Structure of 45,46,47-trinorhomoyessotoxin, a new yessotoxin analog, from Protoceratium reticulatum which represents the first detection of a homoyessotoxin analog in Japan

Effects of salinity, temperature and nutrients on growth, cellular characteristics and yessotoxin production of Protoceratium reticulatum

“…reticulatum is common in different geographical areas all over the world and many reports exist about accumulation of YTX in several molluscan shellfish species (e.g. Aasen et al, 2005;Ciminiello et al, 1997Ciminiello et al, , 2003Finch et al, 2005;Krock et al, 2006;MacKenzie et al, 1998;Paz et al, 2004Paz et al, , 2006Paz et al, , 2007Paz et al, , 2008Ramstad et al, 2001;Samdal et al, 2004;Satake et al, 1997Satake et al, , 1999Satake et al, , 2006Suzuki et al, 2007;Yasumoto and Takizawa, 1997). The P. reticulatum strain used in this study was isolated in the North Sea and identified as YTX producer (Hoppenrath, 2004).…”

“…: Gonyaulax polyedra) (Tubaro et al, 1998;Draisci et al, 1999) and Gonyaulax spinifera (Claparè de & Lachmann) Diesing (Rhodes et al, 2006;Riccardi et al, 2009). Meanwhile, the production of YTX by the dinoflagellate P. reticulatum has been reported in New Zealand, Japan, Norway, UK, Canada, USA, Chile, Spain, Italy, and southern Africa Bay (Ciminiello et al, 2003;Finch et al, 2005;Krock et al, 2006Krock et al, , 2009Paz et al, 2004Paz et al, , 2006Paz et al, , 2007Ramstad et al, 2001;Samdal et al, 2004;Satake et al, 1997Satake et al, , 1999Satake et al, , 2006. Different concentrations of YTX were found in cultures of dinoflagellates around the world.…”

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.…”

Yessotoxins, a Group of Marine Polyether Toxins: an Overview

“…Other analogues recently isolated from this dinoflagellate are: homo-YTX (=1a-homo-YTX) [13], noroxo-YTX [13, 49] (=42,43,44,45,46,47,55-heptanor-41-oxo-YTX or 41-keto-YTX), 40- epi -41-keto-YTX and 41-keto-YTXenone [59]; also 41a-homo-YTX, 9-methyl-41a-homo-YTX, four nor-ring-A-YTXs [60], 9-methyl-41-keto-YTXenone [11], 44,55-dihydroxy-YTX, 44,55-dihydroxy-41a-homo-YTX and 44,55-dihydroxy-9-Methyl-41a-homo-YTX [62], the hydroxyamide-YTXs derived from 41a-homo-YTX and 9-methyl-41a-YTX [61]. In more recent studies 45-OHdinor-YTX, 44-oxotrinor-YTX, 41a-homo-44-oxotrinor-YTX [11] and 45,46,47-trinorhomo-YTX [16, 53] (Figure 3) have been identified.…”