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Natural Product Studies of Marine Organisms from the Western Atlantic

The projects described in this dissertation are focused on compounds derived
from marine organisms collected from the western Atlantic marine environment.
Chapter 1 provides an introduction to the study of natural products chemistry,
marine natural products, and overview of the research undertaken from natural product
chemists.
Chapter 2 describes the isolation and structure elucidation of a series of rare
diterpenoids from the gorgonian Briareum asbestinum, together with their conformational
analysis and biosynthetic interconversions. These rare diterpenes from Briareum
asbestinum are linked by an unusual transannular oxa-6π electrocyclization which is
described in detail and this work demonstates the biomimetic hemisynthesis of
briareolate esters L (19) to B (22) achieved via an intermediary, briareolate ester G (2),
through a controlled set of photoinduced isomerizations and a unique photochromic
transannular oxa-6π electrocyclization. This work focuses largely on the mechanistic understanding of the photochemical production of these briarane diterpenoids and
illustrates a unique UVA/UVC, photochromic switch which induces a transannular oxa-
6π electrocyclization.
Chapter 3 describes the assay-guided isolation of marine antioxidants. This
chapter focuses on the screening of marine organism extracts using the Ferric Reducing
Antioxidant Power (FRAP) assay for antioxidant activity guided isolation of marine
natural products. The chapter concludes with the activity guided isolation and structural
elucidation of 1-O-palmitoyl-2-O-myristoyl-3-O-(6-sulfo-α-D-quinovopyranosyl)-
glycerol (40) to show direct antioxidant potential through FRAP analysis.
Chapter 4 describes the isolation, structural elucidation and pharmacological
evaluation of the novel secondary metabolites iso-PsA(45), Iso-PsC (46), iso-PsD (47) as
well as known Pseudopterosins A(41), B(42), C(43), D(44), K(48), K2’OAc(49),
K2’OAc(50). These secondary metabolites were evaluated for both cytotoxicity. The
chapter concludes with the screening of these compounds as αβ-amyloid fibril modulators
utilizing atomic force microcopy (AFM). / Includes bibliography. / Dissertation (Ph.D.)--Florida Atlantic University, 2016. / FAU Electronic Theses and Dissertations Collection

Identiferoai:union.ndltd.org:fau.edu/oai:fau.digital.flvc.org:fau_33680
ContributorsHall, Andrew (author), West, Lyndon (Thesis advisor), Florida Atlantic University (Degree grantor), Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
PublisherFlorida Atlantic University
Source SetsFlorida Atlantic University
LanguageEnglish
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation, Text
Format159 p., application/pdf
RightsCopyright © is held by the author, with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder., http://rightsstatements.org/vocab/InC/1.0/

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