Naringin

Not to be confused with Naringenin.

Naringin

Names
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 Naringoside 4',5,7-Trihydroxyflavanone-7-rhamnoglucoside Naringenin 7-O-neohesperidoside
Identifiers
CAS Number	10236-47-2 Y
ChEBI	CHEBI:28819 N
ChEMBL	ChEMBL451512 N
ChemSpider	4447695 Y
IUPHAR/BPS	4738
Jmol 3D model	Interactive image
PubChem	442428
UNII	N7TD9J649B Y
InChI InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1 Y Key: DFPMSGMNTNDNHN-CSIAVLANSA-N Y InChI=1/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16+,18-,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1 Key: DFPMSGMNTNDNHN-CSIAVLANBN
SMILES O=C4c5c(O)cc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)C)cc5O[C@H](c3ccc(O)cc3)C4
Properties
Chemical formula	C27H32O14
Molar mass	580.54 g/mol
Melting point	166 °C (331 °F; 439 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Naringin is a flavanone-7-O-glycoside between the flavanone Naringenin and the disaccharide neohesperidose. The flavonoids naringenin and hesperetin, which form the aglycones of naringin and hesperidin, occur 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 created by naringin. In humans the naringin is metabolized to the flavanone naringenin.

Biological activity

Naringin inhibits some drug-metabolizing cytochrome P450 enzymes, including CYP3A4 and CYP1A2, which may result in drug-drug interactions. Ingestion of naringin and related flavonoids can also affect the intestinal absorption of certain drugs, leading to either an increase or decrease in circulating drug levels. To avoid interference with drug absorption and metabolism, the consumption of citrus (especially grapefruit) and other juices with medications is contraindicated.

A variety of other pharmacological effects have been observed in vitro or in animal studies, but their relevance to human health in unknown. These effects include:

• Naringin is an inhibitor of vascular endothelial growth factor (VEGF) release, which causes angiogenesis.

• Naringin reduced diabetes-induced neuropathy in rats.
• Naringin ameliorates memory deficits in ICV-STZ-induced experimental paradigm of Alzheimer's disease through attenuating mitochondrial dysfunction.
• Naringin has shown protective effects against cognitive dysfunction and oxidative damage in rats.

Uses

When naringin is treated with potassium hydroxide or another strong base, and then catalytically hydrogenated, it becomes a naringin dihydrochalcone, a compound roughly 300–1800 times sweeter than sugar at threshold concentrations.