title: 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.
abstract: 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.
authors.affiliation: AgResearch Ltd, Department of Toxinology, Ruakura Research Centre, Private Bag 3123, East Street, Hamilton, New Zealand. chris.miles@agresearch.co.nz
authors.forename: Christopher O
authors.initials: CO
authors.lastname: Miles
authors.forename: Alistair L
authors.initials: AL
authors.lastname: Wilkins
authors.forename: Allan D
authors.initials: AD
authors.lastname: Hawkes
authors.forename: Andrew I
authors.initials: AI
authors.lastname: Selwood
authors.forename: Dwayne J
authors.initials: DJ
authors.lastname: Jensen
authors.forename: Janine M
authors.initials: JM
authors.lastname: Cooney
authors.forename: Veronica
authors.initials: V
authors.lastname: Beuzenberg
authors.forename: A Lincoln
authors.initials: AL
authors.lastname: MacKenzie
mesh_terms: 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*
chemical_list: D004988:Ethers, Cyclic; D008978:Mollusk Venoms; D035964:Oxocins; C066632:yessotoxin