Prunin
Chemical compound
From Wikipedia, the free encyclopedia
Prunin is a flavanone glycoside found in immature citrus fruits[1][2] and in tomatoes.[3] Its aglycone form is called naringenin.
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| Names | |
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| IUPAC name
(2S)-7-(β-D-Glucopyranosyloxy)-4′,5-dihydroxyflavan-4-one | |
| Systematic IUPAC name
(2S)-5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-4H-1-benzopyran-4-one | |
| Other names
Naringenin-7-O-glucoside | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.696 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C21H22O10 | |
| Molar mass | 434.397 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
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 chalcones, which contain two phenyl rings.[4] In the main pathway, the enzymes chalcone synthase and chalcone isomerase produce (S)-naringenin which is the immediate precursor for prunin.[5][6]
Flavanone 7-O-beta-glucosyltransferase uses UDP-glucose to transfer a sugar group to one of the phenolic hydroxyl groups of (S)-naringenin.[7]
In some citrus fruits, the product prunin is converted to naringin, a compound which is responsible for the bitter taste of grapefruit.[7][8]
Flavanone 7-O-glucoside 2"-O-beta-L-rhamnosyltransferase uses UDP-rhamnose to add the second sugar component.[9]
Metabolism in the human gut
Glucosidase breaks dietary prunin back into glucose and naringenin.[4][10][11]
