naringin
Sign in to saveAlso known as Naringoside, Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside, Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]
Naringin is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness (debittering) created by naringin. In humans naringin is metabolized to the aglycone naringenin (not bitter) by naringinase present in the gut.
Wikidata facts
- Mass
- 580.179206
Show 4 more facts
- chemical formula
- C₂₇H₃₂O₁₄
- isomeric SMILES
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
- canonical SMILES
- CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
- Commons category
- Naringin
via Wikidata · CC0
~5 min read
Article
8 sectionsContents
- Structure
- Biosynthesis
- Metabolism
- Toxicity
- Uses
- Commercial
- References
- External links
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 444022951 | Name = Naringin | ImageFile = Naringin.svg | ImageSize = 250px | ImageName = Naringin | ImageFile2 = Naringin 3D BS.png | ImageSize2 = 250px | ImageName2 = Naringin 3D | IUPACName = (2S)-4′,5-Dihydroxy-7-[α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyloxy]flavan-4-one | SystematicName = (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | OtherNames = NaringinNaringoside4′,5,7-Trihydroxyflavanone-7-rhamnoglucosideNaringenin 7-O-neohesperidoside |Section1= |Section2= }} Naringin is a flavanone-7-O-glycoside between the flavanone naringenin and the disaccharide neohesperidose. The flavonoid naringin occurs naturally in citrus fruits, especially in grapefruit, where naringin is responsible for the fruit's bitter taste. In commercial grapefruit juice production, the enzyme naringinase can be used to remove the bitterness (debittering) created by naringin. In humans naringin is metabolized to the aglycone naringenin (not bitter) by naringinase present in the gut.
==Structure== Naringin belongs to the flavonoid family which are characterised by the presence of 15 carbon atoms in three rings: two benzene rings are connected by a three-carbon chain. Naringin contains the basic flavonoid structure along with one rhamnose and one glucose unit attached to the phenol, naringenin. The steric hindrance provided by the two sugar units makes naringin less potent as an antioxidant than this aglycone. Flavonoid base structure|250x250px