Bioactive secondary metabolites from marine algae and study of oxidized anandamide derivatives Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/dj52w770x

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  • 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.
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  • description.provenance : Submitted by Kirsten Clark (kcscannerosu@gmail.com) on 2012-09-17T23:33:32Z No. of bitstreams: 1 YooHye-Dong1998.pdf: 4946451 bytes, checksum: ed0c89822979dc01cf4c2bf8cf93d3fa (MD5)
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