Naringenin chalcone
Chemical compound
From Wikipedia, the free encyclopedia
Naringenin chalcone[1] is a common chalconoid (or chalcone, not to be confused with the compound chalcone). It is synthesized from 4-coumaroyl-CoA and malonyl-CoA by chalcone synthase (CHS), a key enzyme in the phenylpropanoid pathway. Naringenin chalcone can spontaneously cyclize to naringenin (a flavanone). In plant cells, this process is catalyzed by chalcone isomerase.
| |
| Names | |
|---|---|
| Preferred IUPAC name
2′,4,4′,6′-Tetrahydroxychalcone | |
| Other names
Chalconaringenin; Chalcononaringenin; Isosalipurpol | |
| Identifiers | |
| |
3D model (JSmol) |
|
| ChEBI | |
| ChemSpider | |
| KEGG | |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C15H12O5 | |
| Molar mass | 272.256 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Biosynthesis and metabolism
Flavonoid biosynthesis in plants uses a phenylpropanoid metabolic pathway in which the amino acid phenylalanine is converted to 4-coumaroyl-CoA. This is combined with three units of malonyl-CoA to yield a group of compounds called chalconoids, which contain two phenyl rings.[2] Naringenin chalcone is produced directly in this pathway by the enzyme chalcone synthase.[3]
It can cyclise spontaneously to naringenin but would provide racemic material. The enzyme chalcone isomerase constrains the reaction to give only the (S) isomer of the flavanone.[2][4]
Naringenin is then further transformed into naringin and other plant metabolites including anthocyanins.[5]