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N Use By Plants
Nitrate Assimilation
Ammonia Assimilation
Glu, Gln, Asn, Gly, Ser
Aminotransferases
Asp, Ala, GABA
Val, Leu, Ileu, Thr, Lys
Pro, Arg, Orn
Polyamines
Non-protein AAs
Alkaloids
Sulfate Assimilation
Cys, Met, AdoMet, ACC
His, Phe, Tyr, Tryp
Secondary Products
Onium Compounds
Enzymes
Methods
Simulation
References
HORT640 - Metabolic Plant Physiology

References, nicotine

Belbahri L, Chevalier L, Bensaddek L, Gillet F, Fliniaux MA, Boerjan W, Inze D, Thomas D, Thomasset B. Different expression of an S-adenosylmethionine synthetase gene in transgenic tobacco callus modifies alkaloid biosynthesis. Biotechnol. Bioeng. 69: 11-20 (2000).

Biastoff S, Brandt W, Drager B. Putrescine N-methyltransferase - the start for alkaloids. Phytochemistry Aug 1 [Epub ahead of print] (2009).

Burtin D, Michael AJ. Overexpression of arginine decarboxylase in transgenic plants. Biochem. J. 325: 331-337 (1997).

Chakrabarti M, Bowen SW, Coleman NP, Meekins KM, Dewey RE, Siminszky B. CYP82E4-mediated nicotine to nornicotine conversion in tobacco is regulated by a senescence-specific signaling pathway. Plant Mol. Biol. 66: 415-427 (2008).

Chakrabarti M, Meekins KM, Gavilano LB, Siminszky B. Inactivation of the cytochrome P450 gene CYP82E2 by degenerative mutations was a key event in the evolution of the alkaloid profile of modern tobacco. New Phytol. 175: 565-574 (2007).

Chintapakorn Y, Hamill JD. Antisense-mediated reduction in ADC activity causes minor alterations in the alkaloid profile of cultured hairy roots and regenerated transgenic plants of Nicotiana tabacum. Phytochemistry 68: 2465-2479 (2007).

Chintapakorn Y, Hamill JD. Antisense-mediated down-regulation of putrescine N-methyltransferase activity in transgenic Nicotiana tabacum L. can lead to elevated levels of anatabine at the expense of nicotine. Plant Mol. Biol. 53: 87-105 (2003).

Cipollini DF, Sipe ML. Jasmonic acid treatment and mammalian herbivory differentially affect chemical defenses and growth of wild mustard (Brassica kaber). Chemoecology 11: 137-143 (2001).

Cooper DA, Moore JM. Femtogram on-column detection of nicotine by isotope dilution gas chromatography/negative ion detection mass spectrometry. Biol. Mass Spectrom. 22: 590-594 (1993).

De Luca V, St Pierre B. The cell and developmental biology of alkaloid biosynthesis. Trends Plant Sci. 5: 168-173 (2000).

De Sutter V, Vanderhaeghen R, Tilleman S, Lammertyn F, Vanhoutte I, Karimi M, Inze D, Goossens A, Hilson P. Exploration of jasmonate signalling via automated and standardized transient expression assays in tobacco cells. Plant J. 44: 1065-1076 (2005).

Deboer KD, Lye JC, Aitken CD, Su AK, Hamill JD. The A622 gene in Nicotiana glauca (tree tobacco): evidence for a functional role in pyridine alkaloid synthesis. Plant Mol. Biol. 69: 299-312 (2009).

Deutsch J, Hegedus L, Greig NH, Rapoport SI, Soncrant TT. Electron-impact and chemical ionization detection of nicotine and cotinine by gas chromatography-mass spectrometry in rat plasma and brain. J. Chromatogr. 579: 93-98 (1992).

Fritz C, Palacios-Rojas N, Feil R, Stitt M. Regulation of secondary metabolism by the carbon-nitrogen status in tobacco: nitrate inhibits large sectors of phenylpropanoid metabolism. Plant J. 46: 533-548 (2006).

Ganas P, Sachelaru P, Mihasan M, Igloi GL, Brandsch R. Two closely related pathways of nicotine catabolism in Arthrobacter nicotinovorans and Nocardioides sp. strain JS614. Arch. Microbiol. 189: 511-517 (2008).

Gavilano LB, Coleman NP, Bowen SW, Siminszky B. Functional analysis of nicotine demethylase genes reveals insights into the evolution of modern tobacco. J. Biol. Chem. 282: 249-256 (2007).

Gavilano LB, Coleman NP, Burnley LE, Bowman ML, Kalengamaliro NE, Hayes A, Bush L, Siminszky B. Genetic engineering of Nicotiana tabacum for reduced nornicotine content. J. Agric. Food Chem. 54: 9071-9078 (2006).

