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Recent Advances in Brassinosteroid Research

  • Volker Marquardt
  • Günter Adam
Part of the Chemistry of Plant Protection book series (PLANT PROTECTIO, volume 7)

Abstract

The brassinosteroids represent a class of steroidal plant growth regulators with high growth-promoting activity. Evidence is accumulating that they are of ubiquitous occurrence and constitute a new group of phytohormones. The article gives a comprehensive survey on the hitherto known brassinosteroids isolated from plants, their analysis as well as the synthesis of members of the class and structural analogs, including labelled compounds. Recent advances in the studies on bioactivity, structural-activity relationships and physiology are also discussed. Experiments for practical use indicate a broad spectrum of bioregulatory and antistress effects which seem to prove the brassinosteroids as ecologically beneficial plant regulators for future application in agriculture and horticulture. An up-to-date overview of the research in this rapidly developing field covering the literature up to 1990 is given.

Keywords

Physiol Plant Lithium Salt Allylic Alcohol Vicinal Diol Phenyl Sulfone 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Grove MD, Spencer GF, Rohwedder WK, Mandava NB, Worley JF, Warthen JD, Steffens GL, Flippen-Anderson JL, Cook JC (1979) Nature (London) 281: 216Google Scholar
  2. 2.
    Mori K (1985) Yuki Gosei Kagaku Kyokaishi 43: 849Google Scholar
  3. 3.
    Adam G, Marquardt V (1987) Z Chem 27: 41Google Scholar
  4. 4.
    Khripach VA (1990) Pure Appl Chem 62: 1319Google Scholar
  5. 5.
    McMorris TC (1989) Analysis of brassinosteroids, antheridiol and oogoniols. In: Nes WD, Parrish EJ (eds) Analysis of sterols and other biologically significant steroids. Academic, San Diego, Calif., p. 61Google Scholar
  6. 6.
    Sembdner G, Schneider G, Schreiber K (eds) (1987) Methoden der Pflanzenhormon-analyse. Springer, Berlin Heidelberg New YorkGoogle Scholar
  7. 7.
    Yokota T, Takahashi N (1986) Chemistry, physiology and agricultural application of brassinolide and related steroids. In: Bopp M (ed) Plant growth substances 1985. Springer, Berlin Heidelberg New York, p 129Google Scholar
  8. 8.
    Adam, G, Marquardt V (1986) Phytochemistry 25: 1787Google Scholar
  9. 9.
    Meudt WJ (1987) Chemical and biological aspects of brassinolide. In: Fuller G, Ness WD (eds) Ecology and metabolism of plant lipids. ACS Symposium Series No 325, p 53Google Scholar
  10. 10.
    Mandava NB (1988) Annu Rev Plant Physiol Plant Mol Biol 39: 23Google Scholar
  11. 11.
    Yokota T, Kim SK, Takahashi N (1988) Abstr 13th Int Conf on Plant Growth Substances, Calgary, Abstr 168Google Scholar
  12. 12.
    Kim SK, Akihisa T, Tamura T, Matsumoto T, Yokota T, Takahashi N (1988) Phytochemistry 27: 629Google Scholar
  13. 13.
    Kim SK, Yokota T, Takahashi N (1987) Agric Biol Chem 51: 2303Google Scholar
  14. 14.
    Yokota T, Kim SK, Kosaka Y, Ogino Y, Takahashi N (1987) Conjugation of brassinosteroids. In: Schreiber K, Schuette HR, Sembdner G (eds) Conjugated plant hormones — structure, metabolism and function. Institute of Plant Biochemistry Halle, Academy of Sciences GDR p 288 (Proceedings of the International Symposium Conjugated Plant Hormones, 3–7 Nov 1986 at Gera)Google Scholar
  15. 15.
    Yokota T, Kim SK, Ogino Y, Takahashi N (1987) Proc. 14th Meeting Plant Growth Regulator Soc Amer p 28Google Scholar
  16. 16.
    Sakakibara M, Okada K, Ichikawa Y, Mori K (1982) Heterocycles 17: 301Google Scholar
  17. 17.
    Ikekawa N, Takatsuto S (1984) Shitsuryo Bunseki 32: 55Google Scholar
  18. 18.
    Thompson MJ, Meudt WJ, Mandava NB, Dutky SR, Lusby WR, Spaulding DW (1982) Steroids 39: 89PubMedGoogle Scholar
  19. 19.
    Abe H, Morishita T, Uchiyama M, Takatsuto S, Ikekawa N, Ikeda M, Sassa T, Kitsuwa T, Marumo S (1983) Experientia 39: 351Google Scholar
  20. 20.
    Takatsuto S, Ying B, Morisaki M, Ikekawa N (1981) Chem Pharm Bull 29: 903Google Scholar
  21. 21.
