Novel 1-O-indole-3-acetyl-β-d-glucose-dependent acyltransferase transferring indoleacetyl moiety to some mono- di- and oligosaccharides

Acta Physiologiae Plantarum

Volumn 34, Issue 1, 2012, Pages 53-63

  Starzyńska, Ewelina ^a   Kowalczyk, Stanisław ^a  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

Author keywords

1 O IA glucose; 1 O IA glucose dependent acyltransferases; Indole 3 acetic acid; Zea mays

Indexed keywords

ZEA MAYS;

EID: 84855244295     PISSN: 01375881     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11738-011-0804-y     Document Type: Article

References (59)

1. Bandurski RS, Cohen JD, Slovin JP, Reinecke DM (1995) Auxin biosynthesis and metabolism. In: Davies PJ (ed) Plant hormones: physiology, biochemistry and molecular biology. Kluwer Academic Publishers, Dordrecht, pp 39-65.
2. Baumert A, Milkowski J, Schmidt M, Nimtz M, Wray V, Strack D (2005) Formation of a complex pattern of sinapate esters in Brassica napus seeds, catalyzed by enzymes of a serine carboxypeptidase-like acyltransferase family? Phytochemistry 66: 1334-1345.
3. Bialek K, Cohen JD (1989) Free and conjugated indole-3-acetic acid in developing bean seeds. Plant Physiol 91: 775-779.
4. Blakesly RW, Boezi JA (1977) A new staining technique for proteins in polyacrylamide gels using Coomassie Brilliant Blue G250. Anal Biochem 82: 580-582.
5. Bollag DM, Edelstein SJ (1991) Protein methods. Wiley, Inc, Publication.
6. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254.
7. Caboche M, Aranda G, Poll AM, Huet J-C, Leguay J-J (1984) Auxin conjugation by tobacco mesophyll protoplasts. Correlations between auxin cytotoxicity under low density growth conditions and induction of conjugation processes at high density. Plant Physiol 75: 54-59.
8. Catalá C, Östin A, Chamarro J, Sandberg G, Crozier A (1992) Metabolism of indole-3-acetic acid by pericarp discs from immature and mature tomato (Lycopersicon esculentum Mill.). Plant Physiol 100: 1457-1463.
9. Chisnell JR (1984) Myo-inositol esters of indole-3-acetic acid are endogenous components of Zea mays L. shoot tissue. Plant Physiol 74: 278-283.
10. Corcuera LJ, Bandurski RS (1982) Biosynthesis of indol-3-yl-acetyl-myo-inositol arabinoside in kernels of Zea mays L. Plant Physiol 70: 1664-1666.
11. Corcuera LJ, Michalczuk L, Bandurski RS (1982) Enzymic synthesis of indol-3-ylacetyl-myo-inositol galactoside. Biochem J 207: 283-290.
12. Delbarre A, Muller P, Imhoff V, Morgat J-L, Barbier-Brygoo H (1994) Uptake, accumulation and metabolism of auxins in tobacco leaf protoplasts. Planta 195: 159-167.
13. Ehmann A (1974) Identification of 2-O-(indole-3-acetyl)-d-glucopyranose, 4-O-(indole-3-acetyl)-d-glucopyranose and 6-O-(indole-3-acetyl)-d-glucopyranose from kernels of Zea mays by gas-liquid chromatography-mass spectrometry. Carbohydr Res 34: 99-114.
14. Ehmann A (1977) The van Urk-Salkowski reagent-a sensitive and specific chromogenic reagent for silica gel thin-layer chromatographic detection and identification of indole derivatives. J Chromatogr 132: 267-276.
15. Epstein E, Cohen JD, Bandurski RS (1980) Concentration and metabolic turnover of indoles in germinating kernels of Zea mays L. Physiol Plant 65: 415-421.
16. Ganguly T, Ganguly SN, Sircar PK, Sircar SM (1974) Rhamnose bound indole-3-acetic acid in the floral parts of Peltophorum ferrugineum. Physiol Plant 31: 330-332.
