title: Structural confirmation of ostreocin-D by application of negative-ion fast-atom bombardment collision-induced dissociation tandem mass spectrometric methods.
abstract: Negative-ion fast-atom bombardment collision-induced dissociation tandem mass spectrometric (FAB-CID-MS/MS) methodology was successfully applied to verify the highly complex structure of ostreocin-D (MW 2633), a new palytoxin analog isolated from the marine dinoflagellate Ostreopsis siamensis and proposed to be 42-hydroxy-3,26-didemethyl-19,44-dideoxypalytoxin based on NMR data. The charge-remote fragmentations were facilitated by a negative charge introduced to a terminal amino group or to a hydroxyl group at the other terminus by a reaction with 2-sulfobenzoic acid cyclic anhydride. Product ions generated from the [M - H](-) ions provided information on the structural details of ostreocin-D. Comparisons between the spectral data for ostreocin-D and palytoxin also provided a rational basis for the assignments of product ions.
authors.affiliation: Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aobaku, Sendai 981-8555, Japan.
authors.forename: Takanori
authors.initials: T
authors.lastname: Ukena
authors.forename: Masayuki
authors.initials: M
authors.lastname: Satake
authors.forename: Masaya
authors.initials: M
authors.lastname: Usami
authors.forename: Yasukatsu
authors.initials: Y
authors.lastname: Oshima
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Fujita
authors.forename: Hideo
authors.initials: H
authors.lastname: Naoki
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yasumoto
mesh_terms: D000178:Acrylamides / Q000737:chemistry; D000818:Animals; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry* / Q000302:isolation & purification; D003064:Cnidarian Venoms; D004141:Dinoflagellida / Q000737:chemistry*; D007477:Ions; D008387:Marine Toxins / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry* / Q000302:isolation & purification; D016339:Spectrometry, Mass, Fast Atom Bombardment / Q000379:methods*; D000095702:Polyether Toxins
chemical_list: D000178:Acrylamides; D019086:Bridged Bicyclo Compounds, Heterocyclic; D003064:Cnidarian Venoms; D007477:Ions; D008387:Marine Toxins; D011714:Pyrans; C010272:palytoxin; D000095702:Polyether Toxins; C459585:ostreocin D