    Yokota T, Baba J, Takahashi N (1982) Tetrahedron Lett 23: 4965Google Scholar
  22. 22.
    Yokota T, Baba J, Koba S, Takahashi N (1984) Agric Biol Chem 48: 2529Google Scholar
  23. 23.
    Mori K, Sakakibara M, Okada K (1984) Tetrahedron 40: 1767Google Scholar
  24. 24.
    Yokota T, Baba J, Takahashi N (1983) Agric Biol Chem 47: 1409Google Scholar
  25. 25.
    Mori K (1985) Rev Latinoam Quim 16: 55Google Scholar
  26. 26.
    Ikekawa N, Nishiyama F, Fujimoto Y (1988) Chem Pharm Bull 36: 405Google Scholar
  27. 27.
    Thompson MJ, Mandava N, Flippen Anderson JL, Worley JF, Dutky SR, Robbins WE, Lusby W (1979) J Org. Chem 44: 5002Google Scholar
  28. 28.
    Yokota T, Arima M, Takahashi N (1982) Tetrahedron Lett 23: 1275Google Scholar
  29. 29.
    Anastasia M, Ciuffreda P, Del Puppo M, Fiecchi A (1983) J Chem Soc, Perkin Trans I 383Google Scholar
  30. 30.
    Yokota T, Kim SK, Fukui Y, Takahashi N, Takeuchi Y, Takematsu T (1987) Phytochemistry 26: 503Google Scholar
  31. 31.
    Takatsuto S, Ikekawa N (1984) J Chem Soc, Perkin Trans I 439Google Scholar
  32. 32.
    Okada K, Mori K (1983) Agric Biol Chem 47: 925Google Scholar
  33. 33.
    Anastasia M, Ciuffreda P, Fiecchi A (1983) J Chem Soc Perkin Trans I 379Google Scholar
  34. 34.
    Mori K, Takeuchi T (1988) Liebigs Ann Chem 815Google Scholar
  35. 35.
    Schneider JA, Yoshihara K, Nakanishi K, Kato N (1983) Tetrahedron Lett 24: 3859Google Scholar
  36. 36.
    Suzuki Y, Yamaguchi I, Yokota T, Takahashi N (1986) Agric Biol Chem 50: 3133Google Scholar
  37. 37.
    Yokota T, Morita M, Takahashi N (1983) Agric Biol Chem 47: 2149Google Scholar
  38. 38.
    Yokota T, Koba S, Kim SK, Takatsuto S, Ikekawa N, Sakakibara M, Okada K, Mori K, Takahashi N (1987) Agric Biol Chem 51: 1625Google Scholar
  39. 39.
    Mori K, Sakakibara M, Ichikawa Y, Ueda H, Okada K, Umemura T, Yabuta G, Kuwahara S, Kondo M, Minobe M, Sogabe A (1982) Tetrahedron 38: 2099Google Scholar
  40. 40.
    Takatsuto S, Ikekawa N (1986) J Chem Soc Perkin Trans I 2269Google Scholar
  41. 41.
    Ikekawa N, Takatsuto S, Kitsuwa T, Saito H, Morishita T, Abe H (1984) J Chromatogr 290: 289Google Scholar
  42. 42.
    Arima M, Yokota T, Takahashi N (1984) Phytochemistry 23: 1587Google Scholar
  43. 43.
    Plattner RD, Taylor SL, Grove MD (1986) J Nat Prod 49: 540Google Scholar
  44. 44.
    Cao H, Chen S, Jing J (1987) Zhiwan Zazho 952Google Scholar
  45. 45.
    Ikekawa N, Takatsuto S, Marumo S, Abe H, Morishita T, Uchiyama M, Ikeda M, Sasa T, Kitsuwa T (1983) Proc Jpn Acad Ser B 59: 9Google Scholar
  46. 46.
    Ikeda M, Takatsuto S, Sassa T, Ikekawa N, Nukina M (1983) Agric Biol Chem 47: 655Google Scholar
  47. 47.
    Park KH, Saimoto H, Nakagawa S, Sakurai A, Yokota T, Takahashi N, Syono K (1989) Agric Biol Chem 53: 805Google Scholar
  48. 48.
    Tada E (1987) JP 1–117 899Google Scholar
  49. 49.
    Yokota T (1987) Shokubutsu no Kagaku Chosetsu 22: 10Google Scholar
  50. 50.
    Baba J, Yokota T, Takahashi N (1983) Agric Biol Chem 47: 659Google Scholar
  51. 51.
    Takatsuto S, Abe H, Gamoh K (1990) Agric Biol Chem 54: 1057Google Scholar
  52. 52.
    Takatsuto S, Omote K, Gamoh K, Ishibashi M (1990) Agric Biol Chem 54: 757Google Scholar
  53. 53.
