Auxin biosynthesis and storage forms

Journal of Experimental Botany

Volumn 64, Issue 9, 2013, Pages 2541-2555

  Korasick, David A ^a   Enders, Tara A ^a   Strader, Lucia C ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

auxin; auxin biosynthesis; auxin conjugates; development; IAA; IBA.

Indexed keywords

AUXIN; INDOLEACETIC ACID; INDOLEACETIC ACID DERIVATIVE; PHYTOHORMONE;

AUXIN BIOSYNTHESIS; AUXIN CONJUGATES; BIOSYNTHESIS; CHEMISTRY; DEVELOPMENT; IBA.; METABOLISM; PLANT; REVIEW; TRANSPORT AT THE CELLULAR LEVEL;

AUXIN; AUXIN BIOSYNTHESIS; AUXIN CONJUGATES; DEVELOPMENT; IAA; IBA.;

BIOLOGICAL TRANSPORT; BIOSYNTHETIC PATHWAYS; INDOLEACETIC ACIDS; METABOLIC NETWORKS AND PATHWAYS; PLANT GROWTH REGULATORS; PLANTS;

EID: 84878300025     PISSN: 00220957     EISSN: 14602431     Source Type: Journal    
DOI: 10.1093/jxb/ert080     Document Type: Review

References (168)

1. Abe H, Uchiyama M, Sato R. 1974. Isolation of phenylacetic acid and its p-hydroxy derivative as auxin-like substances from Undaria pinnatifida. Agricultural and Biological Chemistry 38, 897-898.
2. Andreae WA, Good NE. 1955. the formation of indoleacetylaspartic acid in pea seedlings. Plant Physiology 30, 380-382.
3. Aung LH. 1972. The nature of root-promoting substances in Lycopersicon esculentum seedlings. Physiologia Plantarum 26, 306-309.
4. Badenoch-Jones J, Summons RE, Rolfe BG, Letham DS. 1984. Phytohormones, Rhizobium mutants, and nodulation in legumes. IV. Auxin metabolites in pea root nodules. Journal of Plant Growth Regulation 3, 23-39.
5. Bajguz A, Piotrowska A. 2009. Conjugates of auxin and cytokinin. Phytochemistry 70, 957-969.
6. Bak S, Nielsen HL, Halkier BA. 1998. The presence of CYP79 homologues in glucosinolate-producing plants shows evolutionary conservation of the enzymes in the conversion of amino acid to aldoxime in the biosynthesis of cyanogenic glucosides and glucosinolates. Plant Molecular Biology 38, 725-734. (Pubitemid 29053611)
7. Bak S, Tax FE, Feldmann KA, Galbraith DW, Feyereisen R. 2001. CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis. Plant Cell 13, 101-111. (Pubitemid 32177036)
8. Bandurski RS, Cohen JD, Slovin JP, Reinecke DM. 1995. Auxin biosynthesis and metabolism. In Davies PJ, ed. Plant Hormones . Dordrecht: Kluwer Academic Publishers, 39-65.
9. Barkawi LS, Tam YY, Tillman JA, Pederson B, Calio J, Al-Amier H, Emerick M, Normanly J, Cohen JD. 2008. A high-throughput method for the quantitative analysis of indole-3-acetic acid and other auxins from plant tissue. Analytical Biochemistry 372, 177-188. (Pubitemid 350116764)
10. Barratt NM, Dong W, Gage DA, Magnus V, Town CD. 1999. Metabolism of exogenous auxin by Arabidopsis thaliana: identification of the conjugate Nα-(indol-3-ylacetyl)-glutamine and initiation of a mutant screen. Physiologia Plantarum 105, 207-217.
11. Bartel B, Fink GR. 1995. ILR1, an amidohydrolase that releases active indole-3-acetic acid from conjugates. Science 268, 1745-1748.
12. Bayer MH. 1969. Gas chromatographic analysis of acidic indole auxins in Nicotiana. Plant Physiology 44, 267-271.
13. Bialek K, Cohen JD. 1986. Isolation and partial characterization of the major amide-linked conjugate of indole-3-acetic acid from Phaseolus vulgaris L. Plant Physiology 80, 99-104.
14. Bitto E, Bingman CA, Bittova L, Houston NL, Boston RS, Fox BG, Phillips GN Jr. 2009. X-ray structure of ILL2, an auxin-conjugate amidohydrolase from Arabidopsis thaliana. Proteins 74, 61-71.
15. Blommaert K. 1954. Growth- and inhibiting-substances in relation to the rest period of the potato tuber. Nature 174, 970-972.
16. Böttcher C, Boss PK, Davies C. 2011. Acyl substrate preferences of an IAA-amido synthetase account for variations in grape (Vitis vinifera L.) berry ripening caused by different auxinic compounds indicating the importance of auxin conjugation in plant development. Journal of Experimental Botany 62, 4267-4280.
17. Bower PJ, Brown HM, Purves WK. 1978. Cucumber seedling indoleacetaldehyde oxidase. Plant Physiology 61, 107-110.
18. Campanella JJ, Ludwig-Müller J, Town CD. 1996. Isolation and characterization of mutants of Arabidopsis thaliana with increased resistance to growth inhibition by indoleacetic acid-amino acid conjugates. Plant Physiology 112, 735-745.
