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

doi:10.1016/j.steroids.2014.07.016

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

Steroids. 2014 Nov:89:56-62. doi: 10.1016/j.steroids.2014.07.016. Epub 2014 Aug 20.

Authors

Affiliations

¹ Institute of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary; Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC.
² Institute of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary.
³ Department of Medical Chemistry, University of Szeged, 6720 Szeged, Hungary.
⁴ Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC.
⁵ Laser Department, National Institute for Laser, Plasma and Radiation Physics, Bucharest, Romania.
⁶ Department of Inorganic and Analytical Chemistry, NMR Group, Budapest University of Technology and Economics, 1111 Budapest, Hungary.
⁷ Travel Medicine of the Center for Malaria and Other Tropical Diseases (CMDT), Instituto de Higiene e Medicina Tropical, Universidade Nova de Lisboa, 1349-008 Lisbon, Portugal; Department of Microbiology and Immunobiology, University of Szeged, 6720 Szeged, Hungary.
⁸ Department of Inorganic and Analytical Chemistry, NMR Group, Budapest University of Technology and Economics, 1111 Budapest, Hungary. Electronic address: drtothgabor@t-online.hu.
⁹ Institute of Pharmacognosy, University of Szeged, 6720 Szeged, Hungary. Electronic address: hunyadi.a@pharm.u-szeged.hu.

PMID: 25150016
DOI: 10.1016/j.steroids.2014.07.016

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.

Keywords: 20-Hydroxyecdysone; Ecdysteroid; Enone photochemistry; Laser flash photolysis; NMR; Stereochemistry.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Asteraceae / chemistry
Ecdysterone / analogs & derivatives
Ecdysterone / chemistry*
Lasers*
Magnetic Resonance Spectroscopy
Molecular Structure
Photochemical Processes*
Photolysis

Substances

Ecdysterone