    Takatsuto S, Yokota T, Omote K, Gamoh K, Takahashi N (1989) Agric Biol Chem 53: 2177Google Scholar
  54. 54.
    Suzuki Y, Yamaguchi I, Takahashi N (1985) Agric Biol Chem 49: 49Google Scholar
  55. 55.
    Yokota T, Arima M, Takahashi N, Crozier A (1985) Phytochemistry 24: 1333Google Scholar
  56. 56.
    Yokota T, Arima M, Takahashi N, Takatsuto S, Ikekawa N, Takematsu T (1983) Agric Biol Chem 47: 2419Google Scholar
  57. 57.
    Schmidt J, Yokota T, Adam G, Takahashi N (1991) Phytochemistry 30: 364Google Scholar
  58. 58.
    Morishita T, Abe H, Uchiyama M, Marumo S, Takatsuto S, Ikekawa N (1983) Phytochemistry 22: 1051Google Scholar
  59. 59.
    Park KH, Yokota T, Sakurai A, Takahashi N (1987) Agric Biol Chem 51: 3081Google Scholar
  60. 60.
    Park KH, Hyun KH (1987) Han’guk Nonghwa Hakhoechi 30: 54Google Scholar
  61. 61.
    Wada K, Marumo S, Abe H, Morishita T, Nakamura K, Uchiyama M, Mori K (1984) Agric Biol Chem 48: 719Google Scholar
  62. 62.
    Takatsuto S, Ying B, Morisaki M, Ikekawa N (1982) J Chromatogr 239: 233Google Scholar
  63. 63.
    Takatsuto S, Ikekawa N (1986) Chem Pharm Bull 34: 3435Google Scholar
  64. 64.
    Abe H, Nakamura K, Morishita T, Uchiyama M, Takatsuto S, Ikekawa N (1984) Agric Biol Chem 48: 1103Google Scholar
  65. 65.
    Schmidt J, Vorbrodt HM, Adam G (1986) Biomed Environ Mass Spectrom 13: 663Google Scholar
  66. 66.
    Gamoh K, Okamoto N, Takatsuto S, Tejima I (1990) Anal Chim Acta 228: 101Google Scholar
  67. 67.
    Gamoh K, Omote K, Okamoto N, Takatsuto S (1989) J Chromatogr 469: 424Google Scholar
  68. 68.
    Gamoh K, Kitsuwa T, Takatsuto S, Fujimoto Y, Ikekawa N (1988) Anal Sci 533Google Scholar
  69. 69.
    Horgen PA, Nakagawa CH, Irvin RT (1984) Can J Biochem Cell Biol 62: 715Google Scholar
  70. 70.
    Schlagnhaufer C, Arteca RN, Phillips AT (1988) Plant Physiol (Suppl) 86: 4Google Scholar
  71. 70a.
    Yokota T, Watanabe S, Ogino Y, Yamaguchi I, Takahashi N (1990) J Plant Growth Regul 9: 151Google Scholar
  72. 70b.
    Zeigan D, Adam G, Porzel A, Kutschabsky L (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle, 29 October-2 November 1990 p 38Google Scholar
  73. 71.
    Kutschabsky L, Adam G, Vorbrodt HM (1990) Z Chem 30: 136Google Scholar
  74. 72.
    Kutschabsky L, Marquardt V, Adam G Z Chem in preparationGoogle Scholar
  75. 73.
    Ishiguro M, Takatsuto S, Morisaki M, Ikekawa N (1980) J Chem Soc Chem Commun 962Google Scholar
  76. 74.
    Fung S, Siddall JB (1980) J Am Chem Soc 102: 6580Google Scholar
  77. 75.
    Takatsuto S, Ikekawa N (1984) Chem Pharm Bull 32: 2001Google Scholar
  78. 76.
    Mori K (1980) Agric Biol Chem 44: 1211Google Scholar
  79. 77.
    Wada K, Marumo S (1981) Agric Biol Chem 45: 2579Google Scholar
  80. 78.
    Akhrem AA, Lakhvich FA, Khripach VA, Zhabinskii VN, Kovganko NV (1984) Dokl Akad Nauk SSSR 275: 1089Google Scholar
  81. 79.
    Takatsuto S, Kobayashi K, Watanabe T, Kuriyama H, Furuse T (1988) Agric Biol Chem 52: 3217Google Scholar
  82. 80.
    Watanabe T,. Kuriyama H, Furuse T, Kobayashi K, Takatsuto S (1988) Agric Biol Chem 52:2117Google Scholar
  83. 81.
    Aburatani M, Takeuchi T, Mori K (1987) Synthesis 181Google Scholar
  84. 82.
    Aburatani M, Takeuchi T, Mori K (1986) Agric Biol Chem 50: 3043Google Scholar
  85. 83.
