Advertisement

Plant Growth Regulation

, Volume 32, Issue 2–3, pp 219–230 | Cite as

Indole-3-butyric acid in plant growth and development

  • Jutta Ludwig-Müller
Article

Abstract

Within the last ten years it has been established by GC-MS thatindole-3-butyric acid (IBA) is an endogenous compound in a variety ofplant species. When applied exogenously, IBA has a variety of differenteffects on plant growth and development, but the compound is stillmainly used for the induction of adventitious roots. Using moleculartechniques, several genes have been isolated that are induced duringadventitious root formation by IBA. The biosynthesis of IBA in maize(Zea mays L.) involves IAA as the direct precursor. Microsomalmembranes from maize are able to convert IAA to IBA using ATP andacetyl-CoA as cofactors. The enzyme catalyzing this reaction wascharacterized from maize seedlings and partially purified. The invitro biosynthesis of IBA seems to be regulated by several externaland internal factors: i) Microsomal membranes from light-grownmaize seedlings directly synthesize IBA, whereas microsomal membranesfrom dark-grown maize plants release an as yet unknown reaction product,which is converted to IBA in a second step. ii) Drought and osmoticstress increase the biosynthesis of IBA maybe via the increaseof endogenous ABA, because application of ABA also results in elevatedlevels of IBA. iii) IBA synthesis is specifically increased byherbicides of the sethoxydim group. iv) IBA and IBA synthesizingactivity are enhanced during the colonization of maize roots with themycorrhizal fungus Glomus intraradices. The role of IBA forcertain developmental processes in plants is discussed and somearguments presented that IBA is per se an auxin and does notact via the conversion to IAA.

