Identification of 45-hydroxy-46,47-dinoryessotoxin, 44-oxo-45,46,47-trinoryessotoxin, and 9-methyl-42,43,44,45,46,47,55-heptanor-38-en-41-oxoyessotoxin, and partial characterization of some minor yessotoxins, from Protoceratium reticulatum.
Preparative HPLC purification of a side-fraction obtained during purification of 44,55-dihydroxyyessotoxin (6) afforded fractions containing previously unidentified yessotoxin analogues. Careful analysis of these fractions by HPLC-UV, LC-MS3, and NMR spectroscopy, revealed the identities of some of these analogues as 45-hydroxy-46,47-dinoryessotoxin (1), 44-oxo-45,46,47-trinoryessotoxin (2) and 9-methyl-42,43,44,45,46,47,55-heptanor-38-en-41-oxoyessotoxin (5). Numerous other analogues were present but could only be characterized by HPLC-UV and LC-MS3 due to their low abundance. The HPLC-UV and LC-MS3 data confirm the presence of large numbers of yessotoxin analogues, some of which may be oxidative degradation products, in extracts of Protoceratium reticulatum. Compound-1 is the first 46,47-dinoryessotoxin to be identified.
Miles
Christopher O
CO
AgResearch Ltd, Department of Toxinology, Ruakura Research Centre, Private Bag 3123, East Street, Hamilton, New Zealand. chris.miles@agresearch.co.nz
Wilkins
Alistair L
AL
Hawkes
Allan D
AD
Selwood
Andrew I
AI
Jensen
Dwayne J
DJ
Cooney
Janine M
JM
Beuzenberg
Veronica
V
MacKenzie
A Lincoln
AL
D000818:Animals; D004141:Dinoflagellida / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D008978:Mollusk Venoms; D035964:Oxocins / Q000737:chemistry* / Q000302:isolation & purification*
D004988:Ethers, Cyclic; D008978:Mollusk Venoms; D035964:Oxocins; C066632:yessotoxin