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Title: Isolation and Relative Configuration Determination of Two Pairs of Bioactive diastereomers from Cacospongia cf. linteiformis.
Creator: Zhang, Long, West, Lyndon, Graduate College
Abstract/Description: Cacospongia cf. linteiformis is a marine sponge collected from Bahamas possessing various bioactive compounds. Two pairs of diastereomers spongianolides E&F were isolated for the first time through function group modification acetylation, and their relative configurations were determined based on Nuclear Overhauser Effect Spectroscopy NOESY. The mixture of isomers of spongianolides E&F are exhibiting inhibition against Schnurri-3. Bioassays will be repeated to unveil the assignment of the...
Show moreCacospongia cf. linteiformis is a marine sponge collected from Bahamas possessing various bioactive compounds. Two pairs of diastereomers spongianolides E&F were isolated for the first time through function group modification acetylation, and their relative configurations were determined based on Nuclear Overhauser Effect Spectroscopy NOESY. The mixture of isomers of spongianolides E&F are exhibiting inhibition against Schnurri-3. Bioassays will be repeated to unveil the assignment of the bioactivities for the four isomers.
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Date Issued: 2014
PURL: http://purl.flvc.org/fau/fd/FA00005865
Format: Document (PDF)

Title: Novel compounds isolated from the marine sponge Clathria sp.
Creator: Rueda de Leon, Rolando, Gupta, Prasoon, West, Lyndon, Graduate College
Date Issued: 2011-04-08
PURL: http://purl.flvc.org/fcla/dt/3164772
Subject Headings: Sponges, Stereochemistry, Marine pharmacology
Format: Document (PDF)

Title: Climate change impacts on the secondary metabolite production in Caribbean coral reef sponges.
Creator: Vansach, Tifanie, Duckworth, Alan R., Hard, M., Stubler, A., West, Lyndon, Graduate College
Date Issued: 2011-04-08
PURL: http://purl.flvc.org/fcla/dt/3164802
Subject Headings: Climatic changes --Environmental aspects, Metabolism, Sponges --Caribbean Sea
Format: Document (PDF)

Title: Cornoside A, a new monoterpenoid glucoside with an unusual skeleton from cornus controversa.
Creator: He, Yangqing, Peng, Jiangnan, Ma, Guoyi, Ma, Zhanying, West, Lyndon, Hamann, Mark T., Graduate College
Date Issued: 2012-03-30
PURL: http://purl.flvc.org/fcla/dt/3342376
Format: Document (PDF)

Title: Isolation and Biomimetic Synthesis of Marine Natural Products.
Creator: Williams, Shakia, Gulino, Stephanie, Bari, Arafat, West, Lyndon, Office of Undergraduate Research and Inquiry
Abstract/Description: While natural products have served as a prolific source of unique chemistry, supply remains a significant obstacle for drug discovery. The overall goal of this project is to determine whether isolation and semi-synthesis can provide adequate quantities for biological evaluation. Erythropodium caribaeorum is an abundant gorgonian in the Caribbean that produces two unique marine diterpenoids, erythrolides A and B, which have been shown to undergo photochemical transformations to yield more...
Show moreWhile natural products have served as a prolific source of unique chemistry, supply remains a significant obstacle for drug discovery. The overall goal of this project is to determine whether isolation and semi-synthesis can provide adequate quantities for biological evaluation. Erythropodium caribaeorum is an abundant gorgonian in the Caribbean that produces two unique marine diterpenoids, erythrolides A and B, which have been shown to undergo photochemical transformations to yield more complex chemistry. In this project, erythrolides A and B will be isolated from E. caribaeorum collected off the coast of Boca Raton, Florida. These compounds will be exposed to ultraviolet light and analyzed to identify any chemical changes. New compounds will then be subjected to biological screening for cytotoxicity against human cancer cell lines. This project will not only identify new bioactive compounds but also provide a novel route for the large-scale production of medically relevant marine natural products.
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Date Issued: 2017
PURL: http://purl.flvc.org/fau/fd/FA00005640
Subject Headings: College students --Research --United States.
Format: Document (PDF)

Title: Briareolate Esters from the Gorgonian Briareum asbestinum.
Creator: Meginley, Rian J., Gupta, Prasoon, Schulz, Thomas C., McLean, Amanda B., Robins, Allan J., West, Lyndon
Date Issued: 2012-08-10
PURL: http://purl.flvc.org/fau/fd/FAUIR000200
Format: Citation

