Investigation of novel secondary metabolites of colophospermum mopane

Thesis (M.S.) University of Alaska Fairbanks, 2005Labdanes are a large and important class of diterpenes. Colophospermum mopane seems to be a source of 'primitive' 9, 13-epoxylabdanes. The structures of these compounds are 'missing links' in the biogenesis of 9, 13-epoxylabdanes. This research reports a new compound extracted from the seeds of C. mopane. The structures of this compound has been completely elucidated by NMR spectroscopy, and the stereochemistry of the compound supports predictions based on biosynthetic arguments. Furthermore, this thesis also corrects NMR assignments previously reported by another group.Introduction -- Description of mopane -- Distribution of mopane -- Uses of mopane -- Known terpenoid chemistry of mopane -- Results and discussion -- Compound I -- Isolation and identification of compound I -- Conversion to a methyl ester -- Compound II -- Isolation and identification of compound II -- Conversion to a methyl ester -- Summary of compounds I and II -- Correction of peak assignments for compound I reported by Mebe (2001) -- Conclusions -- Experimental -- Sample collection and extraction -- Analysis and purification -- Methyl ester formation -- References -- Appendix A : NMR data -- Appendix B : All HMBC and NOESY correlations for compound I in CDCl₃ -- Appendix C : All HMBC and NOE correlations for compound I in d₆-benzene -- Appendix D : All HMBC and NOESY correlations for compound II in CDCl₃ -- Appendix E : All HMBC and NOESY correlations for compound II in d₆-benzene -- Appendix F : HMBC and NOESY correlations for compound Ia -- Appendix G : HMBC and NOESY correlations for compound IIa -- Appendix H : Stereoviews