Indolylfuran, a potent aryl hydrocarbon receptor agonist from sauerkraut, interacts with the oestrogen pathway

Numerous ligands of the aryl hydrocarbon receptor (AhR) have been found in plants, especially edible plants, such as cruciferous vegetables, which exert beneficent health effects. A potent activator of the AhR was found in sauerkraut juice. The isolated active ingredient was identified as the novel AhR ligand, (1-(2-furanyl)2-(3-indolyl)ethanone, common name indolylfuran. The isolated and the synthesised compound exerted similar potencies; their EC50-values in an AhR transactivation assay were 160 and 123 nM, respectively. Our in vivo studies confirm and enlighten basic interactions between the AhR and oestrogen receptors (ERs). Further anti-oestrogenic effects of sauerkraut extract were shown. Indolylfuran regulates ER α and β expression, most likely via the AhR pathway, since indolylfuran had no effect on uterus weight and did not agonise ERα. Sauerkraut and indolylfuran may have potential for the prevention or treatment of diseases through modulation of AhR regulation and, indirectly, the ER pathway.

Research highlights
► Isolation of a novel compound from sauerkraut (common name indolylfuran).
► Identification as (1-(2-furanyl)2-(3-indolyl)ethanone via NMR techniques.
► Establishment of a structure function relationship.
► Indolylfuran is in vitro a potent agonist of the aryl hydrocarbon receptor.
► Sauerkraut acts in vivo anti-oestrogenic and regulates anti-proliferative genes.