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 significantl...

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Bibliographic Details
Published in:Industrial crops and products 2019-12, Vol.142, p.111859, Article 111859
Main Authors: Graça, V.C., Calhelha, Ricardo C., Nunes, Fernando M., Berthet, Jérôme, Ferreira, Isabel C.F.R., Santos, P.F.
Format: Article
Language:English
Subjects:
Cytotoxic activity
Geranium molle L
Phenolic compounds
Secondary metabolites
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Summary:•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.
ISSN:0926-6690
1872-633X
DOI:10.1016/j.indcrop.2019.111859