Study of structural characteristic features of phenanthriondolizidine alkaloids by fast atom bombardment with tandem mass spectrometry.
The mass spectrometric behavior of phenanthroindolizidine alkaloids has been investigated in detail by positive ion fast atom bombardment tandem mass spectrometry (FAB-MS/MS) combined with collision-induced dissociation (CID). The fragmentation has been correlated with the skeleton structure and positions of substituents. The product ions arising from retro-Diels-Alder cleavages differ clearly for compounds with different skeletons. The substituents at C-14 were observed to markedly influence the fragmentation pathway of [M + H](+) ions. A diversity of dissociation behavior initiated by the variation of substituents on the aromatic ring was also observed in the CID spectra. Product ions resulting from loss of CH(4) were obtained for compounds in which both C-6 and C-7 are occupied by methoxy groups. FAB-MS/MS spectra can reflect the connection between the fragmentation behavior and structural features of these phenanthroindolizidine alkaloids rapidly and effectively, and should prove to be a powerful method to determine the structures of related compounds.
Xiang
Yun
Y
Institute of Materia Medica, Chinese Academy of Medical Science and Peking Union Medical College, Beijing 100050, China.
Abliz
Zeper
Z
Li
Li-jun
LJ
Huang
Xue-shi
XS
Yu
Shi-shan
SS
D000470:Alkaloids / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry*; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000470:Alkaloids; D000970:Antineoplastic Agents; D004365:Drugs, Chinese Herbal; D010936:Plant Extracts