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Planta Med 2004; 70(10): 936-941
DOI: 10.1055/s-2004-832620
Original Paper
Physiology, in vitro Biotechnology
© Georg Thieme Verlag KG Stuttgart · New York

Anatalline and Other Methyl Jasmonate-Inducible Nicotine Alkaloids from Nicotiana tabacum cv. BY-2 Cell Cultures

Suvi T. Häkkinen1 , 4 , Heiko Rischer1 , 4 , Into Laakso2 , Hannu Maaheimo3 , Tuulikki Seppänen-Laakso1 , Kirsi-Marja Oksman-Caldentey1
  • 1VTT Biotechnology, Espoo, Finland
  • 2Department of Pharmacognosy, Faculty of Pharmacy, University of Helsinki, Finland
  • 3VTT Biotechnology, Helsinki, Finland
  • 4These authors have contributed equally to this publication
Further Information

Publication History

Received: May 5, 2004

Accepted: July 7, 2004

Publication Date:
18 October 2004 (online)

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Abstract

Anatalline [2,4-di(3-pyridyl)piperidine] accumulation was shown to be induced by methyl jasmonate in Nicotiana tabacum cv. BY-2 cell cultures. Beside anatabine, anatalline represented the most abundant alkaloid, moreover, it was always present in two isomeric forms occurring always in similar concentrations. Both isomers could be completely separated by GC-MS. For structural analysis, the isolation of both isomers was performed using a semi-preparative HPLC system. The structures of anatalline [cis-2,4-di(3-pyridyl)piperidine] and its stereoisomer trans-2,4-di(3-pyridyl)piperidine were confirmed by MS and 1D and 2D NMR spectral data. The biosynthetic origin of anatalline was studied by feeding alkaloid precursors to BY-2 cell cultures.

Key words

Nicotiana tabacum BY-2 - Solanaceae - alkaloids - anatalline - anatabine - cell cultures

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Dr. K.-M. Oksman-Caldentey

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