Evidence for numerous analogs of yessotoxin in Protoceratium reticulatum

Growth and bioactive secondary metabolites of arctic Protoceratium reticulatum (Dinophyceae)

“…Even though its identity due to the lack of an analytical standard cannot be confirmed, it is obvious that this compound with a smaller molecular mass as YTX most likely is a truncated or not fully developed YTX and might be a precursor or side product of YTX biosynthesis. The same applies to m/z 1047 which could be 41-keto YTX or one of its isomers (Miles et al, 2005a) with its almost 100 Da lower molecular weight in comparison to YTX. In contrast the other four minor congeners seem to be substituted forms of YTX: m/z 1157 a hydroxylated and m/z 1175 a dihydroxylated variant.…”

“…The most abundant of the minor YTX was a compound with m/z 1101 consistent with nor-YTX (Miles et al, 2005a). Even though its identity due to the lack of an analytical standard cannot be confirmed, it is obvious that this compound with a smaller molecular mass as YTX most likely is a truncated or not fully developed YTX and might be a precursor or side product of YTX biosynthesis.…”

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

“…76 Despite recent evidence that YTXs may have no significant acute toxicity when administered orally to mice, [14][15][16] MBA positives due to low level contamination of bivalves by YTXs has been a worldwide problem causing serious economic hardship to bivalve industries. YTXs are produced by the dinoflagellates Protoceratium reticulatum, [77][78][79][80][81][82] Lingulodinium polyedrum 83,84 and possibly Gonyaulax spinifera, 85 and accumulate in filter-feeding bivalves feeding on the toxic dinoflagellates. Recently, several new YTX analogues have been identified in bivalves or dinoflagellate.…”

“…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.…”

Synthesis of a PbTx-2 photoaffinity and fluorescent probe and an alternative synthetic route to photoaffinity probes

“…The yessotoxins contain 11 trans-fused polyether rings, two sulfate groups on one end and an unsaturated side chain on the opposite end. The number of yessotoxin analogs reported range from 30 to over 90 15 . These analogues arise as a result of hydroxylations, carboxylations, desulfations, methylations, oxidations, changes in the length of the carbon side chain and even an absence of the A-ring.…”