Nonenzymatic reduction of thymoquinone in physiological conditions

References

• Halliwell B, Aeschbach R, Loliger J, Aruoma OI. The characterization of antioxidants. Food Chem Toxicol 1995; 33: 601–617
   PubMed Web of Science ®Google Scholar
• Jung HA, Park JC, Chung HY, Kim J, Choi JS. Antioxidant flavonoids and chlorogenic acid from the leaves of Eriobotrya japonica. Arch Pharm Res 1999; 22: 213–218
   PubMed Web of Science ®Google Scholar
• Pietta P, Simonetti P, Mauri P. Antioxidant activity of selected medicinal plants. J Agric Food Chem 1998; 46: 4487–4490
   Web of Science ®Google Scholar
• Yen G-C, Chen H-Y. Antioxidant activity of various tea extracts in relation to their antimutagenicity. J Agric Food Chem 1995; 43: 27–32
   Web of Science ®Google Scholar
• Miyake Y, Shimoi K, Kumazawa S, Yamamoto K, Kinae N, Osawa T. Identification and antioxidant activity of flavonoid metabolites in plasma and urine of eriocitrin-treated rats. J Agric Food Chem 2000; 48: 3217–3224
   PubMed Web of Science ®Google Scholar
• Pulido R, Bravo L, Saura-Calixto F. Antioxidant activity of dietary polyphenols as determined by a modified ferric reducing/antioxidant power assay. J Agric Food Chem 2000; 48: 3396–3402
   PubMed Web of Science ®Google Scholar
• Gyamfi MA, Yonamine M, Aniya Y. Free-radical scavenging action of medicinal herbs from Ghana Thonningia sanguinea on experimentally-induced liver injuries. Gen Pharmacol 1999; 32: 661–667
   PubMedGoogle Scholar
• Rchida H, Chevassusb H, Nmilac R, Guiralb C. Nigella sativa seed extracts enhance glucose-induced insulin release from rat-isolated Langerhans islets. Fundam Clin Pharmacol 2004; 18: 525–529
   PubMedGoogle Scholar
• Mohamed F, Ramadan L, Lothar WK, JO RG-T, Morsel RJ. Radical scavenging activity of black cumin (Nigella sativa L.),Coriander (Coriandrum sativum L.), and Niger (Guizotia abyssinica Cass.) crude seed oils and oil fractions. J Agric Food Chem 2003; 51: 6961–6969
   PubMedGoogle Scholar
• Burits M, Bucar F. Antioxidant activity of Nigella sativa essential oil. Phytother Res 2000; 14: 323–328
   PubMed Web of Science ®Google Scholar
• Kruk I, Michalska T, Lichszteld K, Kladna A, Aboul-Enein HY. The effect of thymol and its derivatives on reactions generating reactive oxygen species. Chemosphere 2000; 41: 1059–1064
   PubMed Web of Science ®Google Scholar
• Ali BH, Blunden G. Pharmacological and toxicological properties of Nigella sativa. Phytother Res 2003; 17: 299–305
   PubMed Web of Science ®Google Scholar
• Houghton PJ, Zarka R, de las Heras B, Hoult JRS. Fixed oil of Nigella sativa and derived thymoquinone inhibit eicosanoid generation in leukocytes and membrane lipid peroxidation. Planta Med 1995; 61: 33–36
   PubMed Web of Science ®Google Scholar
• Burits M, Bucar F. Antioxidant activity of Nigella sativa essential oil. Phytother Res 2000; 14: 323–328
   PubMed Web of Science ®Google Scholar
• Mansour MA, Nagi MN, El-Khatib AS, Al-Bekairi AMR. Effects of thymoquinone on antioxidant enzyme activities, lipid peroxidation and DT-diaphorase in different tissues of mice: A possible mechanism of action. Cell Biochem Funct 2002; 20(2)143–151, Jun
   PubMed Web of Science ®Google Scholar
