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

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" Bioactive secondary metabolites from marine algae and study of oxidized anandamide derivatives "
H.-D. Yoo

Document Type	:	Latin Dissertation
Language of Document	:	English
Record Number	:	1113508
Doc. No	:	TLpq304384755
Main Entry	:	H.-D. Yoo
Title & Author	:	Bioactive secondary metabolites from marine algae and study of oxidized anandamide derivatives\ H.-D. Yoo
College	:	Oregon State University
Date	:	1997
student score	:	1997
Degree	:	Ph.D.
Page No	:	148
Abstract	:	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 usd\omega6usd-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.
Subject	:	curacin
	:	Health and environmental sciences
	:	Laminaria saccharina
	:	Lyngbya majuscula
	:	Pure sciences
	:	Vidalia