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Caccamese, S. et al.

Caccamese, Scivoli, Bianca, López-Romero, Ortiz-López,

Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids.

The HPLC enantiomeric separation of the racemic cularinoid alkaloids N-p-methoxy-1,alpha-dihydroaristoyagonine (1) and 4',5'-demethoxy-1,alpha-dihydroaristoyagonine (2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugative effect strongly affect the different enantioselectivity of the compounds 1 and 2 on the various CSPs investigated. Single enantiomers of 1 were isolated by repeated injections on an analytical HPLC column, and their circular dichroism spectra and optical rotations were measured. The cytotoxicity of the isolated enantiomers was measured on a human colon carcinoma cell line and compared with that of the racemic compound.[1]

References

Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids. Caccamese, S., Scivoli, G., Bianca, S., López-Romero, J.M., Ortiz-López, F.J. Journal of chromatography. A. (2006) [Pubmed]

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