    Anastasia M, Allevi P, Ciuffreda P, Oleotti A (1985) Steroids 45: 561PubMedGoogle Scholar
  86. 84.
    Aburatani M, Takeuchi T, Mori K (1987) Agric Biol Chem 51: 1909Google Scholar
  87. 85.
    Barton DHR, Lusinchi X, Magdzinski L, Ramirez JS (1984) J Chem Soc Chem Commun 1236Google Scholar
  88. 86.
    Anastasia M, Allevi P, Ciuffreda P, Fiecchi A, Scala A (1984) J Org Chem 49: 4297Google Scholar
  89. 87.
    Ferrer JC, Lalueza R, Saavedra O, Brosa C (1990) Tetrahedron Lett 31: 3941Google Scholar
  90. 88.
    Anastasia M, Ciuffreda P, Fiecchi A (1982) J Chem Soc Chem Commun 1169Google Scholar
  91. 89.
    Takatsuto S, Yazawa N, Ishiguro M, Morisaki M, Ikekawa N (1984) J Chem Soc Perkin Trans I 139Google Scholar
  92. 90.
    Zhou WS, Jiang B, Pan XF (1988) J Chem Soc Chem Commun 791Google Scholar
  93. 91.
    Zhou WS, Zhou YP, Jiang B (1989) Synthesis 426Google Scholar
  94. 92.
    Brooks CJW, Ekhato IV (1982) J Chem Soc Chem Commun 943Google Scholar
  95. 93.
    Zhou WS (1989) Pure Appl Chem 61: 431Google Scholar
  96. 94.
    Akhrem AA, Lakhvich FA, Khripach VA, Kovganko NV (1983) J Org Chem SSSR 19: 1249Google Scholar
  97. 95.
    Takatsuto S, Ikekawa N (1987) Chem Pharm Bull 35: 829Google Scholar
  98. 96.
    Takatsuto S, Ikekawa N (1987) Chem Pharm Bull 35: 3006Google Scholar
  99. 97.
    Takatsuto S, Muramatsu M, Ohya Y, Hayashi S, Shida A (1988) Agric Biol Chem 52: 2059Google Scholar
  100. 98.
    Cerny V (1989) Collect Czech Chem Commun 54: 2211Google Scholar
  101. 99.
    Edwards JE, Mills JS, Sundeen J, Freed JH (1969) J Am Chem Soc 91: 1248PubMedGoogle Scholar
  102. 100.
    Hutchins RF, Thompson MJ, Svoboda JA (1970) Steroids 15: 113PubMedGoogle Scholar
  103. 101.
    Salmond WG, Sobala MC (1977) Tetrahedron Lett 1695Google Scholar
  104. 102.
    Takatsuto S, Ikekawa N (1983) J Chem Soc, Perkin Trans I 2133Google Scholar
  105. 103.
    Takatsuto S, Yazawa N, Ikekawa N (1984) Phytochemistry 23: 525Google Scholar
  106. 104.
    Takatsuto S, Ikekawa N (1983) Tetrahedron Lett 24: 773Google Scholar
  107. 105.
    Donaubauer JR, Greaves AM, McMorris TC (1984) J Org Chem 49: 2833Google Scholar
  108. 106.
    Hayami H, Sato M, Kanemoto S, Morizawa Y, Oshima K, Nozaki H (1983) J Am Chem Soc 105: 4491Google Scholar
  109. 107.
    Kametani T, Kigawa M, Tsubuki M, Honda T (1988) J Chem Soc Perkin Trans I 1503Google Scholar
  110. 108.
    Kametani T, Katoh T, Tsubuki M, Honda T (1986) J Am Chem Soc 108: 7055Google Scholar
  111. 109.
    Kametani T, Keino K, Kigawa M, Tsubuki M, Honda T (1989) Tetrahedron Lett 30:3141Google Scholar
  112. 110.
    Zhou WS (1988) Acta Chim Sin 46: 598Google Scholar
  113. 111.
    Zhou WS, Tian WS (1987) Tetrahedron 43: 3705Google Scholar
  114. 112.
    Zhou WS, Jiang B, Pan XF (1989) J Chem Soc Chem Commun 612Google Scholar
  115. 112a.
    Zhou WS, Jiang B, Pan XF (1990) Tetrahedron 46: 3173Google Scholar
  116. 113.
    Yamamoto Y, Nishii S, Maruyama K (1986) J Chem Soc Chem Commun 102Google Scholar
  117. 114.
    Back TG, Brunner K, Krishna MV, Lai EKY (1989) Can J Chem 67: 1032Google Scholar
  118. 115.
    Takahashi T, Ootake A, Yamada H, Tsuji J (1985) Tetrahedron Lett 26: 69Google Scholar
  119. 116.
