Naringin

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Naringin
Naringin
IUPAC name 7-[[2-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-
glucopyranosyl]]oxy]-2,3-dihydro-5-hydroxy-
2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names Naringin
4',5,7-Trihydroxyflavanone-7-rhamnoglucoside
4',5,7-Trihydroxyflavanone-7-rutinoside
Identifiers
CAS number [10236-47-2]
SMILES OC(C=C3)=CC=[C@@]3[C@@H]2CC(C1=C(O)
C=C(O[C@H]4[C@H](O[C@]5([H])O[C@@H]
(C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)
[C@H](O)[C@@H](CO)O4)C=C1O2)=O
Properties
Molecular formula C27H32O14
Molar mass 580.541 g/mol
Density  ? g/cm3
Melting point

166 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. It is metabolized to the flavanone naringenin in humans. Both naringenin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits.

[edit] Activity

Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro.[1]

[edit] References

  1. ^ Grapefruit Juice and Medications
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Types of Glycosides
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Aglycone:
Alcoholic glycoside | Anthraquinone glycoside | Coumarin glycoside | Cyanogenic glycoside | Flavonoid glycoside | Phenolic glycoside | Saponin | Cardiac glycoside | Steviol glycoside | Thioglycoside | Glycosylamine | Bufanolide | Cardenolide
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