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extraction optimization and determination of the absolute configuartion of clathric acid
Title
An extraction optimization and determination of the absolute configuartion of clathric acid.
Creator
Rueda de Leon, Rolando, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description
Current research in natural products has heavily focused on the identification of potent biologically active compounds, specifically for drug development. The project detailed in this thesis focuses on the extraction of compounds from marine invertebrates as well as defining the absolute configuration for a compound. Utilizing marine invertebrates, the sonications method developed in this thesis provides an alternative approach to rapidly extract compounds for primary screening. This method...
Show moreCurrent research in natural products has heavily focused on the identification of potent biologically active compounds, specifically for drug development. The project detailed in this thesis focuses on the extraction of compounds from marine invertebrates as well as defining the absolute configuration for a compound. Utilizing marine invertebrates, the sonications method developed in this thesis provides an alternative approach to rapidly extract compounds for primary screening. This method is viable compared to a traditional overnight extraction method, without suffering compound degredation... Previously, clathric acid was isolated from an unknown Clathria sp. This compound is a bibyblic C-21 terpenoid shown to have mild antimicrobial activity against gram positive bacteria. With only its relative configuration established, additional amounts of clathric acid were required to define the overall absolute configuration. Identifying the Clathria sp. to be Clathria compressa, through spicule analysis, additional sponge tissues were then collected off the coast of Boca Raton, Florida to isolate additional quatities of clathric acid. The absolulte configuration was determined through circular dichroism and the octant rule to establish a final configuration for clathric acid's four carbon stereocenters to be: (3S, 7S, 8R, and 12S).
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Date Issued
2012
PURL
http://purl.flvc.org/FAU/3355874
Subject Headings
Organic compounds, Analysis, Extraction (Chemistry), Natural products, Therapeutic use, Marine biotechology, Marine resources, Research, Sponges, Ecology
Format
Document (PDF)
Isolation and structure elucidation of novel compounds from marine cyanobacteria
Title
Isolation and structure elucidation of novel compounds from marine cyanobacteria.
Creator
Meickle, Theresa, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description
The work of this dissertation examined the secondary metabolites of several blooms of the marine cyanobacterium Lyngbya collected in Guam and Florida with an emphasis on the isolation and structure elucidation of novel biologically active compounds. The introduction in Chapter One provides a brief history of marine natural products, a description of cyanobacteria and a summary of peptides isolated from Lyngbya collected in the Caribbean. In Chapter Two, a bioassay-guided fractionation of a...
Show moreThe work of this dissertation examined the secondary metabolites of several blooms of the marine cyanobacterium Lyngbya collected in Guam and Florida with an emphasis on the isolation and structure elucidation of novel biologically active compounds. The introduction in Chapter One provides a brief history of marine natural products, a description of cyanobacteria and a summary of peptides isolated from Lyngbya collected in the Caribbean. In Chapter Two, a bioassay-guided fractionation of a Floridian collection of Lyngbya polychroa led to the isolation and structural determination of the cytotoxin desacetylmicrocolin B and the known compounds microcolins A and B. The structures were established by nuclear magnetic resonance (NMR) spectroscopic analysis. All three compounds inhibited the growth of cancer cell lines HT-29 and IMR-32 at nanomolar concentrations. Microcolins A and B were found to have little activity in the ecological assay against the marine fungus Dendryphiella salina. Chapter Three describes the isolation and structure elucidation of the glycosidic, acyl proline derivative tumonoic acid J from a sample Lyngbya sp. collected in Guam. The planar structure was determined by 1D and 2D NMR spectroscopy in conjunction with high resolution-mass spectrometry (HR-MS) data. Tumonoic acid J showed moderate activity in the ecological assay against the marine fungus D. salina. In Chapter Four, NMR-guided fractionation of a Floridian sample of Lyngbya majuscula led to the isolation of two novel cyclic peptides porpoisamides A and B. The planar structures were determined by 1D and 2D NMR spectroscopy with HR-MS data. The absolute configurations of these two compounds were defined through chiral chromatographic methods and derivatization techniques., The porpoisamides showed only moderate activity in cytotoxicity assays against cancer cell lines HCT-116 and U2OS. Finally, Chapter Five examines a potential ecological role of compounds isolated from marine cyanobacte ria. These secondary metabolites may function as chemical defenses against competing microorganisms within marine environments. Compounds isolated from cyanobacteria were tested for anti-fungal activity against the saprophytic marine fungus D. salina. Three of the six compounds tested produced inhibitory activity at or below their natural concentration.
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Date Issued
2010
PURL
http://purl.flvc.org/FAU/2978991
Subject Headings
Sponges, Ecology, Cyanobacteria, Biological control, Aquatic ecology
Format
Document (PDF)
Therapeutic potential, mechanism of action, and ecology of novel marine natural products
Title
Therapeutic potential, mechanism of action, and ecology of novel marine natural products.
Creator
Winder, Priscilla L., Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description
The projects described in this dissertation are focused on compounds derived from the marine environment. Chapter 1 gives an introduction to the study of marine natural products to treat human ailments and a thorough review on compounds from lithistid sponges that have been isolated or synthesized since 2000. Chapter 2 describes the isolation and structure elucidation of two sesquiterpene substituted benzoquinone derivatives, petrosiquinones A and B, from a deep-water marine sponge from the...
Show moreThe projects described in this dissertation are focused on compounds derived from the marine environment. Chapter 1 gives an introduction to the study of marine natural products to treat human ailments and a thorough review on compounds from lithistid sponges that have been isolated or synthesized since 2000. Chapter 2 describes the isolation and structure elucidation of two sesquiterpene substituted benzoquinone derivatives, petrosiquinones A and B, from a deep-water marine sponge from the Family Petrosiidae. Although initially purified following activity in a (Sb(B-catenin/Tcf4 assay they were later followed using tumor cell line cytotoxicity assays. Petrosiquinone A was the more active of the two compounds with moderate cytotoxicity in the DLD-1, PANC-1, and AsPC-1 cell lines. In Chapter 3, the isolation and structure elucidation of two new marine-derived macrolides, madeirolide A and B, isolated from a deep-water lithistid sponge of the genus Leiodermatium is described., They were isolated using numerous chromatographic techniques and the structures were elucidated on the basis of 1D and 2D NMR spectra coupled with high resolution-mass spectrometry (HR-MS) data. Madeirolide A and B inhibited the growth of the fungal pathogen Candida albicans with minimum inhibitory concentrations (MIC) of 12.5 and 25 (So(Bg/mL, respectively, but were not cytotoxic in tumor cell assays under the conditions tested. Chapter 4 describes work performed to determine the molecular target of lasonolide A using affinity chromatography. The target of lasonolide A is of interest since lasonolide A is known to kill cancer cells in vitro through a unique mechanism., This chapter highlights the research performed to create an affinity matrix with immobilized lasonolide. A target has not been confirmed but there are a number of interesting hits that are being pursued. In Chapter 5, a liquid chromatography-mass spectrometry (LC-MS) screening method was established in order to rapidly identify the metabolites from numerous collections of Lyngbya spp. obtained from Broward and Lee County, Florida sites that may help marine ecologists assess the effects of Lyngbya spp. blooms on the environment. A link between the metabolites produced and nutrients from both the algal tissue and water column was also explored.
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Date Issued
2009
PURL
http://purl.flvc.org/FAU/369392
Subject Headings
Natural products, Therapeutic use, Sponges, Ecology, Marine resources, Research, Marine biotechnology
Format
Document (PDF)