    Kametani T, Katoh T, Tsubuki M, Honda T (1987) Chem Pharm Bull 35: 2334Google Scholar
  120. 117.
    Kametani T, Katoh T, Fujio J, Nogiwa I, Tsubuki M, Hondo T (1988) J Org Chem 53: 1982Google Scholar
  121. 118.
    Mikami K, Loh TP, Nakai T (1988) J Chem Soc Chem Commun 1430Google Scholar
  122. 119.
    Mikami K, Kawamoto K, Nakai T (1986) Tetrahedron Lett 27: 4899Google Scholar
  123. 120.
    Mikami K, Kawamoto K, Nakai T (1985) Tetrahedron Lett 26: 5799Google Scholar
  124. 121.
    Takatsuto S, Ikekawa N (1986) J Chem Soc, Perkin Trans I 591Google Scholar
  125. 122.
    Takatsuto S, Ikekawa N (1986) Chem Pharm Bull 34: 1415Google Scholar
  126. 123.
    Takatsuto S, Ikekawa N (1986) Chem Pharm Bull 34: 4045Google Scholar
  127. 124.
    Allevi P, Anastasia M, Cerana R, Ciuffreda P, Lado P (1988) Phytochemistry 27:1309Google Scholar
  128. 125.
    Seo S, Nagasaki T, Katsuyama Y, Matsubara F, Sakata T, Yoshioka M, Makisumi Y (1989) J Labelled Compd Radiopharm 27: 1383Google Scholar
  129. 126.
    Yokota T, Ogino Y, Suzuki H, Takahashi N, Saimoto H, Fujioka S, Sakurai A (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990, p 5Google Scholar
  130. 127.
    Kohout L, Velgova H, Strnad M, Kaminek M (1987) Coll Czech Chem Comm 52:476Google Scholar
  131. 128.
    Kohout L, Strnad M (1989) Collect Czech Chem Commun 54: 1019Google Scholar
  132. 129.
    Kohout L (1989) Coll Czech Chem Commun 54: 3348Google Scholar
  133. 130.
    Adam G, Vorbrodt HM, Marquardt V, Kien NT, Porzel A (1989) Proc 5th Conf Chem Biotechnol Biol Active Nat Prod, Warna 18–23 September 1989, 3: 159Google Scholar
  134. 131.
    Marquardt V, Adam G, Alonso E, Coll F, Creuzburg D (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 10Google Scholar
  135. 132.
    Takatsuto S, Ikekawa N (1987) Chem Pharm Bull 35: 986Google Scholar
  136. 133.
    Takatsuto S, Ikekawa N, Morishita T, Abe H (1987) Chem Pharm Bull 35: 211Google Scholar
  137. 134.
    Akhrem AA, Lakhvich FA, Khripach VA, Zhabinskii VN, Kovganko NV (1984) Dokl Akad Nauk SSSR 275: 626Google Scholar
  138. 135.
    Akhrem AA, Lakhvich FA, Khripach VA, Kovganko NV, Zhabinskii VN (1985) Dokl Akad Nauk SSSR 283: 130Google Scholar
  139. 135a.
    Vorbrodt HM, Kien NT, Porzel A, Adam G (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 16Google Scholar
  140. 136.
    Hoerhold C, Vorbrodt HM, Boehme H, Porzel A, Adam G (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 24Google Scholar
  141. 137.
    Mandava NB, Sasse JM, Yopp JH (1981) Physiol Plant 53: 453Google Scholar
  142. 138.
    Hamada K (1986) FFTC Book Ser 34: 188Google Scholar
  143. 139.
    Strnad M, Kaminek M (1985) Biol Plant 27: 209Google Scholar
  144. 140.
    Mitchell JW, Livingston GA (1968) Agric Handb US Dept Agric 336Google Scholar
  145. 141.
    Yopp JH, Mandava NB, Sasse JM (1981) Physiol Plant 53: 445Google Scholar
  146. 142.
    Hewitt FR, Hough T, O’Neill P, Sasse JM, Williams EG, Rowan KS (1985) Aust J Plant Physiol 12: 201Google Scholar
  147. 143.
    Wada K, Kondo H, Marumo S (1985) Agric Biol Chem 49: 2249Google Scholar
  148. 144.
    Takatsuto S, Yazawa N, Ikekawa N, Takematsu T, Takeuchi Y, Koguchi M (1983) Phytochemistry 22: 2437Google Scholar
  149. 145.
    Strnad M (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990, p 37Google Scholar
  150. 146.
    Ikekawa N (1986) Structure and Function of Natural Sterols. In: Imura H, Goto T, Murachi T, Nakajima T (eds) Natural Products and Biological Activities. Univ Tokyo Press, Tokyo p 75Google Scholar
  151. 146a.
    Takatsuto S, Ikekawa N, Morishita T, Abe H (1987) Chem Pharm Bull 35: 211Google Scholar
  152. 147.