Arabidopsis thaliana arbuscular mycorrhiza biosynthesis indole-3-acetic acid indole-3-butyric acid regulation Zea mays 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Alvarez R, Nissen SJ and Sutter EG (1989) Relationship between indole-3-acetic acid levels in apple (Malus pumila Mill) rootstocks cultured in vitro and adventitious root formation in the presence of indole-3-butyric acid. Plant Physiol 89: 439-443Google Scholar
  2. 2.
    Babczinski P and Fischer R (1991) Inhibition of acetylcoenzyme A carboxylase by the novel grass-selective herbicide 3-(2,4-dichlorophenyl)-perhydroindolizine-2,4-dione. Pestic Sci 33: 455-466Google Scholar
  3. 3.
    Badenoch-Jones J, Summons RE, Rolfe BG and Letham DS (1984) Phytohormones, Rhizobium mutants and nodulation in legumes. IV. Auxin metabolism in pea root nodules. J Plant Growth Regul 3: 23-29Google Scholar
  4. 4.
    Baraldi R, Cohen JD, Bertazza D and Predieri S (1993) Uptake and metabolism of indole-3-butyric acid during the in vitro rooting phase in pear cultivars (Pyrus communis L.). Acta Hort 329: 289-291Google Scholar
  5. 5.
    Bartel B (1997) Auxin biosynthesis. Annu Rev Plant Physiol Plant Mol Biol 48: 51-66Google Scholar
  6. 6.
    Biddington NL and Dearman AS (1982) The effect of abscisic acid on root and shoot growth of cauliflower plants. Plant Growth Regul 1: 15-24Google Scholar
  7. 7.
    Blazkova A, Sotta B, Tranvan H, Maldiney R, Bonnet M, Einhorn JH, Kerhoas L and Miginiac E (1997) Auxin metabolism and rooting in young and mature clones of Sequoia sempervirens. Physiol Plant 99: 73-80Google Scholar
  8. 8.
    Blommaert KLJ (1954) Growth-and inhibiting substances in relation to the rest period of the potato tuber. Nature 174: 970-972Google Scholar
  9. 9.
    Buchala AJ and Schmid A (1979) Vitamin D and its analogues as a new class of plant growth substances affecting rhizogenesis. Nature 280: 230-231Google Scholar
  10. 10.
    Burton JD, Gronwald JW, Somers DA, Gengenbach BG and Wyse DL (1989) Inhibition of corn acetyl-CoA carboxylase by cyclohexanedione and aryloxyphenoxypropionate herbicides. Pestic Biochem Physiol 34: 76-85Google Scholar
  11. 11.
    Caboche M, Muller J-F, Chanut F, Aranda G and Cirakoglu S (1987) Comparison of the growth promoting activities and toxicities of various auxin analogs on cells derived from wildtype and a non-rooting mutant of tobacco. Plant Physiol 83: 795-800Google Scholar
  12. 12.
    Cabrera HL, Poch C, Peto CA and Chory J (1993) A mutation in the Arabidopsis DET3 gene uncouples photoregulated leaf development from gene expression and chloroplast biogenesis. Plant J 4: 671-682Google Scholar
  13. 13.
    Chory J and Peto CA (1990) Mutations in the DET1 gene affect cell-type-specific expression of light-regulated genes and chloroplast development in Arabidopsis. Proc Natl Acad Sci USA 87: 8776-8780Google Scholar
  14. 14.
    Chory J, Nagpal P and Peto CA (1991) Phenotypic and genetic analysis of det2, a new mutant that affects light-regulated seedling development in Arabidopsis. Plant Cell 3: 445-460Google Scholar
  15. 15.
    Cohen JD and Bandurski RS (1982) Chemistry and physiology of the bound auxins. Annu Rev Plant Physiol 33: 403-430Google Scholar
  16. 16.
    Cohen JD, Baldi BG and Slovin JP (1986) 13C6-[Benzene ring]-indole-3-acetic acid. Plant Physiol 80: 14-19Google Scholar
  17. 17.
    Cooper WC (1935) Hormones in relation to root formation on stem cuttings. Plant Physiol 10: 789-794Google Scholar
  18. 18.
    CosgroveDJandLiZC1993Roleofexpansinincellenlargementofoatcoleoptiles.Analysisofdevelopmentalgradientsandphotocontrol.PlantPhysiol 103: 1321-132Google Scholar
  19. 19.
    Dannenberg G, Latus C, Zimmer W, Hundeshagen B, Schneider-Poetsch H-J and Bothe H (1992) Influence of vesicular-arbuscular mycorrhiza on phytohormone balances in maize (Zea mays L.). J Plant Physiol 141: 33-39Google Scholar
  20. 20.