• El-Saleh SC, Al-Sagair OA, Al-Khalaf MI. Thymoquinone and Nigella sativa oil protection against methionine-induced hyperhomocysteinemia in rats. Int J Cardiol 2004; 93(1)19–23, January
   PubMedGoogle Scholar
• Marsik P, Kokoska L, Landa P, Nepovim A, Soudek P, T. In vitro inhibitory effects of thymol and quinones of Nigella sativa seed on cyclooxigenase -1 and -2 catalyzed prostaglandin E2 biosyntheses. Plant Med 2005; 71: 739–742
   PubMed Web of Science ®Google Scholar
• Sies H. Glutathione and its role in cellular functions. Free Radic Biol Med 1999; 27: 916–921
   PubMed Web of Science ®Google Scholar
• Flohe' L. Glutathione peroxidase : Fact and function. Ciba Found Symp 1978; 267: 95–122
   Google Scholar
• Ferreira AM, Ciriolo MR, Marcocci L, Rotilio G. Copper (I) transfer into metallothionein mediated by glutathione. Biochem J 2000; 292: 673–676
   Google Scholar
• Ciriolo MR, Desideri A, Paci M, Rotilio G. Reconstitution of Cu-Zn superoxide dismutase by the CuI-glutathione complex. J Biol Chem 1990; 265: 11030–11034
   PubMed Web of Science ®Google Scholar
• Smith LI, Tess RW. Dithymoquinone. J Am Chem Soc 1944; 66: 1323–1325
   Google Scholar
• El-Alfy TS, El-Fattatry HM, Toama MA. Isolation and structure assignment of an antimicrobial principle from the volatile oil of Nigella sativa L seeds. Pharmazie 1975; 30: 109–111
   PubMed Web of Science ®Google Scholar
• Peskin AV, Winterbourn CC. Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate. Free Rad Res Med 2001; 30(5)572–579
   PubMed Web of Science ®Google Scholar
• Blois MS. Antioxidant determinations by the use of stable free radical. Nature 1958; 181: 1199–1200
   Web of Science ®Google Scholar
• Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying ab improved ABTS radical cation decolourization assay. Free Rad Biol Med 1999; 26: 1231–1237
   PubMed Web of Science ®Google Scholar
• Sanchez-Moreno C. Methods used to evaluate the free radical scavenging activity in foods and biological systems. Food Sci Technol Int 2002; 44: 743–745
   Google Scholar
• Friaa O, Brault D. Kinetics of the reaction between the antioxidant Trolox R_ and the free radical DPPH√ in semi-aqueous solution. Org Biomol Chem 2006; 4: 2417–2423
   PubMed Web of Science ®Google Scholar
• Badary OA, Nagi MN, Al-Shabandah OA, Al-Sawaf HA, Al-Sohaibani MO, Al-Bakairi AM. Thymoquinone ameliorates the nephrotoxicity induced by cisplatin in rodents and potentates its antitumor activity. Can J Physiol Pharmacol 1997; 75: 1356–1361
   PubMed Web of Science ®Google Scholar
• Houghton PJ, Zarka R, Heras B, Hoult RS. Fixed oil of Nigella sati6a and derived thymoquinone inhibit eicosanoid generation in leucocytes and membrane lipid peroxidation. Planta Med 1995; 61: 33–36
   PubMed Web of Science ®Google Scholar
• Mordente A, Martorana GE, Minotti G, Giardina B. Antioxidant properties of 2,3-dimethoxy-5-methyl- 6-(10-hydroxydecyl)-1,4-benzoquinone (Idebenone). Chem Res Toxicol 1998; 11: 54–63
   PubMed Web of Science ®Google Scholar
• Stocker R, Suarna C. Extracellular reduction of ubiquinone-1 and -10 by human Hep G2 and blood cells. Biochim Biophys Acta 1993; 1158: 15–22
   PubMedGoogle Scholar
• Valliant F, Larm JA, McMullen GL, Wolvetang EJ, Lawen A. Effectors of the mammalian plasma membrane NADH-oxidoreductase system. Short-chain ubiquinone analogues as potent stimulators. J Bioenerg Biomembr 1996; 28: 531–540