Title: Pseudopterosin A: Protection of Synaptic Function and Potential as a Neuromodulatory Agent.
Creator: Caplan, Stacee Lee, Zheng, Bo, Dawson-Scully, Ken, White, Catherine, West, Lyndon
Date Issued: 2016-03-10
PURL: http://purl.flvc.org/fau/fd/FAUIR000130
Format: Citation

Title: Chemical Studies of Caribbean Marine Organisms.
Creator: Vansach, Tifanie, West, Lyndon M., Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: The projects described in this dissertation concentrated on investigating Caribbean species for qualitative and quantitative chemical differences. Chapter one includes a brief update on the status of natural products as drugs, a discussion of the biodiversity of Caribbean marine organisms as well as a discussion about the chemistry of algae and sponges. In chapter two, an experiment to test for possible effects of warmer, more acidic water and how that will impact coral reef organisms was...
Show moreThe projects described in this dissertation concentrated on investigating Caribbean species for qualitative and quantitative chemical differences. Chapter one includes a brief update on the status of natural products as drugs, a discussion of the biodiversity of Caribbean marine organisms as well as a discussion about the chemistry of algae and sponges. In chapter two, an experiment to test for possible effects of warmer, more acidic water and how that will impact coral reef organisms was conducted. Six common Caribbean coral reef sponge species were grown in seawater for 24 days ranging from values experienced at summer-maxima (temperature = 28 ºC; pH = 8.1) to those predicted for the year 2100 (T = 31 ºC; pH = 7.8). For each species, attachment rates, growth, and survival were similar between temperature and pH levels. Only two metabolite concentrations varied significantly between treatments but were similar to baseline levels. In chapter three, a chemical survey of Florida Keys algae was performed using MeOH extraction and HP-20 SPE with varying Me2CO:H2O solutions. 1H NMR spectra were collected for each fraction and analyzed for interesting signals. A Laurencia sp. was extracted and found to contain the known compound isodactylyne (61) with the structure determined using spectroscopic analyses. In chapter four, a Laurencia obtusa specimen was investigated to determine the compound causing oxygenated signals between 4.50 – 4.80 ppm in the 1H NMR spectra observed in chapter three. A large scale extraction and fractionation was performed and the compound was determined to be 1-O-palmitoyl-2-O-myristoyl-3-O-(6-sulfo-α- D-quinovo-pyranosyl)-glycerol (63). In chapter five, the isolation and structural elucidation of a new compound, furocaespitanenone (64) and two known compounds (10R)- and (10S)-10-O-methylfurocaespitanelactol 65 and 66, from a Laurencia sp. collected off of the Florida Keys using MeOH extraction and HP-20 column chromatography is described. A potential biosynthesis of 64 from furocaepsitane (68) is proposed.
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Date Issued: 2019
PURL: http://purl.flvc.org/fau/fd/FA00013274
Subject Headings: Marine organisms, Caribbean, Algae--chemistry, Sponges--Caribbean Sea, Chemistry
Format: Document (PDF)

Title: Isolation and structure elucidation of new compounds from Cornus Controversa and Delphinium Chrysotrichum.
Creator: He, Yangqing, West, Lyndon, Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: The aim of this dissertation was to explore structurally unique secondary metabolites from herb medicinal plants Cornus controversa and Delphinium chrysotrichum. The introduction in the first chapter provides a detailed review about the research progress of chemical constitutents of the genus Cornus. In addition, its pharmacological activities were also summarized in this chapter to provide a framework for understanding the roles of medicinal herbs belong to genus Cornus as anti-diabetes...
Show moreThe aim of this dissertation was to explore structurally unique secondary metabolites from herb medicinal plants Cornus controversa and Delphinium chrysotrichum. The introduction in the first chapter provides a detailed review about the research progress of chemical constitutents of the genus Cornus. In addition, its pharmacological activities were also summarized in this chapter to provide a framework for understanding the roles of medicinal herbs belong to genus Cornus as anti-diabetes therapeutics and to deliver useful information for further research. In chapter two, seven new compounds, including one iridoid glucoside, cornoside A (59), five iridoid aglycones, cornolactones A – E (60 – 64) and one indenone glucoside, cornoside B (65), together with 10 known compounds have been isolated from the leaves of Cornus controversa. The structures of these compounds were established by interpretation of spectroscopic data. Cornolactone A (61) is the first natural cis-fused tricyclic dilactone iridoid containing both a five- and six-membered lactone ring. Cornoside B (65) is the first alkaloid isolated from the genus Cornus bearing an indole-3-lactic acid-11--D-glucopyranoside skeleton. In chapter three, we described the structure elucidation of three new diterpenoid alkaloids delphatisine D (77), chrysotrichumines A (78) and B (79), as well as 11 known compounds from the whole plants of Delphinium chrysotrichum. Delphatisine D (77) is a rare atisine-type alkaloid from genus Delphinium and is the C-15 epimer of spiramine C which bears an internal carbinolamine ether linkage (NCOC) between C-7 and C-20. Chrysotrichumine A (78) is a rare natural C19-diterpenoid alkaloid possessing a nitrone group between C-17 and C-19. In addition, their cytotoxic activity against human breast cancer cell lines of MCF-7 and MDA-MB-231 were also reported. In chapter four, the detailed extraction and isolation procedures of the new compounds, cornosides A and B, cornolactones A – E, delphatisine D, chrysotrichumine A and B, as well as of all the known compounds were described. In addition, the experimental procedures for the determination of PPARγ and LXR agonistic activities and the MTT cytotoxicity assay were listed in this chapter.
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Date Issued: 2014
PURL: http://purl.flvc.org/fau/fd/FA00004121
Subject Headings: Medicinal plants., Delphinium., Cornus (Plants)
Format: Document (PDF)