17. Hall PJ (1980) Indole-3-acetyl-myo-inositol in kernels of Oryza sativa. Phytochemistry 19: 2121-2123.
18. Harlow E, Lane D (1988) Antibodies. A laboratory manual. Cold Spring Harbor Laboratory Press, New York.
19. Iyer M, Slovin JP, Epstein E, Cohen JD (2005) Transgenic tomato plants with a modified ability to synthesize indole-3-acetyl-β-1-O-d-glucose. J Plant Growth Regul 24: 142-152.
20. Jackson RG, Lim E-K, 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. J Biol Chem 276: 4350-4356.
21. 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. Plant J 32: 573-583.
22. Jakas A, Magnus V, Horvat S, Sandberg G (1993) Synthesis of the β-d glucosyl ester of [carbonyl-13C]-indole-3-acetic acid. J Label Comp Radiopharmac XXXIII: 933-939.
23. 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. J Exp Bot 55: 791-801.
24. 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. J Plant Physiol 162: 207-213.
25. Jakubowska A, Kowalczyk S, Leźnicki AJ (1993) Enzymatic hydrolysis of 4-O and 6-O-indol-3-ylacetyl-β-d-glucose in plant tissues. J Plant Physiol 142: 61-66.
26. Jensen PJ, Bandurski RS (1994) Metabolism and synthesis of indole-3-acetic acid (IAA) in Zea mays. Levels of IAA during kernel development and the use of in vitro endosperm systems for studying IAA biosynthesis. Plant Physiol 106: 343-351.
27. Kai K, Horita J, Wakasa K, Miyagawa H (2007) Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana. Phytochemistry 68: 1651-1663.
28. Ke{ogonek}sy JM, Bandurski RS (1990) Partial purification and characterization of indol-3-ylacetylglucose: myo-inositol indol-3-ylacetyltransferase (indoleacetic acid-inositol synthase). Plant Physiol 94: 1598-1604.
29. Kowalczyk S, Bandurski RS (1990) Isomerization of 1-O-indol-3-ylacetyl-β-d-glucose. Enzymatic hydrolysis of 1-O, 4-O, and 6-O- indol-3-ylacetyl-β-d-glucose and the enzymatic synthesis of indole-3-acetyl glycerol by a hormone metabolizing complex. Plant Physiol 94: 4-12.
30. Kowalczyk S, Bandurski RS (1991) Enzymic synthesis of 1-O-(indol-3-ylacetyl)-β-d-glucose. Purification of the enzyme from Zea mays, and preparation of antibodies to the enzyme. Biochem J 279: 509-514.
31. 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. Physiol Plant 119: 165-174.
32. Leźnicki AJ, Bandurski RS (1988) Enzymic synthesis of indole-3-acetyl-1-O-β-d-glucose. I. Partial purification and characterization of the enzyme form Zea mays. Plant Physiol 88: 1474-1480.
33. Leznicki AJ, Bandurski RS (2001) The new pathway for the biosynthesis of ester linked IAA conjugates. XXXVI Meeting of the Polish Biochemical Society, Abstract, pp 302-303.
34. Li AX, Steffens JC (2000) An acyltransferase catalyzing the formation of diacylglucose is a serine carboxypeptidase-like protein. Proc Natl Acad Sci USA 97: 6902-6907.
35. Ljung K, Östin A, Lioussanne L, Sandberg G (2001) Developmental regulation of indole-3-acetic acid turnover in Scots pine seedlings. Plant Physiol 125: 464-475.
36. 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 Molec Biol 49: 249-272.
37. Ludwig-Müller J (2011) Auxin conjugates: their role for plant development and in the evolution of land plants. J Exp Bot 62: 1757-1773.
38. Ludwig-Müller J, Walz A, Slovin JP, Epstein E, Cohen JD, Dong W, Town CD (2005) Overexpression of maize IAGLU in Arabidopsis thaliana alters plant growth and sensitivity to IAA but not IBA and 2, 4-D. J Plant Growth Regul 24: 127-141.
