Isolation of a 1,3-enone isomer of heptanor-41-oxoyessotoxin from Protoceratium reticulatum cultures.
The 1,3-enone isomer (1) of heptanor-41-oxoyessotoxin (2) was isolated from extracts of Protoceratium reticulatum during large-scale production of yessotoxin (4). We found that 2 readily isomerizes to 1 in the presence of dilute ammonia and present evidence for the existence of 40-epi-2 (3) that also isomerizes to 1. 1-3 were detected by LC-MS methods both in extracts of P. reticulatum cultures and in mussels contaminated with yessotoxins. The isomerization of 2 and 3 into 1 occurs so readily that purification on basic alumina needs to be conducted carefully. No toxic effects were recorded in mice injected intraperitoneally with 1 at a dose of 5,000 microg/kg.
Miles
Christopher O
CO
AgResearch Ltd, Ruakura Research Centre, Department of Toxinology, Private Bag 3123, Hamilton, New Zealand. chris.miles@agresearch.co.nz
Wilkins
Alistair L
AL
Hawkes
Allan D
AD
Selwood
Andrew
A
Jensen
Dwayne J
DJ
Aasen
John
J
Munday
Rex
R
Samdal
Ingunn A
IA
Briggs
Lyn R
LR
Beuzenberg
Veronica
V
MacKenzie
A Lincoln
AL
D000641:Ammonia / Q000378:metabolism; D000818:Animals; D001681:Biological Assay; D049872:Bivalvia / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D004141:Dinoflagellida / Q000378:metabolism*; D004784:Environmental Monitoring; D004988:Ethers, Cyclic / Q000737:chemistry* / Q000302:isolation & purification* / Q000633:toxicity; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D008958:Models, Molecular; D009520:New Zealand; D009664:Norway; D023382:Toxicity Tests, Acute
C432526:42,43,44,45,46,47,55-heptanor-41-oxohomoyessotoxin; D004988:Ethers, Cyclic; D000641:Ammonia