Structural confirmation of ostreocin-D by application of negative-ion fast-atom bombardment collision-induced dissociation tandem mass spectrometric methods.
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.
Ukena
Takanori
T
Graduate School of Life Sciences, Tohoku University, 1-1 Tsutsumidori-Amamiya, Aobaku, Sendai 981-8555, Japan.
Satake
Masayuki
M
Usami
Masaya
M
Oshima
Yasukatsu
Y
Fujita
Tsuyoshi
T
Naoki
Hideo
H
Yasumoto
Takeshi
T
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
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