By Horace G. Cutler, Gunter Adam, Takao Yokota
content material: U.S. division of Agriculture brassins venture, 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 --
common 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 sensible points of brassinosteroids / V.A. Khripach, V.N. Zhabinskii, and R.P. Litvinovskaya --
kinds of brassinosteroids and their bioassays / L. Kohout, M. Strnad, and M. Kaminek --
facets 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 --
construction of brassinosteroids in plant-cell cultures / Akira Sakurai, Shozo Fujioka, and Hiroshi Saimoto --
Microanalysis of certainly 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 adjustments of plasmalemma energization and shipping and of assimilate uptake through plant tissues / I. Dahse, U. Petzold, C.M. Willmer, and E. Grimm --
Brassinosteroids in particular inhibit progress of tobacco tumor cells / Thomas J. Bach, Petra S. Roth, and Malcolm J. Thompson --
Stimulation of progress prompted via 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 --
effect of brassinosteroids on organ kin and enzyme actions of sugar-beet vegetation / Günther Schilling, Christiane Schiller, and Steffan Otto --
results of brassinolide on progress 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 --
program of 24-epibrassinolide in agriculture / Nobuo Ikekawa and Yu-Ju Zhao --
strength for and difficulties of functional 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, okay. Hirai, and H. Saka --
influence of brassinolide on degrees of indoleacetic acid and abscisic acid in squash hypocotyls : attainable program for combating fruit abortion / S. Kuraishi, N. Sakurai, J.-S. Eun, and ok. Sugiyama --
Brassinosteroids : U.S. division of Agriculture contributions and Environmental safeguard corporation registration necessities / 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
In extending our s t u d i e s i n n a t u r a l and transformed s t e r o i d s , BS s y n t h e s i s was the subject i n our l a b o r a t o r y f o r a number of years. During t h i s p e r i o d , d i f f e r e n t s y n t h e t i c approaches s t a r t i n g with a c c e s s i b l e natural s t e r o i d s have been developed, and a l o t of n a t u r a l BS and t h e i r analogues have been synthesized and b i o l o g i c a l l y t e s t e d i n laboratory and f i e l d c o n d i t i o n s .
From large scale experiments with seeds ( 136 kg ), over sixty kinds of brassinosteroids have been found (30, 31). ch003 5 l OH , OH X HO HO- f £ 13 F fi 14 HC Figure 1. Structures of free brassinosteroids from plants. 1; brassinolide, 2; dolicholide, 3; castasterone, 4; dolichosterone, 5; 6-deoxodihydrocastasterone, 6; 6deoxodihydrodolichosterone, 7; typhasterol, 8; teasterone, 9; 24-epicastasterone, 10; homodolicholide 11; homodolichosterone, 12; 24-ethylbrassinone, 13; 6deoxodihydrohomodolichosterone, 14; 28-norbrassinolide, 15; brassinone, 16; 2epiacstasterone, 17; 3-epicastasterone, 18; 2,3-diepicastasterone, 19; 3,24-diepicastasterone, 20; 3-epi-6-deoxodihydrocastasterone, 21; ip-hydroxycastasterone, 22; 3epi-l-a-hydroxycastasterone, 23; 25-methyldolichosterone, 24; 2-epi-25-methyldolichosterone, 25; 2,3-diepi-25-methyldolichosterone, 26; 2-deoxy-25-methyldolichosterone, 27; 3-epi-2-deoxy-25-methyldolichosterone, 28; 6-deoxodihydro-25methyldolichosterone, 29; 24-epibrassinolide.
Another s y n t h e s i s of 5 was a l s o accomplished (Figure 2) (6-9). I t e l i m i n a t e d the n e c e s s i t y of p r o t e c t i n g and d e p r o t e c t i n g the hydroxyl groups and gave a r e l a t i v e l y good y i e l d of F i g u r e 1. ch005 5. KHRIPACH ET AL. 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 .