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Stereochemical Studies on Ovatoxin‐a
Author(s) -
Ciminiello Patrizia,
Dell'Aversano Carmela,
Dello Iacovo Emma,
Fattorusso Ernesto,
Forino Martino,
Grauso Laura,
Tartaglione Luciana
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201357
Subject(s) - computer science
Ovatoxin‐a is the main toxin produced by Ostreopsis ovata , a benthic dinoflagellate that has bloomed massively across the Mediterranean basin over the past years, inflicting both human and environmental suffering. Ovatoxin‐a has recently been isolated from cultures of O. ovata and structurally identified as an analogue of palytoxin: in comparison with palytoxin, ovatoxin‐a lacks three hydroxy groups at the 17‐, 44‐ and 64‐positions, but features an extra hydroxy functionality at the 42‐position. Herein we report on the NMR‐based elucidation of the stereochemistry of ovatoxin‐a, which includes 7 stereogenic double bonds and 62 asymmetric carbon atoms. Understanding the full stereochemistry of ovatoxin‐a is a step towards the elucidation of its mechanism of action on a molecular level.