|Systematic (IUPAC) name|
|CAS Registry Number|
|Molecular mass||272.257 g/mol|
|(what is this?)|
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.
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.
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.
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.
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 in vitro experiments in mice. This suggests, but does not conclusively prove, that naringenin would elicit the same response when administered to humans. More research will be needed to determine if naringenin has any clinically significant effects (including medical applications) in human subjects.
Like many other flavonoids, naringenin has been found to possess activity at the opioid receptors. It specifically acts as a non-selective antagonist of all three opioid receptors, albeit with somewhat weak affinity.
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. A full glass of orange juice will supply about enough naringenin to achieve a [blood plasma?] concentration of about 0.5 micromoles per liter.
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.
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- A Pilot Study of the Grapefruit Flavonoid Naringenin for HCV Infection
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