19. Campanella JJ, Olajide AF, Magnus V, Ludwig-Müller J. 2004. A novel auxin conjugate hydrolase from wheat with substrate specificity for longer side-chain auxin amide conjugates. Plant Physiology 135, 2230-2240. (Pubitemid 39182801)
20. Campanella JJ, Smith SM, Leibu D, Wexler S, Ludwig-Müller J. 2008. The auxin conjugate hydrolase family of Medicago truncatula and their expression during the interaction with two symbionts. Journal of Plant Growth Regulation 27, 26-38. (Pubitemid 351640770)
21. Chamarro J, Östin A, Sandberg G. 2001. Metabolism of indole- 3-acetic acid by orange (Citrus sinensis) flavedo tissue during fruit development. Phytochemistry 57, 179-187. (Pubitemid 32458376)
22. Cheng Y, Dai X, Zhao Y. 2006. Auxin biosynthesis by the YUCCA flavin monooxygenases controls the formation of floral organs and vascular tissues in Arabidopsis. Genes & Development 20, 1790-1799. (Pubitemid 43992887)
23. Cheng Y, Dai X, Zhao Y. 2007. Auxin synthesized by the YUCCA flavin monooxygenases is essential for embryogenesis and leaf formation in Arabidopsis. Plant Cell 19, 2430-2439. (Pubitemid 47583835)
24. Chisnell Jr. 1984. Myo-inositol esters of indole-3-acetic acid are endogenous components of Zea mays L. shoot tissue. Plant Physiology 74, 278-283.
25. Chiwocha S, von Aderkas P. 2002. Endogenous levels of free and conjugated forms of auxin, cytokinins and abscisic acid during seed development in Douglas fir. Plant Growth Regulation 36, 191-200.
26. Cohen JD. 1982. Identification and quantitative analysis of indole-3- acetyl-L-aspartate from seeds of Glycine max L. Plant Physiology 70, 749-753.
27. Cohen JD, Bandurski RS. 1982. Chemistry and physiology of the bound auxins. Annual Review of Plant Physiology 33, 403-430.
28. Cohen JD, Ernstsen A. 1991. Indole-3-acetic acid and indole-3- acetylaspartic acid isolated from seeds of Heracleum laciniatum Horn. Plant Growth Regulation 10, 95-101.
29. Cooney TP, Nonhebel HM. 1989. The measurement and mass spectral identification of indole-3-pyruvate from tomato shoots. Biochemical and Biophysical Research Communications 162, 761-796.
30. Dai X, Mashiguchi K, Chen Q, Kasahara H, Kamiya Y, Ojha S, Dubois J, Ballou D, Zhao Y. 2013. The biochemical mechanism of auxin biosynthesis by an Arabidopsis YUCCA flavin-containing monooxygenase. Journal of Biological Chemistry 288, 1448-1457.
31. Davies RT, Goetz DH, Lasswell J, Anderson MN, Bartel B. 1999. IAR3 encodes an auxin conjugate hydrolase from Arabidopsis. Plant Cell 11, 365-376.
32. De Rybel B, Audenaert D, Xuan W, et al. 2012. A role for the root cap in root branching revealed by the non-auxin probe naxillin. Nature Chemical Biology 8, 798-805.
33. Engvild KC, Egsgaard H, Larsen E. 1980. Determination of 4-chloroindole-3-acetic acid methyl ester in Lathyrus, Vicia and Pisum by gas chromatography-mass spectrometry. Physiologia Plantarum 48, 499-503.
34. Engvild KC, Egsgaard H, Larsen E. 1981. Determination of 4-chloroindoleacetic acid methyl ester in Vicieae species by gas chromatography-mass spectrometry. Physiologia Plantarum 53, 79-81.
35. Epstein E, Chen KH., Cohen JD. 1989. Identification of indole- 3-butyric acid as an endogenous constituent of maize kernels and leaves. Plant Growth Regulation 8, 215-223.
36. Epstein E, Nissen SJ, Sutter EG. 1991. Indole-3-acetic acid and indole-3-butyric acid in tissues of carrot inoculated with Agrobacterium rhizogenes. Journal of Plant Growth Regulation 10, 97-100.
37. Ernstsen A, Sandberg G. 1986. Identification of 4-chloroindole- 3-acetic acid and indole-3-aldehyde in seeds of Pinus sylvestris. Physiologia Plantarum 68, 511-518.
38. Ernstsen A, Sandberg G, Lundström K. 1987. Identification of oxindole-3-acetic acid, and metabolic conversion of indole-3-acetic acid to oxindole-3-acetic acid in Pinus sylvestris seeds. Planta 172, 47-52.
39. Fries L, Iwasaki H. 1976. p-Hydroxyphenylacetic acid and other phenolic compounds as growth stimulators of the red alga Porphyra tenera. Plant Science Letters 6, 299-307.