    Cerny V, Strnad M, Kaminek M (1986) Collect Czech Chem Commun 51: 687Google Scholar
  153. 148.
    Kakiuchi T, Kamuro Y, Takatsuto S, Kobayashi K (1988) Agric Biol Chem 52:2381Google Scholar
  154. 149.
    Takatsuto S, Futatsuya F, Kobayashi K, Satoh H (1989) Agric Biol Chem 53: 263Google Scholar
  155. 150.
    Hayashi S, Hohjoh T, Shida A, Ikekawa N (1988) EP O 282 984Google Scholar
  156. 151.
    Arteca RN, Tsai DS, Schlagnhaufer C, Mandava NB (1983) Physiol Plant 59: 539Google Scholar
  157. 152.
    Arteca RN, Schlagnhaufer C (1984) Physiol Plant 62: 445Google Scholar
  158. 153.
    Schlagnhaufer C, Arteca RN, Yopp JH (1984) Physiol Plant 61: 555Google Scholar
  159. 154.
    Schlagnhaufer C, Arteca RN, Yopp JH (1984) Physiol Plant 60: 347Google Scholar
  160. 155.
    Wu YM, Bao YW, Liu Y (1987) Acta Phytophysiologica Sinica 13: 107Google Scholar
  161. 156.
    Arteca RN, Bachman JM, Mandava NB (1988) J Plant Physiol 133: 430Google Scholar
  162. 157.
    Arteca RN, Bachman JM, Tsai DS, Mandava NB (1988) Physiol Plant 74: 631Google Scholar
  163. 158.
    Arteca RN, Bachman JM (1987) J Plant Physiol 129: 13Google Scholar
  164. 159.
    Eun JS, Kuraishi S, Sakurai N (1989) Plant Cell Physiol 30: 807Google Scholar
  165. 160.
    Schlagnhaufer CD, Arteca RN (1985) Physiol Plant 65: 151Google Scholar
  166. 161.
    Schlagnhaufer CD, Arteca RN (1985) Plant Physiol 78: 300PubMedGoogle Scholar
  167. 162.
    Schubert S, Matzke H (1985) Physiol Plant 64: 285Google Scholar
  168. 163.
    Romani G, Marre MT, Bonetti A, Cerana R, Lado P, Marre E (1983) Physiol Plant 59: 528Google Scholar
  169. 164.
    Marre E (1985) Fusicoccin-induced and hormone-induced changes of hydrogen extrusion physiological implications. In: St. John JB, Berlin E and Jackson PC (eds) Beltsville Symposia in Agricultural Research, 9. Frontiers of Membrane Research in Agriculture; Beltsville, MD, USA, 20–24 May 1984 p 439Google Scholar
  170. 165.
    Cerana R, Colombo R, Lado P (1983) Physiol Veg 21: 875Google Scholar
  171. 166.
    Cerana R, Bonetti A, Marre MT, Romani G, Lado P, Marre E (1983) Physiol Plant 59:23Google Scholar
  172. 167.
    Cerana R, Lado P, Anastasia M, Ciuffreda P, Allevi P (1984) Z Pflanzenphysiol 114:221Google Scholar
  173. 168.
    Cerana R, Spelta M, Bonetti A, Lado P (1985) Plant Sci 38: 99Google Scholar
  174. 169.
    De Michelis MI, Lado P (1986) Physiol Plant 68: 603Google Scholar
  175. 170.
    Dahse I, Sack H, Bernstein M, Petzold U, Mueller E, Vorbrodt HM, Adam G (1990) Plant Physiol 93: 1268PubMedGoogle Scholar
  176. 171.
    Dahse I, Willmer CM, Grammatikopoulus G, Nikolopoulos D (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 34Google Scholar
  177. 172.
    Kalinich JF, Mandava NB, Todhunter JA (1985) J Plant Physiol 120: 207Google Scholar
  178. 173.
    Kalinich JF, Mandava NB, Todhunter JA (1986) J Plant Physiol 125: 345Google Scholar
  179. 174.
    Mandava NB, Thompson MJ, Yopp JH (1987) J Plant Physiol 128: 53Google Scholar
  180. 175.
    Xu RJ, Zhao YJ (1989) Acta Phytophysiologica Sinica 15: 263Google Scholar
  181. 176.
    Henry EW, Dungy LJ, Bracciano DM (1981) Proc Plant Growth Regul Soc Amer p 146Google Scholar
  182. 177.
    Beinhauer K, Andreas W, Creuzburg D, Lang S, Vorbrodt HM, Adam G (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 22Google Scholar
  183. 178.
    Mai Y, Lin J, Zeng X, Pan R (1989) Zhiwu Shenglixue Tongxun 50Google Scholar
  184. 179.
