Structure and relative potency of several karlotoxins from Karlodinium veneficum.
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.
Van Wagoner
Ryan M
RM
Center for Marine Science, University of North Carolina Wilmington, 5600 Marvin Moss Lane, Wilmington, North Carolina 28409, USA.
Deeds
Jonathan R
JR
Tatters
Avery O
AO
Place
Allen R
AR
Tomas
Carmelo R
CR
Wright
Jeffrey L C
JL
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*
D053878:Hemolytic Agents; D018942:Macrolides; D008387:Marine Toxins; D011090:Polyenes; D061065:Polyketides; D011714:Pyrans; C552184:karlotoxin 1; C552185:karlotoxin 3
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