Coumestan is a

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products of

pterocarpan Pterocarpans are derivatives of isoflavonoids found in the family Fabaceae. It is a group of compounds which can be described as benzo-pyrano-furano-benzenes (i.e. 6''H''- enzofuro ,2-chromene skeleton) which can be formed by coupling of the B rin ...

that are similar to

coumarin Coumarin () or 2''H''-chromen-2-one is an aromatic organic chemical compound with formula . Its molecule can be described as a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain , forming a second six-membered h ...

. Coumestans, including

coumestrol Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. Coumestrol was first identified as a compound with estrogenic properties by E. M. Bickoff in ladino clover and alfalfa in 1957. It has garnered research ...

, a

phytoestrogen A phytoestrogen is a plant-derived xenoestrogen (see estrogen) not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonstero ...

, are found in a variety of plants. Food sources high in coumestans include

split pea Split peas are an agricultural or culinary preparation consisting of the dried, peeled and split seeds of ''Pisum sativum'', the pea. Harvesting The peas are spherical when harvested, with an outer skin. The peas are dried and the dull-coloure ...

pinto beans The pinto bean () is a variety of Phaseolus vulgaris, common bean (''Phaseolus vulgaris''). In Spanish language, Spanish they are called , literally "painted bean" (compare pinto horse). It is the most popular bean by crop production in Northern M ...

lima beans A lima bean (''Phaseolus lunatus''), also commonly known as the butter bean, sieva bean, double bean, Madagascar bean, or wax bean is a legume grown for its edible seeds or beans. Origin and uses ''Phaseolus lunatus'' is found in Meso- and Sou ...

, and especially

alfalfa Alfalfa () (''Medicago sativa''), also called lucerne, is a perennial flowering plant in the legume family Fabaceae. It is cultivated as an important forage crop in many countries around the world. It is used for grazing, hay, and silage, as w ...

and

clover Clover or trefoil are common names for plants of the genus ''Trifolium'' (from Latin ''tres'' 'three' + ''folium'' 'leaf'), consisting of about 300 species of flowering plants in the legume or pea family Fabaceae originating in Europe. The genus ...

sprouts.

Coumestrol Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. Coumestrol was first identified as a compound with estrogenic properties by E. M. Bickoff in ladino clover and alfalfa in 1957. It has garnered research ...

has about the same binding affinity for the ER-β

estrogen receptor Estrogen receptors (ERs) are a group of proteins found inside cells. They are receptors that are activated by the hormone estrogen ( 17β-estradiol). Two classes of ER exist: nuclear estrogen receptors (ERα and ERβ), which are members of the ...

as 17β-estradiol, but much less affinity than 17α-estradiol, although the estrogenic potency of coumestrol at both receptors is much less than that of 17β-estradiol. Because of the estrogenic activity of some coumestans, a variety of syntheses have been developed that allow the preparation of coumestans so that their pharmacological effects can be explored.

Coumestans

Image:coumestrol.png,

Image:wedelolactone.png,

Wedelolactone Wedelolactone is an organic chemical compound classified as a coumestan that occurs in '' Eclipta alba'' (false daisy) and in '' Wedelia calendulacea''. References Catechols Coumestans Phenol ethers {{aromatic-stub ...

Image:plicadin.png,

Plicadin Plicadin is a coumestan Coumestan is a heterocyclic organic compound. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products of pterocarpan that are similar to coum ...

References

{{Xenoestrogens