Isolation and structure of prorocentrolide B, a fast-acting toxin from Prorocentrum maculosum.
A new toxin, prorocentrolide B (1), has been isolated following bioassay-guided fractionation of a BuOH extract of the tropical dinoflagellate, Prorocentrum maculosum Faust. This compound produces a rapid toxic response in the mouse bioassay, a type of activity not accounted for by other diarrhetic shellfish poisoning toxins produced by P. maculosum. The structure 1 was established by NMR and MS and is similar to prorocentrolide (2), a toxin from a strain of Prorocentrum lima. NMR data and the modeling program ConGen have been used to establish the relative stereochemistry of some individual ether ring systems and the hexahydroisoquinoline ring.
Hu
T
T
Institute for Marine Biosciences, National Research Council of Canada, Halifax, Nova Scotia, Canada.
deFreitas
A S
AS
Curtis
J M
JM
Oshima
Y
Y
Walter
J A
JA
Wright
J L
JL
D000818:Animals; D002240:Carbohydrate Sequence; D004141:Dinoflagellida / Q000737:chemistry*; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000302:isolation & purification* / Q000633:toxicity; D013058:Mass Spectrometry; D051379:Mice; D008969:Molecular Sequence Data; D011714:Pyrans / Q000302:isolation & purification* / Q000633:toxicity
D008387:Marine Toxins; D011714:Pyrans; C103447:prorocentrolide B