Metabolites isolated from moorea producens, nostoc sphaericum, and spongia sp.

Date
2013-05
Authors
Parrish, Stephen Michael
Contributor
Advisor
Department
Instructor
Depositor
Speaker
Researcher
Consultant
Interviewer
Journal Title
Journal ISSN
Volume Title
Publisher
[Honolulu] : [University of Hawaii at Manoa], [May 2013]
Volume
Number/Issue
Starting Page
Ending Page
Alternative Title
Abstract
People have been interacting with natural products for centuries. The metabolites held within organisms have been the most valuable source of drug leads and continue to develop a complex scaffolding and bioactivity. In my thesis, I present data from a cyanobacterium strain, Moorea producens, in the bioactivity-guided isolation of a new lipophilic molecule, trans-7-methoxytetradec-5-ene-4-oneioic acid (2.1) and a few known non-active molecules majusculamides A and B (2.2, 2.3). Next, another cyanobacterium, Nostoc sphaericum, is extracted to obtain three known indolocarbazoles (2.4-2.6), separating two similar regioisomers for the first time allowing us to obtain distinct IR data. I will also present the isolation and characterization of one known (3.4) and three new spongians (3.1-3.3). One novel diterpene, spongiapyridine (3.3), has a unique pyridine ring in the D ring of the molecule. Its structure elucidation was complicated by a methylene that exchanged its proton with the deuterated solvent. 19-nor-3,5α,17-trihydroxyspongia-3,13(16),14-triene-2-one (3.2) showed weak aromatase inhibition at 34 μM and moderate quinone reductase induction with a CD of 11.2 μM. Data of these structures are presented via NMR and LC-MS spectroscopic data, as well as the bioactivity, biosynthesis and implications associated with these molecules.
Description
M.S. University of Hawaii at Manoa 2013.
Includes bibliographical references.
Keywords
Moorea producens
Citation
Extent
Format
Geographic Location
Time Period
Related To
Theses for the degree of Master of Science (University of Hawaii at Manoa). Chemistry.
Rights
Rights Holder
Collections
Email libraryada-l@lists.hawaii.edu if you need this content in ADA-compliant format.