Biochemical analyses of indole-3-acetaldoximedependent auxin biosynthesis in Arabidopsis

Proceedings of the National Academy of Sciences of the United States of America

Volumn 106, Issue 13, 2009, Pages 5430-5435

  Sugawara, Satoko ^a,b   Hishiyama, Shojiro ^c   Jikumaru, Yusuke ^a   Hanada, Atsushi ^a   Nishimura, Takeshi ^b   Koshiba, Tomokazu ^b   Zhao, Yunde ^a   Kamiya, Yuji ^d   Kasahara, Hiroyuki ^a  

^a RIKEN Center for Sustainable Resource Science   (Japan)

^b TOKYO METROPOLITAN UNIVERSITY   (Japan)

^c FORESTRY AND FOREST PRODUCTS RESEARCH INSTITUTE   (Japan)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETALDOXIME; ARABIDOPSIS PROTEIN; AUXIN; INDOLE 3 ACETALDOXIME; INDOLE 3 ACETONITRILE; INDOLE DERIVATIVE; INDOLEACETAMIDE; PROTEIN CYP79B2; PROTEIN CYP79B3; PROTEIN YUC; UNCLASSIFIED DRUG;

ARABIDOPSIS; ARTICLE; CONTROLLED STUDY; MUTATIONAL ANALYSIS; NONHUMAN; PHENOTYPE; PLANT GENE; PLANT GROWTH; PLANT ROOT; PRIORITY JOURNAL;

ARABIDOPSIS; INDOLEACETIC ACIDS; INDOLES; METABOLIC NETWORKS AND PATHWAYS; OXIMES;

ARABIDOPSIS; NICOTIANA TABACUM; ZEA MAYS;

EID: 65249099043     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.0811226106     Document Type: Article

References (36)

