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An unusual reduction on the quinonoid ring of 5‐amino‐8‐hydroxy‐1,4‐naphthoquinone by Staphylococcus aureus
Author(s) -
Medina L.F.C.,
Stefani V.,
Brandelli A.
Publication year - 2006
Publication title -
letters in applied microbiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.698
H-Index - 110
eISSN - 1472-765X
pISSN - 0266-8254
DOI - 10.1111/j.1472-765x.2006.01863.x
Subject(s) - staphylococcus aureus , naphthoquinone , chemistry , antimicrobial , quinone , bacteria , biochemistry , stereochemistry , microbiology and biotechnology , biology , organic chemistry , genetics
Aims: The objective of this study was to investigate the interactions between 5‐amino‐8‐hydroxy‐1,4‐naphthoquinone (ANQ) and Staphylococcus aureus . Methods and Results: The compound ANQ display antimicrobial activity against S. aureus . During incubation with 50 μ g ml −1 of ANQ, an unusual reduction reaction takes place and leads to the isolation of 2,3‐dihydro‐5‐amino‐8‐hydroxy‐1,4‐naphthoquinone (ANQ‐H 2 ), fully characterized by means of 13 C‐NMR and 1 H‐NMR, plus infrared, UV–visible and mass spectroscopy. Oxygen uptake by S. aureus cells was inhibited by ANQ, but in a significantly minor extent by ANQ‐H 2 . Conclusions: The ability of S. aureus to reduce the double bond at C2–C3 of the ANQ is a unusual behaviour for biological transformation of naphthoquinones. Significance and Impact of the Study: This uncommon reaction may provide valuable understanding of the S. aureus regarding to the antimicrobial effect and the acquisition of resistance to naphthoquinones.