Naringenin
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| Names
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| IUPAC name
(2S)-4′,5,7-Trihydroxyflavan-4-one
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Preferred IUPAC name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one |
| Other names
Naringetol; Salipurol; Salipurpol
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| Identifiers
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| ChEBI
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| ChEMBL
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| ChemSpider
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| DrugBank
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| ECHA InfoCard
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100.006.865 
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| UNII
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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  NKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N N
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O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
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| Properties
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C15H12O5
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| Molar mass
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272.256 g·mol−1
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| Melting point
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251 °C (484 °F; 524 K)[1]
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475 mg/L[1]
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Chemical compound
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]
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.
Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable.[5][6] Racemization of S(-)-naringenin has been shown to occur fairly quickly.[7]
Sources and bioavailability
Naringenin and its glycoside has been found in a variety of herbs and fruits, including grapefruit,[8] bergamot,[9] sour orange,[10] tart cherries,[11] tomatoes,[12][13] cocoa,[14] Greek oregano,[15] water mint,[16] as well as in beans.[17] Ratios of naringenin to naringin vary among sources,[12] as do enantiomeric ratios.[6]
The naringenin-7-glucoside form seems less bioavailable than the aglycol form.[18]
Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.[19] 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 are 3.8 mg of naringenin in 150 grams of tomato paste.[20]
Potential biological effects
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.[23][24] The effect is believed to be due to a protein present in neurons known as CRMP2 that naringenin binds to.[25]
Antibacterial, antifungal, and antiviral
Naringenin has an antimicrobial effect on S. epidermidis, as well as Staphylococcus aureus, Bacillus subtilis, Micrococcus luteus, and Escherichia coli.[26] Further research has added evidence for antimicrobial effects against Lactococcus lactis,[27] lactobacillus acidophilus, Actinomyces naeslundii, Prevotella oralis, Prevotella melaninogencia, Porphyromonas gingivalis,[28] as well as yeasts such as Candida albicans, Candida tropicalis, and Candida krusei.[29] 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.[30]
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.[31] The antiviral effects of naringenin are currently under clinical investigation.[32] Reports of antiviral effects on polioviruses, HSV-1 and HSV-2 have also been made, though replication of the viruses has not been inhibited.[33][34] In in vitro experiments Naringenin also showed a strong antiviral activity against SARS-CoV-2.
[35]
Anti-inflammatory
Despite evidence of anti-inflammatory activity of naringin,[36] the anti-inflammatory activity of naringenin has been observed to be poor to nonexistent.[37][38]
Antioxidant
Naringenin has been shown to have significant antioxidant properties.[39][40] It has been shown to reduce oxidative damage to DNA in vitro and in animal studies.[41][42]
Anticancer
Cytotoxicity has been induced reportedly by naringenin in cancer cells from breast, stomach, liver, cervix, pancreas, and colon tissues, along with leukaemia cells.[43][44] The mechanisms behind inhibition of human breast carcinoma growth have been examined, and two theories have been proposed.[45] The first theory is that naringenin inhibits aromatase, thus reducing growth of the tumor.[46] The second mechanism proposes that interactions with estrogen receptors is the cause behind the modulation of growth.[47] New derivatives of naringenin were found to be active against multidrug-resistant cancer.[48]
