Revisiting anabasine biosynthesis in tobacco hairy roots expressing plant lysine decarboxylase gene by using 15N-labeled lysine

Plant Biotechnology

Volumn 31, Issue 5, 2014, Pages 511-518

  Bunsupa, Somnuk ^a   Komastsu, Kana ^a   Nakabayashi, Ryo ^b   Saito, Kazuki ^a,b   Yamazaki, Mami ^a  

^a CHIBA UNIVERSITY   (Japan)

^b RIKEN Center for Sustainable Resource Science   (Japan)

Author keywords

Anabasine; Lys derived alkaloids; Lysine ornithine decarboxylase; Tobacco alkaloids

Indexed keywords

LUPINUS ANGUSTIFOLIUS; NICOTIANA; NICOTIANA TABACUM;

EID: 84923423037     PISSN: 13424580     EISSN: 13476114     Source Type: Journal    
DOI: 10.5511/plantbiotechnology.14.1008a     Document Type: Article

References (31)

1. Bunsupa S, Katayama K, Ikeura E, Oikawa A, Toyooka K, Saito K, Yamazaki M (2012a) Lysine decarboxylase catalyzes the first step of quinolizidine alkaloid biosynthesis and coevolved with alkaloid production in Leguminosae. Plant Cell 24: 1202-1206
2. Bunsupa S, Yamazaki M, Saito K (2012b) Quinolizidine alkaloid biosynthesis: recent advances and future prospects. Front Plant Sci 3: 239
3. Campbell IM (1974) Incorporation and dilution values—Their calculation in mass spectrally assayed stable isotope labeling experiments. Bioorg Chem 3: 386-397
4. DeBoer KD, Dalton HL, Edward FJ, Ryan SM, Hamill JD (2013) RNAi-mediated down-regulation of ornithine decarboxylase (ODC) impedes wound-stress stimulation of anabasine synthesis in Nicotiana glauca. Phytochemistry 86: 21-28
5. DeBoer KD, Lye JC, Aitken CD, Su AK-K, Hamill JD (2009) The A622 gene in Nicotiana glauca (tree tobacco): evidence for a functional role in pyridine alkaloid synthesis. Plant Mol Biol 69: 299-312
6. Dewey RE, Xie J (2013) Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry 94: 10-27
7. Eich E (2008) Solanaceae Convolvulaceae: Secondary Metabolites. Springer, Berlin
8. Faccini PJ (2001) Alkaloid biosynthesis in plants: Biochemistry, cell biology, molecular regulation, and metabolic engineering application. Annu Rev Plant Physiol Plant Mol Biol 52: 29-66
9. Fecker LF, Rügenhagen C, Berlin J (1993) Increased production of cadaverine and anabasine in hairy root cultures of Nicotiana tabacum expressing a bacterial lysine decarboxylase gene. Plant Mol Biol 23: 11-21
10. Furer V, Hersch M, Silvetzki N, Breuer GS, Zevin S (2011) Nicotiana glauca (tree tobacco) intoxication-two cases in one family. J Med Toxicol 7: 47-51
11. Hashimoto T, Yamada Y (1994) Alkaloid biogenesis: molecular aspects. Annu Rev Plant Physiol 45: 257-285
12. Hashimoto T, Yamada Y (2003) New genes in alkaloid metabolism and transport. Curr Opin Biotechnol 14: 163-168
13. Herminghaus S, Tholl D, Rügenhagen C, Fecker LF, Leuschner C, Berlin J (1996) Improved metabolic action of a bacterial lysine decarboxylase gene in tobacco hairy root cultures by its fusion to a rbcS transit peptide coding sequence. Transgenic Res 5: 193-201
14. Kajikawa M, Hirai N, Hashimoto T (2009) A PIP-family protein is required for biosynthesis of tobacco alkaloids. Plant Mol Biol 69: 287-298
15. Lee YS, Cho YD (2001) Identification of essential active-site residues in ornithine decarboxylase of Nicotiana glutinosa decarboxylating both L-ornithine and L-lysine. Biochem J 360: 657-665
16. Leeper FJ, Grue-S0rensen G, Spenser ID (1981) Biosynthesis of quinolizidine alkaloids. Incorporation of A1-piperideine into matrine. Can J Chem 59: 106-115
17. Leete E (1956) The biogenesis of nicotine and anabasine. J Am Chem Soc 78: 3520-3523
18. Leete E (1958) The biogenesis of the Nicotiana alkaloids. VI. The piperidine ring of anabasine. J Am Chem Soc 80: 4393-4394
19. Leete E, Gros EG, Gilbertson TJ (1964) The Biosynthesis of anabasine. Origin of the nitrogen of the piperidine ring. J Am Chem Soc 86: 3907-3908
20. Leete E, Siegfried KJ (1957) The biogenesis of nicotine. III. Further observations on the incorporation of ornithine into the pyrrolidine ring. J Am Chem Soc 79: 4529-4531
21. Leistner E, Spenser ID (1973) Biosynthesis of the piperidine nucleus. Incorporation of chirally labeled [1-3H] cadaverine. J Am Chem Soc 95: 4715-4725
22. Nakabayashi R, Sawada Y, Yamada Y, Suzuki M, Hirai MY, Sakurai T, Saito K (2013) Combination of liquid chromatography-fourier transform ion cyclotron resonance-mass spectrometry with 13C-labeling for chemical assignment of sulfur-containing metabolites in onion bulbs. Anal Chem 85: 1310-1315
23. Saitoh F, Nona M, Kawashima N (1985) The alkaloid contents of sixty Nicotiana species. Phytochemistry 24: 477-480
24. Shitan N, Morita M, Yazaki K (2009) Identification of a nicotine transporter in leaves vacuoles of Nicotiana tabacum. Plant Signal Behav 4: 530-532
25. Shoji T, Hashimoto T (2008) Why does anatabine, but not nicotine, accumulate in jasmonate-elicited cultured tobacco BY-2 cells? Plant Cell Physiol 49: 1209-1216
26. Shoji T, Yamada Y, Hashimoto T (2000) Jasmonate induction of putrescine N-methyltransferase genes in the root of Nicotiana sylvestris. Plant Cell Physiol 41: 831-839
27. Sinclair SJ, Johnson R, Hamill JD (2004) Analysis of wound-induced gene expression in Nicotiana species with contrasting alkaloid profiles. Funct Plant Biol 31: 1-9
28. Sisson VA, Severson RF (1990) Alkaloid composition of the Nicotiana species. Beitr Tabakforsch 14: 327-339
29. Steppuhn A, Gase K, Krock B, Halitschke R, Baldwin IT (2004) Nicotine's defensive function in nature. PLoS Biol 2: 1074-1080
30. Walton NJ, Robins RJ, Rhodes MJC (1988) Perturbation of alkaloid production by cadaverine in hairy root cultures of Nicotiana rustica. Plant Sci 54: 125-131
31. Zhang Y-HP (2011) Substrate channeling and enzyme complexes for biotechnological applications. Biotechnol Adv 29: 715-725