Coumestrol is a natural organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 in the class of phytochemical

Phytochemical

Phytochemicals are biologically active chemical compounds that occur naturally in plants . Phytochemicals are the molecules responsible for the color and organoleptic properties . For example, the deep purple color of blueberries and the smell of garlic...

s known as coumestan

Coumestan

Coumestan is an organic compound that is a derivative of coumarin. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans, including coumestrol, a phytoestrogen, are found in a variety of plants...

s. It has garnered research interest because of its estrogenic activity and its prevalence in some foods, such as soybean

Soybean

The soybean or soya bean is a species of legume native to East Asia, widely grown for its edible bean which has numerous uses...

s.

Coumestrol was first identified by E. M. Bickoff in alfalfa

Alfalfa

Alfalfa is a flowering plant in the pea family Fabaceae cultivated as an important forage crop in the US, Canada, Argentina, France, Australia, the Middle East, South Africa, and many other countries. It is known as lucerne in the UK, France, Australia, South Africa and New Zealand, and known as...

 in 1957. It has since be found in a variety of legumes, soybean

Soybean

The soybean or soya bean is a species of legume native to East Asia, widely grown for its edible bean which has numerous uses...

s, brussels sprout

Brussels sprout

The Brussels sprout is a cultivar of wild cabbage grown for its edible buds. The leafy green vegetables are typically 2.5–4 cm in diameter and look like miniature cabbages. The sprout is Brassica oleracea, in the "gemmifera" group of the family Brassicaceae...

s, and spinach

Spinach

Spinach is an edible flowering plant in the family of Amaranthaceae. It is native to central and southwestern Asia. It is an annual plant , which grows to a height of up to 30 cm. Spinach may survive over winter in temperate regions...

. Clover

Clover

Clover , or trefoil, is a genus of about 300 species of plants in the leguminous pea family Fabaceae. The genus has a cosmopolitan distribution; the highest diversity is found in the temperate Northern Hemisphere, but many species also occur in South America and Africa, including at high altitudes...

 and soybeans have the highest concentrations.

Coumestrol is a phytoestrogen, mimicking the biological activity of estrogen

Estrogen

Estrogens , oestrogens , or œstrogens, are a group of compounds named for their importance in the estrous cycle of humans and other animals. They are the primary female sex hormones. Natural estrogens are steroid hormones, while some synthetic ones are non-steroidal...

s. The chemical shape of coumestrol orients its two hydroxy

Hydroxyl

A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...

 groups in the same position as the two hydroxy groups in estradiol

Estradiol

Estradiol is a sex hormone. Estradiol is abbreviated E2 as it has 2 hydroxyl groups in its molecular structure. Estrone has 1 and estriol has 3 . Estradiol is about 10 times as potent as estrone and about 80 times as potent as estriol in its estrogenic effect...

, allowing it to inhibit the activity of aromatase

Aromatase

Aromatase is an enzyme responsible for a key step in the biosynthesis of estrogens. It is a member of the cytochrome P450 superfamily , which are monooxygenases that catalyze many reactions involved in steroidogenesis. In particular, aromatase is responsible for the aromatization of androgens into...

 and hydroxysteroid dehydrogenase

Hydroxysteroid dehydrogenase

The Hydroxysteroid dehydrogenases are a group of alcohol oxidoreductases that catalyze the dehydrogenation of hydroxysteroids.There are four types, classified by the number of the carbon acted upon:...

. These enzymes are involved in the biosynthesis of steroid

Steroid

A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...

hormones, and inhibition of these enzymes results in the modulation of hormone production.