Rapid, laser-induced conversion of 20-hydroxyecdysone-A follow-up study on the products obtained

Wan Chun Lai, Balázs Dankó, József Csábi, Zoltán Kele, Fang Rong Chang, Mihail L. Pascu, Tamás Gáti, András Simon, Leonard Amaral, Gábor Tóth, Attila Hunyadi

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Abstract

We have recently reported the set-up of an experimental system for the laser-induced photochemical modification of bioactive substances, where two ecdysteroids, 20-hydroxyecdysone (20E) and its diacetonide derivative served as probes. As a direct continuation of our previous work, three new compounds together with five other ecdysteroid derivatives, have been identified from the novel, laser-induced photo-transformation reaction of 20E. The structures and NMR signal assignment were established by comprehensive one- and two-dimensional NMR spectroscopy supported by mass spectroscopy. Possible ways for the formation of each species is also discussed. Similar to their parental compound, the products obtained are potentially bioactive and worthy for further investigations; due to the low yields, however, a different approach for their higher scale production is suggested.

Original languageEnglish
Pages (from-to)56-62
Number of pages7
JournalSteroids
Volume89
DOIs
Publication statusPublished - Nov 2014

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Keywords

  • 20-Hydroxyecdysone
  • Ecdysteroid
  • Enone photochemistry
  • Laser flash photolysis
  • NMR
  • Stereochemistry

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Lai, W. C., Dankó, B., Csábi, J., Kele, Z., Chang, F. R., Pascu, M. L., Gáti, T., Simon, A., Amaral, L., Tóth, G., & Hunyadi, A. (2014). Rapid, laser-induced conversion of 20-hydroxyecdysone-A follow-up study on the products obtained. Steroids, 89, 56-62. https://doi.org/10.1016/j.steroids.2014.07.016