40. García Sánchez F, Navas Díaz A, García Pareja A. 1996. Micellar liquid chromatography of plant growth regulators detected by derivative fluorometry. Journal of Chromatography A 723, 227-233. (Pubitemid 26071213)
41. Glawischnig E, Tomas A, Eisenreich W, Spiteller P, Bacher A, Gierl A. 2000. Auxin biosynthesis in maize kernels. Plant Physiology 123, 1109-1119. (Pubitemid 30466863)
42. Gouthu S, Morre J, Maier CS, Deluc LG. 2013. An analytical method to quantify three plant hormone families in grape berry using liquid chromotography and multiple reaction monitoring mass spectrometry. In: Gang DR, ed. Phytochemicals, Plant Growth, and the Environment, vol. 42. New York: Springer Science+Business Media, 19-36.
43. Hall PJ. 1980: Indole-3-acetyl-myo-inositol in kernels of Oryza sativa. Phytochemistry 19, 2121-2123.
44. Hull AK, Vij R, Celenza JL. 2000. Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis. Proceedings of the National Academy of Sciences, USA 97, 2379-2384. (Pubitemid 30134077)
45. Ilić N, Normanly J, Cohen JD. 1996. Quantification of free plus conjugated indoleacetic acid in Arabidopsis requires correction for the nonenzymatic conversion of indolic nitriles. Plant Physiology 111, 781-788. (Pubitemid 126450553)
46. Jackson RG, Kowalczyk M, Li Y, Higgins G, Ross J, Sandberg G, Bowles DJ. 2002. Over-expression of an Arabidopsis gene encoding a glucosyltransferase of indole-3-acetic acid: phenotypic characterization of transgenic lines. The Plant Journal 32, 573-583. (Pubitemid 36814964)
47. Jackson RG, Lim EK. Li Y, Kowalczyk M, Sandberg G, Hoggett J, Ashford DA, Bowles DJ. 2001. Identification and biochemical characterization of an Arabidopsis indole-3-acetic acid glucosyltransferase. Journal of Biological Chemistry 276, 4350-4356.
48. Jakubowska A, Kowalczyk S. 2004. The auxin conjugate 1-O-indole-3-acetyl- β-d-glucose is synthesized in immature legume seeds by IAGlc synthase and may be used for modification of some high molecular weight compounds. Journal of Experimental Botany 55, 791-801. (Pubitemid 38492526)
49. Jakubowska A, Kowalczyk S. 2005. A specific enzyme hydrolyzing 6-O(4-O)-indole-3-ylacetyl-β-d-glucose in immature kernels of Zea mays. Journal of Plant Physiology 162, 207-213. (Pubitemid 40191581)
50. Jones ERH, Henbest HB, Bentley JA. 1952. 3-Indolylacetonitrile: a naturally occurring plant growth hormone. Nature 169, 485-487.
51. Kai K, Horita J, Wakasa K, Miyagawa H. 2007. Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana. Phytochemistry 68, 1651-1663. (Pubitemid 46894706)
52. Kim JI, Sharkhuu A, Jin JB, et al. 2007. yucca6, a dominant mutation in Arabidopsis, affects auxin accumulation and auxin-related phenotypes. Plant Physiology 145, 722-735. (Pubitemid 350127609)
53. Kojima M, Kamada-Nobusada T, Komatsu H, et al. 2009. Highly sensitive and high-throughput analysis of plant hormones using MS-probe modification and liquid chromatography-tandem mass spectrometry: an application for hormone profiling in Oryza sativa. Plant and Cell Physiology 50, 1201-1214.
54. Koshiba T, Saito E, Ono N, Yamamoto N, Sato M. 1996. Purification and properties of flavin- and molybdenum-containing aldehyde oxidase from coleoptiles of maize. Plant Physiology 110, 781-789.
55. Kowalczyk M, Sandberg G. 2001. Quantitative analysis of indole- 3-acetic acid metabolites in Arabidopsis. Plant Physiology 127, 1845-1853. (Pubitemid 34050048)
56. Kowalczyk S, Jakubowska A, Zielińska E, Bandurski RS. 2003. Bifunctional indole-3-acetyl transferase catalyses synthesis and hydrolysis of indole-3-acetyl-myo-inositol in immature endosperm of Zea mays. Physiologia Plantarum 119, 165-174. (Pubitemid 37189985)
57. Larsen P. 1949. Conversion of indole acetaldehyde to indoleacetic acid in excised coleoptiles and in coleoptile juice. Americal Journal of Botany 36, 32-41.
58. Larsen P. 1951. Enzymatic conversion of indole acetaldehyde and naphthalene acetaldehyde to auxins. Plant Physiology 26, 697-707.
59. Lasswell J, Rogg LE, Nelson DC, Rongey C, Bartel B. 2000. Cloning and characterization of IAR1, a gene required for auxin conjugate sensitivity in Arabidopsis. Plant Cell 12, 2395-2408. (Pubitemid 32106414)
60. LeClere S, Rampey RA, Bartel B. 2004. IAR4, a gene required for auxin conjugate sensitivity in Arabidopsis, encodes a pyruvate dehydrogenase E1α homolog. Plant Physiology 135, 989-999. (Pubitemid 38819042)
61. LeClere S, Tellez R, Rampey RA, Matsuda SPT., Bartel B. 2002. Characterization of a family of IAA-amino acid conjugate hydrolases from Arabidopsis. Journal of Biological Chemistry 277, 20446-20452. (Pubitemid 34967341)
62. Li L, Hou X, Tsuge T, Ding M, Aoyama T, Oka A, Gu H, Zhao Y, Qu LJ. 2008. The possible action mechanisms of indole-3-acetic acid methyl ester in Arabidopsis. Plant Cell Reports 27, 575-584. (Pubitemid 351629489)
63. Liu X, Hegeman AD, Gardner G, Cohen JD. 2012. Protocol: highthroughput and quantitative assays of auxin and auxin precursors from minute tissue samples. Plant Methods 8, 31.