   PubMedGoogle Scholar
• Ponsoda X, Jover R, Lechon Gomez MJ, Fabra R, Trullenque R, Castell JV. Intracellular glutathione in human hepatocytes incubated with S-adenosyl-l-methionine and GSH-depleting drugs. Toxicology 1991; 70: 293–302
   PubMedGoogle Scholar
• Boots AW, Kubben N, Haenen Guido RMM, Bast A. Oxidized quercetin react with thiols rather than with ascorbate: Implication for quercetin supplementation. 2003; 308: 560–565
   Google Scholar
• Filomeni G, Rotilio G, Circolo MR. Cell signalling and the glutathione redox system. Biochem Pharmacol 2002; 1057–1064
   PubMedGoogle Scholar
• Daba MH, Abdel-Rahman MS. Hepatoprotective activity of thymoquinone in isolated rat hepatocytes. Toxicol Lett 1998; 95: 23–29
   PubMed Web of Science ®Google Scholar
• Nickerson WJ, Falcone G, Strauss G. Studies on quinone-thioethers. I. Mechanism of formation and properties of thiodione. Biochemistry 1963; 2: 537–543
   PubMed Web of Science ®Google Scholar
• Wefers H, Sies H. Hepatic low-level chemiluminescence during redox cycling of menadione and the menadione-glutathione conjugate: Relation to glutathione and NAD(P)H:quinone reductase (DT-diaphorase) activity. Arch Biochem Biophys 1983; 224: 568–578
   PubMed Web of Science ®Google Scholar
• Kim BH, Yoo J, Park SH, Jung JK, Cho H, Chung Y. Synthesis and evaluation of antitumor activity of novel 1,4-naphthoquinone derivatives (IV). Arch Pharm Res 2006; 29(2)123–130, Feb
   PubMedGoogle Scholar
• Cysyk RL, Parker RJ, Barchi JJ, Jr., Steeg PS, Hartman NR, Strong JM. Reaction of geldanamycin and C17-substituted analogues with glutathione: Product identifications and pharmacological implications. Chem Res Toxicol 2006; 19: 376–381
   PubMed Web of Science ®Google Scholar
• Dai J, Park G, Wright MW, Adams M, Akman SA, Manderville RA. Detection and characterization of a glutathione conjugate of ochratoxin A. Chem Res Toxicol 2002; 15: 1581–1588
   PubMed Web of Science ®Google Scholar
• Johnson BM, van Breemen RB. In vitro formation of quinoid metabolites of the dietary supplement cimicifuga racemosa (Black Cohosh). Chem Res Toxicol 2003; 16: 838–846
   PubMed Web of Science ®Google Scholar
• Cai XH, Luo XD, Zhou J, Hao XJ. Quinones from Chirita eburnea. J Nat Prod 2005; 68: 797–799
   PubMedGoogle Scholar
• Takahashi N, Schreiber J, Fisher V, Mason R. Formation og glutathione-conjugated semiquinones by the reaction of quinones with glutathione: An ESR study. Arch Biochem Biophys 1987; 252: 41–48
   PubMed Web of Science ®Google Scholar
• Li WW, Heinze J, Haehnel W. Site-specific binding of quinones to proteins through thiol addition and addition-elimination reaction. J Am Chem Soc 2005; 127: 6140–6141
   PubMed Web of Science ®Google Scholar
• Wefers H, Sies H. Hepatic low-level chemiluminescence during redox cycling of menadione and the menadione-glutathione conjugate: Relation to glutathione and NAD(P)H:quinone reductase (DT-diaphorase) activity. Arch Biochem Biophys 1983; 235: 334–342
   Google Scholar
• Takahashi N, Schreiber J, Fischer V, Mason RP. Formation of glutathione-conjugated semiquinones by the reaction of quinones with glutathione: An ESR study. Arch Biochem Biophys 1987; 252(1)41–48, Jan
   PubMedGoogle Scholar