.
47. Hermann R., Niebch G., Borbe H. O., Fieger H., Ruus P., Nowak H., Riethmller-Winzen H., Peukert M. and Blume H. (1996) Enantio selective pharmacokinetics and bioavailability of different racemic α-lipoic acid formulations in healthy volunteers. Eur. J. Pharm. Sci. 4, 167-174.
48. Holmgren A. (1979) Thioredoxin catalyses the reduction of insulin disulfides by dithiothreitol and dihydrolipoamide. J. Biol. Chem. 254, 9627-9632.
49. Jayanthi S. and Varalakshmi P. (1992) Alterations in rat erythrocyte membrane parameters during calcium oxalate lithiasis and the effect of α-lipoic acid. Indian J. Clin. Biochem. 7, 115-120.
50. Kagan V. E., Shvedova A., Serbinova E., Khan S., Swanson C., Powell R. and Packer L. (1992) Dihydrolipoic acid: a universal antioxidant both in the membrane and in the aqueous phase. Biochem. Pharmac. 44, 1637-1649.
51. Kaiser S., Di Mascio P. and Sies H. (1989) Lipoate und Singulettsauerstoff. In Thioctsäure: Neue biochemische, pharmakologische und klinische Erkenntnisse zur Thioctsäure. (Edited by Borbe H. O. and Ulrich H.) pp. 69-76. pmi Verlag, Frankfurt am Main.
52. Kawabata T., Tritschler H.-J. and Packer L. (1995) Reaction of (R,S)-dihydrolipoic acid and homologs with iron. Methods Enzymol. 251, 325-332.
53. Kleemann A., Borbe H. O. and Ulrich H. (1989) Thioctsäure: α-liponsäure. In Thioctsäure: Neue biochemische, pharmakologische und klinische Erkenntnisse zur Thioctsäure. (Edited by Borbe H. O. and Ulrich H.) pp. 11-26. pmi Verlag, Frankfurt am Main.
54. Lewis R. L. and Sweet D. V. (1985) Registry of Toxic Effects of Chemical Substances 1983-84. U.S. Department of Health and Human Services, Cincinnati.
55. Locher M., Busker E. and Borbe H. O. (1995) Metabolism of a-lipoic acid in human volunteers. Naunyn-Schmiedeberg's Arch. Pharmac. 351, R52 (abstract).
56. Löffelhardt S., Bonaventura C., Locher M., Borbe H. O. and Bisswanger H. (1995) Interaction of α-lipoic acid enantiomers and homologues with the enzyme components of the mammalian pyruvate dehydrogenase complex. Biochem. Pharmac. 50, 637-646.
57. Maier K. L., Matejkova E., Hinze H., Leuschel L., Weber H. and Beck-Speier I. (1989) Different selectivities of oxidants during oxidation of methionine residues in the α-1-proteinase inhibitor. FEBS Lett. 250, 221-226.
58. Maitra I., Serbinova E., Tritschler H. J. and Packer L. (1995) α-Lipoic acid prevents buthionine sulfoximine-induced cataract formation in newborn rats. Free Radical Biol. Med. 18, 823-829.
59. Maitra I., Serbinova E., Tritschler H. J. and Packer L. (1996) Stereospecific effects of R-lipoic acid on buthionine sulfoxinine-induced cataract formation in newborn rats. Biochem. Biophys. Res. Commun. 221, 422-429.
60. Matsugo S., Yan L. J., Han D., Trischler H. J. and Packer L. (1995) Elucidation of antioxidant activity of α-lipoic acid toward hydroxyl radical. Biochem. Biophys. Res. Commun. 208, 161-167.
61. Mattulat A. (1992) Determination of the lipoic acid content of animal tissue. In Thioctsäure: International Thioctic Acid Workshop. (Edited by Schmidt K. and Ulrich H.) pp. 69-73. Universimed Verlag, Frankfurt am Main.
62. Mattulat A. and Baltes W. (1992) Determination of lipoic acid in meat of commercial quality. Z. Lebensm.-Unters.-Forsch. 194, 326-329.
63. Morris T. W., Reed K. E. and Cronan J. E. (1995) Lipoic acid metabolism in Escherichia coli: the lplA and lipB genes define redundant pathways for ligation of lipoyl groups to apoptotein. J. Bacteriol. 177, 1-10.
64. Moskovitz J., Rahman M. A., Strassman J., Yancey S.O., Kushner S. R., Brot N. and Weisbach H. (1995) Escherichia coli peptide methionine sulfoxide reductase gene: regulation of expression and role in protecting against oxidative damage. J. Bacterial. 177, 502-507.
65. Müller L. (1989) Protective effects of DL-α-lipoic acid on cadmium-induced deterioration of rat hepatocytes. Toxicology 58, 175-185.
66. 2+ toxicity in isolated hepatocytes. Biochim. Biophys. Acta 1052, 386-391.
67. Nagamatsu M., Nickander K. K., Schmelzer J. D., Raya A., Wittrock D. A., Tritschler H. and Low P. A. (1995) Lipoic acid improves nerve blood flow, reduces oxidative stress, and improves distal nerve conduction in experimental diabetic neuropathy. Diabetes Care 18, 1160-1167.
