COUMESTROL

Description

Coumestrol is a phytoestrogen that occurs naturally in soybeans, spinach, and clover. It competitively (vs. 17β-estradiol, ) binds the estrogen receptors ERα (IC₅₀ = 11 nM) and ERβ (IC₅₀ = 2 nM) and can induce ER-dependent gene expression in isolated cells. Coumestrol is also a weak antagonist of pregnane X receptor (IC₅₀ = 12 μM) as well as a potential inverse agonist of the constitutive androstane receptor (EC₅₀ = 30 μM).

Chemical Properties

Yellow to Beige Powder

Uses

This compound has estrogenic activity. It exhibits bright blue fluorescence in neutral or acid solution, and greenish-yellow fluorescence in strong alkali solution.

Definition

ChEBI: A member of the class of coumestans that is coumestan with hydroxy substituents at positions 3 and 9.

Synthesis Reference(s)

Tetrahedron Letters, 4, p. 1151, 1963 DOI: 10.1039/jr9630005127

Biochem/physiol Actions

Coumestrol has anti-estrogenic actions in the brain and pituitary, mediated through estrogen receptor-α.

Safety Profile

An experimental teratogen. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

References

[1]. chen hy, dykstra kd, birzin et, et al. estrogen receptor ligands. part 1: the discovery of flavanoids with subtype selectivity. bioorg med chem lett. 2004 mar 22;14(6):1417-21.
[2]. hopert ac, beyer a, frank k, et al. characterization of estrogenicity of phytoestrogens in an endometrial-derived experimental model. environ health perspect. 1998 sep;106(9):581-6.
[3]. wang h, li h, moore lb, et al. the phytoestrogen coumestrol is a naturally occurring antagonist of the human pregnane x receptor. mol endocrinol. 2008 apr;22(4):838-57.