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Isolation of 41a-homoyessotoxin and the identification of 9-methyl-41a-homoyessotoxin and nor-ring A-yessotoxin from Protoceratium reticulatum.

Authors
  • Miles, Christopher O
  • Wilkins, Alistair L
  • Jensen, Dwayne J
  • Cooney, Janine M
  • Quilliam, Michael A
  • Aasen, John
  • MacKenzie, A Lincoln
Type
Published Article
Journal
Chemical research in toxicology
Publication Date
Nov 01, 2004
Volume
17
Issue
11
Pages
1414–1422
Identifiers
PMID: 15540939
Source
Medline
License
Unknown

Abstract

41a-homoyessotoxin (1), a new analogue of yessotoxin (7), was isolated from extracts of Protoceratium reticulatum grown in culture. In addition, 9-methyl-41a-homoyessotoxin (2) and a nor-ring A-yessotoxin (3) were identified as the major components of a mixed fraction. The structural information was initially obtained from LC-UV and LC-MS3 chromatograms, with subsequent definitive structure determination by NMR, LC-MS/MS, and high-resolution MS. Full 1H and indirectly detected 13C NMR assignments for all but two carbon atoms were obtained from ca. 100 microg of 1. Full 1H NMR assignments for 2 and 3 and identification of three new heptanor-41-oxo-analogues of 3 (4-6) during LC-MS3 analysis of a fraction containing 1-3 and 7 are also reported.

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