Planta Med 2022; 88(15): 1534
DOI: 10.1055/s-0042-1759246
Poster Session II

Antitrypanosomal activity of semisyntetic enone-type derivatives

M Háznagy∗
1   University of Szeged, Szeged, Hungary
,
M Vágvölgyi
1   University of Szeged, Szeged, Hungary
,
S R Krishnan
2   University of Bern, Bern, Switzerland
,
J Gertsch
2   University of Bern, Bern, Switzerland
,
A Hunyadi
1   University of Szeged, Szeged, Hungary
› Author Affiliations
› Further Information
 

The protozoan Trypanosoma cruzi (T. cruzi) causes Chagas disease, a neglected tropical disease, which aggravates between 6 and 7 million patientsʼ life in global. Mostly it is spreaded via vectoral infection of Triatominae bugs [1].

In our previous study, 52 ecdysteroidsʼ antitrypanosomal activity was tested on T. cruzi epimastigotes. Cinnamic ester derivatives of 20-hydroxyecdysone (20-E) and E and Z 6-tert-butyl-oxime ethers of 20E 2,3 : 20,22-diacetonide possessed promising selective antiparasitic activity at 5 µM [2], [3].

The aim of our current work was to prepare new antitrypanosomal compounds from further natural enones. Our first target compound group was eccdysteroids derivatives that contain both previously identified pharmacophores, i.e., cinnamic ester and t-butyl-oxime ether moieties. The esterification of the two 6-t-butyl-oxime ether isomers were carried out applying cinnamic acid, EDAC, DMAP in dry dichloromethane. RP-HPLC methods were used to isolate the compounds. Four new ecdysteroid derivatives were obtained, and they were identified by NMR as the 2-, the 2,22-, and the 2,3,22-cinnamic ester of the E isomer and the 2-cinnamic ester of the Z isomer. Secondly, a set of new protoflavonoid derivatives were prepared, including ethers, oximes, semicarbazides, thiosemicarbazides.

The testing of altogether 16 compounds against T. cruzi is currently ongoing.

Acknowledgements

NKFIH K-134704, UNKP-21-4-SZTE-281


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Publication History

Article published online:
12 December 2022

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