Prunin
Chemical compound
Prunin is a flavanone glycoside found in immature citrus fruits and in tomatoes. Its aglycone form is called naringenin.
01Biosynthesis
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. In the main pathway, the enzymes chalcone synthase and chalcone isomerase produce (S)-naringenin which is the immediate precursor for prunin.
Flavanone 7-O-beta-glucosyltransferase uses UDP-glucose to transfer a sugar group to one of the phenolic hydroxyl groups of (S)-naringenin.
naringenin + UDP-glucose prunin + UDPIn some citrus fruits, the product prunin is converted to naringin, a compound which is responsible for the bitter taste of grapefruit.
prunin + UDP-rhamnose naringin + UDPFlavanone 7-O-glucoside 2"-O-beta-L-rhamnosyltransferase uses UDP-rhamnose to add the second sugar component.
02Metabolism in the human gut
Glucosidase breaks dietary prunin back into glucose and naringenin.
Sources and credits
This article is adapted from the Wikipedia article “Prunin”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Prunin.svg by No machine-readable author provided. Ayacop assumed (based on copyright claims)., Public domain
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