68. Nathan C. (1992) Nitric oxide as a secretory product of mammalian cells. FASEB J. 6, 3051-3064.
69. O'Neill C. A., Halliwell B., van der Vliet A., Davis P.A., Packer L., Tritschler H., Strohman W. J., Rieland T., Cross C. E. and Reznick A. Z. (1994) Aldehyde-induced protein modifications in human plasma: protection by glutathione and dihydrolipoic acid. J. Lab. Clin. Med. 124, 359-370.
70. Ou P. M., Tritschler H. J. and Wolff S. P. (1995) Thioctic (lipoic) acid: a therapeutic metal-chelating antioxidant? Biochem. Pharmac. 50, 123-126.
71. Packer L., Witt E. H. and Tritschler H. J. (1995) α-Lipoic acid as biological antioxidant. Free Radical Biol. Med. 19, 227-250.
72. Panigrahi M., Sadguna Y., Shivakumar B. R., Kolluri S. V. R., Roy S., Packer L. and Ravindranath V. (1996) α-Lipoic acid protects against reperfusion injury following cerebral ischemia in rats. Brain Res. 717, 184-188.
73. Pick U., Haramaki N., Constantinescu A., Handelman G. J., Tritschler H. J. and Packer L. (1995) Glutathione reductase and lipoamide dehydrogenase have opposite stereospecificities for α-lipoic acid enantiomers. Biochem. Biophys. Res. Commun. 206, 724-730.
74. Pruijn F. B., Haenen G. R. M. M. and Bast A. (1991) Interplay between vitamin E, glutathione and dihydrolipoic acid in protection against lipid peroxidation. Fat Sci. Technol. 6, 216-221.
75. Rosenberg H. R. and Culik R. (1959) Effect of α-lipoic acid on vitamin C and vitamin E deficiencies. Arch. Biochem. Biophys. 80, 86-93.
76. Salonen J. T., Nyyssnen K., Tuomainen T.-P., Menp P. H., Korpela H., Kaplan G. A., Lynch J., Helmrich S. P. and Salonen R. (1995) Increased risk of non-insulin dependent diabetes mellitus at low plasma vitamin E concentrations: a four year follow up study in men. Br. Med. J. 311, 1124-1126.
77. Scheer B. and Zimmer G. (1993) Dihydrolipoic acid prevents hypoxic/ reoxygenation and peroxidative damage in rat heart mitochondria. Arch. Biochem. Biophys. 302, 385-390.
78. Scholich H., Murphy M. E. and Sies H. (1989) Antioxidant activity of dihydrolipoate against microsomal lipid peroxidation and its dependence on α-tocopherol. Biochim. Biophys. Acta 1001, 256-261.
79. Scott B. C., Aruoma O. I., Evans P. J., O'Neill C., van der Vliet A., Cross C. E., Tritschler H. and Halliwell B. (1994) Lipoic and dihydrolipoic acids as antioxidants: a critical evaluation. Free Radical Res. 20, 119-133.
80. Serbinova E., Reznick S. K. A. Z. and Packer L. (1992) Thioctic acid protects against ischemia-reperfusion injury in the isolated perfused Langendorf heart. Free Radicas Res. Commun. 17, 49-58.
81. Sigel H. (1982) Die hydrophoben und Metallionen-koordinierenden Eigenschaften von A-Liposäure: ein Beispiel für intramolekulare Gleichgewichte in Metallionen-Komplexen. Angew. Chem. 94, 421-432.
82. 2+ in solution. Arch. Biochem. Biophys. 187, 208-214.
83. Spector A., Huang R.-R. C., Yan G.-Z. and Wang R.-R. (1988) Thioredoxin fragment 31-36 is reduced by dihydrolipoamide and reduces oxidized protein. Biochem. Biophys. Res. Commun. 150, 156-162.
84. Spence J. T. and McCormick D. B. (1976) Lipoic acid metabolism in the rat. Arch. Biochem. Biophys. 174, 13-19.
85. Spoto G., Dupre S. and Cavallini D. (1982) Biosynthesis of lipoic acid: endocellular localization and some properties of the involved enzymatic system. IRCS Med. Sci. 10, 626.
86. Stary F. E., Jindal S. L. and Murray R. W. (1975) Oxidation of aα-lipoic acid. J. Org. Chem. 40, 58-62.
87. Stevens B., Perez S. R. and Small R. D. (1974) The photoperoxidation of unsaturated organic molecules IX: lipoic acid inhibition of rubrene autoperoxidation. Photochem. Photobiol. 19, 315-316.
88. Stroman F., Herold H., Erdmann R., Ulrich H. and Szelenyi I. (1989) Zur protekiven Wirkung der Thioctsäure bei myocardialer Ischmie. In Thioctsäure: Neue biochemische, pharmakologische und klinische Erkenntnisse zur Thioctsäure. (Edited by Borbe H. O. and Ulrich H.) pp. 279-288. pmi-Verlag, Frankfurt am Main.
