title: Brevisin: an aberrant polycyclic ether structure from the dinoflagellate Karenia brevis and its implications for polyether assembly.
abstract: Brevisin is an unprecedented polycyclic ether isolated from the dinoflagellate Karenia brevis, an organism well-known to produce complex polycyclic ethers. The structure of brevisin was determined by detailed analyses of MS and 2D NMR spectra and is remarkable in that it consists of two separate fused polyether ring assemblies linked by a methylene group. One of the polycyclic moieties contains a conjugated aldehyde side chain similar to that recently observed in other K. brevis metabolites, though the "interrupted" polyether structure of brevisin is novel and provides further insight into the biogenesis of such fused-ring polyether systems. On the basis of the unusual structure of brevisin, principles underlying the initiation of polyether assemblies are proposed. Brevisin was found to inhibit the binding of [(3)H]-PbTx-3 to its binding site on the voltage-sensitive sodium channels in rat brain synaptosomes.
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin K. Moss Lane, Wilmington, North Carolina 28409, USA.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Satake
authors.forename: Anna
authors.initials: A
authors.lastname: Campbell
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Van Wagoner
authors.forename: Andrea J
authors.initials: AJ
authors.lastname: Bourdelais
authors.forename: Henry
authors.initials: H
authors.lastname: Jacocks
authors.forename: Daniel G
authors.initials: DG
authors.lastname: Baden
authors.forename: Jeffrey L C
authors.initials: JL
authors.lastname: Wright
mesh_terms: D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry; D004988:Ethers, Cyclic / Q000737:chemistry* / Q000302:isolation & purification; D011083:Polycyclic Compounds / Q000737:chemistry* / Q000302:isolation & purification; D011108:Polymers / Q000737:chemistry*
chemical_list: D004988:Ethers, Cyclic; D011083:Polycyclic Compounds; D011108:Polymers; C550958:brevisin