title: Structure and relative potency of several karlotoxins from Karlodinium veneficum.
abstract: The karlotoxins are a family of amphidinol-like compounds that play roles in avoiding predation and in prey capture for the toxic dinoflagellate Karlodinium veneficum. The first member of the toxin group to be reported was KmTx 1 (1), and here we report an additional five new members of this family (3-7) from the same strain. Of these additional compounds, KmTx 3 (3) differs from KmTx 1 (1) in having one less methylene group in the saturated portion of its lipophilic arm. In addition, 64-E-chloro-KmTx 3 (4) and 10-O-sulfo-KmTx 3 (5) were identified. Likewise, 65-E-chloro-KmTx 1 (6) and 10-O-sulfo-KmTx 1 (7) were also isolated. Comparison of the hemolytic activities of the newly isolated compounds to that of KmTx 1 shows that potency correlates positively with the length of the lipophilic arm and is disrupted by sulfonation of the polyol arm.
authors.affiliation: Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin Moss Lane, Wilmington, North Carolina 28409, USA.
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Van Wagoner
authors.forename: Jonathan R
authors.initials: JR
authors.lastname: Deeds
authors.forename: Avery O
authors.initials: AO
authors.lastname: Tatters
authors.forename: Allen R
authors.initials: AR
authors.lastname: Place
authors.forename: Carmelo R
authors.initials: CR
authors.lastname: Tomas
authors.forename: Jeffrey L C
authors.initials: JL
authors.lastname: Wright
mesh_terms: D004141:Dinoflagellida / Q000737:chemistry*; D004912:Erythrocytes / Q000187:drug effects; D053878:Hemolytic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006801:Humans; D018942:Macrolides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D008387:Marine Toxins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011090:Polyenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D061065:Polyketides; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D053878:Hemolytic Agents; D018942:Macrolides; D008387:Marine Toxins; D011090:Polyenes; D061065:Polyketides; D011714:Pyrans; C552184:karlotoxin 1; C552185:karlotoxin 3
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