Enzymatic synthesis of phenolic acid glucosyl esters to test activities on cholangiocarcinoma cells.

While glycoside hydrolase family 1 (GH1) enzymes mostly catalyze hydrolysis reactions, rice Os9BGlu31 preferentially catalyzes transglycosylation to transfer a glucosyl moiety to another aglycone moiety to form a new glycosylated compound through a retaining mechanism. In this study, Os9BGlu31 was used to synthesize eight phenolic acid glucosyl esters, which were evaluated for activities in cholangiocarcinoma cells. The transglycosylation products of Os9BGlu31 wild type and its mutant variants were detected, produced on a milligram scale, and purified, and their structures were characterized by NMR spectroscopy.

Semi-synthesis of phenolic-amides and their cytotoxicity against THP-1, HeLa, HepG2 and MCF-7 cell lines.

In the present study, we derivatized several hydroxycinnamic and hydroxybenzoic acids to phenolic amides (PAMs) one step BOP mediated amide coupling reactions. Fifteen PAMs were synthesized in >40% yields and were screened for their cytotoxic activities against four cancer cell lines: THP-1 (leukaemia), HeLa (cervical), HepG2 (liver), and MCF-7 (breast), in comparison to 5-flurouracil (5-FU). Four amides showed IC ranging from 5 to 55 µM against all four cell lines.