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Spectrophotometric study of time stability and acid-base characteristics of chelerythrine and dihydrochelerythrine

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Central European Journal of Chemistry

Abstract

Time stability, acid-base and UV-VIS spectral properties of dihydrochelerythrine (DHCHE) were studied spectrophotometrically in water:methanol and water:ethanol media. DHCHE is stable in strongly acid milieu (pH < 3) and at the higher amounts (60% v/v) alcohol. Acid-base characteristics and UV-VIS spectral properties of chelerythrine (CHE) were studied in aqueous solutions in the presence of different concentrations of HCl, HNO3, H2SO4, H3PO4 and their mixtures. Remarkable shifts of formation parts of absorbance-pH (A-pH) curves to the alkaline medium were observed depending on the type and concentration of inert electrolyte (most remarkable for HNO3 and HCl). The corresponding equilibrium constants pKR+ of the transition reaction between charged iminium Q+ and uncharged QOH (pseudo-base, 6-hydroxy-dihydro derivative) forms of chelerythine were calculated using a numerical interpretation of A-pH curves by a SQUAD-G computer program which ranged from 8.51–9.31. The highest changes of ΔpK R+ (0.75 and 0.53) were observed for H3PO4 and H2SO4, respectively. The priority effect of ionic species and ionic strength was confirmed in the presence of additions of NaCl and KCl. The strength of interaction of CHE with biomacromolecular compounds (i.e., peptides, proteins, nucleic acids etc.) may be affected because of the observed influence of both cation and anion of the inert electrolyte on acid-base behavior.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, Mendel University, 613 00, Brno, Czech Republic

    Helena Absolínová & Irena Jančářová

  2. Department of Chemistry, Masaryk University, 611 37, Brno, Czech Republic

    Luděk Jančář & Vlastimil Kubáň

  3. Department of Medical Chemistry and Biochemistry, Palacky University, 775 15, Olomouc, Czech Republic

    Jaroslav Vičar

  4. Department of Biochemistry and Food Analysis, Tomas Bata University, 762 72, Zlín, Czech Republic

    Vlastimil Kubáň

Authors
  1. Helena Absolínová
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  2. Luděk Jančář
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  3. Irena Jančářová
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  4. Jaroslav Vičar
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  5. Vlastimil Kubáň
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Correspondence to Vlastimil Kubáň.

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Absolínová, H., Jančář, L., Jančářová, I. et al. Spectrophotometric study of time stability and acid-base characteristics of chelerythrine and dihydrochelerythrine. cent.eur.j.chem. 8, 626–632 (2010). https://doi.org/10.2478/s11532-010-0038-7

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  • DOI: https://doi.org/10.2478/s11532-010-0038-7

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