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

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.