期刊
INTERNATIONAL JOURNAL OF MASS SPECTROMETRY
卷 341, 期 -, 页码 28-33出版社
ELSEVIER SCIENCE BV
DOI: 10.1016/j.ijms.2013.03.002
关键词
Matrine-type alkaloid; Stereoisomer; Electrospray; Four-centered H rearrangement; RDA reaction; McLafferty-type rearrangement
资金
- West Light Foundation of the Chinese Academy of Sciences [Y2C6031100]
- National Natural Science Foundation of China [20932007, 21172214]
- National New Drug Innovation Major project of China [2011ZX09307-002-02]
A series of six matrine-type alkaloids, including a pair of stereoisomers, was investigated using electrospray ionization quadrupole time-of-flight tandem mass spectrometry (ESI-QTOF-MS/MS) in positive-ion mode. Protonated molecules were fragmented by collision-induced dissociation (CID) and the products identified. The identity of the major product ions was also supported by deuterium-labeling experiments. It was found that sequential four-centered H rearrangements play a significant role in the fragmentation of the piperidine-ring; the RDA reaction dominates the dissociations for sophocarpine and sophocarpidine; and the McLafferty-type rearrangement occurs with neosophoramine. Interestingly, a pair of stereoisomers matrine and sophoridine, can be unambiguously distinguished using CID, and this characterization was supported by the DFT calculations of the potential energy profiles for protonated matrine and sophoridine before dissociation to the product ion at m/z 152. (C) 2013 Elsevier B.V. All rights reserved.
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