Isolation of 41a-Homoyessotoxin and the Identification of 9-Methyl-41a-homoyessotoxin and Nor-ring A-yessotoxin from Protoceratium reticulatum

CO Miles, AL Wilkins, DJ Jensen… - Chemical research in …, 2004 - ACS Publications
CO Miles, AL Wilkins, DJ Jensen, JM Cooney, MA Quilliam, J Aasen, AL MacKenzie
Chemical research in toxicology, 2004ACS Publications
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 …
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 μg of 1. Full 1H NMR assignments for 2 and 3 and identification of three new heptanor-41-oxo-analogues of 3 (46) during LC-MS3 analysis of a fraction containing 13 and 7 are also reported.
ACS Publications
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