An unusual reduction on the quinonoid ring of 5-amino-8-hydroxy-1,4- naphthoquinone by Staphylococcus aureus

Letters in Applied Microbiology

Volumn 42, Issue 4, 2006, Pages 381-385

  Medina, L F C ^a   Stefani, V ^a   Brandelli, A ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

Author keywords

Antimicrobial; Hydroquinone; Oxygen uptake; Redox reaction; Staphylococci

Indexed keywords

BACTERIA; KETONES; MASS SPECTROMETRY; OXYGEN; REDUCTION;

% REDUCTIONS; ANTI-MICROBIAL ACTIVITY; ANTIMICROBIAL; HYDROQUINONE; NAPHTHOQUINONES; OXYGEN UPTAKE; QUINONOIDS; S. AUREUS; STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS;

REDOX REACTIONS;

5 AMINO 8 HYDROXY 1,4 NAPHTHOQUINONE; CARBON 13; NAPHTHOQUINONE; UNCLASSIFIED DRUG;

BACTERIA; BACTERIOLOGY; CHEMICAL BONDS; KETONES; MICROBIOLOGY; REDOX REACTIONS; REDUCTION;

OXYGEN CONSUMPTION; REDOX CONDITIONS;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL CELL; INFRARED RADIATION; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE IMAGING; OXYGEN CONSUMPTION; REDUCTION; STAPHYLOCOCCUS AUREUS; ULTRAVIOLET RADIATION;

BACTERIA (MICROORGANISMS); STAPHYLOCOCCUS; STAPHYLOCOCCUS AUREUS;

EID: 33645053555     PISSN: 02668254     EISSN: 1472765X     Source Type: Journal    
DOI: 10.1111/j.1472-765X.2006.01863.x     Document Type: Article

References (17)

1. Bogdanov P.M. Albesa I. Sperandeo N.R. Luna C. De Bertorello M.M. 1996 Antibacterial effect of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4- naphthoquinone-4-imine on Staphylococcus aureus Experientia 52 600 604
2. Brandelli A. Bizani D. Martinelli M. Stefani V. Gerbase A.E. 2004 Antimicrobial activity of 1,4-naphthoquinones by metal complexation Braz J Pharm Sci 40 247 253
3. Buffinton G.D. Öllinger K. Brunmark A. Cadenas E. 1989 DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates Biochem J 257 561 571
4. Fariña F. Martinez-Utrilla R. Paredes M.C. Stefani V. 1985 Synthesis of 5-amino-8-hydroxy-1,4-naphthoquinone and derivatives Synthesis 8 781 784
5. Iyanagi T. 1987 On the mechanisms of one-electron and two-electron transfer by flavin enzymes Chem Scr 27A 31 36
6. Iyanagi T. 1990 On the mechanism of one-electron reduction of quinones by microsomal flavin enzymes - the kinetic analysis between cytochrome-B5 and menadione Free Radic Res Commun 8 259 268
7. Le Texier L. Roy S. Fosse C. Neuwels M. Azerad R. 2001 A biosynthetic microbial ability applied for the oxidative ring cleavage of non-natural heterocyclic quinones Tetrahedron Lett 42 4135 4137
8. Maruyama A. Kumagai Y. Morikawa K. Taguchi K. Hayashi H. Otha T. 2003 Oxidative-stress-inducible qorA encodes an NADPH-dependent quinone oxidoreductase catalysing a one-electron reduction in Staphylococcus aureus Microbiology 149 389 398
9. Medina L.F.C. Stefani V. Brandelli A. 2004 Use of 1,4-naphthoquinones for control of Erwinia carotovora Can J Microbiol 50 951 956
10. Monks T.J. Hanzlik R.P. Cohen G.M. Ross D. Graham D.G. 1992 Quinone chemistry and toxicity Toxicol Appl Pharmacol 112 2 16
11. O'Brien P.J. 1991 Molecular mechanisms of quinone cytotoxicity Chem Biol Interact 80 1 41
12. Öllinger K. Brunmark A. 1991 Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes J Biol Chem 266 21496 21503
13. Oppermann U.C.T. Maser T. 2000 Molecular and structural aspects of xenobiotic carbonyl metabolyzing enzymes. Role of reductases and dehydrogenases in xenobiotic phase I reactions Toxicology 144 71 81
14. Papageorgiou V.P. Assimopoulou A.N. Couladouros E.A. Hepworth D. Nicolaou K.C. 1999 The chemistry and biology of alkannin, shikonin, and related naphthazarin natural products Angew Chem Int 38 270 300
15. Riffel A. Medina L.F. Stefani V. Santos R.C. Bizani D. Brandelli A. 2002 In vitro antimicrobial activity of a new series of 1,4-naphthoquinones Braz J Med Biol Res 35 811 818
16. Slabas A.R. Brown A. Sinden B.S. Swinhoe R. Simon J.W. Ashton A.K. Whitfeld P.R. Elborough K.M. 1994 Pivotal reactions in fatty acid synthesis Prog Lipid Res 33 39 46
17. Zhang R. Hirsch O. Mohsen M. Samuni A. 1994 Effects of nitroxide stable radicals on Juglone citotoxicity Arch Biochem Biophys 312 385 391