title: Structure and absolute stereochemistry of hectochlorin, a potent stimulator of actin assembly.
abstract: 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.
authors.affiliation: College of Pharmacy, Oregon State University, Corvallis, Oregon 97331, USA.
authors.forename: Brian L
authors.initials: BL
authors.lastname: Marquez
authors.forename: Karl Shawn
authors.initials: KS
authors.lastname: Watts
authors.forename: Alexandre
authors.initials: A
authors.lastname: Yokochi
authors.forename: Mary Ann
authors.initials: MA
authors.lastname: Roberts
authors.forename: Pascal
authors.initials: P
authors.lastname: Verdier-Pinard
authors.forename: Jorge I
authors.initials: JI
authors.lastname: Jimenez
authors.forename: Ernest
authors.initials: E
authors.lastname: Hamel
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Scheuer
authors.forename: William H
authors.initials: WH
authors.lastname: Gerwick
mesh_terms: D000199:Actins / Q000187:drug effects* / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D018360:Crystallography, X-Ray; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides; D016650:Fluorescein-5-isothiocyanate; D020128:Inhibitory Concentration 50; D007563:Jamaica; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008235:Lyngbya Toxins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010176:Panama; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013844:Thiazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000199:Actins; D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D047630:Depsipeptides; D007783:Lactones; D008235:Lyngbya Toxins; D010456:Peptides, Cyclic; D013844:Thiazoles; C454807:hectochlorin; C410925:lyngbyabellin A; C416586:lyngbyabellin B; C057531:jasplakinolide; D016650:Fluorescein-5-isothiocyanate