Analysis of benzylisoquinoline-type alkaloids by electrospray tandem mass spectrometry and atmospheric pressure photoionization

Eur. J. Mass Spectrom. 11, 325–334 (2005)
DOI: 10.1255/ejms.745

Analysis of benzylisoquinoline-type alkaloids by electrospray tandem mass spectrometry and atmospheric pressure photoionization

Jürgen Schmidt,^a, Klaus Raith,^b, Chotima Boettcher^c and Meinhart H. Zenk^c
^aLeibniz-Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, D-06120 Halle/S., Germany. E-mail: jschmidt@ipb-halle.de
^bInstitute of Pharmaceutics and Biopharmaceutics, Martin-Luther-University, Wolfgang-Langenbeck-Strasse 4, D-06120 Halle/S., Germany
^cBiocenter, Martin-Luther-University, Weinbergweg 22, D-06120 Halle/S., Germany

ABSTRACT:

Benzylisoquinoline alkaloids found in the Papaveraceae family play a major role in pharmaceutical biology. This is the first systematic study dealing with electrospray tandem mass spectrometry (ESI-MS/MS) of all benzylisoquinolines found as biogenetic precursors of morphinan alkaloids. Tandem mass spectral data are presented for norlaudanosoline, laudanosoline, 4′-O-methyl-norlaudanosoline, 6-O-methyl-norlaudanosoline, norcoclaurine, coclaurine, N– methylcoclaurine, N-methyl-3′-hydroxycoclaurine, N-methyl-3′-O-methylcoclaurine, norreticuline and reticuline. This study compares results obtained using an ion trap mass spectrometer with those obtained using a triple quadrupole one. The results highlight the differences of the tandem-in-time versus the tandem-in- space principle, often hampering the development of ESI-MS/MS libraries. Additionally, the use of the atmospheric pressure photoionisation technique for the analysis of such substances is discussed.

Keywords: MS/MS; benzylisoquinoline alkaloids, atmospheric pressure photoionization; mass spectral fragmentation

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