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

Parrish, Stephen Michael
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[Honolulu] : [University of Hawaii at Manoa], [May 2013]
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.
M.S. University of Hawaii at Manoa 2013.
Includes bibliographical references.
Moorea producens
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