عنوان

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

Number

TLpq304384755

.Language of Text, Soundtrack etc

انگلیسی

Title Proper

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

General Material Designation

[Thesis]

First Statement of Responsibility

H.-D. Yoo

Name of Publisher, Distributor, etc.

Oregon State University

Date of Publication, Distribution, etc.

1997

Specific Material Designation and Extent of Item

148

Dissertation or thesis details and type of degree

Ph.D.

Body granting the degree

Oregon State University

Text preceding or following the note

1997

Text of Note

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.

curacin

Health and environmental sciences

Laminaria saccharina

Lyngbya majuscula

Pure sciences

Vidalia

H.-D. Yoo

Electronic name

p

[Thesis]

276903

a

Y