Photochemical transformation of 20-hydroxyecdysone: production of monomeric and dimeric ecdysteroid analogues

Add time:08/22/2019    Source:sciencedirect.com

Structural modification of 20-hydroxyecdysone (20E) based on photochemical transformation yielded dimeric ecdysteroid 7αH,7′αH-bis-[(20R,22R)-2β,3β,20,22,25-pentahydroxy-5β-cholest-8(14)-en-6-one-7-yl] as a main product. Its structure was determined by detailed NMR analysis. Furthermore, two new monomeric analogues: 14-epi-20-hydroxyecdysone and 14-deoxy-14,18-cyclo-20-hydroxyecdysone were identified in addition to the earlier described 14-deoxy and 14-hydroperoxy derivatives of 20E. Formation of the specific and so far unique ecdysteroid dimer has not been observed in earlier photo-transformation studies. The transformed dimeric analogue of 20-hydroxyecdysone retained the high agonistic activity on the ecdysone receptor in the BII-bioassay compared with the original 20E.

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