    Krizek DT, Mandava NB (1983) Physiol Plant 57: 324Google Scholar
  185. 180.
    Krizek DT, Mandava NB (1983) Physiol Plant 57: 317Google Scholar
  186. 181.
    Kamuro Y, Inada K (1987) Proc Ann Plant Growth Regul Soc Amer 1987 p 221Google Scholar
  187. 182.
    Meudt WJ, Porath D (1986) Proc Plant Growth Regul Soc Amer p 129Google Scholar
  188. 183.
    Meudt J (1986) Plant Physiol (Suppl 4) 80: 9Google Scholar
  189. 184.
    Meudt WJ (1987) Plant Physiol 83: 195PubMedGoogle Scholar
  190. 185.
    Sasse JM (1990) Abstr 200th ACS National Meeting, Symposium on Brassinosteroids, Washington 26–31 Aug 1990 Abst No 119Google Scholar
  191. 186.
    Braun P, Wild A (1984) J Plant Physiol 116: 189Google Scholar
  192. 187.
    Braun P, Wild A (1984), Proc Int Congr Photosynth, 6th, Nijhoff, The Hague, Neth p 461Google Scholar
  193. 188.
    Fujii S, Hirai K, Saka M (1990) Abstr 200th ACS National Meeting, Symposium on Brassinosteroids, Washington 26–31 Aug 1990 Abstr No 79Google Scholar
  194. 189.
    Kulaeva ON, Burkhanova EA, Fedina AB, Danilowa NV, Adam G, Vorbrodt HM, Khripach VA (1989) Dokl Akad Nauk SSSR 305: 1277Google Scholar
  195. 190.
    Clouse S, Zurek D, Hall A (1990) Abstr 200th ACS National Meeting, Symposium on Brassinosteroids, Washington 26–31 Aug 1990, Abstr No 139Google Scholar
  196. 191.
    Roddick JG, Guan M (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 19Google Scholar
  197. 192.
    Guan M, Roddick JG (1988) Physiol Plant 73: 426Google Scholar
  198. 193.
    Guan M, Roddick JG (1988) Physiol Plant 74: 720Google Scholar
  199. 194.
    Radi SH, Maeda E (1988) Japanese Journal of Crop Science 57: 191Google Scholar
  200. 195.
    Sathiyamoorthy P, Nakamura S (1990) Plant Growth Regul 9: 73Google Scholar
  201. 196.
    Vorbrodt HM, Donath P, Adam G, Luckner M, Neumann D, Beinhauer K (1988) Ger (East) DD 271 445Google Scholar
  202. 197.
    Bellincampi D, Morpurgo G (1988) Plant Science, 54: 153Google Scholar
  203. 198.
    Chang JQ, Cai DT (1988) Oil Crops of China 18Google Scholar
  204. 199.
    Chen JC, Chi JF (1986) Plant Physiol Commun 51Google Scholar
  205. 200.
    Roth PS, Bach TJ, Thompson MJ (1989) Plant Science (Shannon) 59: 63Google Scholar
  206. 201.
    Bach TJ, Roth PS, Thompson MJ (1990) Abstr Int Workshop Brassinosteroids-Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 47Google Scholar
  207. 202.
    Gartz J, Adam G, Vorbrodt HM (1990) Naturwissenschaften 77: 388Google Scholar
  208. 203.
    Graefe U (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 23Google Scholar
  209. 204.
    Hetru C, Roussel JP, Mori K, Nakatani Y (1986) C R Acad Sci, Ser 2 302: 417Google Scholar
  210. 205.
    Richter K (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 51Google Scholar
  211. 206.
    Lehmann M, Vorbrodt HM, Adam G, Koolman J (1988) Experientia 44: 355Google Scholar
  212. 207.
    Genma T (1989) JP 1-106802Google Scholar
  213. 208.
    Kajita F, Furushima M, Takematsu T (1985) JP 62-77305 (1986) EP 0220514Google Scholar
  214. 209.
    Kaneda T et al (1989) JP 1-256330Google Scholar
  215. 210.
    Kuraishi S, Eun JS, Sakurai N, Kojima K, Sugiyama K, Sumi T (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 42Google Scholar
  216. 211.
    Kumura A, Ishii R, Luo BS, Adachi M, Hamada K, Fujita F (1985) JP 60-116537Google Scholar
  217. 212.
    Kumura A et al (1986) JP 61-76402Google Scholar
  218. 213.
    Hirai Y, Fujii S, Kamuro Y (1985) JP 62-63502Google Scholar
  219. 214.
    Hirai Y, Fujii S (1985) JP 62-67005Google Scholar
  220. 215.
    Mori K, Kishi M (1985) JP 62-135459Google Scholar
  221. 216.
    Takematsu T, Ikekawa N, Shida A (1986) EP 218945 (1988) JP 63-54302Google Scholar
  222. 217.