89. Sumathi R., Baskaran G. and Varalakshmi P. (1996) Relationship between glutathione and DL α-lipoic acid against cadmium-induced hepatotoxicity. Jpn. J. Med. Sci. Biol. 49, 39-48.
90. Sumathi R., Devi V. K. and Varalakshmi P. (1994) DL-α-Lipoic acid protection against cadmium induced tissue lipid peroxidation. Med. Sci. Res. 22, 23-25.
91. Sumathi R., Jayanthi S. and Varalakshmi P. (1993) DL-α-Lipoic acid as a free radical scavenger in glyoxylate-induced lipid peioxidation. Med. Sci. Res. 21, 135-137.
92. Suzuki Y. J. and Packer L. (1994) α-Lipoic acid is a potent inhibitor of NF-KB activation in human T cells: does the mechanism involve anti-oxidant activities? In Biological Oxidants and Antioxidants (Edited by Packer L. and Cadenas E.) pp. 87-96. Hippokrates Verlag, Stuttgart.
93. Suzuki Y. J., Tsuchiya M. and Packer L. (1991) Thioctic acid and dihydrolipoic acid are novel antioxidants which interact with reactive oxygen species. Free Radical Res. Commun. 15, 255-263.
94. Suzuki Y. J., Tsuchiya M. and Packer L. (1993) Antioxidant activities of dihydrolipoic acid and its structural homologues. Free Radical Res. Commun. 18, 115-122.
95. Swaim M. W. and Pizzo S. V. (1988) Methionine sulfoxide and the oxidative regulation of plasma proteinase inhibitors. J. Leukocyte Biol. 43, 365-379.
96. Teichert J. and Preiß R. (1995) Determination of lipoic acid in human plasma by high-performance liquid chromatography with electrochemical detection. J. Chromatogr. B 672, 277-281.
97. Tuaillon N., Andre C., Briand J.-P., Penner E. and Muller S. (1992) A lipoyl synthetic octadecapeptide of dihydrolipoamide acetyltransferase specifically recognized by the anti-M2 autoantibodies in primary biliary cirrhosis. J. Immunol. 148, 445-450.
98. van der Vliet A., O'Neill C. A., Eiserich J. P. and Cross C. E. (1995) Oxidative damage to extracellular fluids by ozone and possible protective effects of thiols. Arch. Biochem. Biophys. 321, 43-50.
99. Vertommen J., van den Enden M., Simoens L. and de Leeuw I. (1994) Flavonoid treatment reduces glycation and lipid peroxidation in exeprimental diabetic rats. Phytother. Res. 8, 430-432.
100. von Schreiber F.-K. (1961) Zur Behandlung der Neuropathia diabetica. Dtsch. Med. Wochenschr. 12, 531-536.
101. Whiteman M., Tritschler H. and Halliwell B. (1996) Protection against peroxynitrite-dependent tyrosine nitration and α(1)-antiproteinase inactivation by oxidized and reduced lipoic acid. FEBS Lett. 379, 74-76.
102. Winkler B. S., Orselli S. M. and Rex T. S. (1995) Comments on the glutathione-ascorbic acid redox couple. Free Radical Biol. Med. 18, 955-956.
103. Winterbourn C. C. (1985) Comparative reactivities of various biological compounds with myeloperoxidase-hydrogen peroxide-chloride, and similarity of the oxidant to hypochlorite. Biochim. Biophys. Acta 840, 204-210.
104. Wolff S. P., Jiang Z. Y. and Hunt J. V. (1991) Protein glycation and oxidative stress in diabetes mellitus and ageing. Free Radical Biol. Med. 10, 339-352.
105. Xie C.-I., Lin R. C., Antony V., Lumeng L., Li T.-K., Mai K., Liu C., Wang Q.-d., Zhao Z.-h. and Wang G.-f. (1994) Daidzin, an antioxidant isoflavonoid, decreases blood alcohol levels and shortens sleep time induced by ethanol intoxication. Alcohol. Clin. Exp. Res. 18, 1443-1447.
106. Xu D. P. and Wells W. W. (1996) α-Lipoic acid dependent regeneration of ascorbic acid from dehydroascorbic acid in rat liver mitochondria. J. Bioenerg. Biomembr. 28, 77-85.
107. Yan L. J., Traber M. G., Kobuchi H., Matsugo S., Tritschler H. J. and Packer L. (1996) Efficacy of hypochlorous acid scavengers in the prevention of protein carbonyl formation. Arch. Biochem. Biophys. 327, 330-334.
108. Ziegler D., Hanefeld M., Ruhnau K. J., Meißner H. P., Lobisch M., Schütte K. and Gries F. A. (1995) Treatment of symptomatic diabetic peripheral neuropathy with the anti-oxidant α-lipoic acid. Diabetologia 38, 1425-1433.
109. Zimmer G., Beikler T. K., Schneider M., Ibel J., Tritschler H. and Ulrich H. (1995) Dose/response curves of lipoic acid R- and S-forms in the working rat heart during reoxygenation: superiority of the R-enantiomer in enhancement of aortic flow. J. Mol. Cell. Cardiol. 27, 1895-1903.