My investigations of the natural products of marine algae have resulted in
the discovery of several new secondary metabolites. Bioassay-guided
fractionation led to the isolation of these new compounds and spectroscopic
analysis was utilized in their structural characterization.
Two new and potent antimitotic metabolites, curacins B and C, were
isolated from a Curacao collection of Lyngbya majuscula. In addition, four
curacin A analogs were prepared by semisynthetic methods. The structures of
the new curacins and the curacin A analogs were determined by spectroscopic
analysis in comparison with curacin A. The biological properties of the new
natural products and synthetic derivatives of curacin A were examined.
Investigations of another Curacao collection of L. majuscula revealed a
new cytotoxic lipopeptide, microcolin C. Microcolin C was found to have an
interesting profile of cytotoxicity to human cancer-derived cell lines.
A new metabolite, vidalenolone, was isolated from an Indonesian red
alga Vidalia sp. The structure of this new cyclopentenolone-containing
compound was determined by a combination of spectroscopic methods.
Filamentous cells isolated from female gametophytes of the brown alga
Laminaria saccharina were cultured in flasks or bioreactors. These cultures
produced a variety of w6-lipoxygenase metabolites: 13-hydroxy-9,11-octadecadienoic acid (13-HODE), 13-hydroxy-6,9,11,15-octadecatetraenoic acid (13-HODTA), and 15-hydroxy-5,8,11,13-eicosatetraenoic acid (15-HETE).
Five oxidized anandamide derivatives were prepared from anandamide through autoxidation in an exploration of ligand binding to the cannabinoid receptor. Their structures were determined by a combination of NMR spectroscopy and GC-MS. The cannabinoid receptor binding affinity of these derivatives was evaluated. This study revealed the following trend in activity: anandamide > 15- > 9- > 8- > 11- > 5-hydroxyanandamide. / Graduation date: 1998
|13 October 1997
|Gerwick, William H.
|Oregon State University
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