Diesters of glycosylglycerols active in cancer chemoprevention.
Enzymatic transesterification, mediated by Pseudomonas cepacia lipase (lipase PS), led to the pure 1,6'-diacylderivatives of 2-O-beta-D-glucosyl-sn-glycerol and 2-O-beta-D-galactosyl-sn-glycerol, the acyl chains being derived from short-medium length fatty acids. A study of the in vitro inhibitory effects of these diacylderivatives on Epstein-Barr virus early antigen activation induced by the tumour promoter 12-O-tetradecanoylphorbol-13-acetate revealed that maximum activity was reached for the hexanoyl chain and that the introduction of a second acyl chain did not significantly modify the inhibitory potential referring to the corresponding 1- or 6'-monoesters.
Colombo
D
D
Dipartimento di Chimica e Biochimica Medica, facoltà di medicina e chirugia, Università degli studi di Milano, Via Saldini 50, I-20133, Milan, Italy. diego.colombo@unimi.it
Compostella
F
F
Ronchetti
F
F
Scala
A
A
Tokuda
H
H
Nishino
H
H
D000956:Antigens, Viral / Q000187:drug effects* / Q000378:metabolism; D016956:Burkholderia cepacia / Q000201:enzymology; D004952:Esters / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism; D005960:Glucosides / Q000378:metabolism / Q000494:pharmacology*; D005990:Glycerol / Q000031:analogs & derivatives / Q000378:metabolism / Q000494:pharmacology*; D006017:Glycolipids / Q000378:metabolism; D006801:Humans; D008071:Lipoprotein Lipase / Q000378:metabolism; D009374:Neoplasms, Experimental / Q000139:chemically induced / Q000503:physiopathology / Q000517:prevention & control*; D013755:Tetradecanoylphorbol Acetate / Q000031:analogs & derivatives* / Q000378:metabolism*; D014407:Tumor Cells, Cultured / Q000187:drug effects / Q000378:metabolism
C445528:1-O-butanoyl-2-O-(6-O-butanoyl-glucopyranosyl)-glycerol; D000956:Antigens, Viral; C033305:Epstein-Barr virus early antigen; D004952:Esters; D005227:Fatty Acids; D005960:Glucosides; D006017:Glycolipids; C034727:glucosylglycerol; C032975:12-O-tetradeca-2,4,6,8-tetranoylphorbol-13-acetate; D008071:Lipoprotein Lipase; D013755:Tetradecanoylphorbol Acetate; D005990:Glycerol