4-Chloroindole-3-acetic acid and plant growth

Plant Growth Regulation

Volumn 27, Issue 1, 1999, Pages 3-13

  Reinecke, Dennis M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

4 chloroindole 3 acetic acid; 4 substituted IAA; Auxin; Pisum sativum; Structure activity relationship; Vicia faba

Indexed keywords

ACETIC ACID; BIOASSAY; BIOSYNTHESIS; HORMONES;

AUXIN; PISUM SATIVUM; PLANT GROWTH; STRUCTURE ACTIVITY RELATIONSHIP; VICIA FABA;

PLANTS (BOTANY);

PINUS SYLVESTRIS; PISUM SATIVUM; VICIA FABA;

EID: 0033052658     PISSN: 01676903     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1006191917753     Document Type: Article

References (68)

1. Ahmad A, Andersen AS and Engvild KC (1987) Rooting, growth and ethylene evolution of pea cuttings in response to chloroindole auxins. Physiol Plant 69: 137-140
2. Antolić S, Kojić-Prodić B, Tomić S, Nigović B, Magnus V and Cohen JD (1996) Structural studies on monofluorinated derivatives of the phytohormone indole-3-acetic acid (auxin). Acta Crystallogr B52: 651-661
3. Antolić, Salopek B, Kojić-Prodić B, Magnus V and Cohen JD (1998) Structural characterization and auxin properties of dichlorinated indole-3-acetic acids. Plant Growth Regulation 27: 21-31
4. Baldi BG, Slovin JP and Cohen JD (1985) Synthesis of 14C-labeled halogen substituted indole-3-acetic acids. J Label Comp Radiopharm 22: 279-285
5. Bandurski RS, Cohen JD, Slovin JP and Reinecke DM (1995) Auxin biosynthesis and metabolism. In: Davies PJ (ed) Plant Hormones Physiology, Biochemistry and Molecular Biology, 2nd edn. Dordrecht: Kluwer Academic Publishers, pp 39-65
6. Böttger M, Engvild KC and Soll H (1978) Growth of Avena coleoptiles and pH drop of protoplast suspensions induced by chlorinated indoleacetic acids. Planta 140: 89-92
7. Brenner ML and Cheikh N (1995) Hormones in photosynthate partitioning and seed filling. In: Davies PJ (ed) Plant Hormones Physiology, Biochemistry and Molecular Biology, 2nd edn. Dordrecht: Kluwer Academic Publishers, pp 649-670
8. 6-[Benzene Ring]-indole-3-acetic acid. Plant Physiol 80: 14-19
9. Davies PJ (1995) The plant hormones: Their nature, occurrence, and functions. In: Davies PJ (ed) Plant Hormones Physiology, Biochemistry and Molecular Biology, 2nd edn. Dordrecht: Kluwer Academic Publishers, pp 1-12
10. Eeuwens CJ and Schwabe WW (1975) Seed and pod wall development in Pisum sativum L. in relation to extracted and applied hormones. J Exp Bot 26: 1-14
11. Engvild KC (1975) Natural chlorinated auxins labelled with radioactive chloride in immature seeds. Physiol Plant 34: 286-287
12. Engvild KC (1978) Substituted indoleacetic acids tested in tissue cultures. Physiol Plant 44: 345-346
13. Engvild KC (1985) The chloroindole auxins of pea and related species. In: Purohit SS (ed) Hormonal Regulation of Plant Growth and Development, Vol II. Dordrecht: Martinus Nijhoff, pp 221-234
14. Engvild KC (1989) The death hormone hypothesis. Physiol Plant 77: 282-285
15. Engvild KC (1994) The Chloroindole Auxins of Pea, strong Plant Growth Hormones or Endogenous Herbicides? Denmark: Risø National Laboratory
16. Engvild KC (1996) Herbicidal activity of 4-chloroindoleacetic acid and other auxins on pea, barley and mustard. Physiol Plant 96: 333-337
17. Engvild KC, Egsgaard H and Larsen E (1978) Gas chromatographic-mass spectrometric identification of 4-chloroindolyl-3-acetic acid methyl ester in immature green peas. Physiol Plant 42: 365-368
18. Engvild KC, Egsgaard H and Larsen E (1980) Determination of 4-chloroindole-3-acetic acid methyl ester in Lathyrus, Vicia, and Pisum by gas chromatography-mass spectrometry. Physiol Plant 48: 499-503
19. Engvild KC, Egsgaard H and Larsen E (1981) Determination of 4-chloroindoleacetic acid methyl ester in Vicieae species by gas chromatography-mass spectrometry. Physiol Plant 53: 79-81
20. Ernstsen A and Sandberg G (1986) Identification of 4-chloroindole-3-acetic acid and indole-3-aldehyde in seeds of Pinus sylvestris. Physiol Plant 68: 511-518
21. Fischer C, Lüthen H, Böttger M and Hertel R (1992) Initial transient growth inhibition in maize coleoptiles following auxin application. J Plant Physiol 141: 88-92
