Not to be confused with naringin.
IUPAC name
Other names
Naringetol; Salipurol; Salipurpol; 4',5,7-Trihydroxyflavanone
480-41-1 YesY
3D model (Jmol) Interactive image
ChemSpider 388383 N
DrugBank DB03467 N
ECHA InfoCard 100.006.865
PubChem 439246
Molar mass 272.26 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).
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Infobox references

Naringenin is a flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit.[2]

Sources and bioavailability

Naringenin can be found in grapefruit, oranges, tomatoes (skin)[3] and in water mint.

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.[4]

Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.[5] 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.[6]

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.[7] 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.[8]

Naringenin has also been shown to reduce oxidative damage to DNA in vitro and in animal studies.[9]

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.[10] The antiviral effects of naringenin are currently under clinical investigation.[11]

Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet.[12]

Naringenin lowers the plasma and hepatic cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.[13]

It also produces BDNF-dependent antidepressant-like effects in mice.[14]

Like many other flavonoids, naringenin has been found to possess weak activity at the opioid receptors.[15] It specifically acts as a non-selective antagonist of all three opioid receptors, albeit with weak affinity.[15]


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


Cunninghamella elegans, a fungal model organism of the mammalian metabolism, can be used to study the naringenin sulfation.[16]


  1. 1 2 "Naringenin". ChemIDplus.
  2. Felgines C, Texier O, Morand C, Manach C, Scalbert A, Régerat F, Rémésy C (December 2000). "Bioavailability of the flavanone naringenin and its glycosides in rats". Am. J. Physiol. Gastrointest. Liver Physiol. 279 (6): G1148–54. PMID 11093936.
  3. Vallverdú-Queralt, A; Odriozola-Serrano, I; Oms-Oliu, G; Lamuela-Raventós, RM; Elez-Martínez, P; Martín-Belloso, O (2012). "Changes in the polyphenol profile of tomato juices processed by pulsed electric fields". J Agric Food Chem. 60 (38): 9667–9672. doi:10.1021/jf302791k. PMID 22957841.
  4. Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA (November 1999). "Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation". Biochem. Biophys. Res. Commun. 265 (2): 410–5. doi:10.1006/bbrc.1999.1695. PMID 10558881.
  5. Erlund I, Meririnne E, Alfthan G, Aro A (February 2001). "Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice". J. Nutr. 131 (2): 235–41. PMID 11160539.
  6. Bugianesi R, Catasta G, Spigno P, D'Uva A, Maiani G (November 2002). "Naringenin from cooked tomato paste is bioavailable in men". J. Nutr. 132 (11): 3349–52. PMID 12421849.
  7. Fuhr U, Klittich K, Staib AH (April 1993). "Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man". Br J Clin Pharmacol. 35 (4): 431–6. doi:10.1016/0024-3205(96)00417-1. PMC 1381556Freely accessible. PMID 8485024.
  8. Ueng YF, Chang YL, Oda Y, Park SS, Liao JF, Lin MF, Chen CF (1999). "In vitro and in vivo effects of naringin on cytochrome P450-dependent monooxygenase in mouse liver". Life Sci. 65 (24): 2591–602. doi:10.1016/s0024-3205(99)00528-7. PMID 10619367.
  9. Sumit Kumar & Ashu Bhan Tiku (2016). "Biochemical and Molecular Mechanisms of Radioprotective Effects of Naringenin, a Phytochemical from Citrus Fruits". J. Agric. Food Chem. 64 (8): 1676–1685. doi:10.1021/acs.jafc.5b05067.
  10. Nahmias Y, Goldwasser J, Casali M, van Poll D, Wakita T, Chung RT, Yarmush ML (May 2008). "Apolipoprotein B-dependent hepatitis C virus secretion is inhibited by the grapefruit flavonoid naringenin". Hepatology. 47 (5): 1437–45. doi:10.1002/hep.22197. PMID 18393287.
  11. A Pilot Study of the Grapefruit Flavonoid Naringenin for HCV Infection
  12. Mulvihill EE, Allister EM, Sutherland BG, Telford DE, Sawyez CG, Edwards JY, Markle JM, Hegele RA, Huff MW (October 2009). "Naringenin prevents dyslipidemia, apolipoprotein B overproduction, and hyperinsulinemia in LDL receptor-null mice with diet-induced insulin resistance". Diabetes. 58 (10): 2198–210. doi:10.2337/db09-0634. PMC 2750228Freely accessible. PMID 19592617.
  13. Lee SH, Park YB, Bae KH, Bok SH, Kwon YK, Lee ES, Choi MS (1999). "Cholesterol-lowering activity of naringenin via inhibition of 3-hydroxy-3-methylglutaryl coenzyme A reductase and acyl coenzyme A:cholesterol acyltransferase in rats". Ann. Nutr. Metab. 43 (3): 173–80. doi:10.1159/000012783. PMID 10545673.
  14. Yi LT, Liu BB, Li J, Luo L, Liu Q, Geng D, Tang Y, Xia Y, Wu D (October 2013). "BDNF signaling is necessary for the antidepressant-like effect of naringenin". Prog. Neuropsychopharmacol. Biol. Psychiatry. 48C: 135–141. doi:10.1016/j.pnpbp.2013.10.002. PMID 24121063.
  15. 1 2 Katavic PL, Lamb K, Navarro H, Prisinzano TE (August 2007). "Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships". J. Nat. Prod. 70 (8): 1278–82. doi:10.1021/np070194x. PMC 2265593Freely accessible. PMID 17685652.
  16. Ibrahim AR (January 2000). "Sulfation of naringenin by Cunninghamella elegans". Phytochemistry. 53 (2): 209–12. doi:10.1016/S0031-9422(99)00487-2. PMID 10680173.
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