Stereoselective synthesis and moulting activity of 2,3-diepi-20-hydroxyecdysone and 2,3-diepi-5α-20-hydroxyecdysone |
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Authors: | Sureeporn Homvisasevongsa Nitirat Chimnoi |
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Institution: | a Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Huamark, Bangkapi, Bangkok 10240, Thailand b Chulabhorn Research Institute, Vipavadee-Rangsit Highway, Bangkok 10210, Thailand |
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Abstract: | The ecdysteroid analogues 2,3-diepi-20-hydroxyecdysone and 2,3-diepi-5α-20-hydroxyecdysone have been synthesized from the readily available ecdysteroid, 20-hydroxyecdysone, and moulting activity has been determined using the Musca bioassay. As expected, the 2,3-diepi-analogue was less active than the parent ecdysteroid, 20-hydroxyecdysone. However, the 2,3-diepi-5α-analogue, which was expected to be inactive in the assay, exhibited moulting activity though it was approximately 1.5-fold less active than its 5β-analogue. The activity of the 5α-analogue could possibly result from the ability of this compound to bind to the ecdysteroid receptor. Alternatively, a possible in vivo C-5 epimerization of the 2,3-diepi-5α-analogue to the corresponding 5β-analogue could account for its activity. |
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Keywords: | Ecdysteroid 2 3-diepi-20-Hydroxyecdysone 2 3-diepi-5α-20-Hydroxyecdysone Synthesis Moulting activity |
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