Apigetrin
Chemical compound
From Wikipedia, the free encyclopedia
Apigetrin is a chemical compound that can be found in dandelion coffee and in Teucrium gnaphalodes.[1]
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| Names | |
|---|---|
| IUPAC name
7-(β-D-Glucopyranosyloxy)-4′,5-dihydroxyflavone | |
| Systematic IUPAC name
5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one | |
| Other names
Apigetrin; Cosmosiine; Cosmetin; Cosmosiin; Cosmosioside; Thalictiin; Cosmosin; Apigenin 7-glucoside; Apigenin 7-O-glucoside | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.574 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C21H20O10 | |
| Molar mass | 432.381 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biosynthesis and metabolism
Apigetrin is a glycoside of the flavone, apigenin. Its biosynthesis in plants involves a sequence of enzymes, with chalcone synthase being the one that forms the ring system of the natural product naringenin. Naringenin is then oxidised to apigenin:[2][3]
Next, the enzyme flavone 7-O-beta-glucosyltransferase transfers the glucose sugar fragment from UDP-glucose, giving apigetrin, with uridine diphosphate (UDP) as byproduct:[2][4]
Apigetrin is further metabolised to apiin when a second apiose sugar is added by the enzyme flavone apiosyltransferase:[3]
