title: Anatalline and other methyl jasmonate-inducible nicotine alkaloids from Nicotiana tabacum cv. By-2 cell cultures.
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.
authors.affiliation: VTT Biotechnology, Espoo, Finland.
authors.forename: Suvi T
authors.initials: ST
authors.lastname: Häkkinen
authors.forename: Heiko
authors.initials: H
authors.lastname: Rischer
authors.forename: Into
authors.initials: I
authors.lastname: Laakso
authors.forename: Hannu
authors.initials: H
authors.lastname: Maaheimo
authors.forename: Tuulikki
authors.initials: T
authors.lastname: Seppänen-Laakso
authors.forename: Kirsi-Marja
authors.initials: KM
authors.lastname: Oksman-Caldentey
mesh_terms: D000085:Acetates / Q000494:pharmacology; D000470:Alkaloids / Q000096:biosynthesis* / Q000737:chemistry; D002478:Cells, Cultured / Q000187:drug effects / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003517:Cyclopentanes / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009538:Nicotine / Q000096:biosynthesis* / Q000737:chemistry; D054883:Oxylipins; D008517:Phytotherapy; D010880:Piperidines / Q000097:blood*; D018515:Plant Leaves; D011725:Pyridines / Q000097:blood*; D014026:Nicotiana / Q000737:chemistry* / Q000166:cytology
chemical_list: D000085:Acetates; D000470:Alkaloids; D003517:Cyclopentanes; D054883:Oxylipins; D010880:Piperidines; D011725:Pyridines; C493473:anatalline; D009538:Nicotine; C072239:methyl jasmonate