Literature DB >> 16107747

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

Jürgen Schmidt1, Klaus Raith, Chotima Boettcher, Meinhart H Zenk.   

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.

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Year:  2005        PMID: 16107747     DOI: 10.1255/ejms.745

Source DB:  PubMed          Journal:  Eur J Mass Spectrom (Chichester)        ISSN: 1469-0667            Impact factor:   1.067


  8 in total

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Journal:  Plant Cell       Date:  2010-10-29       Impact factor: 11.277

2.  Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy.

Authors:  Thu-Thuy T Dang; Peter J Facchini
Journal:  Plant Physiol       Date:  2012-04-25       Impact factor: 8.340

3.  Nitrogen-Containing Constituents of Black Cohosh: Chemistry, Structure Elucidation, and Biological Activities.

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Journal:  Recent Adv Phytochem       Date:  2015

4.  De novo production of the key branch point benzylisoquinoline alkaloid reticuline in yeast.

Authors:  Isis J Trenchard; Michael S Siddiqui; Kate Thodey; Christina D Smolke
Journal:  Metab Eng       Date:  2015-07-10       Impact factor: 9.783

5.  Integration of deep transcript and targeted metabolite profiles for eight cultivars of opium poppy.

Authors:  Isabel Desgagné-Penix; Scott C Farrow; Dustin Cram; Jacek Nowak; Peter J Facchini
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6.  Mass spectrometric dereplication of nitrogen-containing constituents of black cohosh (Cimicifuga racemosa L.).

Authors:  Dejan Nikolić; Tanja Gödecke; Shao-Nong Chen; Jerry White; David C Lankin; Guido F Pauli; Richard B van Breemen
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7.  Dioxygenases catalyze O-demethylation and O,O-demethylenation with widespread roles in benzylisoquinoline alkaloid metabolism in opium poppy.

Authors:  Scott C Farrow; Peter J Facchini
Journal:  J Biol Chem       Date:  2013-08-08       Impact factor: 5.157

8.  Untargeted Metabolomics Sheds Light on the Diversity of Major Classes of Secondary Metabolites in the Malpighiaceae Botanical Family.

Authors:  Helena Mannochio-Russo; Rafael F de Almeida; Wilhan D G Nunes; Paula C P Bueno; Andrés M Caraballo-Rodríguez; Anelize Bauermeister; Pieter C Dorrestein; Vanderlan S Bolzani
Journal:  Front Plant Sci       Date:  2022-04-14       Impact factor: 5.753

  8 in total

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