By Horace G. Cutler, Gunter Adam, Takao Yokota
content material: U.S. division of Agriculture brassins undertaking, 1970-1980 / G.L. Steffens --
Brassinosteroids in leaves of Distylium racemosum Sieb. et Zucc. : the start of brassinosteroid examine in Japan / Hiroshi Abe and Shingo Marumo --
typical occurrences of brassinosteroids / Seong-Ki Kim --
Synthesis of brassinolide / T.C. McMorris, J.R. Donaubauer, M.H. Silveira, and T.F. Molinski --
Synthesis and a few functional points of brassinosteroids / V.A. Khripach, V.N. Zhabinskii, and R.P. Litvinovskaya --
varieties of brassinosteroids and their bioassays / L. Kohout, M. Strnad, and M. Kaminek --
points of synthesis and bioactivity of brassinosteroids / Günter Adam, V. Marquardt, H.M. Vorbrodt, C. Hörhold, W. Andreas, and J. Gartz --
Metabolism and biosynthesis of brassinosteroids / Takao Yokota, Y. Ogino, H. Suzuki, N. Takahashi, Hiroshi Saimoto, Shozo Fujioka, and Akira Sakurai --
creation of brassinosteroids in plant-cell cultures / Akira Sakurai, Shozo Fujioka, and Hiroshi Saimoto --
Microanalysis of clearly taking place brassinosteroids / Suguru Takatsuto --
Molecular research of brassinolide motion in plant development and improvement / S.D. Clouse and D. Zurek --
influence of brassinosteroids on protein synthesis and plant-cell ultrastructure below rigidity stipulations / O.N. Kulaeva, E.A. Burkhanova, A.B. Fedina, V.A. Khokhlova, G.A. Bokebayeva, H.M. Vorbrodt, and Günter Adam --
The case for brassinosteroids as endogenous plant hormones / Jenneth M. Sasse --
Brassinosteroid-induced alterations of plasmalemma energization and shipping and of assimilate uptake through plant tissues / I. Dahse, U. Petzold, C.M. Willmer, and E. Grimm --
Brassinosteroids particularly inhibit progress of tobacco tumor cells / Thomas J. Bach, Petra S. Roth, and Malcolm J. Thompson --
Stimulation of progress prompted by way of brassinosteroid and conditioning components in plant-cell cultures / Daniela Bellincampi and Giorgio Morpurgo --
Rice-lamina inclination, endogenous degrees in plant tissues and accumulation in the course of pollen improvement of brassinosteroids / Hiroshi Abe --
impression of brassinosteroids on organ relatives and enzyme actions of sugar-beet crops / Günther Schilling, Christiane Schiller, and Steffan Otto --
results of brassinolide on development and chilling resistance of maize seedlings / Ruo-yun He, Guan-jie Wang, and Xue-shu Wang --
Brassinosteroids and root improvement / J.G. Roddick and M. Guan --
Physiological modes of brassinolide motion in cucumber hypocotyl progress / Masayuki Katsumi --
Brassinolide-induced elongation / Jenneth M. Sasse --
Antiecdysteroid results of brassinosteroids in bugs / Klaus Richter and Jan Koolman --
software of 24-epibrassinolide in agriculture / Nobuo Ikekawa and Yu-Ju Zhao --
strength for and difficulties of sensible makes use of of brassinosteroids / Yasuo Kamuro and Suguru Takatsuto --
results of brassinolide on conditioning and germination of witchweed (Striga asiatica) seeds / Y. Takeuchi, A.D. Worsham, and A.E. Awad --
Growth-regulating motion of brassinolide in rice vegetation / S. Fujii, ok. Hirai, and H. Saka --
influence of brassinolide on degrees of indoleacetic acid and abscisic acid in squash hypocotyls : attainable program for fighting fruit abortion / S. Kuraishi, N. Sakurai, J.-S. Eun, and okay. Sugiyama --
Brassinosteroids : U.S. division of Agriculture contributions and Environmental safeguard organization registration standards / N. Bhushan Mandava --
Brassinosteroids during the taking a look glass : an appraisal / Horace G. Cutler.
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Extra info for Brassinosteroids. Chemistry, Bioactivity, and Applications
Ch004 Department of Chemistry (0506), University of California—San Diego, La Jolla, CA 92093-0506 Several reported syntheses of brassinolide, (22R,23R,24S)2α,3α,22,23-tetrahydroxy-24-methyl-B-homo-7-oxa-5α-cholestan6-one, involve a C-22 aldehyde derived from stigmasterol, which is used for construction of the sidechain with chiral centers at C-22, C-23 and C-24. In our synthesis, (20 S)-6β-methoxy-3α,5-cyclo5α-pregnane-20-carboxaldehyde was reacted with the anion of 2,3dimethylbutenolide at -78 °C to give a lactone which was readily converted to the desired sidechain.
Soc. Perkin Trans 1 1984, 139. ; Ikekawa, N . J. Chem. Soc. Perkin Trans 1 1983, 2133. ; Yazawa, N . ; Ikekawa, N . Phytochemistry 1984, 23, 525. ; Morizawa, Y . ; Nozaki, H . J. Am. Chem. Soc. 1983, 105, 4491. ; Ootake, A . ; Yamada, H . ; Tsuji, J. Tetrahedron Letters 1985, 26, 69. ; Greaves, A . M . C. J. Org. Chem. 1984, 49, 2833. A. Tetrahedron, 1980, 36, 2. ; Honda, T. J. Org. Chem. 1988, 53, 1982. ; Honda, T. J. Chem. Soc. Perkin Trans 1 1988, 1503. ; Tian, W-S. Tetrahedron 1987, 45, 3705.
Synthesis and Some Practical Aspects 45 Figure 2 . A l t e r n a t i v e s y n t h e s i s of 22S,23S-homobrassinolide the d e s i r e d product. The key step to t h i s approach was the r e g i o s e l e c t i v e a d d i t i o n of bromine and hydrogen bromide to the double bond and cyclopropane of 2, r e s p e c t i v e l y . Subsequent B a e y e r - V i l l i g e r o x i d a t i o n of the tribromoketone 6 and debromination with simultaneous dehydrobromination of 7 under the a c t i o n of l i t h i u m carbonate i n b o i l i n g DMF l e d to the dienolactone 8.
Brassinosteroids. Chemistry, Bioactivity, and Applications by Horace G. Cutler, Gunter Adam, Takao Yokota