Document Detail

The ecdysteroid agonist/antagonist and brassinosteroid-like activities of synthetic brassinosteroid/ecdysteroid hybrid molecules.
MedLine Citation:
PMID:  11529505     Owner:  NLM     Status:  MEDLINE    
A series of synthetic hybrid brassinosteroid/ecdysteroid structures has been assessed for their ecdysteroid agonist/antagonist activities in the Drosophila melanogaster B(II) cell bioassay and for brassinosteroid-like activity in the rice lamina inclination test. Most of the compounds proved inactive for ecdysteroid agonist activity, demonstrating the specificity of the ecdysteroid receptor for compounds closely structurally related to 20-hydroxyecdysone. However, compound 18, with 14alpha-hydroxy-7-en-6-one and 22S-hydroxy functionalities (as in most active ecdysteroids), possessed distinct agonist activity (median effective concentration = 1.4 x 10(-5) M), although this is still almost 2000-fold less active than 20-hydroxyecdysone (25). Compounds 13 and 15 possessed weak agonist activity. Compounds 5, 11 and 14 weakly antagonised the action of 20-hydroxyecdysone (at 5 x 10(-8) M) on B(II) cells. In the brassinosteroid bioassay, most of the tested compounds showed activity. This may reflect the metabolic capability of plant tissue to convert test compounds to more active analogues. However, it is clear that biological activity declines as the structure of the test compound deviates further from that of castasterone (16). Three ecdysteroids (25, 26 and 27) are completely inactive in the rice lamina inclination test. These studies demonstrate the high specificities of the insect ecdysteroid receptor and the plant brassinosteroid receptor and indicate that phytoecdysteroids, even in high concentrations, would not interfere with brassinosteroid signalling pathways in plants where the two classes of compounds co-occur. Equally, brassinosteroids would not interfere with ecdysteroid signalling in insects, especially if one takes into account the low concentrations of brassinosteroids in the diet of phytophagous insects.
B Voigt; P Whiting; L Dinan
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Cellular and molecular life sciences : CMLS     Volume:  58     ISSN:  1420-682X     ISO Abbreviation:  Cell. Mol. Life Sci.     Publication Date:  2001 Jul 
Date Detail:
Created Date:  2001-08-31     Completed Date:  2001-10-18     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9705402     Medline TA:  Cell Mol Life Sci     Country:  Switzerland    
Other Details:
Languages:  eng     Pagination:  1133-40     Citation Subset:  IM    
Institut für Pflanzenbiochemie, Abteilung Natur- und Wirkstoffchemie, Halle/Saale, Germany.
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MeSH Terms
Biological Assay
Drosophila melanogaster
Molecular Structure
Steroids / agonists*,  antagonists & inhibitors*
Reg. No./Substance:
0/Ecdysteroids; 0/Steroids

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