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.
Caccamese
Salvatore
S
Dipartimento di Scienze Chimiche, Università di Catania, viale A. Doria 6, 95125 Catania, Italy. scaccamese@dipchi.unict.it
Scivoli
Giovanna
G
Bianca
Salvatore
S
López-Romero
Juan Manuel
JM
Ortiz-López
Francisco Javier
FJ
D000470:Alkaloids / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002942:Circular Dichroism / Q000379:methods*; D019073:HT29 Cells; D006801:Humans; D007546:Isoquinolines / Q000032:analysis* / Q000737:chemistry / Q000494:pharmacology; D015203:Reproducibility of Results; D013237:Stereoisomerism
D000470:Alkaloids; D007546:Isoquinolines; C499203:aristocularine