64. Ljung K, Hull AK, Kowalczyk M, Marchant A, Celenza J, Cohen JD, Sandberg G. 2002. Biosynthesis, conjugation, catabolism and homeostasis of indole-3-acetic acid in Arabidopsis thaliana. Plant Molecular Biology 50, 309-332. (Pubitemid 38458823)
65. Lu Q, Chen L, Lu M, Chen G, Zhang L. 2010. Extraction and analysis of auxins in plants using dispersive liquid-liquid microextraction followed by high-performance liquid chromatography with fluorescence detection. Journal of Agricultural and Food Chemistry 58, 2763-2770.
66. Ludwig-Müller J. 2011. Auxin conjugates: their role for plant development and in the evolution of land plants. Journal of Experimental Botany 62, 1757-1773.
67. Ludwig-Müller J, Cohen JD. 2002. Identification and quantification of three active auxins in different tissues of Tropaeolum majus. Physiologia Plantarum 115, 320-329. (Pubitemid 34667556)
68. Ludwig-Müller J, Epstein E. 1994. Indole-3-butyric acid in Arabidopsis thaliana. III. In vivo biosynthesis. Plant Growth Regulation 14, 7-14. (Pubitemid 2045654)
69. Ludwig-Müller J, Hilgenberg W. 1988. A plasma membrane-bound enzyme oxidizes l-tryptophan to indole-3-acetaldoxime. Physiologia Plantarum 74, 240-250.
70. Ludwig-Müller J, Jülke S, Bierfreund NM, Decker EL, Reski R. 2009. Moss (Physcomitrella patens) GH3 proteins act in auxin homeostasis. New Phytologist 181, 323-338. (Pubitemid 352840369)
71. Ludwig-Müller J, Sass S, Sutter EG, Wodner M, Epstein E. 1993. Indole-3-butyric acid in Arabidopsis thaliana. I. Identification and quantification. Plant Growth Regulation 13, 179-187.
72. Luo Y, Qin G, Zhang J, et al. 2011. d-myo-inositol-3-phosphate affects phosphatidylinositol-mediated endomembrane function in Arabidopsis and is essential for auxin-regulated embryogenesis. Plant Cell 23, 1352-1372.
73. Marsch-Martinez N, Greco R, Van Arkel G, Herrera-Estrella L, Pereira A. 2002. Activation tagging using the En-I maize transposon system in Arabidopsis. Plant Physiology 129, 1544-1556. (Pubitemid 34923218)
74. Martens DA, Franckenbeger WT. 1994. Assimilation of exogenous 2'-14C-indole-3-acetic acid and 3'-14C-tryptophan exposed to the roots of three wheat varieties. Plant and Soil 166, 281-290.
75. Mashiguchi K, Tanaka K, Sakai T, et al. 2011. The main auxin biosynthesis pathway in Arabidopsis. Proceedings of the National Academy of Sciences, USA 108, 18512-18517.
76. Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA. 2000. Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid. Journal of Biological Chemistry 275, 33712-33717.
77. Mikkelsen MD, Naur P, Halkier BA. 2004. Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis. The Plant Journal 37, 770-777. (Pubitemid 38300521)
78. Monteiro AM, Crozier A, Sandberg G. 1988. The biosynthesis and conjugation of indole-3-acetic acid in germinating seed and seedlings of Dalbergia dolichopetala. Planta 174, 561-568.
79. Morris DA, Johnson CF. 1987. Regulation of auxin transport in pea (Pisum sativum L.) by phenylacetic acid: inhibition of polar auxin transport in intact plants and stem segments. Planta 172, 408-416.
80. Müller A, Weiler EW. 2000. Indolic constituents and indole-3-actic acid biosynthesis in the wild-type and a tryptophan auxotroph mutant of Arabidopsis thaliana. Planta 211, 855-863.
81. Nakazawa M, Yabe N, Ichikawa T, Yamamoto YY, Yoshizumi T, Hasunuma K, Matsui M. 2001. DFL1, an auxin-responsive GH3 gene homologue, negatively regulates shoot cell elongation and lateral root formation, and positively regulates the light response of hypocotyl length. The Plant Journal 25, 213-221. (Pubitemid 32122755)
82. Narasimhan K, Basheer C, Bajic VB, Swarup S. 2003. Enhancement of plant-microbe interactions using a rhizosphere metabolomics-driven approach and its application in the removal of polychlorinated biphenyls. Plant Physiology 132, 146-153. (Pubitemid 36599272)
83. Nicholls PB. 1967. The isolation of indole-3-acetyl-3-O-myo-inositol from Zea mays. Planta 10, 2207-2209.
84. Norcini JG, Heuser CW. 1988. Changes in the level of [14C]indole-3- acetic acid and [14C]indoleacetylaspartic acid during root formation in mung bean cuttings. Plant Physiology 86, 1236-1239.