Gavilano LB, Siminszky B. Isolation and characterization of the cytochrome P450 gene CYP82E5v2 that mediates nicotine to nornicotine conversion in the green leaves of tobacco. Plant Cell Physiol. 48: 1567-1574 (2007).

Hakkinen ST, Moyano E, Cusido RM, Palazon J, Pinol MT, Oksman-Caldentey KM. Enhanced secretion of tropane alkaloids in Nicotiana tabacum hairy roots expressing heterologous hyoscyamine-6beta-hydroxylase. J. Exp. Bot. 56: 2611-2618 (2005).

Hakkinen ST, Tilleman S, Swiatek A, De Sutter V, Rischer H, Vanhoutte I, Van Onckelen H, Hilson P, Inze D, Oksman-Caldentey KM, Goossens A. Functional characterisation of genes involved in pyridine alkaloid biosynthesis in tobacco. Phytochemistry 68: 2773-2785 (2007).

Halitschke R, Baldwin IT. Antisense LOX expression increases herbivore performance by decreasing defense responses and inhibiting growth-related transcriptional reorganization in Nicotiana attenuata. Plant J. 36: 794-807 (2003).

Heim WG, Jelesko JG. Association of diamine oxidase and S-adenosylhomocysteine hydrolase in Nicotiana tabacum extracts. Plant Mol. Biol. 56: 299-308 (2004).

Hibi N, Higashiguchi S, Hashimoto T, Yamada Y. Gene expression in tobacco low-nicotine mutants. Plant Cell 6: 723-735 (1994).

Imanishi S, Hashizume K, Nakakita M, Kojima H, Matsubayashi Y, Hashimoto T, Sakagami Y, Yamada Y, Nakamura K. Differential induction by methyl jasmonate of genes encoding ornithine decarboxylase and other enzymes involved in nicotine biosynthesis in tobacco cell cultures. Plant Mol. Biol. 38: 1101-1111 (1998).

Jacob P 3d, Shulgin AT, Yu L, Benowitz NL. Determination of the nicotine metabolite trans-3'-hydroxycotinine in urine of smokers using gas chromatography with nitrogen-selective detection or selected ion monitoring. J. Chromatogr. 583: 145-154 (1992).

Jacob P 3d, Yu L, Wilson M, Benowitz NL. Selected ion monitoring method for determination of nicotine, cotinine and deuterium-labeled analogs: absence of an isotope effect in the clearance of (S)-nicotine-3',3'-d2 in humans. Biol. Mass. Spectrom. 20: 247-252 (1991).

Jiang K, Pi Y, Hou R, Jiang L, Sun X, Tang K. Promotion of nicotine biosynthesis in transgenic tobacco by overexpressing allene oxide cyclase from Hyoscyamus niger. Planta 229: 1057-1063 (2009).

Jones D, Curvall M, Abrahamsson L, Kazemi-Vala E, Enzell C. Quantitative analysis of plasma nicotine using selected ion monitoring at high resolution. Biomed. Mass Spectrom. 9: 539-545 (1982).

Kahl J, Siemens DH, Aerts RJ, Gabler R, Kuhnemann F, Preston CA, Baldwin IT. Herbivore-induced ethylene suppresses a direct defense but not a putative indirect defense against an adapted herbivore. Planta 210: 336-342 (2000).

Kajikawa M, Hirai N, Hashimoto T. A PIP-family protein is required for biosynthesis of tobacco alkaloids. Plant Mol. Biol. 69: 287-298 (2009).

Kang JH, Wang L, Giri A, Baldwin IT. Silencing threonine deaminase and JAR4 in Nicotiana attenuata impairs jasmonic acid-isoleucine-mediated defenses against Manduca sexta. Plant Cell 18: 3303-3320 (2006).

Kaplan I, Halitschke R, Kessler A, Sardanelli S, Denno RF. Constitutive and induced defenses to herbivory in above- and belowground plant tissues. Ecology 89: 392-406 (2008).

Katoh A, Shoji T, Hashimoto T. Molecular cloning of N-methylputrescine oxidase from tobacco. Plant Cell Physiol. 48: 550-554 (2007).

Kessler D, Baldwin IT. Making sense of nectar scents: the effects of nectar secondary metabolites on floral visitors of Nicotiana attenuata. Plant J. 49: 840-854 (2007).

Kessler D, Gase K, Baldwin IT. Field experiments with transformed plants reveal the sense of floral scents. Science 321: 1200-1202 (2008).

Kidd SK, Melillo AA, Lu RH, Reed DG, Kuno N, Uchida K, Furuya M, Jelesko JG. The A and B loci in tobacco regulate a network of stress response genes, few of which are associated with nicotine biosynthesis. Plant Mol. Biol. 60: 699-716 (2006).

