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Structural determination of monoacylglycerols extracted from marine sponge by fast atom bombardment tandem mass spectrometry
Author(s) -
Gil JiHye,
Hong JooYeon,
Jung Jee H.,
Kim KangJin,
Hong Jongki
Publication year - 2007
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.2948
Subject(s) - chemistry , fast atom bombardment , tandem mass spectrometry , mass spectrometry , collision induced dissociation , fragmentation (computing) , dissociation (chemistry) , mass spectrum , ion , chromatography , molecule , analytical chemistry (journal) , organic chemistry , computer science , operating system
Five new monoacylglycerols (MAGs) were isolated from the marine sponge Stelletta sp. by reversed‐phase high‐performance liquid chromatography and analyzed by positive ion fast atom bombardment mass spectrometry (FAB‐MS). FAB mass spectra of these compounds produced abundant sodium‐adducted molecules [M+Na] + from a mixture of 3‐nitrobenzyl alcohol and sodium iodide. The structural elucidation of these sponge MAGs was carried out by FAB tandem mass spectrometry (MS/MS). To find diagnostic ions for the characterization of the MAGs, authentic MAGs were initially analyzed by collision‐induced dissociation (CID) MS/MS. The CID MS/MS of [M+Na] + precursor ions resulted in the formation of numerous characteristic product ions via a series of dissociative processes. The product ions formed by charge‐remote fragmentation (CRF) provided important information for the characterization of acyl chains substituted at the glycerol backbone, and product ions at m/z 84, 97, 113 and 139 were diagnostic for the sodiated glycerol backbone. On the basis of these fragmentation patterns, the structures of five MAGs extracted from marine sponge were elucidated. In addition, high‐resolution mass measurement was performed to obtain the elemental compositions of the MAGs. Copyright © 2007 John Wiley & Sons, Ltd.