85. Normanly J. 2010. Approaching cellular and molecular resolution of auxin biosynthesis and metabolism. Cold Spring Harbor Perspectives in Biology 2, a001594.
86. Normanly J, Cohen JD, Fink GR. 1993. Arabidopsis thaliana auxotrophs reveal a tryptophan-independent biosynthetic pathway for indole-3-acetic acid. Proceedings of the National Academy of Sciences, USA 90, 10355-10359. (Pubitemid 23328311)
87. Normanly J, Grisafi P, Fink GR, Bartel B. 1997. Arabidopsis mutants resistant to the auxin effects of indole-3-acetonitrile are defective in the nitrilase encoded by the NIT1 gene. Plant Cell 9, 1781-1790.
88. Normanly J, Slovin JP, Cohen JD. 2004. Auxin biosynthesis and metabolism. In: Davies PJ, ed. Plant Hormones: Biosynthesis, Signal Transduction, Action . Dordrecht: Kluwer Academic Publishers, 36-62.
89. Novák O, Hényková E, Sairanen I, Kowalczyk M, Pospíšil T, Ljung K. 2012. Tissue-specific profiling of the Arabidopsis thaliana auxin metabolome. The Plant Journal 72, 523-536.
90. Okamoto T, Isogai Y, Koizumi T. 1967. Studies on plant growth regulators. 2. isolation of indole-3-acetic acid phenylacetic acid and several plant growth inhibitors from etiolated seedlings of Phaseolus. Chemical and Pharmaceutical Bulletin 15, 159-163.
91. Östin A, Kowalyczk M, Bhalerao RP, Sandberg G. 1998. Metabolism of indole-3-acetic acid in Arabidopsis. Plant Physiology 118, 285-296. (Pubitemid 128652991)
92. Östin A, Moritz T, Sandberg G. 1992. Liquid chromatography/mass spectrometry of conjugates and oxidative metabolites of indole-3- acetic acid. Biological Mass Spectrometry 21, 292-298.
93. Ouyang J, Shao X, Li J. 2000. Indole-3-glycerol phosphate, a branchpoint of indole-3-acetic acid biosynthesis from the tryptophan biosynthetic pathway in Arabidopsis thaliana. The Plant Journal 24, 327-333.
94. Park S, Cohen JD, Slovin JP. 2006. Strawberry fruit protein with a novel indole-acyl modification. Planta 224, 1015-1022. (Pubitemid 44435852)
95. Park S, Ozga JA, Cohen JD, Reinecke DM. 2010. Evidence of 4-Cl-IAA and IAA bound to proteins in pea fruit and seeds. Journal of Plant Growth Regulation 28, 184-193.
96. Park WJ, Kriechbaumer V, Müller A, Piotrowski M, Meeley RB, Gierl A, Glawischnig E. 2003. The nitrilase ZmNIT2 converts indole-3-acetonitrile to indole-3-acetic acid. Plant Physiology 133, 794-802. (Pubitemid 37325688)
97. Peat TS, Bottcher C, Newman J, Lucent D, Cowieson N, Davies C. 2012. Crystal structure of an indole-3-acetic acid amido synthetase from grapevine involved in auxin homeostasis. Plant Cell 24, 4525-4538.
98. Pedras MS, Nycholat CM, Montaut S, Xu Y, Khan AQ. 2002. Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip. Phytochemistry 59, 611-625. (Pubitemid 34229375)
99. Penčík A, Rolčík J, Novák O, Magnus V, Barták P, Buchtík R, Salopek-Sondi B, Strnad M. 2009. Isolation of novel indole-3-acetic acid conjugates by immunoaffinity extraction. Talanta 80, 651-655.
100. Percival FW, Bandurski RS. 1976. Esters of indole-3-acetic acid from Avena seeds. Plant Physiology 58, 60-67.
101. Phillips KA, Skirpan AL, Liu X, Christensen A, Slewinski TL, Hudson C, Barazesh S, Cohen JD, Malcomber S, McSteen P. 2011. vanishing tassel2 encodes a grass-specific tryptophan aminotransferase required for vegetative and reproductive development in maize. Plant Cell 23, 550-566.
102. Pollmann S, Müller A, Piotrowski M, Weiler EW. 2002. Occurrence and formation of indole-3-acetamide in Arabidopsis thaliana. Planta 216, 155-161. (Pubitemid 36761559)
103. Pollmann S, Neu D, Weiler EW. 2003. Molecular cloning and characterization of an amidase from Arabidopsis thaliana capable of converting indole-3-acetamide into the plant growth hormone, indole- 3-acetic acid. Phytochemistry 62, 293-300. (Pubitemid 36168929)
104. Purves WK, Hollenberg SM. 1982. Metabolism of exogenous indoleacetic acid to its amide conjugates in Cucumis sativus L. Plant Physiology 70, 283-286.
105. Qin G, Gu H, Zhao Y, et al. 2005. An indole-3-acetic acid carboxyl methyltransferase regulates Arabidopsis leaf development. Plant Cell 17, 2693-2704.
106. Quittenden LJ, Davies NW, Smith JA, Molesworth PP, Tivendale ND, Ross JJ. 2009. Auxin biosynthesis in pea: characterization of the tryptamine pathway. Plant Physiology 151, 1130-1138.