22. Fock A, Kettner J and Böttger M (1992) The occurrence of 4-chlorotryptophane in Vicia faba. Phytochemistry 31: 2327-2328
23. Gandar JC (1960) Evolution des substances de croissance de la graine et de la gousse du pois au cours de leur development. Ann Physiol Vég 4: 255-260
24. Gandar JC and Nitsch C (1967) Isolement de l'ester méthylique d'un acide chloro-3-indolylacétique à partir de graines immatures de Pois, Pisum sativum L. C R Acad Sci, Paris, Ser D 265: 1795-1798
25. Gandar JC and Nitsch JP (1964) In: Régulateurs naturels de la croissance végetale. Extraction d'une substance de croissance à partir des jeunes graines de Pisum sativum. CNRS, Paris 123: 169-178
26. Hatano T, Katayama M and Marumo S (1987) 5,6-dichloroindole-3-acetic acid as a potent auxin: its synthesis and biological activity. Experientia 43: 1237-1239
27. Hattori H and Marumo S (1972) Monomethyl-4-chloroindolyl-3-acetyl-L-aspartate and absence of indolyl-3-acetic acid in immature seeds of Pisum sativum. Planta 102: 85-90
28. Higashi M, Hatori M, Manabe K and Sakagami Y (1998) Biosynthesis studies on Chlorinated indoles in Vicia faba. Plant Growth Regulation 27: 15-19
29. Hirasawa E (1989) Auxins induce α-amylase activity in pea cotyledons. Plant Physiol 91: 484-486
30. Hoffmann OL, Fox SW and Bullock MW (1952) Auxin-like activity of systematically substituted indoleacetic acid. J Biol Chem 196: 437-441
31. Hofinger M and Böttger M (1979) Identification by GC-MS of 4-chloroindolylacetic acid and its methyl ester in immature Vicia faba seeds. Phytochemistry 18: 653-654
32. Jensen JB, Egsgaard H and Van Onckelen H (1995) Catabolism of indole-3-acetic acid and 4- and 5-chloroindole-3-acetic acid in Bradyrhizobium japonicum. J Bact 177: 5762-5766
33. Katayama M, Thiruvikraman SV and Marumo S (1987) Identification of 4-chloroindole-3-acetic acid and its methyl ester in immature seeds of Vicia amurensis (the tribe Vicieae), and their absence from three species of Phaseoleae. Plant Cell Physiol 28: 383-386
34. Katayama M, Thiruvikraman SV and Marumo S (1988) Localization of 4-chloroindole-3-acetic acid in seeds of Pisum sativum and its absence from all other organs. Plant Cell Physiol 29: 889-891
35. Katekar GF (1979) Auxins: On the nature of the receptor site and molecular requirements for auxin activity. Phytochemistry 18: 223-233
36. Katekar GF and Geissler AE (1982) Auxins II: The effect of chlorinated indolylacetic acids on pea stems. Phytochemistry 21: 257-260
37. Katekar GF and Geissler AE (1983) Structure-activity differences between indoleacetic acid auxins on pea and wheat. Phytochemistry 22: 27-31
38. Magnus V, Ozga JA, Reinecke DM, Pierson GL, Larue TA, Cohen JD and Brenner ML (1997) 4-Chloroindole-3-acetic acid and indole-3-acetic acid in Pisum sativum. Phytochemistry 46: 675-681
39. Marumo S, Abe H, Hattori H and Munakata K (1968) Isolation of a novel auxin, methyl 4-chloroindoleacetate from immature seeds of Pisum sativum. Agr Biol Chem 32: 117-118
40. Marumo S and Hattori H (1970) Isolation of D-4-chlorotryptophane derivatives as auxin-related metabolites from immature seed of Pisum sativum. Planta 90: 208-211
41. Marumo S, Hattori H, Abe H and Munakata K (1968) Isolation of 4-Chloroindolyl-3-acetic acid from immature seeds of Pisum sativum. Nature 219: 959-960
42. Marumo S, Hattori H and Yamamoto A (1974) Biological activity of 4-chloroindolyl-3-acetic acid. In: Plant Growth Substances 1973. Tokyo: Hirokawa Publishing Co, pp 419-428
43. Nigović B, Kojić-Prodić B, Antolić S, Tomić S, Puntarec V and Cohen JD (1996) Structural studies on monohalogenated derivatives of the phytohormone indole-3-acetic acid (auxin). Acta Crystallogr B52: 332-343
44. Ozga JA, Brenner ML and Reinecke DM (1992) Seed effects on gibberellin metabolism in pea pericarp. Plant Physiol 100: 88-94
45. Ozga JA and Reinecke DM (1998) Interaction of 4-chloroindole-3-acetic acid and gibberellins in early pea fruit development. Plant Growth Regulation 27: 33-38
46. Parker CW, Entsch B and Letham DS (1986) Inhibitors of two enzymes which metabolize cytokinins. Phytochemistry 25: 303-310
