Anatalline and other methyl jasmonate-inducible nicotine alkaloids from Nicotiana tabacum cv. By-2 cell cultures.
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.
Häkkinen
Suvi T
ST
VTT Biotechnology, Espoo, Finland.
Rischer
Heiko
H
Laakso
Into
I
Maaheimo
Hannu
H
Seppänen-Laakso
Tuulikki
T
Oksman-Caldentey
Kirsi-Marja
KM
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
D000085:Acetates; D000470:Alkaloids; D003517:Cyclopentanes; D054883:Oxylipins; D010880:Piperidines; D011725:Pyridines; C493473:anatalline; D009538:Nicotine; C072239:methyl jasmonate