Naringenin

Not to be confused with naringin.

Naringenin

Names
IUPAC name 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
Other names Naringetol; Salipurol; Salipurpol; 4',5,7-Trihydroxyflavanone
Identifiers
CAS Number	480-41-1 Y
ChEBI	CHEBI:50202 N
ChEMBL	ChEMBL9352 N
ChemSpider	388383 N
DrugBank	DB03467 N
Jmol 3D model	Interactive image
PubChem	439246
UNII	HN5425SBF2 N
InChI InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1 N Key: FTVWIRXFELQLPI-ZDUSSCGKSA-N N
SMILES O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
Properties
Chemical formula	C15H12O5
Molar mass	272.26 g·mol−1
Melting point	251 °C (484 °F; 524 K)
Solubility in water	475 mg/L
Vapor pressure	{{{value}}}
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

Naringenin is a flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit.

Sources and bioavailability

Naringenin can be found in grapefruit, oranges, and tomatoes (skin).

This bioflavonoid is difficult to absorb on oral ingestion. In the best-case scenario, only 15% of ingested naringenin will get absorbed in the human gastrointestinal tract.

The naringenin-7-glucoside form seems less bioavailable than the aglycol form.

Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice. Also found in grapefruit is the related compound kaempferol, which has a hydroxyl group next to the ketone group.

Naringenin can be absorbed from cooked tomato paste.

Potential biological effects

Naringenin has been shown to have an inhibitory effect on the human cytochrome P450 isoform CYP1A2, which can change pharmacokinetics in a human (or orthologous) host of several popular drugs in an adverse manner, even resulting in carcinogens of otherwise harmless substances. The National Research Institute of Chinese Medicine in Taiwan conducted experiments on the effects of the grapefruit flavanones naringin and naringenin on CYP450 enzyme expression. Naringenin proved to be a potent inhibitor of the benzo(a)pyrene metabolizing enzyme benzo(a)pyrene hydroxylase (AHH) in experiments in mice.

Naringenin has also been shown to reduce oxidative damage to DNA in vitro and in animal studies.

Naringenin has also been shown to reduce hepatitis C virus production by infected hepatocytes (liver cells) in cell culture. This seems to be secondary to naringenin's ability to inhibit the secretion of very-low-density lipoprotein by the cells. The antiviral effects of naringenin are currently under clinical investigation.

Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet.

Naringenin lowers the plasma and hepatic cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.

It also produces BDNF-dependent antidepressant-like effects in mice.

Like many other flavonoids, naringenin has been found to possess weak activity at the opioid receptors. It specifically acts as a non-selective antagonist of all three opioid receptors, albeit with weak affinity.

Metabolism

The enzyme naringenin 8-dimethylallyltransferase uses dimethylallyl diphosphate and (−)-(2S)-naringenin to produce diphosphate and 8-prenylnaringenin.

Biodegradation

Cunninghamella elegans, a fungal model organism of the mammalian metabolism, can be used to study the naringenin sulfation.