Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity

Fifteen new galactoglycerolipid analogues, in which one or two branched, alicyclic or aromatic acyl chains are linked to 2-O-β-d-galactosylglycerol (6′-position or 1,6′ positions), were prepared and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein–Barr virus early antigen (EBV-EA) activation. All compounds were active in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the branched compounds resulting in the most active glycoglycerolipid analogues of the series. The branched 2-O-[6-O-(3-methylbutanoyl)-β-d-galactopyranosyl]-sn-glycerol (1a) and the structurally related alicyclic 2-O-[6-O-(2-cyclohexylethanoyl)-β-d-galactopyranosyl]-sn-glycerol (1d), when tested in an in vivo two-stage carcinogenesis test, exhibited inhibitory effects on mouse skin tumor promotion.

Graphical abstractA series of branched, alicyclic or aromatic galactoglycerolipid analogues were prepared and tested for their in vitro and in vivo anti-tumor-promoting activities.Figure optionsDownload full-size imageDownload as PowerPoint slide