Title: Isolation and Structural Elucidation of Novel Bioactive Natural Products from Marine Organisms of the Western Atlantic Ocean.
Creator: Zhang, Long, West, Lyndon, Florida Atlantic University, Charles E. Schmidt College of Science, Department of Chemistry and Biochemistry
Abstract/Description: The aim of this dissertation was to elaborate the exploration of biologically active secondary metabolites from the marine sponge Cacospongia cf. linteiformis collected from the Bahamas and the soft coral Briareum asbestinum collected from two different sites in Florida State, Boca Raton and Dry Tortugas. In chapter one, a review on previous chemical and biological studies of the marine sponge C. cf. linteiformis and soft coral B. asbestinum is provided. Particular attention is given to...
Show moreThe aim of this dissertation was to elaborate the exploration of biologically active secondary metabolites from the marine sponge Cacospongia cf. linteiformis collected from the Bahamas and the soft coral Briareum asbestinum collected from two different sites in Florida State, Boca Raton and Dry Tortugas. In chapter one, a review on previous chemical and biological studies of the marine sponge C. cf. linteiformis and soft coral B. asbestinum is provided. Particular attention is given to spongianolides and briarellins, two important classes of compounds isolated from C. cf. linteiformis and B. asbestinum, respectively, and their structural features and diverse bioactivities. In chapter two, the isolation and relative configuration determination of four epimeric sesterterpenoids, spongianolides E & F (18c, 18d, 19c, 19d) from C. cf. linteiformis collected from the Bahamas are discussed. Thanks to chemical modification (acetylation), diastereomeric 18c&18d and 19c&19d, respectively, were able to be isolated using chromatographic techniques for the first time, and then the relative configurations of 18c, 18d, 19c, 19d were determined based on NOESY NMR experiments. The bioactivity of mixture of compounds 18c, 18d, 19c, 19d were tested and it exhibited inhibition against Schnurri-3 (a regulator of postnatal bone mass). In chapter three, the isolation and structural elucidation of four new compounds, florellins A-D (49-52), from B. asbestinum collected off the coast of Boca Raton, FL are discussed. The molecular structures of these compounds were established by spectroscopic analysis. Compounds 49-52 are the first briarellins containing an acyl group at C-13, while 49 and 50 are the first briarellins possessing acylation at C-15. Florellins A–C (49-51) were screened and found cytotoxic against three human cell lines, BT474, WM266−4 and HEK293. In chapter four, the isolation and structural elucidation of four new compounds, florellins E-H (57-60), from B. asbestinum collected in Dry Tortugas, FL are discussed. The molecular structures of these compounds were established by spectroscopic analysis. Florellins F (58) and H (60) were screened against three human cell lines, BT474, WM266−4 and HEK293, but no cytotoxicity was exhibited. In chapter five, all the experimental procedures are described, including analytical instruments, animal materials, extraction and isolation processes, spectroscopic data and protocols of bioassays.
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Date Issued: 2017
PURL: http://purl.flvc.org/fau/fd/FA00004850, http://purl.flvc.org/fau/fd/FA00004850
Subject Headings: Pharmacognosy., Natural products--Analysis., Marine pharmacology., Marine biotechnology., Marine algae--Biotechnology., Bioactive compounds.
Format: Document (PDF)

