Structural Studies of Isoquinoline Alkaloids

People involved:
 
Staff:
Doc. RNDr. Radek Marek, Ph.D.
Mgr. Jaromír Toušek, Dr.
Prof. RNDr. Vladimír Sklenář, DrSc.
 
Diploma, Ph.D. and postdoctoral fellows:
Mgr. Lenka Baraková
 

Project description:

This project is focused on the structural studies of benzo[c]phenanthridine, protoberberine, and other isoquinoline plant alkaloids found in families Papaveraceae, Berberidaceae, Fumariaceae, and Rutaceae. The spectra obtained using advanced two-dimensional NMR techniques are used to extract structural parameters from chemical shifts, spin-spin scalar coupling constants and coherence transfer pathways of ¹H, ¹³C and ¹⁵N nuclei. The experimental data together with quantum-chemical calculations (DFT calculations of chemical shielding and scalar spin-spin couplings) are employed to determine the molecular structure with high accuracy and the results are correlated with the geometry determined by x-ray diffraction. Interactions of isoquinoline alkaloids with basic building blocks of biomacromolecules and intermolecular interactions in the solid state are current hot topics.
 

Diploma and Ph.D. theses offered:

• Interactions of isoquinoline alkaloids with basic building blocks of biomacromolecules
• Intermolecular interactions in the solid state

List of selected publications:

• Sečkářová, P.; Marek, R.; Dostál, J.; Dommisse, R.; Esmans, E.L. 2002. Magn. Reson. Chem. 40: 147 - 152.

• Marek, R.; Marek, J.; Dostál, J.; Táborská; E., Slavík; J.; Dommisse, R. 2002. Isoquinoline alkaloids: a ¹⁵N NMR and x-ray study. Magn. Reson. Chem. 40: 687 - 692.

• Marek, R.; Sečkářová, P.; Hulová, D.; Marek, J.; Dostál, J.; Sklenář, V. 2003. Palmatine and Berberine Isolation Artifacts. J. Nat. Prod. 66: 481 - 486.

• Marek, J.; Hulová, D.; Dostál, J.; Marek, R. 2003. Berberine formate - succinic acid (1/1). Acta Crystallogr. C59: o583 - o585.

• Dostál, J.; Man, S.; Sečkářová, P.; Hulová, D.; Nečas, M.; Potáček, M.; Toušek, J.; Dommisse, R.; Van Dongen, W.; Marek, R. 2004. Berberine and coptisine free bases. J. Mol. Struct. 687: 135 - 142.

Cooperations:

• Jiří Dostál, Masaryk University, Brno, Czech Republic

• Roger Dommisse and Luc Pieters, University of Antwerp, Antwerp, Belgium

Financial sources:

• Ministry of Education, Youth and Sports

 

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