    Davies PJ (ed.) (1995) Plant Hormones. Physiology, Biochemistry and Molecular Biology. Dordrecht, The Netherlands: Kluwer Academic Publishers. ISBN 0-7923-2985-6Google Scholar
  21. 21.
    Dunberg A, Hsihan S and Sandberg G (1981) Auxin dynamics and the rooting of cuttings of Pinus sylvestris. Plant Physiol Suppl 67: 5Google Scholar
  22. 22.
    Epstein E and Lavee S (1984) Conversion of indole-3-butyric acid to indole-3-acetic acid by cuttings of grapevine (Vitis vinifera) and olive (Olea europea). Plant Cell Physiol 25: 697-703Google Scholar
  23. 23.
    Epstein E, Muszkat L and Cohen JD (1988) Identification of indole-3-butyric acid (IBA) in leaves of cypress and maize by gas-chromatography-mass spectrometry. Alon HaNotea 42: 917-919Google Scholar
  24. 24.
    Epstein E, Chen K-H and Cohen JD (1989) Identification of indole-3-butyric acid as an endogenous constituent of maize kernels and leaves. Plant Growth Regul 8: 215-223Google Scholar
  25. 25.
    Epstein E, Nissen SJ and Sutter EG (1991) Indole-3-acetic acid and indole-3-butyric acid in tissues of carrot inoculated with Agrobacterium rhizogenes. J. Plant Growth Regul. 10: 97-100Google Scholar
  26. 26.
    Epstein E and Sagee O (1992) Effect of ethylene treatment on transport and metabolism of indole-3-butyric acid in citrus leaf midribs. Plant Growth Regul 11: 357-362Google Scholar
  27. 27.
    Epstein E and Ackerman A (1993) Transport and metabolism of indole-3-butyric acid in cuttings of Leucadendron discolor. Plant Growth Regul 12: 17-22Google Scholar
  28. 28.
    Epstein E and Ludwig-Müller J (1993) Indole-3-butyric acid in plants: occurrence, biosynthesis, metabolism, and transport. Physiol Plant 88: 382-389Google Scholar
  29. 29.
    Epstein E, Sagee O and Zelcer A (1993) Uptake and metabolism of indole-3-butyric acid and indole-3-acetic acid by Petunia cell suspension cultures. Plant Growth Regul 13: 31-40Google Scholar
  30. 30.
    Epstein E, Zilkah S, Faingersh G and Rotebaum A (1993) Transport and metabolism of indole-3-butyric acid in sterile easy-to-root and difficult-to-root cuttings of sweet cherry (Prunus avium L.). Acta Hort 329: 292-295Google Scholar
  31. 31.
    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: 511-518Google Scholar
  32. 32.
    Esch H, Hundeshagen B, Schneider-Poetsch H-J and Bothe H (1994) Demonstration of abscisic acid in spores and hyphae of the arbuscular-mycorrhizal fungus Glomus and in the N2-fixing cyanobacterium Anabaena variabilis. Plant Sci 99: 9-16Google Scholar
  33. 33.
    Fallik E, Okon Y, Epstein E, Goldman A and Fischer M(1989) Identification and quantification of IAA and IBA in Azospirillum brasilense-inoculated maize roots. Soil Biol Biochem 21: 147-153Google Scholar
  34. 34.
    Harbage JF and Stimart DP (1996) Effect of pH and 1H-indole-3-butyric acid (IBA) on rooting of apple microcuttings. J Amer Soc Hort Sci 121: 1049-1053Google Scholar
  35. 35.
    Hartmann HT, Kester DE and Davies FT (1990) Plant Propagation: Principles and Practices. Englewood Cliffs, NJ: Prentice-Hall, pp 246-247Google Scholar
  36. 36.
    Hartung W and Heilmeier H (1992) The development of the root system of the winter annual desert plant Anastatica hierochuntica L. The significance of soil water content and nutrient supply. Flora 186: 117-125Google Scholar
  37. 37.
    Hartung W, Zhang J and Davies WJ (1994) Does abscisic acid play a stress physiological role in maize plants growing in heavily compacted soil? J Exp Bot 45: 221-226Google Scholar
  38. 38.
    Hobbie LJ (1998) Auxin: Molecular genetic approaches in Arabidopsis. Plant Physiol Biochem 36: 91-102Google Scholar
  39. 39.
    Hertel R, Evans ML, Leopold AC and Sell HM (1969) The specificity of the auxin transport system. Planta 85: 238-249Google Scholar
  40. 40.
    Hutchison KW, Singer PB, McInnis S, Diaz-Sala C and Greenwood MS (1999) Expansins are conserved in conifers and expressed in hypocotyls in response to exogenous auxin. Plant Physiol 120: 827-832Google Scholar
  41. 41.
