A5042839776- Marine Sponges and Natural Products
- Synthetic Organic Chemistry Methods
- Microbial Natural Products and Biosynthesis
- Traditional and Medicinal Uses of Annonaceae
- Marine Biology and Environmental Chemistry
- Phytochemical Studies and Bioactivities
- Computational Drug Discovery Methods
- Coral and Marine Ecosystems Studies
- Molecular spectroscopy and chirality
- Antimicrobial Peptides and Activities
- Chemical synthesis and alkaloids
- Synthesis and Biological Activity
- Alkaloids: synthesis and pharmacology
- Beetle Biology and Toxicology Studies
- Organometallic Complex Synthesis and Catalysis
- Carbohydrate Chemistry and Synthesis
- Biopolymer Synthesis and Applications
- X-ray Diffraction in Crystallography
- Neurobiology and Insect Physiology Research
- Photochromic and Fluorescence Chemistry
- Cocoa and Sweet Potato Agronomy
- Analytical Chemistry and Sensors
- Radioactive element chemistry and processing
- Seaweed-derived Bioactive Compounds
- Enzyme Production and Characterization
Florida Atlantic University
2011-2024
University of Georgia
2009-2016
Victoria University
2000-2010
Bunkyo University
2009
Scripps Institution of Oceanography
2003-2008
University of California, San Diego
2003-2008
The University of Tokyo
2008
Victoria University of Wellington
1999-2005
Center for Cancer Research
2002
Physical Sciences (United States)
2002
A novel, polyoxygenated, pyranose ring containing 16-membered macrolide peloruside (1) exhibiting cytotoxic activity in the nanomolar range was isolated from New Zealand marine sponge Mycale sp. The structure of 1 and relative stereochemistry 10 stereogenic centers were determined on a 3 mg sample using variety spectroscopic methods. Compound along with previously reported cytotoxins mycalamide (2) pateamine (3) single specimen this sponge.
MEPS Marine Ecology Progress Series Contact the journal Facebook (Twitter) RSS Mailing List Subscribe to our mailing list via Mailchimp HomeLatest VolumeAbout JournalEditorsTheme Sections 462:67-77 (2012) - DOI: https://doi.org/10.3354/meps09853 Effects of water temperature and pH on growth metabolite biosynthesis coral reef sponges Alan R. Duckworth1,5,*, Lyndon West2, Tifanie Vansach2, Amber Stubler3, Marah Hardt4 1Blue Ocean Institute, Stony Brook University, New York 11794, USA...
Four new indoles, ancorinolates A−C and bis-ancorinolate B, which contain sulfamate sulfate groups, were isolated from the aqueous extract of sponge Ancorina sp. In addition, ancorinazole, an indolo[3,2-a]carbazole also possessing was two separate New Zealand collections Ancorinazole is first described as a natural product. Ancorinolates A (1) C (3) showed weak HIV-inhibitory activity in XTT-based, anticytopathicity assay.
Peloruside B (2), a natural congener of peloruside A (1), was isolated in sub-milligram quantities from the New Zealand marine sponge Mycale hentscheli. promotes microtubule polymerization and arrests cells G2/M phase mitosis similar to paclitaxel, its bioactivity comparable that A. NMR-directed isolation, structure elucidation, confirmation by total synthesis, are described this article. The synthesis features Sharpless dihydroxylation, Brown's asymmetric allylboration reaction, reductive...
Natural products have provided an invaluable source of inspiration in the drug discovery pipeline. The oceans are a vast biological and chemical diversity. Recently, this untapped resource has been gaining attention search for novel structures development new classes therapeutic agents. Pseudopterosins group marine diterpene glycosides that possess array potent activities several areas. Few studies examined pseudopterosin effects during cellular stress and, to our knowledge, no explored...
A new mycalamide, mycalamide D (3), has been isolated from the New Zealand marine sponge Mycale sp. This metabolite, in which C13-O-methyl group of (1) is replaced by a hydrogen atom, was found to be cytotoxic range mammalian cell lines, with potency approximately 20-fold less than that 1.
Three new bicyclic C21 terpenoids, clathric acid (1) and two N-acyl taurine derivatives, clathrimides A (2) B (3), were isolated from the marine sponge Clathria compressa. The structures of these compounds elucidated by interpretation spectroscopic data. Clathric showed mild antibacterial activity against several Gram-positive bacteria.
A biomimetic synthesis of briareolate ester B (3) from L (1) via the intermediate G (2) has been achieved through a unique transannular oxa-6π electrocyclization induced by UVA light. UVC irradiation 3 triggered rapid retro-6π to establish an unprecedented photochromic switch. In ground state, reaction 1 led formation polycyclic γ-spiroketal γ-lactone 5, architecturally related ether-bridged cembranoids cladiellin class.