47. Pless T, Böttger M, Hedden P and Graebe J (1984) Occurrence of 4-Cl-indoleacetic acid in broad beans and correlation of its levels with seed development. Plant Physiol. 74: 320-323
48. Porter WL and Thimann KV (1965) Molecular requirements for auxin action - I. Halogenated indoles and indoleacetic acids. Phytochemistry 4: 229-243
49. Reinecke DM, Ozga JA, Ilić N, Magnus V and Kojić-Prodić B (1998) Molecular properties of 4-substituted indole-3-acetic acids affecting pea pericarp elongation. Plant Growth Regulation 27: 39-48
50. Reinecke, DM, Ozga JA and Magnus V (1995) Effect of halogen substitution of indole-3-acetic acid on biological activity in pea fruit. Phytochemistry 40: 1361-1366
51. Rescher U, Walther A, Schiebl C and Klämbt D (1996) In vitro binding affinities of 4-chloro-, 2-methyl-, 4-methyl-, and 4-ethylindoleacetic acid to auxin-binding protein 1 (ABP1) correlate with their growth-stimulating activities. J Plant Growth Regul 15: 1-3
52. Sakagami Y, Manabe Y, Aitani T, Thiruvikraman SV and Marumo S (1993) L-4-chlorotryptophan from immature seeds of Pisum sativum and reassignment of the absolute stereochemistry of N-malonyl-4-chlorotryptophan. Tetrahedron Lett 34: 1057-1060
53. Schneider EA, Kazakoff CW and Wightman F (1985) Gas chromatography - mass spectrometry evidence for several endogenous auxins in pea seedling organs. Planta 165: 232-241
54. Sell HM, Wittwer SH, Rebstock TL and Redemann CT (1952) Comparative stimulation of parthenocarpy in the tomato by various indole compounds. Plant Physiol 28: 481-487
55. Slovin JP (1997) Phytotoxic conjugates of indole-3-acetic acid: Potential agents for biochemical selection of mutants in conjugate hydrolysis. Plant Growth Regulation 21: 215-221
56. Stenlid G and Engvild KC (1987) Effects of chlorosubstituted indoleacetic acids on root growth, ethylene and ATP formation. Physiol Plant 70: 109-113
57. Stotz HU and Hertel R (1994) Reevaluation of the role of auxin binding site II. J Plant Growth Regulation 13: 79-85
58. Thiruvikraman SV, Sakagami Y, Katayama M and Marumo S (1988) S-4-chlorotryptophan: Its synthesis via resolution, determination of the absolute stereochemistry and identification in the crude seed protein of the pea, Pisum sativum. Tetrahedron Lett 29: 2339-2342
59. Ulvskov P, Marcussen J, Seiden P and Olsen CE (1992) Immunoaffinity purification using monoclonal antibodies for the isolation of indole auxins from elongation zones of epicotyls of red-light-grown Alaska peas. Planta 188: 182-189
60. van Huizen R, Ozga JA and Reinecke DM (1996) Influence of auxin and gibberellin on in vivo protein synthesis during early pea fruit growth. Plant Physiol 112: 53-59
61. van Huizen R, Ozga JA and Reinecke DM (1997) Seed and hormonal regulation of gibberellin 20-oxidase expression in pea pericarp. Plant Physiol 115: 123-128
62. van Huizen R, Ozga JA, Reinecke DM, Twitchin B and Mander LN (1995) Seed and 4-chloroindole-3-acetic acid regulation of gibberellin metabolism in pea pericarp. Plant Physiol 109: 1213-1217
63. Venis (1995) Auxin binding protein 1 is a red herring? Oh no it isn't! J Exp Botany 46: 463-465
64. Wiesner W, van Pée K-H and Lingens F (1988) Purification and characterization of a novel bacterial non-heme chloroperoxidase from Pseudomonas pyrrocinia. J Biol Chem 263: 13725-13732
65. Yang D, Tannenbaum SR, Büchi G and Lee GCM (1984) 4-Chloro-6-methoxyindole is the precursor of a potent mutagen (4-chloro-6-methoxy-2-hydroxy-1 -nitroso-indolin-3-one oxime) that forms during nitrosation of the faba bean (Vicia faba). Carcinogenesis 5: 1219-1224
66. Yang T, Law DM and Davies PJ (1993) Magnitude and kinetics of stem elongation induced by exogenous indole-3-acetic acid in intact light-grown pea seedlings. Plant Physiol 102:717-724
67. Yoshimatsu K, Hatano T, Katayama M, Marumo S, Kamada H and Shimomura K (1990) IAA derivative induced tropane alkaloid production in root cultures of a Duboisia hybrid. Phytochemistry 29: 3525-3528
68. Zažimalová E and Kutáček M (1985) Auxin-binding site in wheat shoots: interactions between indol-3-ylacetic acid and its halogenated derivatives. Biologia Plantarum 27: 114-118