1. Davies PJ (2004) in Plant Hormones, ed Davies PJ (Kluwer Academic Publishers, Dordrecht), pp 1-15.
2. Cohen JD, Slovin JP, Hendrickson AM (2003) Two genetically discrete pathways convert tryptophan to auxin: more redundancy in auxin biosynthesis. Trends Plant Sci 8:197-199.
3. Ljung K, et al. (2002) Biosynthesis, conjugation, catabolism and homeostasis of indole- 3-acetic acid in Arabidopsis thaliana. Plant Mol Biol 49:249-272.
4. Pollmann S, Muller A, Weiler EW (2006) Many roads lead to "auxin": of nitrilases, synthases, and amidases. Plant Biol (Stuttg) 8:326-333.
5. Strader LC, Bartel B (2008) A new path to auxin. Nat Chem Biol 4:337-339.
6. Hull AK, Vij R, Celenza JL (2000) Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis. Proc Natl Acad Sci USA 97:2379-2384.
7. Mikkelsen MD, HansenCH, WittstockU, HalkierBA (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. J Biol Chem 275:33712-33717.
8. Zhao Y, et al. (2002) Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3. Genes Dev 16:3100-3112.
9. Bak S, et al. (2001) CYP83B1, a cytochrome P450 at the metabolic branch pointinauxin and indole glucosinolate biosynthesis in Arabidopsis. Plant Cell 13:101-111.
10. 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. Plant J 37:770-777.
11. Glawischnig E, Hansen BG, Olsen CE, Halkier BA (2004) Camalexin is synthesized from indole-3-acetaldoxime, a key branching point between primary and secondary metabolism in Arabidopsis. Proc Natl Acad Sci USA 101:8245-8250.
12. Grubb CD, Abel S (2006) Glucosinolate metabolism and its control. Trends Plant Sci 11:89-100.
13. Halkier BA, Gershenzon J (2006) Biology and biochemistry of glucosinolates. Annu Rev Plant Biol 57:303-333.
14. Nafisi M, et al. (2007) Arabidopsis cytochrome P450 monooxygenase 71A13 catalyzes the conversion of indole-3-acetaldoxime in camalexin synthesis. Plant Cell 19:2039-2052.
15. Barlier I, et al. (2000) The SUR2 gene of Arabidopsis thaliana encodes the cytochrome P450 CYP83B1, a modulator of auxin homeostasis. Proc Natl Acad Sci USA 97:14819-14824.
16. ChengY, DaiX, ZhaoY(2007) Auxinsynthesized by the YUCCA flavin mono oxygenases is essential for embryogenesis and leaf formation in Arabidopsis. Plant Cell 19:2430-2439.
17. ChengY, DaiX, ZhaoY(2006) Auxin biosynthesisbythe YUCCAflavin monooxygenases controls the formation of floral organs and vascular tissues in Arabidopsis. Genes Dev 20:1790-1799.
18. Zhao Y, et al. (2001) A role for flavin monooxygenase-like enzymes in auxin biosynthesis. Science 291:306-309.
19. Yamamoto Y, et al. (2007) Auxin biosynthesisby the YUCCA genes in rice. Plant Physiol 143:1362-1371.
20. GallavottiA, etal. (2008)sparse inflorescence1 encodesamonocot-specific YUCCA-like gene required for vegetative and reproductive development in maize. Proc Natl Acad Sci USA 105:15196-15201.
21. Tobena-Santamaria R, et al. (2002) FLOOZY of petunia is aflavin mono-oxygenase-like protein required for the specification of leaf and flower architecture. Genes Dev 16:753-763.
22. 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 Mol Biol 38:725-734.
23. Park WJ, et al. (2003) The nitrilase ZmNIT2 converts indole-3- acetonitrile to indole-3- acetic acid. Plant Physiol 133:794-802.
24. LlicN, NormanlyJ, CohenJD (1996) Quantificationoffree plus conjugated indoleacetic acid in arabidopsis requires correction for the nonenzymatic conversion of indolic nitriles. Plant Physiol 111:781-788.
25. Pollmann S, Muller A, Piotrowski M, Weiler EW (2002) Occurrence and formation of indole-3-acetamide in Arabidopsis thaliana. Planta 216:155-161.
26. Savaldi-Goldstein S, et al. (2008) New auxin analogs with growth-promoting effects in intact plants reveal a chemical strategy to improve hormone delivery. Proc Natl Acad Sci USA 105:15190-15195.
27. 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 bythe NIT1 gene. Plant Cell 9:1781-1790.
28. Ludwig-Muller J, Hilgenberg W (1988) A plasma membrane-bound enzyme oxidizes L-tryptophan to indole-3-acetaldoxime. Physiol Plant 74:240-250.
29. Wittstock U, Halkier BA (2000) Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate. J Biol Chem 275:14659-14666.
30. Nelson DR, et al. (2004) Comparative genomics of rice and Arabidopsis. Analysis of 727 cytochrome P450 genes and pseudogenes from a monocot and a dicot. Plant Physiol 135:756-772.
31. Golander Y, Sternson LA (1979) Metabolic conversion of fluorenone oxime to phenanthridinone by hepatic enzymes. J Pharm Sci 68:820-822.
32. Muller A, Hillebrand H, Weiler EW (1998) Indole-3-acetic acid is synthesized from L-tryptophan in roots of Arabidopsis thaliana. Planta 206:362-369.
33. Romano CP, et al. (1995) Transgene-mediated auxin overproduction in Arabidopsis: hypocotyl elongation phenotype and interactions with the hy6-1 hypocotyl elongation and axr1 auxin-resistant mutants. Plant Mol Biol 27:1071-1083.
34. Tao Y, et al. (2008) Rapid synthesis of auxin via a new tryptophan-dependent pathway is required for shade avoidance in plants. Cell 133:164-176.
35. Stepanova AN, etal. (2008) TAA1-mediated auxin biosynthesisisessential for hormone crosstalk and plant development. Cell 133:177-191.
36. Nishimura T, et al. (2006) Red light causes a reduction in IAA levels at the apical tip by inhibiting de novo biosynthesis from tryptophan in maize coleoptiles. Planta 224:1427-1435.