Biochanin A is an
''O''-methylated isoflavone. It is a natural organic compound in the class of
phytochemical
Phytochemicals are chemical compounds produced by plants, generally to help them resist fungi, bacteria and plant virus infections, and also consumption by insects and other animals. The name comes . Some phytochemicals have been used as poison ...
s known as flavonoids. Biochanin A can be found in
red clover
''Trifolium pratense'', the red clover, is a herbaceous species of flowering plant in the bean family Fabaceae, native to Europe, Western Asia, and northwest Africa, but planted and naturalized in many other regions.
Description
Red clov ...
in
soy
The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses.
Traditional unfermented food uses of soybeans include soy milk, from which tofu and ...
, in
alfalfa sprouts, in
peanut
The peanut (''Arachis hypogaea''), also known as the groundnut, goober (US), pindar (US) or monkey nut (UK), is a legume crop grown mainly for its edible Seed, seeds. It is widely grown in the tropics and subtropics, important to both small ...
s, in
chickpea
The chickpea or chick pea (''Cicer arietinum'') is an annual legume of the family Fabaceae, subfamily Faboideae. Its different types are variously known as gram" or Bengal gram, garbanzo or garbanzo bean, or Egyptian pea. Chickpea seeds are hi ...
(''Cicer arietinum'') and in other legumes.
Biochanin A is classified as 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 nonster ...
and has putative benefits in dietary
cancer prophylaxis. It has also been found to be a weak
inhibitor
Inhibitor or inhibition may refer to:
In biology
* Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity
* Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...
of
fatty acid amide hydrolase
Fatty acid amide hydrolase or FAAH (, oleamide hydrolase, anandamide amidohydrolase) is a member of the serine hydrolase family of enzymes. It was first shown to break down anandamide in 1993. In humans, it is encoded by the gene ''FAAH''.;
Fu ...
''
in vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology and ...
''.
Biochanin A can block the
vasoconstriction
Vasoconstriction is the narrowing of the blood vessels resulting from contraction of the muscular wall of the vessels, in particular the large arteries and small arterioles. The process is the opposite of vasodilation, the widening of blood ve ...
in a dose-dependent manner due to the inhibition of
L-type calcium channel
The L-type calcium channel (also known as the dihydropyridine channel, or DHP channel) is part of the high-voltage activated family of voltage-dependent calcium channel.
"L" stands for long-lasting referring to the length of activation. This c ...
s. Such
vasodilatory
Vasodilation is the widening of blood vessels. It results from relaxation of smooth muscle cells within the vessel walls, in particular in the large veins, large arteries, and smaller arterioles. The process is the opposite of vasoconstriction, ...
effect, in micromolar concentrations, is of potential clinical interest for the management of
cardiovascular pathologies.
[Migkos, T., Pourová, J., Vopršalová, M., Auger, C., Schini-Kerth, V., & Mladěnka, P. (2020). "Biochanin A, the Most Potent of 16 Isoflavones, Induces Relaxation of the Coronary Artery Through the Calcium Channel and cGMP-dependent Pathway". Planta medica, 86(10), 708-716. ]
Metabolism
The enzyme
biochanin-A reductase
In enzymology, a biochanin-A reductase () is an enzyme that catalyzes the chemical reaction
:dihydrobiochanin A + NADP+ \rightleftharpoons biochanin A + NADPH + H+
Thus, the two substrates of this enzyme are dihydrobiochanin A and NADP+, wher ...
uses dihydrobiochanin A and NADP
+ to produce biochanin A, NADPH, and H
+. The enzyme
isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase
In enzymology, an isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase () is an enzyme that catalyzes the chemical reaction
:malonyl-CoA + biochanin A 7-O-beta-D-glucoside \rightleftharpoons CoA + biochanin A 7-O-(6-O-malonyl-beta-D-glucoside)
...
uses malonyl-CoA and biochanin A 7-O-β-
D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-
D-glucoside).
See also
*
List of phytochemicals in food
While there is ample evidence to indicate the health benefits of diets rich in fruits, vegetables, legumes, whole grains and nuts, no specific food has been acknowledged by scientists and government regulatory authorities as providing a health bene ...
*
Prunetin
Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of ''Prunus emarginata'' (the Oregon cherry). Prunetin isolated from pea roots can act as an attractant for '' Ap ...
References
{{Estrogen-related receptor modulators
Aromatase inhibitors
O-methylated isoflavones
Phytoestrogens
Selective ERβ agonists