Bile acids lithocholic acid (LCA) and ursodeoxycholic acid (UDCA) together with trametenolic acid (TMA) were used as starting materials for the preparation of new derivatives bearing a guanidine moiety in their side chain. The derivatives were synthesized through modification at the oxygenated carbon C-3/C-7 and at the carbonyl carbon C-24/C-21. The reactions showed yields ranging from 40 % to 96 %. The structures of all compounds obtained were identified on the basis of their spectral data (IR, MS, 1D- and 2D-NMR). The activity of bile acids, trametenolic acid and derivatives was evaluated against the growth of S. aureus, B. subtilis and M. smegmatis. The derivative 3α-hydroxy-23-guanidino-5β-cholane showed the best activity, with MIC values of 12.5 μM against S. aureus, 5 μM against B. subtilis and 50 μM against M. smegmatis. The cytotoxic activity of bile acids, trametenolic acid and derivatives was also evaluated against HT-29 cell line.

Cholane and Lanostane Derivatives: Antimicrobial Evaluation

CATENI, FRANCESCA;ZACCHIGNA, MARINA;PROCIDA, GIUSEPPE;
2016

Abstract

Bile acids lithocholic acid (LCA) and ursodeoxycholic acid (UDCA) together with trametenolic acid (TMA) were used as starting materials for the preparation of new derivatives bearing a guanidine moiety in their side chain. The derivatives were synthesized through modification at the oxygenated carbon C-3/C-7 and at the carbonyl carbon C-24/C-21. The reactions showed yields ranging from 40 % to 96 %. The structures of all compounds obtained were identified on the basis of their spectral data (IR, MS, 1D- and 2D-NMR). The activity of bile acids, trametenolic acid and derivatives was evaluated against the growth of S. aureus, B. subtilis and M. smegmatis. The derivative 3α-hydroxy-23-guanidino-5β-cholane showed the best activity, with MIC values of 12.5 μM against S. aureus, 5 μM against B. subtilis and 50 μM against M. smegmatis. The cytotoxic activity of bile acids, trametenolic acid and derivatives was also evaluated against HT-29 cell line.
http://dx.doi.org/10.1002/slct.201600556
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11368/2883448
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