Title: Isolation and Semi-synthesis of Marine Diterpenoids.
Creator: Scesa, Paul D., West, Lyndon, Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: Natural products play a historical role in the discovery of medicine but present unique challenges for chemical isolation, identification and production. In this work we describe the identification of twenty novel diterpenoids. These were isolated by use of chromatography, and the structures determined by spectroscopic methods, primarily 1D and 2D NMR. Six of these possess unprecedented diterpenoid skeletons and two of them show significant growth inhibitory effects on cancer cell lines in...
Show moreNatural products play a historical role in the discovery of medicine but present unique challenges for chemical isolation, identification and production. In this work we describe the identification of twenty novel diterpenoids. These were isolated by use of chromatography, and the structures determined by spectroscopic methods, primarily 1D and 2D NMR. Six of these possess unprecedented diterpenoid skeletons and two of them show significant growth inhibitory effects on cancer cell lines in vitro (GI50 < 10 μM). The biomimetic semisynthesis of diterpendoids and analogues is also presented. Access to the bielschowskyane carbon skeleton by dearomatization of a furanocembranoid precursor is described. Highlights include a stereoselective alkene epoxidation, a novel kinetic furan dearomatization method, and an efficient [2+2] photochemical cycloaddition. The role of conformational steering was studied spectroscopically using VT 1H-NMR and NOESY as well as quantum chemical calculations at the DFT level of theory. We also disclose a biomimetic synthesis of providencin using a photochemical Norrish-Yang cyclization. This provided the absolute configuration by chemical correlation with the precursor bipinnatin E, the latter determined by x-ray diffraction. An unexpected, regioisomeric byproduct was observed and a possible mechanism is proposed. A biomimetic synthesis of the diterpene alkaloid aceropterine is also described, using an epoxidation-rearrangement cascade. This work led to a revised structure of aceropterine, formulated by spectroscopic methods. Finally, the isolation and structure elucidation of a novel, cyclic lipopeptide from Pseudomonas sp. is described. The compound was obtained using a unique antibiotic crowd sourcing approach and the structure determined by spectroscopic methods and advanced Marfey’s analysis.
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Date Issued: 2020
PURL: http://purl.flvc.org/fau/fd/FA00013539
Subject Headings: Marine natural products, Diterpenoids, Biomimetics
Format: Document (PDF)

Title: Natural Product Studies of Marine Organisms from the Western Atlantic.
Creator: Hall, Andrew, West, Lyndon, Florida Atlantic University, 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 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...
Show moreThe 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).
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Date Issued: 2016
PURL: http://purl.flvc.org/fau/fd/FA00004666
Subject Headings: Marine natural products., Diterpenes., Marine metabolites
Format: Document (PDF)

Title: Isolation and Biomimetic Synthesis of Marine Natural Products from the Gorgonian Briareum Asbestinum.
Creator: Simpson, Johnathon, West, Lyndon M., Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description: Throughout history, natural products have produced a plethora of biologically active compounds that have established applications in medicine, biology, and pharmacy. The exploration for improved cytotoxic agents has continued to be a crucial path in natural products drug discovery. The focal point of this thesis sheds light on the biosynthetic relationship between the two distinct classes of briarane diterpenoids, the γ-lactone briarane and the briareolate esters. Additionally, this study...
Show moreThroughout history, natural products have produced a plethora of biologically active compounds that have established applications in medicine, biology, and pharmacy. The exploration for improved cytotoxic agents has continued to be a crucial path in natural products drug discovery. The focal point of this thesis sheds light on the biosynthetic relationship between the two distinct classes of briarane diterpenoids, the γ-lactone briarane and the briareolate esters. Additionally, this study elaborates on the discovery and elucidation of structurally unique secondary metabolites from the gorgonian coral Briareum asbestinum. The first chapter of this thesis provides a review of the development and discovery of diverse secondary metabolites. In addition, this chapter describes the role of natural products in drug discovery and summarizes the research progress in marine natural product chemistry in conjunction with a detailed overview of the current marine-derived pharmaceuticals.
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Date Issued: 2021
PURL: http://purl.flvc.org/fau/fd/FA00013857
Subject Headings: Marine natural products, Diterpenoids, Biomimetics, Soft corals
Format: Document (PDF)

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