Cytotoxic steroids of Gelsemium sempervirens.
A new pregnane derivative, 12 beta-hydroxy-5 alpha-pregn-16-ene-3,20-dione, along with the known derivative 12 beta-hydroxy-pregna-4,16-diene-3,20-dione have been isolated from a MeOH extract of the stem of Gelsemium sempervirens and found to be the principal cytotoxic entities. The 13C-nmr spectra of both compounds were assigned by comparison with other pregnane analogs thereby allowing confirmation of the stereochemistry at C-5 in compound. Heteronuclear 2D correlation and selective INEPT experiments indicated the need to revise a number of 13C-nmr assignments of pregn-4,16-dien-3,20-dione. Nine indole alkaloids, gelsemine, gelsevirine, 21-oxogelsemine, gelsedine, 14 beta-hydroxygelsedine, gelsenicine, humantenidine, humantenirine, and koumidine were found to be inactive in the KB and P-388 cytotoxicity test systems.
Schun
Y
Y
Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago 60612.
Cordell
G A
GA
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis / Q000302:isolation & purification*; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D009374:Neoplasms, Experimental / Q000188:drug therapy; D010936:Plant Extracts / Q000032:analysis; D010946:Plants, Medicinal / Q000032:analysis*
D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts