title: Stereochemical studies on ovatoxin-a.
abstract: 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.
authors.affiliation: Department of Chimica delle Sostanze Naturali, University of Napoli "Federico II", Italy.
authors.forename: Patrizia
authors.initials: P
authors.lastname: Ciminiello
authors.forename: Carmela
authors.initials: C
authors.lastname: Dell'Aversano
authors.forename: Emma
authors.initials: E
authors.lastname: Dello Iacovo
authors.forename: Ernesto
authors.initials: E
authors.lastname: Fattorusso
authors.forename: Martino
authors.initials: M
authors.lastname: Forino
authors.forename: Laura
authors.initials: L
authors.lastname: Grauso
authors.forename: Luciana
authors.initials: L
authors.lastname: Tartaglione
mesh_terms: D000178:Acrylamides / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003064:Cnidarian Venoms; D004141:Dinoflagellida / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008387:Marine Toxins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D013058:Mass Spectrometry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D000178:Acrylamides; D003064:Cnidarian Venoms; D008387:Marine Toxins; C573585:ovatoxin-a; C010272:palytoxin; D000095702:Polyether Toxins