Stereoselective synthesis of (22R)- and (22S)-castasterone/ponasterone A hybrid compounds and evaluation of their molting hormone activity

Steroids
Bunta WatanabeHisashi Miyagawa

Abstract

Two stereoisomers of a castasterone/ponasterone A hybrid compound, the (20R,22R) and (20R,22S)-isomers of 2alpha,3alpha,20,22-tetrahydroxy-5alpha-cholestan-6-one, were synthesized stereoselectively and their binding activity to the ecdysteroid receptor was determined. From the concentration-response curve for the inhibition of the incorporation of tritiated ponasterone A into ecdysteroid receptor containing insect cells, the concentration (IC50) required to inhibit 50% of the incorporation of radioactivity into cells was evaluated. The IC50 values of the (22R)- and (22S)-isomers were determined to be 0.30 and 38.9 microM against Kc cells, respectively, indicating that the (22R)-isomer is about 100 times more potent than the corresponding (22S)-isomer. IC50 values of these compounds against lepidopteran Sf-9 cells were determined to be 0.36 and 12.9 microM, respectively. The molting hormonal effect was examined in a Chilo suppressalis integument system and the 50% effective concentration for the stimulation of N-acetylglucosamine incorporation into the cultured integument was determined to be 2.7 microM for the (22R)-isomer, while the (22S)-isomer was inactive. On the other hand, both isomers did not show brassinolide-like activ...Continue Reading

References

Jan 5, 2002·Insect Biochemistry and Molecular Biology·Yoshiaki NakagawaTamio Ueno
Jan 5, 2002·Insect Biochemistry and Molecular Biology·G SmaggheL Tirry
Feb 20, 2003·Phytochemistry·Andrzej Bajguz, Andrzej Tretyn
Jun 1, 2004·Bioscience, Biotechnology, and Biochemistry·Shinya UesusukiHisashi Miyagawa

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Citations

Jul 6, 2013·Expert Opinion on Therapeutic Patents·Jon LorenValentina Molteni
Jul 28, 2009·Bioorganic & Medicinal Chemistry·Toshiyuki HaradaHisashi Miyagawa
Sep 15, 2014·Steroids·Vladimir N ZhabinskiiVladimir A Khripach
Feb 3, 2006·Natural Product Reports·James R Hanson

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