Isodomoic acid C, an unusual amnesic shellfish poisoning toxin from Pseudo-nitzschia australis.
An unusual isomer of domoic acid (1), isodomoic acid C (2), has been found in New Zealand shellfish contaminated by amnesic shellfish poisoning (ASP) toxins and was shown to be produced by a local strain of the pennate diatom Pseudo-nitzschia australis. A bulk culture of this strain was used to isolate 2. The structure was determined from spectroscopic data and was shown to correspond to that of 2 from a Japanese red seaweed, the only other reported occurrence of this compound. The affinity of 2 for GluR6 glutamate receptors was 240-fold lower than for 1, indicating low neurotoxic potential.
Holland
Patrick T
PT
Cawthron Institute, Private Bag 2, Nelson, New Zealand. patrick.holland@cawthron.org.nz
Selwood
Andrew I
AI
Mountfort
Douglas O
DO
Wilkins
Alistair L
AL
McNabb
Paul
P
Rhodes
Lesley L
LL
Doucette
Gregory J
GJ
Mikulski
Christina M
CM
King
Kristen L
KL
D000647:Amnesia / Q000139:chemically induced*; D000818:Animals; D017377:Diatoms / Q000737:chemistry*; D005068:Eutrophication / Q000502:physiology*; D005517:Foodborne Diseases; D006538:Heptanoic Acids / Q000633:toxicity*; D008387:Marine Toxins / Q000633:toxicity*; D009498:Neurotoxins / Q000032:analysis / Q000378:metabolism / Q000633:toxicity; D017470:Receptors, Glutamate / Q000187:drug effects / Q000378:metabolism; D012624:Seaweed / Q000737:chemistry; D012758:Shellfish / Q000469:parasitology*; D057096:Shellfish Poisoning
D006538:Heptanoic Acids; D008387:Marine Toxins; D009498:Neurotoxins; D017470:Receptors, Glutamate; C504322:isodomoic acid C