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Cholane and Lanostane Derivatives: Antimicrobial Evaluation
Author(s) -
Cateni F.,
Zacchigna M.,
Procida G.,
Zilic J.,
Cordone A.,
Zanfardino A.,
Varcamonti M.
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201600556
Subject(s) - moiety , ursodeoxycholic acid , chemistry , lithocholic acid , deoxycholic acid , guanidine , antimicrobial , bile acid , chenodeoxycholic acid , lanostane , organic chemistry , stereochemistry , biochemistry , medicine , alternative medicine , pathology , triterpene
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.