Literature DB >> 17113612

Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding.

Jürgen Schmidt1, Chotima Boettcher, Christine Kuhnt, Toni M Kutchan, Meinhart H Zenk.   

Abstract

Papaver alkaloids play a major role in medicine and pharmacy. In this study, [ring-(13)C(6)]-tyramine as a biogenetic precursor of these alkaloids was fed to Papaver somniferum seedlings. The alkaloid pattern was elucidated both by direct infusion high-resolution ESI-FT-ICR mass spectrometry and liquid chromatography/electrospray tandem mass spectrometry. Thus, based on this procedure, the structure of about 20 alkaloids displaying an incorporation of the labeled tyramine could be elucidated. These alkaloids belong to different classes, e.g. morphinan, benzylisoquinoline, protoberberine, benzo[c]phenanthridine, phthalide isoquinoline and protopine. The valuable information gained from the alkaloid profile demonstrates that the combination of these two spectrometric methods represents a powerful tool for evaluating biochemical pathways and facilitates the study of the flux of distant precursors into these natural products.

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Year:  2006        PMID: 17113612     DOI: 10.1016/j.phytochem.2006.10.003

Source DB:  PubMed          Journal:  Phytochemistry        ISSN: 0031-9422            Impact factor:   4.072


  19 in total

1.  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

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

Authors:  Dejan Nikolić; David C Lankin; Tamara Cisowska; Shao-Nong Chen; Guido F Pauli; Richard B van Breemen
Journal:  Recent Adv Phytochem       Date:  2015

3.  Preparative isolation of alkaloids from Corydalis bungeana Turcz. by high-speed counter-current chromatography using stepwise elution.

Authors:  Lili Niu; Zhensheng Xie; Tanxi Cai; Peng Wu; Peng Xue; Xiulan Chen; Zhiyong Wu; Yoichiro Ito; Famei Li; Fuquan Yang
Journal:  J Sep Sci       Date:  2011-03-08       Impact factor: 3.645

4.  Engineering strategies for the fermentative production of plant alkaloids in yeast.

Authors:  Isis J Trenchard; Christina D Smolke
Journal:  Metab Eng       Date:  2015-05-14       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
Journal:  Plant Mol Biol       Date:  2012-04-24       Impact factor: 4.076

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
Journal:  Fitoterapia       Date:  2011-12-09       Impact factor: 2.882

7.  Microbial production of plant benzylisoquinoline alkaloids.

Authors:  Hiromichi Minami; Ju-Sung Kim; Nobuhiro Ikezawa; Tomoya Takemura; Takane Katayama; Hidehiko Kumagai; Fumihiko Sato
Journal:  Proc Natl Acad Sci U S A       Date:  2008-05-20       Impact factor: 11.205

8.  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

9.  Quantitative 1H nuclear magnetic resonance metabolite profiling as a functional genomics platform to investigate alkaloid biosynthesis in opium poppy.

Authors:  Jillian M Hagel; Aalim M Weljie; Hans J Vogel; Peter J Facchini
Journal:  Plant Physiol       Date:  2008-06-11       Impact factor: 8.340

10.  Assessment of metabolome annotation quality: a method for evaluating the false discovery rate of elemental composition searches.

Authors:  Fumio Matsuda; Yoko Shinbo; Akira Oikawa; Masami Yokota Hirai; Oliver Fiehn; Shigehiko Kanaya; Kazuki Saito
Journal:  PLoS One       Date:  2009-10-16       Impact factor: 3.240

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