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Not to be confused with naringin.
392MetabolicEditor/sandbox
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
UNII
  • 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
  • O=C2c3c(O[C@H](c1ccc(O)cc1)C2)cc(O)cc3O
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 checkY☒N ?)
Tracking categories (test):

Naringenin, a bitter[2], colourless substance[3], is a 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[edit]

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[edit]

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,[10] primarily via high-performance liquid chromatography on polysaccharide-derived chiral stationary phases. [11][12][13][14] 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[edit]

Naringenin and its glycoside has been found in a variety of herbs and fruits, including grapefruit[15],bergamot[16], sour orange[17], tart cherries[18], tomatoes [19][20], cocoa[21], Greek oregano[22], water mint [23], as well as in beans[24]. Ratios of naringenin to naringin vary among sources[19], as do enantiomeric ratios.[7]

Bioavailability[edit]

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]

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.[27]

Metabolism[edit]

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

Biodegradation[edit]

Cunninghamella elegans, a fungal model organism of the mammalian metabolism, can be used to study the naringenin sulfation.[28]

Potential biological effects[edit]

Inhibitory Activity[edit]

Effect on Cytochrome P450[edit]

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]

Antibacterial, antifungal, and antiviral[edit]

Naringenin's potential antibacterial and antifungal behaviour has been investigated. In 1987, it was reported that naringenin had no antibacterial activity against Staphylococcus epidermidis.[31] 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.[32] Further research has added evidence for antimicrobial effects against Lactococcus lactis[33], lactobacillus acidophilus, Actinomyces naeslundii, Prevotella oralis, Prevotella melaninogencia, Porphyromonas gingivalis [34], as well as yeasts such as Candida albicans, Candida tropicalis, and Candida krusei[35]. 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[36].

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.[37] The antiviral effects of naringenin are currently under clinical investigation.[38] Reports of antiviral effects on polioviruses HSV-1 and HSV-2 have also been made, though replication of the viruses has not been inhibited.[39][40][41]

Anti-inflamatory[edit]

Despite evidence of anti-inflammatory activity of naringin[42], the anti-inflammatory activity of naringenin has been observed to be poor to nonexistent.[43][44]

Antioxidant[edit]

Naringenin has been shown to have significant antioxidant properties.[45][46]

Naringenin has also been shown to reduce oxidative damage to DNA in vitro and in animal studies.[47][48]

Anticancer[edit]

Cytotoxicity has been induced reportedly by naringenin in cancer cells from breast, stomach, liver, cervix, pancreas, and colon tissues, along with leukaemia cells.[49] The mechanisms behind inhibition of human breast carcinoma growth have been examined, and two theories have been proposed.[50] The first theory is that naringenin inhibits aromatase, thus reducing growth of the tumor.[51] The second mechanism proposes that interactions with estrogen receptors is the cause behind the modulation of growth. [52]

Antiadipogenic Activity and Cardioprotective Effects[edit]

Naringenin has been reported to induce apoptosis in preadipocytes.[53]

Naringenin seems to protect LDLR-deficient mice from the obesity effects of a high-fat diet.[54]

Naringenin lowers the plasma and hepatic cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.[55]

Other Effects[edit]

Naringenin also produces BDNF-dependent antidepressant-like effects in mice.[56]

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.[57]

Like many other flavonoids, naringenin has been found to possess weak activity at the opioid receptors.[58] It specifically acts as a non-selective antagonist of all three opioid receptors, albeit with weak affinity.[58]

References[edit]