    Kaldorf M and Ludwig-Müller J (2000) AM fungi might affect the root morphology of maize by increasing indole-3-butyric acid biosynthesis. Physiol Plant 109: 58-67Google Scholar
  42. 42.
    Katayama M, Kato K, Kimoto H and Fujii S (1995) (S)-(+)-4,4,4-trifluoro-3-(indole-3-) butyric acid, a novel fluorinated plant growth regulator. Experientia 51: 721-724Google Scholar
  43. 43.
    Katayama M and Gautam RK (1996) Synthesis and biological activities of substituted 4,4,4-trifluoro-3-(indole-3-)butyric acids, novel fluorinated plant growth regulators. Biosci Biotech Biochem 60: 755-759Google Scholar
  44. 44.
    Koornneef M, Jorna ML, Brinkhorst-van der Swan DLC and Karssen CM (1982) The isolation of abscisic acid (ABA) deficient mutant by selection of induced revertants in nongerminating gibberellin sensitive lines of Arabidopsis thaliana (L.) Heynh. Theor Appl Genet 61: 385-393Google Scholar
  45. 45.
    Kreps JA and Town CD (1992) Isolation and characterization of a mutant of Arabidopsis thaliana resistant to alpha methyl tryptophan. Plant Physiol 99: 269-275Google Scholar
  46. 46.
    Kreps JA, Ponappa T, Dong W and Town CD (1996) Molecular basis of α-methyltryptophan resistance in amt-1, a mutant of Arabidopsis thaliana with altered tryptophan metabolism. Plant Physiol 110: 1159-1165Google Scholar
  47. 47.
    Lange T (1997) Cloning gibberellin dioxygenase genes from pumpkin endosperm by heterologous expression of enzyme activities in Escherichia coli. Proc Natl Acad Sci USA 94: 6553-6558Google Scholar
  48. 48.
    LaTorre KA, Harris DM and Rundle SJ (1997) Differential expression of three Arabidopsis genes encoding the B' regulatory subunit of protein phosphatase 2A. Eur J Biochem 245: 156-163Google Scholar
  49. 49.
    Lemieux B, Miquel M, Somerville C and Browse J (1990) Mutants of Arabidopsis with alterations in seed lipid fatty acid composition. Theor Appl Genet 80: 234-240Google Scholar
  50. 50.
    Leyser O (1997) Auxin: Lessons from a mutant weed. Physiol Plant 100: 407-414Google Scholar
  51. 51.
    Ludwig-Müller J (1999) The biosynthesis of auxins. Curr. Topics Plant Biol. 1: 77-88Google Scholar
  52. 52.
    Ludwig-Müller J and Epstein E (1991) Occurrence and in vivo biosynthesis of indole-3-butyric acid in corn (Zea mays L.). Plant Physiol 97: 765-770Google Scholar
  53. 53.
    Ludwig-Müller J and Epstein E (1992) Indole-3-acetic acid is converted to indole-3-butyric acid by seedlings of Zea mays L. In: Karssen CM, van Loon LC and Vreugdenhil D (eds) Progress in Plant Growth Regulation. Boston, MA: Kluwer Academic Publishers, pp 188-193. ISBN 0-7923-1617-7Google Scholar
  54. 54.
    Ludwig-Müller J and Epstein E (1993) Indole-3-butyric acid in Arabidopsis thaliana. II. In vivo metabolism. Plant Growth Regulation 13: 189-195Google Scholar
  55. 55.
    Ludwig-Müller J, Sass S, Sutter EG, Wodner M and Epstein E (1993) Indole-3-butyric acid in Arabidopsis thaliana. I. Identification and quantification. Plant Growth Regul 13: 179-187Google Scholar
  56. 56.
    Ludwig-Müller J and Epstein E (1994) Indole-3-butyric acid in Arabidopsis thaliana. III. In vivo biosynthesis. Plant Growth Regul 14: 7-14Google Scholar
  57. 57.
    Ludwig-Müller J and Hilgenberg W (1995) Characterization and partial purification of indole-3-butyric acid synthetase from maize (Zea mays). Physiol Plant 94: 651-660Google Scholar
  58. 58.
    Ludwig-Müller J, Hilgenberg W and Epstein E (1995) The in vitro biosynthesis of indole-3-butyric acid in maize. Phytochemistry 40: 61-68Google Scholar
  59. 59.
    Ludwig-Müller J, Raisig A and Hilgenberg W (1995) Uptake and transport of indole-3-butyric acid in Arabidopsis thaliana: Comparison with other natural and synthetic auxins. J Plant Physiol 147: 351-354Google Scholar
  60. 60.
    Ludwig-Müller J, Schubert B and Pieper K (1995) Regulation of IBA synthetase by drought stress and abscisic acid. J Exp Bot 46: 423-432Google Scholar
  61. 61.
