Naringenin

Naringenin

Systematic (IUPAC) name
5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	480-41-1 Y
ATC code	None
PubChem	CID 439246
DrugBank	DB03467
ChemSpider	388383 N
UNII	HN5425SBF2 N
ChEMBL	CHEMBL9352 N
Chemical data
Formula	C15H12O5
Mol. mass	272.257 g/mol
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
N (what is this?)  (verify)

Naringenin is a flavanone, a type of flavonoid, that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, anti-inflammatory, carbohydrate metabolism promoter, and immune system modulator. It is the predominant flavanone in grapefruit.^[1]

Biological effects

This substance has also been shown to reduce oxidative damage to DNA in vitro. Scientists^[who?] exposed cells to 80 micromoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24% in that very short period of time^{[citation needed]}.

Naringenin found in grapefruit juice 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.^[2]

Naringenin has also been shown to reduce hepatitis C virus production by infected hepatocytes (liver cells) in cell culture. This seem to be secondary to Naringenin ability to inhibit the secretion of very-low-density lipoprotein by the cells.^[3] The antiviral effects of naringenin are currently under clinical investigation.^[4]

Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet.^[5]

Naringenin lowers the plasma and hepatic cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.^[6]

Sources and bioavailability

It can be found in grapefruits, 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.^{[citation needed]} A full glass of orange juice will supply about enough naringenin to achieve a [blood plasma?] concentration of about 0.5 micromoles per liter.^{[citation needed]}

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

Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.^[8] 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.^[9]

Biodegradation

Cunninghamella elegans, a fungal model organism of the mammalian metabolism, can be used to study the naringenin sulfation.^[10]

References