Structure elucidation and biosynthetic investigations of marine cyanobacterial secondary metabolites Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/bn999968w

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  • This thesis details my investigations of marine cyanobacterial natural products that resulted in the discovery of thirteen new secondary metabolites, the isolation of over fifteen previously reported metabolites and the biosynthetic investigation of two additional cyanobacterial compounds. Two novel lipopeptides were identified from a Lyngbya majuscula and Schizothrix sp. assemblage collected in the Fiji Islands. Somamide A is a depsipeptide consisting of a hexanoate moiety extended by seven amino acids, including two nonstandard units characteristic of cyanobacterial peptides. In contrast, somocystinamide A is a unique linear disulfide dimer displaying potent cytotoxicity against a mammalian neuroblastoma cell line. The organic extract from a Puerto Rican L. majuscula proved remarkably rich in chemistry, producing twelve known compounds as well as four new secondary metabolites. Among these new isolates were the novel sodium channel blocker antillatoxin B, a new chlorinated quinoline derivative and the new α-pyrone malyngamide T. A collection of L. majuscula from Antany Mora, Madagascar, led to the isolation of the previously reported antineoplastic agent dolastatin 16 and the discovery of a new series of lipopeptides, the antanapeptins. These new molecules are characterized by the presence of the unique β-hydroxy acid 3-hydroxy-2-methyloctynoate, or its reduced double- or single-bond equivalent. Wewakazole is a novel cyclic dodecapeptide isolated from a Papua New Guinea collection of L. majuscula. This large molecule contains both a methyloxazole and two oxazoles, residues rarely observed in marine cyanobacterial metabolites. Extensive utilization of 1D and 2D NMR techniques were required to elucidate the structure of this distinctive peptide. Biosynthetic investigations of two halogenated cytotoxins were also conducted on a cultured L. majuscula strain originally isolated from Hector Bay, Jamaica. Stable isotope feeding experiments demonstrated that both jamaicamide A and hectochlorin derive from mixed PKS and NRPS biosynthetic origins but are comprised of primary precursors unique to each molecule.
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