Kintz P. Gas chromatographic analysis of nicotine and cotinine in hair. J. Chromatogr. 580: 347-353 (1992).

Kintz P, Ludes B, Mangin P. Evaluation of nicotine and cotinine in human hair. J. Forensic Sci. 37: 72-76 (1992).

Lehrer M, Karmen A. Chemical ionization mass spectrometry for rapid assay of drugs in serum. J. Chromatogr. 126: 615-623 (1976).

Lelandais-Briere C, Jovanovic M, Torres GA, Perrin Y, Lemoine R, Corre-Menguy F, Hartmann C. Disruption of AtOCT1, an organic cation transporter gene, affects root development and carnitine-related responses in Arabidopsis. Plant J. 51: 154-164 (2007).

Lou Y, Baldwin IT. Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores. Plant Physiol. 140: 1126-1136 (2006).

Lou Y, Baldwin IT. Nitrogen supply influences herbivore-induced direct and indirect defenses and transcriptional responses in Nicotiana attenuata. Plant Physiol. 135: 496-506 (2004).

Malphettes L, Schoenmakers RG, Fussenegger M. 6-Hydroxy-nicotine-inducible multilevel transgene control in mammalian cells. Metab. Eng. 8: 543-553 (2006).

Matros A, Amme S, Kettig B, Buck-Sorlin GH, Sonnewald U, Mock HP. Growth at elevated CO2 concentrations leads to modified profiles of secondary metabolites in tobacco cv. SamsunNN and to increased resistance against infection with potato virus Y. Plant Cell Environ. 29: 126-137 (2006).

Matt P, Krapp A, Haake V, Mock HP, Stitt M. Decreased Rubisco activity leads to dramatic changes of nitrate metabolism, amino acid metabolism and the levels of phenylpropanoids and nicotine in tobacco antisense RBCS transformants. Plant J. 30: 663-677 (2002).

McManus KT, deBethizy JD, Garteiz DA, Kyerematen GA, Vesell ES. A new quantitative thermospray LC-MS method for nicotine and its metabolites in biological fluids. J. Chromatogr. Sci. 28: 510-516 (1990).

Memelink J, Verpoorte R, Kijne JW. ORCAnization of jasmonate-responsive gene expression in alkaloid metabolism. Trends Plant Sci. 6: 212-219 (2001).

Mesnard F, Roscher A, Garlick AP, Girard S, Baguet E, Arroo RR, Lebreton J, Robins RJ, Ratcliffe G. Evidence for the involvement of tetrahydrofolate in the demethylation of nicotine by Nicotiana plumbaginifolia cell-suspension cultures. Planta 214: 911-919 (2002).

Minguet EG, Vera F, Marina A, Carbonell J, Blazquez MA. Evolutionary diversification in polyamine biosynthesis. Mol. Biol. Evol. 25: 2119-2128 (2008).

Moyano E, Fornale S, Palazon J, Cusido RM, Bagni N, Pinol MT. Alkaloid production in Duboisia hybrid hairy root cultures overexpressing the pmt gene. Phytochemistry 59: 697-702 (2002).

Pacifici R, Pichini S, Altieri I, Rosa M, Bacosi A, Caronna A, Zuccaro P. Determination of nicotine and two major metabolites in serum by solid-phase extraction and high-performance liquid chromatography, and high-performance liquid chromatography-particle beam mass spectrometry. J. Chromatogr. 612: 209-213 (1993).

Pandey SP, Baldwin IT. RNA-directed RNA polymerase 1 (RdR1) mediates the resistance of Nicotiana attenuata to herbivore attack in nature. Plant J. 50: 40-53 (2007).

Paschold A, Halitschke R, Baldwin IT. Co(i)-ordinating defenses: NaCOI1 mediates herbivore- induced resistance in Nicotiana attenuata and reveals the role of herbivore movement in avoiding defenses. Plant J. 51: 79-91 (2007).

Pluskota WE, Qu N, Maitrejean M, Boland W, Baldwin IT. Jasmonates and its mimics differentially elicit systemic defence responses in Nicotiana attenuata. J. Exp. Bot. 58: 4071-4082 (2007).

Preston CA, Lewandowski C, Enyedi AJ, Baldwin IT. Tobacco mosaic virus inoculation inhibits wound-induced jasmonic acid-mediated responses within but not between plants. Planta 209: 87-95 (1999).

Ramsey JS, Jander G. Testing nicotine tolerance in aphids using an artificial diet experiment. J. Vis. Exp. 15 pii: 701 (2008).

