Cyclopentenoid Cyanogens: Their Chemistry, Importance in Plant Systematics, and Their Role in the Coevolution of Plants and Insects (Phytochemistry, Cyanogenic, Glycosides, Nmr)

433 p.Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1984.Cyanogenic glycosides containing a cyclopentene ring were investigated chemically. Techniques for their isolation from plant sources were devised, and data accumulated on their spectroscopic properties. The distribution of cyclopentenoid cyanogens in plants was investigated, and it was determined that members of the Passifloraceae, Turneraceae, Malesherbiaceae, Flacourtiaceae and Caricaceae elaborate these compounds. The value of such a distribution in assessing taxonomic relationships was tested numerically in one genus. Cyclopentenoid cyanogens were found to be useful indicators of phylogenetic affinity at all taxonomic levels. A correlation was discovered between the pattern of elaboration of plant cyclopentenoid compounds and the host-plant preference of Heliconiine butterflies in their coevolutionary interaction with species in the genus Passiflora. A number of new structures are described for cyclopentenoid cyanogenic glycosides isolated from natural sources. An investigation into the biological activity of these compounds showed several to possess potential antitumor activity.U of I OnlyRestricted to the U of I community idenfinitely during batch ingest of legacy ETD