Naringenin

Naringenin is a flavorless,[2] colorless[3] flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit,[4] and is found in a variety of fruits and herbs.[5]

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.865
UNII
Properties
C15H12O5
Molar mass 272.256 g·mol−1
Melting point 251 °C (484 °F; 524 K)[1]
475 mg/L[1]
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

Structure

Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4', 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7.

Chirality

Like the majority of flavanones, naringenin has a single chiral center at carbon 2, resulting in enantiomeric forms of the compound.[6] The enantiomers are found in varying ratios in natural sources.[7] Racemization of S(-)-naringenin has been shown to occur fairly quickly.[8] Naringenin has been shown to be resistant to enatiomerization over pH 9-11.[9]

Separation and analysis of the enantiomers has been explored for over 20 years,[6] primarily via high-performance liquid chromatography on polysaccharide-derived chiral stationary phases.[8][10][11][12] There is evidence to suggest stereospecific pharmacokinetics and pharmacodynamics profiles, which has been proposed to be an explanation for the wide variety in naringenin's reported bioactivity.[7]

Sources

Naringenin and its glycoside has been found in a variety of herbs and fruits, including grapefruit,[13] bergamot,[14] sour orange,[15] tart cherries,[16] tomatoes,[17][18] cocoa,[19] Greek oregano,[20] water mint,[21] drynaria[22] as well as in beans.[23] Ratios of naringenin to naringin vary among sources,[17] as do enantiomeric ratios.[7]

Bioavailability

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.[24]

The naringenin-7-glucoside form seems less bioavailable than the aglycol form.[25]

Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.[26] 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. There is 253 mg of naringenin in 10 grams of tomato paste.[27]

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.[28]

Potential biological effects

Inhibitory activity

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.[29] 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.[30]

Alzheimer's disease

Naringenin is being researched as a potential treatment for Alzheimer's disease. Naringenin has been demonstrated to improve memory and reduce amyloid and tau proteins in a study using a mouse model of Alzheimer's disease.[31][32] The effect is believed to be due to a protein present in neurons known as CRMP2 that naringenin binds to.[33]

Antibacterial, antifungal, and antiviral

Naringenin's potential antibacterial and antifungal behaviour has been investigated. In 1987, it was reported that naringenin had no antibacterial activity against Staphylococcus epidermidis.[34] This finding was not replicated in a 2000 study in which naringenin was shown to indeed have an antimicrobial effect on S. epidermidis, as well as Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, and Escherichia coli.[35] Further research has added evidence for antimicrobial effects against Lactococcus lactis,[36] lactobacillus acidophilus, Actinomyces naeslundii, Prevotella oralis, Prevotella melaninogencia, Porphyromonas gingivalis,[37] as well as yeasts such as Candida albicans, Candida tropicalis, and Candida krusei.[38] There is also evidence of antibacterial effects on H. pylori, though naringenin has not been shown to have any inhibition on urease activity of the microbe.[39]

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.[40] The antiviral effects of naringenin are currently under clinical investigation.[41] Reports of antiviral effects on polioviruses, HSV-1 and HSV-2 have also been made, though replication of the viruses has not been inhibited.[42][43][44]

Anti-inflammatory

Despite evidence of anti-inflammatory activity of naringin,[45] the anti-inflammatory activity of naringenin has been observed to be poor to nonexistent.[46][47]

Antioxidant

Naringenin has been shown to have significant antioxidant properties.[48][49] It has been shown to reduce oxidative damage to DNA in vitro and in animal studies.[50][51]

Anticancer

Cytotoxicity has been induced reportedly by naringenin in cancer cells from breast, stomach, liver, cervix, pancreas, and colon tissues, along with leukaemia cells.[52] The mechanisms behind inhibition of human breast carcinoma growth have been examined, and two theories have been proposed.[53] The first theory is that naringenin inhibits aromatase, thus reducing growth of the tumor.[54] The second mechanism proposes that interactions with estrogen receptors is the cause behind the modulation of growth.[55] New derivatives of naringenin were found to be active against multidrug-resistant cancer.[56]

Antiadipogenic activity and cardioprotective effects

Naringenin has been reported to induce apoptosis in preadipocytes.[57]

Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet.[58]

Naringenin lowers the plasma and hepatic cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.[59]

Other effects

Naringenin also produces BDNF-dependent antidepressant-like effects in mice.[60]

In 2006 it was shown to increase the mRNA expression levels of two DNA repair enzymes, DNA pol beta and OGG1, specifically in prostate cancer cells.[61]

Like many other flavonoids, naringenin has been found to possess weak activity at the opioid receptors.[62] It specifically acts as a non-selective antagonist of all three opioid receptors, albeit with weak affinity.[62]

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gollark: Haskell *is* perfect and without flaw, yes.
gollark: Oh bee, it is downloading GHC?!

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