107. Rajagopal R, Tsurusaki K, Kannangara G, Kuraishi S, Sakurai N. 1994. Natural occurrence of indoleacetamide and amidohydrolase activity in etiolated aseptically-grown squash seedlings. Plant and Cell Physiology 35, 329-339. (Pubitemid 2094130)
108. Rampey RA, LeClere S, Kowalczyk M, Ljung K, Sandberg G, Bartel B. 2004. A family of auxin-conjugate hydrolases that contributes to free indole-3-acetic acid levels during Arabidopsis germination. Plant Physiology 135, 978-988. (Pubitemid 38819041)
109. Rampey RA, Woodward AW, Hobbs BN, Tierney MP, Lahner B, Salt DE, Bartel B. 2006. An Arabidopsis basic helix-loop-helix leucine zipper protein modulates metal homeostasis and auxin conjugate responsiveness. Genetics 174, 1841-1857. (Pubitemid 46011577)
110. Rampey RA, Baldridge MT, Farrow DC, Bay SN, Bartel B. 2013. Compensatory mutations in predicted metal transporters modulate auxin conjugate responsiveness in Arabidopsis. G3 3, 131-141.
111. Rashotte AM, Poupart J, Waddell CS, Muday GK. 2003. Transport of the two natural auxins, indole-3-butyric acid and indole- 3-acetic acid, in Arabidopsis. Plant Physiology 133, 761-772. (Pubitemid 37325685)
112. Reinecke DM. 1999. 4-Chloroindole-3-acetic acid and plant growth. Plant Growth Regulation 27, 3-13. (Pubitemid 29096737)
113. Reinecke DM, Bandurski RS. 1983. Oxindole-3-acetic acid, an indole- 3-acetic acid catabolite in Zea mays. Plant Physiology 71, 211-213.
114. Riov J, Bangerth F. 1992. Metabolism of auxin in tomato fruit tissue: formation of high molecular weight conjugates of oxindole-3-acetic acid via the oxidation of indole-3-acetylaspartic acid. Plant Physiology 100, 1396-1402.
115. Riov J, Gottlieb HE. 1980. Metabolism of auxin in pine tissues: indole-3-acetic acid conjugation. Physiologia Plantarum 50, 347-352.
116. Růžička K, Strader LC, Bailly A, et al. 2010. Arabidopsis PIS1 encodes the ABCG37 transporter of auxinic compounds including the auxin precursor indole-3-butyric acid. Proceedings of the National Academy of Sciences, USA 107, 10749-10753.
117. Sasaki K, Shimomura K, Kamada H, Harada H. 1994. IAA metabolism in embryogenic and non-embryonic carrot cells. Plant and Cell Physiology 35, 1159-1164.
118. Savić B, Tomić S, Magnus V, Gruden K, Barle K, Grenković R, Ludwig-Müller J, Salopek-Sondi B. 2009. Auxin amidohydrolases from Brassica rapa cleave the alanine conjugate of indolepropionic acid as a preferable substrate: a biochemical and modeling approach. Plant and Cell Physiology 50, 1587-1599.
119. Schmidt RC, Müller A, Hain R, Bartling D, Weiler EW. 1996. Transgenic tobacco plants expressing the Arabidopsis thaliana nitrilase II enzyme. The Plant Journal 9, 683-691. (Pubitemid 126661049)
120. Schneider EA, Kazakoff CW, Wightman F. 1985. Gas chromatography-mass spectrometry evidence for several endogenous auxins in pea seedling organs. Planta 165, 232-241.
121. Schwartz SH, Léon-Kloosterziel KM, Koornneef M, Zeevaart JAD. 1997. Biochemical characterization of the aba2 and aba3 mutants of Arabidopsis thaliana. Plant Physiology 114, 161-166. (Pubitemid 28110905)
122. Segal LM, Wightman F. 1982. Gas chromatographic and GC-MS evidence for the occurrence of 3-indolylpropionic acid and 3-incolylacetic acid in seedlings of Cucurbita pepo. Physiologia Plantarum 56, 367-370.
123. Seo M, Akaba S, Oritani T, Delarue M, Bellini C, Caboche M, Koshiba T. 1998. Higher activity of an aldehyde oxidase in the auxin-overproducing superroot1 mutant of Arabidopsis thaliana. Plant Physiology 116, 687-693. (Pubitemid 128482296)
124. Sitbon F, Ostin A, Sundberg B, Olsson O, Sandberg G. 1993. Conjugation of indole-3-acetic acid (IAA) in wild-type and IAA-overproducing transgenic tobacco plants, and identification of the main conjugates by frit-fast atom bombardment liquid chromatography-mass spectrometry. Plant Physiology 101, 313-320.
125. Sonner JM, Purves WK. 1985. Natural Occurrence of indole-3- acetylaspartate and indole-3-acetylglutamate in cucumber shoot tissue. Plant Physiology 77, 784-785.
126. Staswick PE. 2009. The tryptophan conjugates of jasmonic and indole-3-acetic acids are endogenous auxin inhibitors. Plant Physiology 150, 1310-1321.
