Structure and Absolute Stereochemistry of Hectochlorin, a Potent Stimulator of Actin Assembly

Hectochlorin (1) was isolated from marine isolates of Lyngbya majuscula collected from Hector Bay, Jamaica, and Boca del Drago Beach, Bocas del Toro, Panama. The planar structure was deduced by one- and two-dimensional NMR spectroscopy. X-ray crystallography was used to determine the absolute stereo...

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Bibliographic Details
Published in:	Journal of natural products (Washington, D.C.) Vol. 65; no. 6; pp. 866 - 871
Main Authors:	Marquez, Brian L, Watts, Karl Shawn, Yokochi, Alexandre, Roberts, Mary Ann, Verdier-Pinard, Pascal, Jimenez, Jorge I, Hamel, Ernest, Scheuer, Paul J, Gerwick, William H
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 01-06-2002 Glendale, AZ American Society of Pharmacognosy
Subjects:	Actins - drug effects Actins - metabolism Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antibiotics (antibacterial agents, antifungal agents) Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Applied microbiology Biological and medical sciences Candida albicans - drug effects Crystallography, X-Ray Cyanobacteria - chemistry Depsipeptides Fluorescein-5-isothiocyanate Fundamental and applied biological sciences. Psychology Inhibitory Concentration 50 Jamaica Lactones - chemistry Lactones - isolation & purification Lactones - pharmacology Lyngbya Toxins - chemistry Lyngbya Toxins - isolation & purification Lyngbya Toxins - pharmacology Microbiology Molecular Conformation Molecular Structure Nuclear Magnetic Resonance, Biomolecular Panama Peptides, Cyclic - chemistry Peptides, Cyclic - isolation & purification Peptides, Cyclic - pharmacology Thiazoles - chemistry Thiazoles - isolation & purification Thiazoles - pharmacology Central America Jamaica Panama America West Indies Candida albicans Oxygen sulfur nitrogen heterocycle Toxicity Contractile protein Cytotoxicity Stimulation Kidney Macrocycle Fungi Marine environment Antifungal agent Actin Chlorine Organic compounds Cyanobacteria Marsupialia Bacteria Fungi Imperfecti Secondary alcohol Acylate Tumor cell Thallophyta Human Burkitt lymphoma Polymerization Lactone Tricyclic compound X ray diffraction In vitro Biological activity Primary alcohol Infection Vertebrata Mammalia Cell line Microbial origin Viral disease Animal Absolute configuration Cytoskeleton Isolation Structural analysis
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Summary:	Hectochlorin (1) was isolated from marine isolates of Lyngbya majuscula collected from Hector Bay, Jamaica, and Boca del Drago Beach, Bocas del Toro, Panama. The planar structure was deduced by one- and two-dimensional NMR spectroscopy. X-ray crystallography was used to determine the absolute stereochemistry of hectochlorin as 2S,3S,14S,22S. Hectochlorin is equipotent to jasplakinolide (5) in its ability to promote actin polymerization, but unlike jasplakinolide, is unable to displace a fluorescent phalloidin analogue from polymerized actin. In addition, hectochlorin shows both a unique profile of cytotoxicity by the COMPARE algorithm and potent inhibitory activity toward the fungus Candida albicans. Structurally, hectochlorin resembles dolabellin and the recently reported lyngbyabellin class of compounds.
Bibliography:	ark:/67375/TPS-L1FQZTX2-M istex:F039AF47C956C8F1D28207A25E09107EEEAD3B7E
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np0106283