A New Analogue of Yessotoxin, Carboxyyessotoxin, Isolated from Adriatic Sea Mussels

Abstract

A new analogue of yessotoxin (YTX), carboxyYTX, 3, was isolated from the digestive glands of mussels cultured on the Italian Adriatic coast. Its structure was determined by MS and NMR spectroscopy.

42,43,44,45,46,47,55-Heptanor-41-oxohomoyessotoxin, a New Biotoxin from Mussels of the Northern Adriatic Sea

“…The ROESY (rotating-frame Overhauser effect spectroscopy) spectrum further confirmed the above planar structure; in addition, it revealed relative stereochemistry of the molecule to be identical to that of YTX (), as well as to that of all other YTXs analogues so far isolated, being observed the same key NOE correlations ( − ) (Figure ). In addition, the NOE correlations between H-36 and Me-42 indicated the diaxial relationship between C-41 and H-36, thus defining the stereochemistry at C-40.…”

Structure−Activity Relationships of Yessotoxins in Cultured Cells

“…The LD 50 's reported in the literature for YTX and its analogues, measured by ip injection in mice, vary according to different experimental conditions (6,7,12,(14)(15)(16)(17)(18)(19)(20)(21). If these LD 50 's are compared with the EC 50 's we have measured in our system (Table 2), then the inspection of data reveals that the values we measured for the EC 50 of YTX analogues in our cellular system are up to 1000fold lower than lethal doses recorded in the mouse bioassay.…”

“…Therefore, the YTX analogues used in the present investigation were obtained from different mussel collections and here we only report the retention time of each compound on the final HPLC column. In particular, yessotoxin (tR 5.15) (6), homoyessotoxin (tR 5.20), and 45-hydroxyhomoyessotoxin (tR 3.91) were obtained in pure forms, while mixtures of carboxyhomoyessotoxin (tR 3.12) (13) and carboxyyessotoxin (tR 3.09) (12) as well as noroxo-homoYTX (tR 2.92) (14) and noroxoYTX (tR 2.89) (15) were not further resolved.…”

The Detection and Identification of 42,43,44,45,46,47,55-Heptanor-41-oxoyessotoxin, a New Marine Toxin from Adriatic Shellfish, by Liquid Chromatography−Mass Spectrometry

“…Formic acid (95-97%, Laboratory grade) and ammonium formate (AR grade) were purchased from Sigma Aldrich, Steinheim, Germany. YTX (6), 45-OHYTX (8), 45-OHhomoYTX (10), carboxyYTX (10), carboxyhomoYTX (11), and noroxohomoYTX (12) were obtained in the course of our studies from Italian contaminated mussels. Analytical standard of YTX was purchased from the Institute of Environmental Science & Research Limited (Wellington Science Center, New Zealand) and used for quantitative studies.…”