Evaluation of fast atom bombardment mass spectrometric and low-energy collisional activation tandem mass spectrometric data for the structural elucidation of bisbenzylisoquinoline alkaloids

✍ Scribed by Gary W. Caldwell; John A. Masucci; Wu-Nan Wu

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 463 KB
• Volume: 29
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/oms.1210290503

✦ Synopsis

The fast atom bombardment (FAB) mass spectra and low-energy collisional activation mass spectra of ions generated under FAB were investigated for twelve bisbenzylisoquinoline (BBI) alkaloids. The relative molecular mass of the free base and diquaternary BBI alkaloids can be obtained from FAB data. However, monoquaternary ammonium salts produce only an [ M -XI + ion and the relative molecular mass cannot be determined. For Type A (single ether linkage) BBI alkaloids, fragmentation occurs primarily from benzylic and ether cleavages. Thus, tlhe total number of aromatic substituents (OH, OCH, or OCH,O) can be determined for rings and. For Type B (two either linkages) BBI alkaloids, fragmentation occurs primarily from double benzylic cleavages. Hence only the total number of aromatic substituents can be determined for the upper half of the Type B BBI alkaloids, i.e. rings A-B and C-D. An unknown alkaloid was examined to illustrate the utility of the fragmentation schemes.