Rayapuram C, Baldwin IT. Increased SA in NPR1-silenced plants antagonizes JA and JA-dependent direct and indirect defenses in herbivore-attacked Nicotiana attenuata in nature. Plant J. 52: 700-715 (2007).

Riechers DE, Timko MP. Structure and expression of the gene family encoding putrescine N-methyltransferase in Nicotiana tabacum: new clues to the evolutionary origin of cultivated tobacco. Plant Mol. Biol. 41: 387-401 (1999).

Roda AL, Oldham NJ, Svatos A, Baldwin IT. Allometric analysis of the induced flavonols on the leaf surface of wild tobacco (Nicotiana attenuata). Phytochemistry 62: 527-536 (2003).

Romisch-Margl W, Schramek N, Radykewicz T, Ettenhuber C, Eylert E, Huber C, Romisch-Margl L, Schwarz C, Dobner M, Demmel N, Winzenhorlein B, Bacher A, Eisenreich W. (13)CO(2) as a universal metabolic tracer in isotopologue perturbation experiments. Phytochemistry 68: 2273-2289 (2007).

Rothe G, Hachiya A, Yamada Y, Hashimoto T, Drager B. Alkaloids in plants and root cultures of Atropa belladonna overexpressing putrescine N-methyltransferase. J. Exp. Bot. 54: 2065-2070 (2003).

Ruiz JM, Blasco B, Rivero RM, Romero L. Nicotine-free and salt-tolerant tobacco plants obtained by grafting to salinity-resistant rootstocks of tomato. Physiol. Plant. 124: 465-475 (2005).

Saedler R, Baldwin IT. Virus-induced gene silencing of jasmonate-induced direct defences, nicotine and trypsin proteinase-inhibitors in Nicotiana attenuata. J. Exp. Bot. 55: 151-157 (2004).

Sato F, Hashimoto T, Hachiya A, Tamura K, Choi KB, Morishige T, Fujimoto H, Yamada Y. Metabolic engineering of plant alkaloid biosynthesis. Proc. Natl. Acad. Sci. U.S.A. 98: 367-372 (2001).

Schaarschmidt S, Kopka J, Ludwig-Muller J, Hause B. Regulation of arbuscular mycorrhization by apoplastic invertases: enhanced invertase activity in the leaf apoplast affects the symbiotic interaction. Plant J. 51: 390-405 (2007).

Schardl CL, Grossman RB, Nagabhyru P, Faulkner JR, Mallik UP. Loline alkaloids: currencies of mutualism. Phytochemistry 68: 980-996 (2007).

Seaton MJ, Vesell ES, Luo H, Hawes EM. Identification of radiolabeled metabolites of nicotine in rat bile. Synthesis of S-(-)-nicotine N-glucuronide and direct separation of nicotine-derived conjugates using high-performance liquid chromatography. J. Chromatogr. 621: 49-53 (1993).

Shi Q, Li C, Zhang F. Nicotine synthesis in Nicotiana tabacum L. induced by mechanical wounding is regulated by auxin. J. Exp. Bot. 57: 2899-2907 (2006).

Shoji T, Hashimoto T. Why does anatabine, but not nicotine, accumulate in jasmonate-elicited cultured tobacco BY-2 cells? Plant Cell Physiol. 49: 1209-1216 (2008).

Shoji T, Inai K, Yazaki Y, Sato Y, Takase H, Shitan N, Yazaki K, Goto Y, Toyooka K, Matsuoka K, Hashimoto T. Multidrug and toxic compound extrusion-type transporters implicated in vacuolar sequestration of nicotine in tobacco roots. Plant Physiol. 149: 708-718 (2009).

Shoji T, Ogawa T, Hashimoto T. Jasmonate-induced nicotine formation in tobacco is mediated by tobacco COI1 and JAZ genes. Plant Cell Physiol. 49: 1003-1012 (2008).

Shoji T, Winz R, Iwase T, Nakajima K, Yamada Y, Hashimoto T. Expression patterns of two tobacco isoflavone reductase-like genes and their possible roles in secondary metabolism in tobacco. Plant Mol. Biol. 50: 427-440 (2002).

Sinclair SJ, Murphy KJ, Birch CD, Hamill JD. Molecular characterization of quinolinate phosphoribosyltransferase (QPRtase) in Nicotiana. Plant Mol. Biol. 44: 603-617 (2000).

Stenzel O, Teuber M, Drager B. Putrescine N-methyltransferase in Solanum tuberosum L., a calystegine-forming plant. Planta 223: 200-212 (2006).

Steppuhn A, Schuman MC, Baldwin IT. Silencing jasmonate signalling and jasmonate-mediated defences reveals different survival strategies between two Nicotiana attenuata accessions. Mol. Ecol. 17: 3717-3732 (2008).

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Number of references = 90

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