127. Staswick PE, Serban B, Rowe M, Tiryaki I, Maldonado MT, Maldonado MC, Suza W. 2005. Characterization of an Arabidopsis enzyme family that conjugates amino acids to indole-3-acetic acid. Plant Cell 17, 616-627. (Pubitemid 41672979)
128. Stepanova AN, Robertson-Hoyt J, Yun J, Benavente LM, Xie DY, Dolezal K, Schlereth A, Jurgens G, Alonso JM. 2008. TAA1- mediated auxin biosynthesis is essential for hormone crosstalk and plant development. Cell 133, 177-191. (Pubitemid 351442990)
129. Stepanova AN, Yun J, Robles LM, Novak O, He W, Guo H, Ljung K, Alonso JM. 2011. The Arabidopsis YUCCA1 flavin monooxygenase functions in the indole-3-pyruvic acid branch of auxin biosynthesis. Plant Cell 23, 3961-3973.
130. Strader LC, Hendrickson Culler A, Cohen JD, Bartel B. 2010. Conversion of endogenous indole-3-butyric acid to indole-3-acetic acid drives cell expansion in Arabidopsis seedlings. Plant Physiology 153, 1577-1586.
131. Strader LC, Monroe-Augustus M, Rogers KC, Lin GL, Bartel B. 2008. Arabidopsis iba response5 (ibr5) suppressors separate responses to various hormones. Genetics 180, 2019-2031.
132. Strader LC, Wheeler DL, Christensen SE, Berens JC, Cohen JD, Rampey RA, Bartel B. 2011. Multiple facets of Arabidopsis seedling development require indole-3-butyric acid-derived auxin. Plant Cell 23, 984-999.
133. Strader LC, Bartel B. 2008. A new path to auxin. Nature Chemical Biology 4, 337-339. (Pubitemid 351694002)
134. Strader LC, Bartel B. 2009. The Arabidopsis PLEIOTROPIC DRUG RESISTANCE8/ABCG36 ATP binding cassette transporter modulates sensitivity to the auxin precursor indole-3-butyric acid. Plant Cell 21, 1992-2007.
135. Strader LC, Bartel B. 2011. Transport and metabolism of the endogenous auxin precursor indole-3-butyric acid. Molecular Plant 4, 477-486.
136. Sugawara S, Hishiyama S, Jikumaru Y, Hanada A, Nishimura T, Koshiba T, Zhao Y, Kamiya Y, Kasahara H. 2009. Biochemical analyses of indole-3- acetaldoxime-dependent auxin biosynthesis in Arabidopsis. Proceedings of the National Academy of Sciences, USA 106, 5430-5435.
137. Sutter EG, Cohen JD. 1992. Measurement of indolebutyric acid in plant tissues by isotope dilution gas chromatography-mass spectrometry analysis. Plant Physiology 99, 1719-1722.
138. Szerszen JB, Szczyglowski K, Bandurski RS. 1994. iaglu, a gene from Zea mays involved in conjugation of growth hormone indole-3- acetic acid. Science 265, 1699-1701.
139. Sztein AE, Cohen JD, de la Fuente IG, Cooke TJ. 1999. Auxin metabolism in mosses and liverworts. American Journal of Botany 86, 1544-1555.
140. Sztein AE, Cohen JD, Cooke TJ. 2000. Evolutionary patterns in the auxin metabolism of green plants. International Journal of Plant Sciences 161, 849-859.
141. Tam YY, Epstein E, Normanly J. 2000. Characterization of auxin conjugates in Arabidopsis. Low steady-state levels of indole-3-acetylaspartate, indole-3-acetyl-glutamate, and indole-3-acetyl-glucose. Plant Physiology 123, 589-595. (Pubitemid 30411143)
142. Tam YY, Normanly J. 1998. Determination of indole-3-pyruvic acid levels in Arabidopsis thaliana by gas chromatography-selected ion monitoring-mass spectrometry. Journal of Chromatography A 800, 101-108. (Pubitemid 28154869)
143. Tao Y, Ferrer JL, Ljung K, et al. 2008. Rapid synthesis of auxin via a new tryptophan-dependent pathway is required for shade avoidance in plants. Cell 133, 164-176. (Pubitemid 351442992)
144. Tivendale ND, Davidson SE, Davies NW, et al. 2012. Biosynthesis of the halogenated auxin, 4-chloroindole-3-acetic acid. Plant Physiology 159, 1055-1063.
145. Tivendale ND, Davies NW, Molesworth PP, Davidson SE, Smith JA, Lowe EK, Reid JB, Ross JJ. 2010. Reassessing the role of N-hydroxytryptamine in auxin biosynthesis. Plant Physiology 154, 1957-1965.
146. Tognetti VB, Van Aken O, Morreel K, et al. 2010. Perturbation of indole-3-butyric acid homeostasis by the UDP-glucosyltransferase UGT74E2 modulates Arabidopsis architecture and water stress tolerance. Plant Cell 22, 2660-2679.
147. Tsurumi S, Wada S. 1980. Metabolism of indole-3-acetic acid and natural occurrence of dioxindole-3-aceticacid derivatives in Vicia roots. Plant and Cell Physiology 21, 1515-1525.
