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Eur. J. Mass Spectrom. 10, 683–689 (2004)
DOI: 10.1255/ejms.660

Electrospray tandem mass spectrometry for structural characterization of aporphine-benzylisoquinoline alkaloids

Wu-Nan Wu* and Michael D. Moyer
Division of Preclinical Drug Evaluation, Johnson & Johnson Pharmaceutical Research & Development, LLC, Spring House, PA 19477, USA. E-mail: jawee@erols.com

ABSTRACT:
Electrospray mass spectrometry and tandem mass spectrometry techniques were utilized to elucidate the structures of ten aporphine- benzylisoquinoline alkaloids, consisting of monoether link between aporphine and benzyltetrahydroisoquinoline units, which were isolated and identified previously from a variety of Thalictrum sp. (Ranunculaceae family) based mainly on the UV, IR, CD, NMR, EI-MS, CI-MS, derivatization, and chemical degradation techniques. In this investigation, protonated molecules, [M+H]+ ions, for nine tertiary alkaloids, a molecular ion, [M+′] ion, for a quaternary alkaloid, and very intense doubly- protonated molecules, [M+2H]2+ ions (100% of relative abundance) in Q1 Scan MS spectra, and prominent as well as diagnostic product ions for structural information in the tandem MS/MS spectra were observed for all investigated alkaloids each in nanogram quantities. More than 10 µg quantities of each investigated alkaloid or other isoquinoline and aporphine analogs needed for the CI-MS, EI-MS and FAB-MS analysis from the previous studies.

Keywords: electrospray, MS and MS/MS, aporphine- benzylisoquinoline alkaloids, structural characterization

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