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.

Key words

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

References

• 1 Facchini P J, Bird D A, St-Pierre B. Can Arabidopsis make complex alkaloids?.  Trends Plant Sci. 2004;  9 116-22
• 2 Leete E. Biosynthesis and metabolism of the tobacco alkaloids. In: Pelletier SW, editor Alkaloids: chemical and biological perspectives. Vol 1 New York; John Wiley & Sons; 1983: pp 85-152
• 3 Leete E, Slattery S A. Incorporation of [2 - ¹⁴ C]- and [6 - ¹⁴ C]nicotinic acid into the tobacco alkaloids. Biosynthesis of anatabine and α,β-dipyridyl.  J Am Chem Soc. 1976;  98 6326-30
• 4 Leete E. Alkaloids derived from ornithine, lysine and nicotinic acid. In: Bell EA, Charlwood BV, editors Encyclopedia of plant physiology, new series, secondary plant products. Vol 8 Berlin; Springer-Verlag 1980: pp 65-91
• 5 Bush L P, Fannin F F, Chelvarajan R L, Burton H R. Biosynthesis and metabolism of nicotine and related alkaloids. In: Garrod JW, Wahren J, editors Nicotine and related alkaloids: absorption, distribution, metabolism and excretion. London; Chapman and Hall 1993: pp 1-30
• 6 Kisaki T, Mizusaki S, Tamaki E. Phytochemical studies on tobacco alkaloids - XI. A new alkaloid in Nicotiana tabacum roots.  Phytochemistry. 1968;  7 323-7
• 7 Nagata T, Hasezawa S, Inzé D. Tobacco BY-2 Cells, Biotechnology in Agriculture and Forestry. Vol 53 Heidelberg; Springer Verlag 2004: 347 p
• 8 Goossens A, Häkkinen S T, Laakso I, Seppänen-Laakso T, Biondi S, De Sutter V, Lammertyn F, Nuutila A M, Söderlund H, Zabeau M, Inzé D, Oksman-Caldentey K -M. A functional genomics approach toward the understanding of secondary metabolism in plant cells.  Proc Natl Acad Sci. 2003;  100 8595-600
• 9 Mueller M J, Brodschelm W, Spannagl E, Zenk M H. Signaling in the elicitation process is mediated through the octadecanoid pathway leading to jasmonic acid.  Proc Natl Acad Sci. 1993;  90 7490-4
• 10 Nagata T, Kumagai F. Plant cell biology through the window of the highly synchronized tobacco BY-2 cell line.  Methods Cell Sci. 1999;  21 123-7
• 11 Glenn D F, Edwards III W B. Synthesis and mass spectrometry of some structurally related nicotinoids.  J Org Chem. 1978;  43 2860-70
• 12 Luaranatana O, Griffin W J. Alkaloids from Duboisia hopwoodii .  Phytochemistry. 1982;  21 449-51
• 13 Ciolino L A, Turner J A, McCauley H A, Smallwood A W, Yi T Y. Optimization study for the reversed-phase ion-pair liquid chromatographic determination of nicotine in commercial tobacco products.  J Chromatogr A. 1999;  852 451-63
• 14 Laatikainen R, Niemitz M, Weber U, Sundelin J, Hassinen T, Vepsäläinen J. General strategies for total-lineshape-type spectral analysis of NMR spectra using integral-transform iterator.  J Magn Res A. 1996;  120 1-10
• 15 Rao H SP, Bharathi B, Jeyalakshmi K. Total synthesis of anatalline.  Ind J Chem. 1997;  36B 557-61
• 16 Miyano M, Yasumatsu N, Matsushita H, Nishida K. 1¹-(6-Hydroxyoctanoyl)nornicotine and 1¹-(7-hydroxyoctanoyl)nornicotine, two new alkaloids from Japanese domestic tobacco.  Agric Biol Chem. 1981;  45 1029-32
• 17 Fujita S, Aoki N. Reports from Hatano, Tobacco Experimental Station.  Japan.. 1965;  55 91-9
• 18 Furuya T, Hisashi K, Syono K. Regulation of nicotine biosynthesis by auxins in tobacco callus tissues.  Phytochemistry. 1971;  10 1529-32
• 19 Friesen J B, Burkhouse P C, Biesdorf D D, Leete E. Influence of alkaloid precursors on the alkaloid content of Nicotiana alata root cultures.  Phytochemistry. 1992;  31 3059-63
• 20 Walton N J, Robins R J, Rhodes M JC. Perturbation of alkaloid production by cadaverine in hairy root cultures of Nicotiana rustica .  Plant Sci. 1988;  54 125-31
• 21 Robins R J, Hamill J D, Parr A J, Smith K, Walton N J, Rhodes M J. Potential for use of nicotinic acid as a selective agent for isolation of high-nicotine producing lines of Nicotiana rustica hairy root cultures.  Plant Cell Rep. 1987;  6 122-6