Chemoenzymatic synthesis and in vitro studies on the hydrolysis of antimicrobial monoglycosyl diglycerides by pancreatic lipase.
Monoglucosyl and monogalactosyl diglycerides (MGDGs) with medium-long length acyl chains, identified as active components in Euphorbiaceae, were synthesized. They were examined for antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. MGDGs with two octanoyl groups at both 1- and 2-positions showed the most potent activity. The stereoselectivity of pancreatic lipase was investigated in vitro where the preference for the 1 position in MGDGs is strictly related to the length of the acyl chains.
Cateni
Francesca
F
Department of Pharmaceutical Sciences, University of Trieste, P.zle Europa 1, 34127 Trieste, Italy. cateni@univ.trieste.it
Bonivento
Paolo
P
Procida
Giuseppe
G
Zacchigna
Marina
M
Scialino
Giuditta
G
Banfi
Elena
E
D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000737:chemistry; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D004075:Diglycerides / Q000737:chemistry*; D015195:Drug Design; D005227:Fatty Acids / Q000737:chemistry; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry*; D008956:Models, Chemical; D008968:Molecular Conformation; D009089:Mucor / Q000378:metabolism; D010179:Pancreas / Q000201:enzymology*; D011549:Pseudomonas / Q000378:metabolism; D013696:Temperature
D000890:Anti-Infective Agents; D000935:Antifungal Agents; D004075:Diglycerides; D005227:Fatty Acids; D008049:Lipase