39. Michalczuk L, Bandurski RS (1980) UDP-glucose: indoleacetic acid glucosyl transferase and indoleacetyl-glucose: myo-inositol indoleacetyl transferase. Biochem Biophys Res Commun 93: 588-592.
40. Michalczuk L, Bandurski RS (1982) Enzymic synthesis of 1-O-indol-3-ylacetyl-β-d-glucose and indol-3-ylacetyl-myo-inositol. Biochem J 207: 273-281.
41. Mugford ST, Qi X, Bakht S, Hill L, Wegel E, Hughes RK, Papadopoulou K, Melton R, Philo M, Sainsbury F, Lomonossoff GP, Roy AD, Goss RJM, Osbourn A (2009) A serine carboxypeptidase-like acyltransferase is required for synthesis of antimicrobial compounds and disease resistance in oats. Plant Cell 21: 2473-2484.
42. Oetiker JH, Aeschbacher G (1997) Temperature-sensitive plant cells with shunted indole-3-acetic acid conjugation. Plant Physiol 114: 1385-1395.
43. Ogita ZI, Markert CL (1979) A miniaturized system for electrophoresis on polyacrylamide gels. Anal Biochem 99: 233-241.
44. Percival FW, Bandurski RS (1976) Esters of indole-3-acetic acid from Avena seeds. Plant Physiol 58: 60-67.
45. Piskornik Z, Bandurski RS (1972) Purification and partial characterization of a glucan containing indole-3-acetic acid. Plant Physiol 50: 176-182.
46. Seidel C, Walz A, Park S, Cohen JD, Ludwig-Müller J (2006) Indole-3-acetic acid protein conjugates: novel players in auxin homeostasis. Plant Biol 8: 340-345.
47. Slovin JP, Bandurski RS, Cohen JD (1999) Auxin. In: Hooykaas PJJ, Hall MA, Libbenga KR (eds) Biochemistry and molecular biology of plant hormones, Elsevier Science BV, pp 115-140.
48. Starzynska, Kowalczyk (2007) Transfer of indole-3-acetic acid from 1-O-IA-glucose to myo-inositol and to some mono- and oligosaccharides. In: 3rd Conference of Polish Society of Exp Plant Biol, Abstract, pp 118.
49. 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.
50. Stehle F, Brandt W, Schmidt J, Milkowski C, Strack D (2008) Activities of Arabidopsis sinapoylglucose: malate sinapoyltransferase shed light on functional diversification of serine carboxypeptidase-like acyltransferases. Phytochemistry 69: 1826-1831.
51. Stehle F, Brandt W, Stubbs MT, Milkowski D, Strack D (2009) Sinapoyltransferases in the light of molecular evolution. Phytochemistry 70: 1652-1662.
52. 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.
53. Szmidt-Jaworska A, Ke{ogonek}sy J, Kopcewicz J (1997) Transformation of 1-O-(indole-3-acetyl)-β-d-glucose into di-O-(indole-3-acetyl)-d-glucose catalysed by enzyme preparation from corn seedlings. Acta Biochim Pol 44: 215-220.
54. Tam YY, Epstein E, Normanly J (2000) Characterization of auxin conjugates in Arabidopsis. Low steady-state levels of indole-3-acetyl-aspartate, indole-3-acetyl-glutamate, and indole-3-acetyl-glucose. Plant Physiol 123: 589-595.
55. Terol J, Domingo C, Taln M (2006) The GH3 family in plants: genome wide analysis in rice and evolutionary history based on EST analysis. Gene 371: 279-290.
56. Ueda M, Bandurski RS (1974) Structure of indole-3-acetic acid myo-inositol esters and pentamethyl-myoinositols. Phytochemistry 13: 243-253.
57. 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. Proc Natl Acad Sci USA 99: 1718-1723.
58. Wang H, Tian C-e, Duan J, Wu K (2008) Research progresses on GH3 s, one family of primary auxin-responsive genes. Plant Growth Regul 6: 225-232.
59. Woodward AW, Bartel B (2005) Auxin: regulation, action, and interaction. Ann Bot 95: 707-735.