Vindoline and 16-demethoxyvindoline: two catharanthus-derived alkaloids.
Vindoline, C(25)H(32)N(2)O(6), and 16-demethoxyvindoline, C(24)H(30)N(2)O(5), both of which are naturally occurring biologically active products derived from plants, are important as possible starting materials for the synthesis of valuable anticancer antibiotics, viz. vincristine and vinblastine, and other pharmaceuticals. The vindoline framework consists of two five- and three six-membered condensed rings. One of the six-membered rings adopts a boat conformation, one adopts a sofa conformation and the third is planar. Both five-membered rings have envelope structures. The intramolecular hydrogen bonds present in the structures are characteristic of vinca alkaloids.
Ruszkowska
Joanna
J
Chemistry Department, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland.
Chrobak
Robert
R
Maurin
Jan K
JK
Czarnocki
Zbigniew
Z
D000470:Alkaloids / Q000737:chemistry*; D000903:Antibiotics, Antineoplastic / Q000096:biosynthesis / Q000737:chemistry; D030008:Catharanthus / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000737:chemistry*
C499421:16-demethoxyvindoline; D000470:Alkaloids; D000903:Antibiotics, Antineoplastic; C009667:vindoline; D014747:Vinblastine