Fig 1.
(A) Structures of 2-phenylethanol and o-xylene. (B) Substrates used for the ToMO-catalyzed biotransformations presented in this study.
Fig 2.
Starting substrates and corresponding hydroxylated products obtained through ToMO-catalyzed biotransformation of (A) 2-phenoxyethanol and (B) phthalan.
Fig 3.
Docking of intermediates in ToMO active site.
Docking of the two possible arenium intermediates (4PT and 5PT) deriving from phthalan in the active site of ToMOA. In the case of 4PT, θ is the torsion angle Fe(2)-O-C4-C9, whereas, in the case of 5PT, θ is the torsion angle Fe(2)-O-C4-C5. Similar arenium intermediates can be hypothesized for the hydroxylation of 2-indanol.
Table 1.
Geometrical parameters and non covalent binding energies (ncBE) of the complexes between ToMO or E103G/F176A-ToMO and the arenium intermediates for the phthalan/1,3-dihydro-4-hydroxyisobenzofuran (4PT), the phthalan/1,3-dihydro-5-hydroxyisobenzofuran (5PT), the 2-indanol/2,4-dihydroxyindan (24I) and the 2-indanol/2,5-dihydroxyindan (25I) reactions.
Fig 4.
E103G/F176A ToMO-catalyzed biotransformation of 2-indanol.
HPLC chromatogram at λ = 280 nm of an aliquot of the exhausted medium deriving from the 16 hrs, E103G/F176A ToMO-catalyzed biotransformation of 2-indanol.
Table 2.
Evaluation of the antioxidant activity using the DPPH assay.
Fig 5.
Effect of sodium arsenite on the formation of stress granules: immunofluorescence and statistical analysis. PABP mAb and Cy3-conjugated goat anti-mouse F(ab’)2 were used to detect SGs in H9c2 cells cultured under normal growth (A) and SA-stress conditions (B). Nuclei are stained with DAPI. Scale bars: 10μm. (C) Effect of pretreatment with hydroxylated compounds in SA-treated H92c cardiomyoblasts. The table reports SGs number for cell (Mean ± SEM) that was obtained by using “Analyze Particles” plugin of the image software ImageJ (pixel unit: 1,5–2,0; Circularity: 0,99–1,00). Statistical analysis (unpaired t test, two tailed; (*, p ≤ 0.05; **, p ≤ 0.01). Tyr: tyrosol; Hyd: hydroxytyrosol.