Isolation of a 1,3-enone isomer of heptanor-41-oxoyessotoxin from Protoceratium reticulatum cultures

Evidence for numerous analogs of yessotoxin in Protoceratium reticulatum

“…Analyses of algal and especially of shellfish samples using an ELISA for YTXs gave much higher results than did analyses for 1 by LC-MS (Aasen et al, 2004;Briggs et al, 2002Briggs et al, , 2004Miles et al, 2004bMiles et al, , 2005Samdal et al, 2004aSamdal et al, , 2005. The possibility that these results were due to matrix effects on the ELISA was excluded by extensive use of dilution series.…”

“…This assay is also suitable for analysis of shellfish for YTXs (Aasen et al, 2004;Briggs et al, 2004;Samdal et al, 2005) and showed an excellent correlation with results obtained by LC-MS methods . However, studies on algal (Briggs et al, 2002;Miles et al, 2004b;Samdal et al, 2004a) and shellfish (Aasen et al, 2004;Samdal et al, 2005) extracts indicate the presence of substantial quantities of unidentified YTXs. We have initiated studies to confirm the presence of large amounts of unknown YTXs in P. reticulatum and, where possible, to identify the most important components.…”

LC-MS/MS Analysis of Diarrhetic Shellfish Poisoning (DSP) Toxins, Okadaic Acid and Dinophysistoxin Analogues, and Other Lipophilic Toxins

“…Recently, several new YTX analogues have been identified in bivalves or dinoflagellate. [86][87][88][89][90][91][92][93][94] The validity of collision-induced dissociation (CID) by negative ion fast atom bombardment (FAB) MS/MS analysis for YTX was established in a previous structural study on YTX 95 and this technique was applied to structural elucidation of YTX analogue. 73 Recently, a number of liquid chromatography-mass spectrometry (LC-MS) methods have been demonstrated as powerful tools for quantification of YTX analogues and structure elucidation of novel toxins in plankton and shellfish.…”

“…73 Recently, a number of liquid chromatography-mass spectrometry (LC-MS) methods have been demonstrated as powerful tools for quantification of YTX analogues and structure elucidation of novel toxins in plankton and shellfish. 72,78,[80][81][82][83][84][85][86][87][88][89][90][91][96][97][98][99][100][101] A hybrid triple-quadrupole/linear ion trap MS/MS technique was proven to be useful for characterization of YTX analogues by our previous study. Figure 17 shows linear ion trap LC-MS/MS spectra obtained for YTX (peak #4) and trinor-1-homoYTX (peak #3) detected in the P. reticulatum isolate extract.…”

The Biosynthesis of Polyketide Metabolites by Dinoflagellates

“…2). These include, 41a-homoyessotoxin, 9-methyl-41a-homoyessotoxin, nor-ring A-yessotoxin (not shown) (Miles et al, 2004b), a 1, 3-enone isomer of heptanor -41-oxo-YTX (Miles et al, 2004a), (44-R,S )-44, 55-dihydroxyyessotoxin (Finch et al, 2005), and the first examples of YTXs having an amide side chain (not shown) (Miles et al, 2005).…”