  1. ^ a b "Naringenin". ChemIDplus.
  2. ^ Esaki, Sachiko; Nishiyama, Kiyotoshi; Sugiyama, Naoko; Nakajima, Ryuta; Takao, Yoshihiro; Kamiya, Shintaro (1994-01-01). "Preparation and Taste of Certain Glycosides of Flavanones and of Dihydrochalcones". Bioscience, Biotechnology, and Biochemistry. 58 (8): 1479–1485. doi:10.1271/bbb.58.1479. ISSN 0916-8451. PMID 7765281.
  3. ^ Shin, W.; Kim, S.; Chun, K. S. (1987-10-15). "Structure of (R,S)-hesperetin monohydrate". Acta Crystallographica Section C Crystal Structure Communications. 43 (10): 1946–1949. doi:10.1107/s0108270187089510. ISSN 0108-2701.
  4. ^ 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.
  5. ^ Yáñez, Jaime A.; Andrews, Preston K.; Davies, Neal M. (2007-04-01). "Methods of analysis and separation of chiral flavonoids". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 848 (2): 159–181. doi:10.1016/j.jchromb.2006.10.052. ISSN 1570-0232. PMID 17113835.
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  7. ^ a b c Yáñez, Jaime A.; Remsberg, Connie M.; Miranda, Nicole D.; Vega-Villa, Karina R.; Andrews, Preston K.; Davies, Neal M. (2008-01-01). "Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices". Biopharmaceutics & Drug Disposition. 29 (2): 63–82. doi:10.1002/bdd.588. ISSN 1099-081X.
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  11. ^ Krause, M.; Galensa, R. (1991-07-01). "Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase". Chromatographia. 32 (1–2): 69–72. doi:10.1007/BF02262470. ISSN 0009-5893.
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  24. ^ Hungria, M.; Johnston, A. W.; Phillips, D. A. (1992-05-01). "Effects of flavonoids released naturally from bean (Phaseolus vulgaris) on nodD-regulated gene transcription in Rhizobium leguminosarum bv. phaseoli". Molecular plant-microbe interactions: MPMI. 5 (3): 199–203. ISSN 0894-0282. PMID 1421508.
  25. ^ 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.
  26. ^ 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.
  27. ^ 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.
  28. ^ 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.
  29. ^ 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 1381556. PMID 8485024.
  30. ^ 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.
  31. ^ Nishino, Chikao; Enoki, Nobuyasu; Tawata, Shinkichi; Mori, Akihisa; Kobayashi, Koji; Fukushima, Masako (1987-01-01). "Antibacterial Activity of Flavonoids against Staphylococcus epidermidis, a Skin Bacterium". Agricultural and Biological Chemistry. 51 (1): 139–143. doi:10.1080/00021369.1987.10867965. ISSN 0002-1369.
  32. ^ Rauha, Jussi-Pekka; Remes, Susanna; Heinonen, Marina; Hopia, Anu; Kähkönen, Marja; Kujala, Tytti; Pihlaja, Kalevi; Vuorela, Heikki; Vuorela, Pia (2000-05-25). "Antimicrobial effects of Finnish plant extracts containing flavonoids and other phenolic compounds". International Journal of Food Microbiology. 56 (1): 3–12. doi:10.1016/S0168-1605(00)00218-X.
  33. ^ Mandalari, G.; Bennett, R. N.; Bisignano, G.; Trombetta, D.; Saija, A.; Faulds, C. B.; Gasson, M. J.; Narbad, A. (2007-12-01). "Antimicrobial activity of flavonoids extracted from bergamot (Citrus bergamia Risso) peel, a byproduct of the essential oil industry". Journal of Applied Microbiology. 103 (6): 2056–2064. doi:10.1111/j.1365-2672.2007.03456.x. ISSN 1364-5072. PMID 18045389.
  34. ^ Koru, Ozgur; Toksoy, Fulya; Acikel, Cengiz Han; Tunca, Yasar Meric; Baysallar, Mehmet; Uskudar Guclu, Aylin; Akca, Eralp; Ozkok Tuylu, Asli; Sorkun, Kadriye (2007-06-01). "In vitro antimicrobial activity of propolis samples from different geographical origins against certain oral pathogens". Anaerobe. 13 (3–4): 140–145. doi:10.1016/j.anaerobe.2007.02.001. ISSN 1075-9964. PMID 17475517.
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  52. ^ Harmon, Anne W.; Patel, Yashomati M. (2004-05-01). "Naringenin Inhibits Glucose Uptake in MCF-7 Breast Cancer Cells: A Mechanism for Impaired Cellular Proliferation". Breast Cancer Research and Treatment. 85 (2): 103–110. doi:10.1023/B:BREA.0000025397.56192.e2. ISSN 0167-6806.
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  57. ^ Gao, K; Henning, S; Niu, Y; Youssefian, A; Seeram, N; Xu, A; Heber, D (2006). "The citrus flavonoid naringenin stimulates DNA repair in prostate cancer cells". The Journal of Nutritional Biochemistry. 17 (2): 89–95. doi:10.1016/j.jnutbio.2005.05.009. PMID 16111881.
  58. ^ a b 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 2265593. PMID 17685652.


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