Acid-base behaviour of sanguinarine and dihydrosanguinarine

• Authors: Helena Absolínová , Luděk Jančář , Irena Jančářová , Jaroslav Vičar , Vlastimil Kubáň
• Languages of publication: EN

Abstracts

EN

Acid-base and optical properties of sanguinarine and dihydrosanguinarine were studied in the presence of HCl, HNO3, H2SO4, H3PO4, CAPSO and acetic acid (HAc) of different concentrations and their mixtures. The equilibrium constants pKR+ of the transition reaction between an iminium cation Q+ of sanguinarine and its uncharged QOH (pseudo-base, 6-hydroxy-dihydroderivative) form were calculated. A numerical interpretation of the A-pH curves by a SQUAD-G computer program was used. Remarkable shifts of formation parts of absorbance-pH (A-pH) curves to alkaline medium were observed. The shifts depend on the type and concentration of inert electrolyte (the most remarkable for HNO3 and HCl). The corresponding pKR+ values ranged from 7.21 to 8.16 in the same manner (ΔpKR+ = 0.81 and 0.73 for HNO3 and HCl, respectively). The priority effect of ionic species and ionic strength was confirmed in the presence of NaCl and KCl. The strength of interaction of SA with bioactive compounds (i.e. receptors, transport proteins, nucleic acids etc.) may be affected because of the observed influence of both cations and anions of the inert electrolytes. [...]

Keywords

EN

Sanguinarine; Dihydrosanguinarine; UV-VIS Spectrophotometry; Equilibrium constants

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2009
• Volume: 7
• Issue: 4
• Pages: 876-883

Dates

published

1 - 12 - 2009

online

6 - 10 - 2009

Contributors

author

Helena Absolínová

• Department of Chemistry and Biochemistry, Mendel University of Agriculture and Forestry, CZ-613 00, Brno, Czech Republic

author

Luděk Jančář

• Department of Chemistry, Masaryk University, CZ-603 00, Brno, Czech Republic

author

Irena Jančářová

• Department of Chemistry and Biochemistry, Mendel University of Agriculture and Forestry, CZ-613 00, Brno, Czech Republic

author

Jaroslav Vičar

• Department of Medical Chemistry and Biochemistry, Palacky University Olomouc, CZ-77515, Olomouc, Czech Republic

author

Vlastimil Kubáň

References

• [1] V. Šimánek, In: A. Brossi (Ed.), The Alkaloids (Academic Press, Orlando, 1985) 26, 185
• [2] D. Walterová et al., Acta Univ. Palacky Olomuc, Fac. Med. 139, 7 (1995)
• [3] R. Verpoorte, In: M.F. Roberts, M. Wink (Eds.), Alkaloids. Biochemistry, Ecology and Medicinal Applications (Plenum Press, New York, 1998) 413
• [4] H. Tenenbaum, N. Dahan, M. Soell, J. Peridontol. 70, 307 (1999) http://dx.doi.org/10.1902/jop.1999.70.3.307[Crossref]
• [5] P. Kosina et al., Food Chem. Toxicol. 42, 85 (2004) http://dx.doi.org/10.1016/j.fct.2003.08.007[Crossref]
• [6] J. Psotová et al., J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 830, 165 (2006) http://dx.doi.org/10.1016/j.jchromb.2005.10.030[Crossref]
• [7] Z. Dvořák et al., Heterocycles 68, 2403 (2006) http://dx.doi.org/10.3987/REV-06-610[Crossref]
• [8] M.E. Perelson, I.V. Persiyanova, T.S. Semenova, I.E. Konylova, Khim. Prirod. Soedin. 3, 337 (1984) (in Russian)
• [9] J. Ulrichová et al., Planta Med. 48, 111 (1983) http://dx.doi.org/10.1055/s-2007-969901[Crossref]
• [10] M.H.A. Bush, L.B. Carels, H.F.M. Boelens, J.C. Kraak, H. Poppe, J. Chromatogr. A 777, 311 (1997) http://dx.doi.org/10.1016/S0021-9673(97)00369-5[Crossref]
• [11] J. Ševčík, J. Vičar, J. Ulrichová, I. Válka, K. Lemr, V. Šimánek, J. Chromatogr. A 866, 293 (2000) http://dx.doi.org/10.1016/S0021-9673(99)01126-7[Crossref]
• [12] E. Vrublová et al., Food Chem. Toxicol. 46, 2546 (2008) http://dx.doi.org/10.1016/j.fct.2008.04.013[Crossref]
• [13] L. Jančář, J. Havel, Scripta Fac. Sci. Nat. Univ. Purk. Brun. Chemia 14, 73 (1984)
• [14] 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]
• [15] J. Kovář, K. Šimek, E. Kožoušková, H. Klukanová, J. Slavík, Collect. Czech. Chem. Commun. 50, 1312 (1985)
• [16] D. Walterová, V. Preininger, F. Grambal, V. Šimánek, F. Šantavý, Heterocycles 14, 597 (1980) http://dx.doi.org/10.3987/R-1980-05-0597[Crossref]
• [17] M.H.A. Bush, L.B. Carels, H.F.M. Boelens, J.C. Kraak, H. Poppe, J. Chromatogr. A 777, 328 (1997)
• [18] J. Ševčík, J. Vičar, J. Ulrichová, I. Válka, K. Lemr, V. Šimánek, J. Chromatogr. A 866, 293 (2000) http://dx.doi.org/10.1016/S0021-9673(99)01126-7[Crossref]
• [19] J. Dostál, E. Táborská, J. Slavík, Fitoterapia 63, 67 (2002)
• [20] M. Vlčková, J. Barták, V. Kubáň, J. Chromatogr. A 1040 (2004) 141 http://dx.doi.org/10.1016/j.chroma.2004.03.064[Crossref]
• [21] M. Hossain, G.S. Kumar, J. Chem. Thermodyn. 41, 764 (2009) http://dx.doi.org/10.1016/j.jct.2008.12.008[Crossref]
• [22] I. Slaninová, J. Slanina, E. Táborská, Chem. Listy 102, 427 (2008) (in Czech)
• [23] M. Vlčková, V. Kubáň, J. Vičar, V. Šimánek, Electrophoresis 26, 1673 (2005) http://dx.doi.org/10.1002/elps.200410193[Crossref]
• [24] Z. Dvořák, V. Šimánek, Curr. Drug Metabol. 8, 173 (2007) http://dx.doi.org/10.2174/138920007779815959[Crossref]
• [25] J. Dostál, H. Bochořáková, E. Táborská, J. Slavík, M. Potáček, M. Buděšínský, E. de Hoffmann, J. Natur. Prod. 59, 599 (1996) http://dx.doi.org/10.1021/np960356h[Crossref]
• [26] R. Vespalec, M. Vlčková, H. Horáková, J. Chromatogr. A 1051, 75 (2004) http://dx.doi.org/10.1016/j.chroma.2004.05.051[Crossref]

Identifiers

DOI

10.2478/s11532-009-0079-y