    Ludwig-Müller J, Kaldorf M, Sutter EG and Epstein E (1997) Indole-3-butyric acid (IBA) is enhanced in young maize (Zea mays L.) roots colonized with the arbuscular mycorrhizal fungus Glomus intraradices. Plant Sci 125: 153-162Google Scholar
  62. 62.
    Ludwig-Müller J, Schubert B, Rademacher W and Hilgenberg W (2000) Indole-3-butyric acid biosynthesis in maize is enhanced by cyclohexanedione herbicides. Physiol Plant, in pressGoogle Scholar
  63. 63.
    Lund ST, Smith AG and Hackett WP (1996) Cuttings of a tobacco mutant, rac, undergo cell division but do not initiate adventitious roots in response to exogenous auxin. Physiol Plant 97: 372-380Google Scholar
  64. 64.
    McCready CC (1963) Movement of growth regulators in plants. I. Polar transport of 2,4-D in segments from petioles of Phaseolus vulgaris. New. Phytol. 62: 3-18Google Scholar
  65. 65.
    McGaw BA (1995) Cytokinin biosynthesis and metabolism. In: Davies PJ (ed.) Plant Hormones. Physiology, Biochemistry and Molecular Biology. The Netherlands: Kluwer Academic Publishers, pp 98-117. ISBN 0-7923-2985-6Google Scholar
  66. 66.
    McQueen-Mason S (1995) Expansins and cell wall expansion. J Exp Bot 46: 1639-1650Google Scholar
  67. 67.
    Merckelbach C, Buchala AJ and Meier H (1991) Adventitious rooting in cuttings of Populus tremula: Metabolism of IAA and IBA. Abstr. 14th Int. Conf. on Plant Growth Substances (Amsterdam, The Netherlands), p 21Google Scholar
  68. 68.
    Mirza JI, Olsen GM, Iversen TH and Maher EP (1984) The growth and gravitropic responses of wild-type and auxinresistant mutants of Arabidopsis thaliana. Physiol Plant 60: 516-522Google Scholar
  69. 69.
    Neuteboom LW, Ng JM, Kuyper M, Clijdesdale OR, Hooykaas PJ and van der Zaal BJ (1999) Isolation and characterization of cDNA clones corresponding with mRNAs that accumulate during auxin-induced lateral root formation. Plant Mol Biol 39: 273-287Google Scholar
  70. 70.
    Neuteboom LW, Veth-Tello LM, Clijdesdale OR, Hooykaas PJ and van der Zaal BJ (1999) A novel subtilisin-like protease gene from Arabidopsis thaliana is expressed at sites of lateral root emergence. DNA Res 6: 13-19Google Scholar
  71. 71.
    Nordström A-C, Jacobs FA and Eliasson L (1991) Effect of exogenous indole-3-acetic acid and indole-3-butyric acid on internal levels of the respective auxins and their conjugation with aspartic acid during adventitious root formation in pea cuttings. Plant Physiol 96: 856-861Google Scholar
  72. 72.
    Normanly J, Slovin JP and Cohen JD (1995) Rethinking auxin biosynthesis and metabolism. Plant Physiol 107: 323-329Google Scholar
  73. 73.
    Östin A, Ilic' N and Cohen JD (1999) An in vitro system from maize seedlings for tryptophan-independent indole-3-acetic acid biosynthesis. Plant Physiol 119: 173-178Google Scholar
  74. 74.
    Ozga JA and Reinecke DM (1998) Interaction of 4-chloroindole-3-acetic acid and gibberellins in early pea fruit development. Plant Growth Regul 27: 33-38Google Scholar
  75. 75.
    Pan R and Gui H (1997) Physiolgical basis of the synergistic effects of IBA and triadimefon on rooting of mung bean hypocotyls. Plant Growth Regul 22: 7-11Google Scholar
  76. 76.
    Poupart J and Waddell C (1999) Characterization of rib1, an IBA Specific Mutant of Arabidopsis. Symposia on Plant Hormones, University of Missouri, April 14-17Google Scholar
  77. 77.
    Pythoud F and Buchala AJ (1989) The fate of vitamin D3 and indolebutyric acid applied to cuttings of Populus tremula L. during adventitious root formation. Plant Cell Environ 2: 489-494Google Scholar
  78. 78.
    Reinecke DM (1999) 4-Chloroindole-3-acetic acid and plant growth. Plant Growth Regul 27: 3-13Google Scholar
  79. 79.
    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: 1361-1366Google Scholar
  80. 80.
    Richmond TA and Bleecker AB (1999) A defect in β-oxidation causes abnormal inflorescence development in Arabidopsis. Plant Cell 11: 1911-1923Google Scholar
  81. 81.
    Riov J and Goren R (1979) Effect of ethylene on auxin transport and metabolism in midrib sections in relation to leaf abscission of woody plants. Plant Cell Environ 2: 83-89Google Scholar
