Isoliquiritigenin is a
phenol
Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...
ic chemical compound found in
licorice
Liquorice (British English) or licorice (American English) ( ; also ) is the common name of ''Glycyrrhiza glabra'', a flowering plant of the bean family Fabaceae, from the root of which a sweet, aromatic flavouring can be extracted.
The liq ...
.
Metabolism
The enzyme
6'-deoxychalcone synthase
In enzymology, a 6'-deoxychalcone synthase () is an enzyme that catalyzes the chemical reaction
:3 malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ \rightleftharpoons 4 CoA + isoliquiritigenin + 3 CO2 + NADP+ + H2O
The 4 substrates of this enzyme are ...
uses
malonyl-CoA
Malonyl-CoA is a coenzyme A derivative of malonic acid.
Functions
It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis.
Fatty acid biosynthesis
Malonyl-CoA provides 2-carbon units to fatty acids and commi ...
,
4-coumaroyl-CoA
Coumaroyl-coenzyme A is the thioester of coenzyme-A and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include Monolignol, lignols (precursors to lignin ...
,
NADPH
Nicotinamide adenine dinucleotide phosphate, abbreviated NADP or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as the Calvin cycle and lipid and nucleic acid syntheses, which require NAD ...
, and H
+ to produce
CoA, isoliquiritigenin,
CO2, NADP
+, and H
2O.
The enzyme
isoliquiritigenin 2'-O-methyltransferase
In enzymology, an isoliquiritigenin 2'-O-methyltransferase () is an enzyme that catalysis, catalyzes the chemical reaction
:S-adenosyl-L-methionine + isoliquiritigenin \rightleftharpoons S-adenosyl-L-homocysteine + 2'-O-methylisoliquiritigenin
Th ...
further transforms isoliquiritigenin into
2'-O-methylisoliquiritigenin.
Mechanism of action
Isoliquiritigenin has been found to be a potent (65 times higher
affinity
Affinity may refer to:
Commerce, finance and law
* Affinity (law), kinship by marriage
* Affinity analysis, a market research and business management technique
* Affinity Credit Union, a Saskatchewan-based credit union
* Affinity Equity Partn ...
than
diazepam)
GABA-A
The GABAA receptor (GABAAR) is an ionotropic receptor and ligand-gated ion channel. Its endogenous ligand is γ-aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Upon opening, the GABAA receptor o ...
benzodiapine receptor
positive allosteric modulator
In pharmacology and biochemistry, allosteric modulators are a group of substances that bind to a receptor to change that receptor's response to stimulus. Some of them, like benzodiazepines, are drugs. The site that an allosteric modulator binds to ...
. It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of
melanoma
Melanoma, also redundantly known as malignant melanoma, is a type of skin cancer that develops from the pigment-producing cells known as melanocytes. Melanomas typically occur in the skin, but may rarely occur in the mouth, intestines, or eye ( ...
growth ''
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 an ...
''.
References
{{chalconoid
Chalconoids
category:Phenols