Synthesis and biological activity of fluorinated brassinosteroids

JAVIER A. RAMIREZ; LYDIA R. GALAGOVSKY

Phytochemistry Research Progress

Nova Science Publishers, Inc

Lugar: Hauppauge - New York; Año: 2007;

Brassinosteroids have attracted considerable interest since 1979, when the isolation and structure determination of brassinolide was reported. Some brassinosteroids display powerful plant growth-regulating activity at doses as low as 1 ng per individual plant. Numerous studies of the chemistry and biology of brassinosteroids, as well as of their potential applications, have been reported. Organofluorine compounds have recently drawn considerable attention in the fields of agrochemistry, pharmaceutical and material science. Fluorinated analogues have been recognized as useful tools for pharmacological and physiological studies of natural products since the introduction of a fluorine atom into a molecule often leads to a significant change in its physical and biological properties. In view of their unique biological properties, fluorinated steroids have been widely studied and several fluoro-substituted compounds are now considered as analogues of plant hormones. This report reviews recent advances on the field of brassinosteroid research, with emphasis made in the work developed by our group and others on fluorinated analogues. The synthetic strategies leading to the introduction of fluorine atoms in the steroidal frame will be discussed. Finally, the biological properties of these fluorinated brassinosteroids, compared to their natural counterparts, will be analysed.