148. Tsurusaki K, Takeda K, Sakurai N. 1997. Conversion of indole- 3-acetaldehyde to indole-3-acetic acid in cell-wall fraction of barley (Hordeum vulgare) seedlings. Plant and Cell Physiology 38, 268-273. (Pubitemid 27210899)
149. Tuominen H, Östin A, Sandberg G, Sundberg B. 1994. A novel metabolic pathway for indole-3-acetic acid in apical shoots of Populus tremula (L.)×Populus tremuloides (Michx.). Plant Physiology 106, 1511-1520. (Pubitemid 24986579)
150. Walz A, Park S, Slovin JP, Ludwig-Müller J, Momonoki YS, Cohen JD. 2002. A gene encoding a protein modified by the phytohormone indoleacetic acid. Proceedings of the National Academy of Sciences, USA 99, 1718-1723. (Pubitemid 34136559)
151. Westfall CS, Herrmann J, Chen Q, Wang S, Jez JM. 2010. Modulating plant hormones by enzyme action: the GH3 family of acyl acid amido synthetases. Plant Signaling & Behavior 5, 1607-1612.
152. Westfall CS, Zubieta C, Herrmann J, Kapp U, Nanao MH, Jez JM. 2012. Structural basis for prereceptor modulation of plant hormones by GH3 proteins. Science 336, 1708-1711.
153. Wightman F, Lighty DL. 1982. Identification of phenylacetic acid as a natural auxin in the shoots of higher plants. Physiologia Plantarum 55, 17-24.
154. Wightman F, Rauthan BS. 1974. Evidence for the biosynthesis and natural occurrence of the auxin, phenylacetic acid, in shoots of higher plants. In: Plant Growth Substances 1973. Tokyo: Hirokawa Publishing Co., 15-27.
155. Won C, Shen X, Mashiguchi K, Zheng Z, Dai X, Cheng Y, Kasahara H, Kamiya Y, Chory J, Zhao Y. 2011. Conversion of tryptophan to indole-3-acetic acid by TRYPTOPHAN AMINOTRANSFERASES OF ARABIDOPSIS and YUCCAs in Arabidopsis. Proceedings of the National Academy of Sciences, USA 108, 18518-18523.
156. Woodward AW, Bartel B. 2005. Auxin: regulation, action, and interaction. Annals of Botany 95, 707-735. (Pubitemid 41238659)
157. Woodward C, Bemis SM, Hill EJ, Sawa S, Koshiba T, Torii KU. 2005. Interaction of auxin and ERECTA in elaborating Arabidopsis inflorescence architecture revealed by the activation tagging of a new member of the YUCCA family putative flavin monooxygenases. Plant Physiology 139, 192-203. (Pubitemid 43951603)
158. Wright AD, Sampson MB, Neuffer MG, Michalczuk L, Slovin JP, Cohen JD. 1991. Indole-3-acetic acid biosynthesis in the mutant maize orange pericarp, a tryptophan auxotroph. Science 254, 998-1000. (Pubitemid 21917427)
159. Yamada M, Greenham K, Prigge MJ, Jensen PJ, Estelle M. 2009. The TRANSPORT INHIBITOR RESPONSE2 gene is required for auxin synthesis and diverse aspects of plant development. Plant Physiology 151, 168-179.
160. Yan H, Wang F, Han D, Yang G. 2012. Simultaneous determination of four plant hormones in bananas by molecularly imprinted solid-phase extraction coupled with high performance liquid chromatography. Analyst 137, 2884-2890.
161. Yang Y, Xu R, Ma CJ, Vlot AC, Klessig DF, Pichersky E. 2008. Inactive methyl indole-3-acetic acid ester can be hydrolyzed and activated by several esterases belonging to the AtMES esterase family of Arabidopsis. Plant Physiology 147, 1034-1045. (Pubitemid 352844260)
162. Zhao Y. 2012. Auxin biosynthesis: a simple two-step pathway converts tryptophan to indole-3-acetic acid in plants. Molecular Plant 5, 334-338.
163. Zhao Y, Christensen SK, Fankhauser C, Cashman JR, Cohen JD, Weigel D, Chory J. 2001. A role for flavin monooxygenase-like enzymes in auxin biosynthesis. Science 291, 306-309. (Pubitemid 32096316)
164. Zhao Y, Hull AK, Gupta NR, Goss KA, Alonso J, Ecker JR, Normanly J, Chory J, Celenza JL. 2002. Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. Genes & Development 16, 3100-3112. (Pubitemid 35424196)
165. Zolman BK, Martinez N, Millius A, Adham AR, Bartel B. 2008. Identification and characterization of Arabidopsis indole-3-butyric acid response mutants defective in novel peroxisomal enzymes. Genetics 180, 237-251.
166. Zolman BK, Nyberg M, Bartel B. 2007. IBR3, a novel peroxisomal acyl-CoA dehydrogenase-like protein required for indole-3-butyric acid response. Plant Molecular Biology 64, 59-72. (Pubitemid 46606920)
167. Zolman BK, Yoder A, Bartel B. 2000. Genetic analysis of indole- 3-butyric acid responses in Arabidopsis thaliana reveals four mutant classes. Genetics 156, 1323-1337.
168. Zubieta C, Ross JR, Koscheski P, Yang Y, Pichersky E, Noel JP. 2003. Structural basis for substrate recognition in the salicylic acid carboxyl methyltransferase family. Plant Cell 15, 1704-1716. (Pubitemid 37078328)