Isoflavonoids are a class of

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as

phytoestrogen A phytoestrogen is a plant-derived xenoestrogen (a type of estrogen produced by organisms other than humans) not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it ...

s, as many isoflavonoid compounds have biological effects via the

estrogen receptor Estrogen receptors (ERs) are proteins found in cell (biology), cells that function as receptor (biochemistry), receptors for the hormone estrogen (17β-estradiol). There are two main classes of ERs. The first includes the intracellular estrogen ...

. Medically, isoflavonoids and related compounds have been used in many

dietary supplement A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...

s but the medical and scientific community is generally skeptical of their use. Recently, some natural isoflavonoids have been identified as toxins, including

biliatresone Biliatresone is an example of a very rare type of a naturally occurring isoflavonoid-related 1,2-diaryl-2-propenone found in '' Dysphania glomulifera'' and ''D. littoralis''. It has been found to cause extrahepatic biliary atresia in a zebrafish m ...

which may cause

biliary atresia Biliary atresia, also known as extrahepatic ductopenia and progressive obliterative cholangiopathy, is a childhood disease of the liver in which one or more bile ducts are abnormally narrow, blocked, or absent. It can be congenital or acquired. ...

when infants are exposed to the plant product. The isoflavonoid group is broad, and includes many structurally similar groups, including: *

isoflavones Isoflavones are a type of naturally-occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans. Although isoflavones and closely-related phytoestrogens are ...

* isoflavanones * isoflavans *

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-c The comma is a punctuation mark that appears in several variants in different languages. Some typefaces render it as a small line, slightly curved or straight, but inclined from the vertical; others give it the appearance of a miniature fille ...

hromene skeleton) which can be formed by coupling of th ...

s *

rotenoids Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno ,4-bhromene nucleus. Many have insecticidal and piscicidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the i ...

Isoflavonoids are derived from the flavonoid biosynthesis pathway via

liquiritigenin Liquiritigenin is a flavanone that was isolated from ''Glycyrrhiza uralensis'', and is found in a variety of plants of the Glycyrrhiza genus, including ''Glycyrrhiza glabra'' (licorice). It is an estrogenic compound which acts as a selective agoni ...

naringenin Naringenin is a flavanone from the flavonoid group of polyphenols. It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit. The fate and biological functions of naringenin in vivo are unknown, remaining und ...

Chemical makeup

While

flavonoids Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

(in the narrow sense) have the 2-phenylchromen-4-one backbone, isoflavonoids have the 3-phenylchromen-4-one backbone with no hydroxyl group substitution at position 2 (case of the isoflavones) or the 3-phenylchroman (isoflavan) backbone (case of isoflavanes, such as

equol Equol (4',7-isoflavandiol) is an isoflavandiolThe structures of 7,4’-dihydroxy-isoflavan and its precursors is shown iStructural Elucidation of Hydroxylated Metabolites of the Isoflavan Equol by GC/MS and HPLC/MSby Corinna E. Rüfer, Hansruedi ...

References

{{GABAergics

Chemical makeup

See also

References