    Meudt WJ, Thompson MJ, Mandava NB, Worley JF (1984) Can 1173659Google Scholar
  223. 218.
    Kumura A et al (1986) JP 61-277601Google Scholar
  224. 219.
    Genma T (1989) JP 1-146805Google Scholar
  225. 220.
    Hayashi S, Hohjoh T, Furuse T, Kuriyama H, Watanabe T, Takatsuto S (1988) EP 261656Google Scholar
  226. 221.
    Kumura et al (1987) JP 62-67006Google Scholar
  227. 222.
    Genma T (1988) JP 63-170306; WO 88/04890Google Scholar
  228. 223.
    Adam G, Bergmann H, Lang S, Meisgeier G, Vorbrodt HM (1989) Ger (East) DD 265316Google Scholar
  229. 224.
    Genma T (1989) JP 1-146806Google Scholar
  230. 225.
    Takahara T, Hirose K, Ono Y, Iwagaki I, Hirai Y (1985) JP 62-63501Google Scholar
  231. 226.
    Genma T (1989) JP 1-163105Google Scholar
  232. 227.
    Genma T (1989) JP 1-146804Google Scholar
  233. 228.
    Ikekawa N (1988) JP 63-243002Google Scholar
  234. 229.
    Maotani T, Suzuki A, Nishimura T, Kumomato O, Oshima K, Yamanaka Y (1989) J Jpn Soc Hortic Sci 58: 557Google Scholar
  235. 230.
    Han JF, Qi QG, Zhang XM, Zhao YY (1988) Proc 9th Intern Tobacco Scientific Congress 9–13 October 1988, Guangzhou, China p 197Google Scholar
  236. 231.
    Lim UK (1985) Proc Plant Growth Regul Soc Amer p 213Google Scholar
  237. 232.
    Nakaseko K, Yoshida K (1989) Mem Fac Agric Hokkaido Univ 16: 347Google Scholar
  238. 233.
    Zhao YJ, Ikekawa N (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 27Google Scholar
  239. 234.
    Hirai Y, Fujii S, Honjo K (1988) JP 63-135303Google Scholar
  240. 235.
    Ikekawa N (1988) JP 63-239201Google Scholar
  241. 236.
    Adachi A, Yamada Y, Fujita F, Nakazawa Y, Amano T, Watanabe K (1984) JP 61-76404Google Scholar
  242. 237.
    Takematsu T (1988) JP 63-66104Google Scholar
  243. 238.
    Takematsu T (1988) JP 63-130504Google Scholar
  244. 239.
    Adachi A, Hamada K, Nishi S, Fujita F, Uesono T, Fujiwara S (1984) JP 61-76403Google Scholar
  245. 240.
    Uesono T, Adachi A, Hamada K, Nishi S, Fujita F, Fujiwara S (1985) JP 62-48602Google Scholar
  246. 241.
    Khokhlova VA, Bokebayeva GA, Adam G, Kulaeva ON (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 44Google Scholar
  247. 242.
    Bokebayeva GA, Khokhlova VA, Khripach VA, Adam G, Kulaeva ON (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 45Google Scholar
  248. 243.
    Hirai K, Fujii S, Kamuro Y (1984) Abstr Ann Meeting Chem Regul of Plants (Tokyo) p 36Google Scholar
  249. 244.
    Sugiyama K, Kuraishi S (1989) Acta Horticulturae 345Google Scholar
  250. 245.
    He RY, Wang XS, Wang GJ Abstr 200 ACS National Meeting, Symposium on Brassinosteroids, Washington 26–31 Aug 1990 Abstr No 100Google Scholar
  251. 246.
    Katsumi M (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 29Google Scholar
  252. 247.
    Yamaguchi T, Wakizuka T, Hirai K, Fujii S, Fujita A (1987) Proc Plant Growth Regul Soc Amer p 26Google Scholar
  253. 248.
    Zhao YJ, Luo WH, Wang YQ, Xu RJ (1987) Acta Phytophysiologica Sinica 13: 129Google Scholar
  254. 249.
    Bergmann H, Meisgeier G, Adam G, Vorbrodt HM, Lang S, Wozniak H Ger (East) DD 277828Google Scholar
  255. 250.
    Schilling G, Schiller C (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 20Google Scholar
  256. 251.
    Korableva N, Sukhova L, Dogonadse (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 32Google Scholar
  257. 252.
    Ikekawa N (1990) Abstr Int Workshop Brassinosteroids — Chemistry, Bioactivity, Application, Halle 29 October-2 November 1990 p 1Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1991

Authors and Affiliations

  • Volker Marquardt
    • 1
  • Günter Adam
    • 1
  1. 1.Institute of Plant BiochemistryHalle/SaaleGermany

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