Isolation of 41a-homoyessotoxin and the identification of 9-methyl-41a-homoyessotoxin and nor-ring A-yessotoxin from Protoceratium reticulatum.
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.
Miles
Christopher O
CO
National Veterinary Institute, PB 8156 Dep., 0033 Oslo, Norway. chris.miles@vetinst.no
Wilkins
Alistair L
AL
Jensen
Dwayne J
DJ
Cooney
Janine M
JM
Quilliam
Michael A
MA
Aasen
John
J
MacKenzie
A Lincoln
AL
D000818:Animals; D005591:Chemical Fractionation; D004141:Dinoflagellida / Q000737:chemistry / Q000378:metabolism*; D004988:Ethers, Cyclic / Q000737:chemistry* / Q000302:isolation & purification*; D015394:Molecular Structure; D008978:Mollusk Venoms / Q000737:chemistry*; D035964:Oxocins / Q000737:chemistry* / Q000302:isolation & purification*; D021241:Spectrometry, Mass, Electrospray Ionization
C497780:41a-homoyessotoxin; D004988:Ethers, Cyclic; D008978:Mollusk Venoms; D035964:Oxocins; C066632:yessotoxin