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

• Autorzy: Helena Absolínová , Luděk Jančář , Irena Jančářová , Jaroslav Vičar , Vlastimil Kubáň
• Języki publikacji: EN

Abstrakty

EN

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 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. [...]

Słowa kluczowe

EN

Chelerythrine; Dihydrochelerythrine; Time stability; UV-VIS spectral characteristics; Equilibrium constants

• Czasopismo: Open Chemistry
• Rocznik: 2010
• Tom: 8
• Numer: 3
• Strony: 626-632

Daty

wydano

2010-06-01

online

2010-04-25

Twórcy

autor

Helena Absolínová

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

autor

Luděk Jančář

• Department of Chemistry, Masaryk University, 611 37, Brno, Czech Republic

autor

Irena Jančářová

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

autor

Jaroslav Vičar

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

autor

Vlastimil Kubáň,

Bibliografia

• [1] V. Šimánek, in: A. Brossi (Ed.), The Alkaloids (Academic Press, Orlando, 1985) 26, 185
• [2] J. Psotová et al., J. Chromatogr. B., Analyt. Technol. Biomed. Life Sci. 830, 427 (2006)
• [3] M. Maiti, G.S. Kumar, Med. Res. Rev. 27, 649 (2007) http://dx.doi.org/10.1002/med.20087[Crossref]
• [4] R. Sinha, M. Hossain, G.S. Kumar, DNA Cell Biol. 28, 209 (2009) http://dx.doi.org/10.1089/dna.2008.0838[Crossref]
• [5] J. Urbanová, P. Lubal, I. Slaninová, E. Táborská, P. Táborský, Anal. Bioanal. Chem. 394, 997 (2009) http://dx.doi.org/10.1007/s00216-009-2601-7[Crossref]
• [6] I. Slaninová, J. Slanina, E. Táborská, Chem. Listy 102, 427 (2008) (in Czech)
• [7] Z. Dvořák et al., Heterocycles 68, 2403 (2006) http://dx.doi.org/10.3987/REV-06-610[Crossref]
• [8] M. Janovská, M. Kubala, V. Šimánek, J. Ulrichová, Anal. Bioanal. Chem. 395, 235 (2009) http://dx.doi.org/10.1007/s00216-009-2903-9[Crossref]
• [9] J. Dostál, J. Slavík, In: Atta-ur-Rahman (Ed.) Studies in Natural Products Chemistry, (Elsevier, Amsterdam, 2002) 27, 155
• [10] M. Vlčková, J. Barták, V. Kubáň, J. Chromatogr. A 1040, 141 (2004) http://dx.doi.org/10.1016/j.chroma.2004.03.064[Crossref]
• [11] M. Vlčková, V. Kubáň, J. Vičar, V. Šimánek, Electrophoresis 26, 1673 (2005) http://dx.doi.org/10.1002/elps.200410193[Crossref]
• [12] R. Vespalec, M. Vlčková, H. Horáková, J. Chromatogr. A 1051, 75 (2004) http://dx.doi.org/10.1016/j.chroma.2004.05.051[Crossref]
• [13] I.G. Motevich, N.D. Strekal, J.W. Nowicky, S.A. Maskevich, J. Appl. Spectrosc. 74, 666 (2007) http://dx.doi.org/10.1007/s10812-007-0107-7[Crossref]
• [14] P. Giri, G.S. Kumar, Biochim. Biophys. Acta 1770, 1419 (2007)
• [15] K. Bhadra, M. Maiti, G.S. Kumar, DNA Cell Biol. 27, 675 (2008) http://dx.doi.org/10.1089/dna.2008.0779[Crossref]
• [16] E. Vrublová et al., J. Food Chem. Toxicol. 46, 2546 (2008) http://dx.doi.org/10.1016/j.fct.2008.04.013[Crossref]
• [17] H. Absolínová, L. Jančář, I. Jančářová, J. Vičar, V. Kubáň, Cent. Eur. J. Chem. 7, 876 (2009) http://dx.doi.org/10.2478/s11532-009-0079-y[Crossref]

Identyfikatory

DOI

10.2478/s11532-010-0038-7