  82. 82.
    Riov J and Yang SF (1989) Ethylene and auxin-ethylene interaction in adventitious root formation in mung bean (Vigna radiata) cuttings. J Plant Growth Regul 8: 131-141Google Scholar
  83. 83.
    Robertson JM, Hubick KT, Yeung EC and Reid DM (1990) Developmental responses to drought and abscisic acid in sun-flower roots. I. Root growth, apical anatomy and osmotic adjustment. J Exp Bot 41: 325-337Google Scholar
  84. 84.
    Sakagami Y, Manabe K, Aitani T, Thiruvikraman SV and Marumo S (1993) L-4-chlorotryptophan from immature seeds of Pisum sativum and reassignment of the absolute stereo230 chemistry of N-malonyl-4-chlorotryptophan. Tetrahedron Lett 43: 1057-1060Google Scholar
  85. 85.
    Schneider EA, Kazakoff CW and Wightman F (1985) Gas chromatography-mass spectrometry evidence for several endogenous auxins in pea seedling organs. Planta 165: 232-241Google Scholar
  86. 86.
    Shoseyov L, Sutter EG, Epstein E and Shoseyov O (1989) IBA induces β-1,3-glucanase activity in 20-day-old mung bean cuttings. Plant Growth Soc Am Quarterly 17: 92Google Scholar
  87. 87.
    Smith RD and Walker JC (1996) Plant protein phosphatases. Annu Rev Plant Physiol Plant Mol Biol 47: 101-125Google Scholar
  88. 88.
    Sponsel VM (1995) Gibberellin biosynthesis and metabolism. In: Davies PJ (ed.) Plant Hormones. Physiology, Biochemistry and Molecular Biology. The Netherlands: Kluwer Academic Publishers, pp 66-97. ISBN 0-7923-2985-6Google Scholar
  89. 89.
    Sutter EG and Cohen JD (1992) Measurement of indolebutyric acid in plant tissues by isotope dilution gas chromatographymass spectrometry analysis. Plant Physiol 99: 1719-1722Google Scholar
  90. 90.
    Tisserant B, Gianinazzi S and Gianinazzi-Pearson V (1996) Relationships between lateral root order, arbuscular mycorrhiza development and the physiological state of the symbiotic fungus in Platanus acerifolia. Can J Bot 74: 1947-1955Google Scholar
  91. 91.
    van der Krieken WM, Breteler H and Visser MHM (1992) The effect of conversion of indolebutyric acid into indoleacetic acid on root formation. Plant Cell Physiol 33: 709-713Google Scholar
  92. 92.
    van der Krieken WM, Breteler H, Visser MHM and Mavridou D (1993) The role of the conversion of IBA into IAA on root generation in apple: introduction of a test system. Plant Cell Rep 12: 203-206Google Scholar
  93. 93.
    Wakil SJ (1989) Fatty acid synthase, a proficient multifunctional enzyme. Biochemistry 28: 4523-4530Google Scholar
  94. 94.
    Wightman F and Lighty DL (1982) Identification of phenylacetic acid as a natural auxin in the shoots of higher plants. Physiol Plant 55: 17-24Google Scholar
  95. 95.
    Wiesman Z, Riov J and Epstein E (1988) Comparison of movement and metabolism of indole-3-acetic acid in mung bean cuttings. Physiol Plant 74: 556-560Google Scholar
  96. 96.
    Wiesman Z, Riov J and Epstein E (1989) Characterization and rooting ability of indole-3-butyric acid conjugates formed during rooting of mung bean cuttings. Plant Physiol 91: 1080-1084Google Scholar
  97. 97.
    Wright AD, Simpson MB, Neuffer MG, Michalczuk L, Slovin JP and Cohen JD (1991) Indole-3-acetic acid biosynthesis in the mutant orange pericarp, a tryptophan auxotroph. Science 254: 998-1000Google Scholar
  98. 98.
    Yano K, Yamauchi A and Kono Y (1996) Localized alteration in lateral root development in roots colonized by an arbuscular mycorrhizal fungus. Mycorrhiza 6: 409-415Google Scholar
  99. 99.
    Zimmerman PW and Wilcoxon F (1935) Several chemical growth substances which cause initiation of roots and other responses in plants. Contrib. Boyce Thompson Inst 7: 209-229Google Scholar

Copyright information

© Kluwer Academic Publishers 2000

Authors and Affiliations

  • Jutta Ludwig-Müller
    • 1
  1. 1.Botanisches Institut, Fakultät Mathematik und NaturwissenschaftenTechnische Universität DresdenDresdenGermany

Personalised recommendations