Novel bisindole derivatives of Catharanthus alkaloids with potential cytotoxic properties.
Pantropical plant Catharanthus roseus (L) G. Don is known as a source of valuable bisindole alkaloids: vinblastine (VBL) and vincristine (VCR), oncolytics widely used as sulfates in therapy of malignant diseases. They are biosynthesized in the plant from monoindolic vindoline and catharanthine, both derived from L-tryptophan and loganine units. In the course of phytochemical screening of this plant cultivated in Poland and considered as a home source of VBL and VCR we developed a new isolation method based on the solid phase extraction. Mild conditions used during the isolation procedure enabled the isolation of some labile compounds and so the monomeric alkaloids with high yields. Vindoline and so its congeners and subjected to various oxidative conditions gave 15,15'-bisindolic derivatives in quite good yield. Biological activities of the above mentioned bisindolic compounds are under study.
Ruszkowska
Joanna
J
Faculty of Chemistry, Warsaw University, L. Pasteur Str. 1, 02-093 Warsaw, Poland. ruszko@chem.uw.edu.pl
Chrobak
Robert
R
Wróbel
Jerzy T
JT
Czarnocki
Zbigniew
Z
D030008:Catharanthus / Q000737:chemistry*; D003603:Cytotoxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D014748:Vinca Alkaloids / Q000737:chemistry / Q000302:isolation & purification; D014750:Vincristine / Q000737:chemistry / Q000302:isolation & purification
D003603:Cytotoxins; D026121:Indole Alkaloids; D014748:Vinca Alkaloids; C009667:vindoline; D014750:Vincristine; D014747:Vinblastine; C017836:catharanthine