Isolation of secondary metabolites from Geranium molle L. with anticancer potential.

• Bioactive fractions of G. molle L. were purified by semipreparative HPLC. • Two flavone glycosides and an anomeric mixture of ellagitannins were isolated for the first time from G. molle. • The isolated compounds were evaluated for their cytotoxic activity. • The mixture of ellagitannins was significantly cytotoxic against cancer cells. Two flavone glycosides, apigenin-6- C -glucoside (1) and lutelin-6- C -glucoside (2), and an anomeric mixture of 2,3-dygalloyl-4,6-HHDP- d -glucose (3a / 3b) were isolated for the first time from Geranium molle L., a medicinal plant used in the folk medicine of northeast of Portugal for the treatment of a variety of ailments, including cancer. The cytotoxic activity of the isolated compounds was assessed against several human tumour cell lines and non-tumour porcine liver primary cells. The anomeric mixture of ellagitannins 3a / 3b , with the two anomers showing considerably different hydrophobicities, was found to be significantly cytotoxic against cancer cells, with only moderate hepatotoxicity. [ABSTRACT FROM AUTHOR]