Koshikamide B (1) has been isolated from two separate collections of the marine sponge Theonella sp. as major cytotoxic constituent. is a 17-residue peptide lactone composed six proteinogenic amino acids, D-isomers seven N-methylated and unusual acid residues. The acids are N(delta)-carbamoylasparagine 2-(3-amino-2-hydroxy-5-oxopyrrolidin-2-yl)propionic (AHPP); former first found constituent peptides, whereas latter new residue. N-terminus koshikamide blocked by methoxyacetyl group....
Three new briarane diterpenoids, briareolate esters L–N (1–3), have been isolated from a gorgonian Briareum asbestinum. Briareolate L (1) and M (2) are the first natural products possessing 10-membered macrocyclic ring with (E,Z)-dieneone exhibit growth inhibition activity against both human embryonic stem cells (BG02) pancreatic cancer cell line (BxPC-3). ester was found to contain "spring-loaded" Michael acceptor group that can form reversible covalent bond model sulfur-based nucleophiles.
Abstract Bielschowskysin ( 1 ), the flagship of furanocembranoid diterpene family, has attracted attention from chemists owing to its intriguing and daunting polycyclic architecture medicinal potential against lung cancer. The high level functionalization poses a considerable challenge synthesis. Herein, stereoselective furan dearomatization strategy furanocembranoids was achieved via intermediacy chlorohydrins. stereochemical course kinetic established, C3 configuration resulting exo ‐enol...
A new iridoid glucoside, cornusoside (1), and four natural product aglycones, cornolactones A–D (2–5), together with 10 known compounds were isolated from the leaves of Cornus florida. The structures 1–5 established by interpretation their spectroscopic data. Cornolactone B (3) is first cis-fused tricyclic dilactone containing both a five- six-membered lactone ring. biosynthesis pathway proposed for C (4) D (5), C-6 epimers 1–3.
Briarellins, a subset of C2-C11 cyclized cembranoids, were proposed to contain C3-C14 ether or lactone bridge, similar asbestinins. However, the total synthesis structure briarellin J revealed misassignment. We revisited briarellins, computationally, with help recently developed hybrid DFT/parametric method, DU8+, and revised structures C14-C3 ε-lactones new structural types containing either C14-C11 C14-C12 bridge. The original asbestinin ethers confirmed.
A biomimetic semisynthesis of the diterpenoid (+)-providencin (2) and unexpected novel C14 regioisomer 3 was achieved by photoirradiation proposed biosynthetic cembranoid precursor (−)-bipinnatin E (1). The absolute configuration assignments 1 2 correlation were established X-ray analysis. combination NOESY data photochemical reaction results revealed that both C2 positions macrocycle (−)-1 are suitable for hydrogen abstraction, thus affording an explanation to mixture cyclobutane...
We present here a surface-enhanced Raman spectroscopy (SERS)-based platform for selectively detecting electrolyte cations. This facilitates the reorientation of chromoionophore I (CHI) molecule positioned on surface silver nanoparticles, regulated by targeted cation within ionophore-based ion-selective sensing framework. When exposed to target ions, leading deprotonation, aromatic plane CHI shifts from an endwise edgewise configuration SERS substrate surface. improves coupling induced dipole...
This paper provides an outline of a collaborative research project between researchers at the University California, San Diego, Rhode Island, and Bristol-Myers Squibb Pharmaceutical Research Institute, with participating members from Developmental Therapeutics Branch National Cancer Institute. The program, formally funded by Institute under Cooperative Drug Discovery Groups (NCDDG) seeks to discover new anticancer drugs marine organisms, in particular invertebrates such as sponges ascidians,...
Abstract The integration of physicochemical profiling screens such as Log P into natural products drug discovery programs is emerging an approach to front-load drug-like properties product libraries for high-throughput screening. In this study a fast-gradient HPLC method using polystyrene-divinylbenzene PRP-1 column was developed estimate the lipophilicity marine products. An excellent correlation found between results experimental determined and literature log values diverse set...
Macrocyclic furanobutenolide-derived cembranoids (FBCs) are the biosynthetic precursors to a wide variety of highly congested and oxygenated polycyclic (nor)diterpenes (e.g. plumarellide, verrillin, bielschowskysin). These architecturally complex metabolites thought originate from site-selective oxidation macrocycle backbone series intricate transannular reactions. Yet development common biomimetic route has been hampered by lack synthetic methods for pivotal furan dearomatization in regio-...
The marine sponge Acanthodendrilla sp. contains the proteasome inhibitor acanthosulfate (4), a disulfated merosesterterpene having scalarane-type skeleton. structure of which possesses an unusual configuration, was elucidated by interpretation spectroscopic data.