Naringenin Explained

Naringenin is a flavanone from the flavonoid group of polyphenols.[1] It is commonly found in citrus fruits, especially as the predominant flavonone in grapefruit.[1]

The fate and biological functions of naringenin in vivo are unknown, remaining under preliminary research, as of 2024.[1] High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability.[1] Taking dietary supplements or consuming grapefruit excessively may impair the action of anticoagulants and increase the toxicity of various prescription drugs.[1]

Similar to furanocoumarins present in citrus fruits, naringenin may evoke CYP3A4 suppression in the liver and intestines, possibly resulting in adverse interactions with common medications.[1] [2] [3] [4]

Structure

Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4′, 5, and 7 carbons.[1] 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, oranges, and lemons,[1] sour orange,[8] sour cherries,[9] tomatoes,[10] cocoa,[11] Greek oregano,[12] water mint,[13] as well as in beans.[14] Ratios of naringenin to naringin vary among sources,[1] as do enantiomeric ratios.

The naringenin-7-glucoside form seems less bioavailable than the aglycol form.[15]

Grapefruit juice can provide much higher plasma concentrations of naringenin than orange juice.[16]

Naringenin can be absorbed from cooked tomato paste. There are 3.8 mg of naringenin in 150 grams of tomato paste.[17]

Biosynthesis and metabolism

Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase.[1] Naringenin is derived from malonyl-CoA and 4-coumaroyl-CoA.[1] The latter is derived from phenylalanine. The resulting tetraketide is acted on by chalcone synthase to give the chalcone that then undergoes ring-closure to naringenin.[18]

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.[19]

Metabolic fate and research

The fate and biological roles of naringenin are difficult to study because naringenin is rapidly metabolized in the intestine and liver, and its metabolites are destined for excretion.[1] [20] The biological activities of naringenin metabolites are unknown, and likely to be different in structure and function from those of the parent compound.[1] [20]

Notes and References

  1. Web site: Flavonoids . Micronutrient Information Center, Linus Pauling Institute, Oregon State University . 9 May 2024 . 2024.
  2. Lohezic-Le Devehat . F. . Marigny . K. . Doucet . M. . Javaudin . L. . 2002 . [Grapefruit juice and drugs: a hazardous combination?]. Therapie . 57 . 5 . 432–445 . 0040-5957 . 12611197.
  3. Singh . B. N. . September 1999 . Effects of food on clinical pharmacokinetics . Clinical Pharmacokinetics . 37 . 3 . 213–255 . 10.2165/00003088-199937030-00003 . 0312-5963 . 10511919.
  4. Fuhr . U. . April 1998 . Drug interactions with grapefruit juice. Extent, probable mechanism and clinical relevance . Drug Safety . 18 . 4 . 251–272 . 10.2165/00002018-199818040-00002 . 0114-5916 . 9565737.
  5. Yáñez JA, Andrews PK, Davies NM . Methods of analysis and separation of chiral flavonoids . Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences . 848 . 2 . 159–181 . April 2007 . 17113835 . 10.1016/j.jchromb.2006.10.052 .
  6. Yáñez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM . Pharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices . Biopharmaceutics & Drug Disposition . 29 . 2 . 63–82 . March 2008 . 18058792 . 10.1002/bdd.588 . 24051610 .
  7. Krause M, Galensa R . July 1991 . Analysis of enantiomeric flavanones in plant extracts by high-performance liquid chromatography on a cellulose triacetate based chiral stationary phase. Chromatographia. en. 32. 1–2. 69–72. 10.1007/BF02262470. 95215634. 0009-5893.
  8. Gel-Moreto N, Streich R, Galensa R . Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis . Electrophoresis . 24 . 15 . 2716–2722 . August 2003 . 12900888 . 10.1002/elps.200305486 . 40261445 .
  9. Wang H, Nair MG, Strasburg GM, Booren AM, Gray JI . Antioxidant polyphenols from tart cherries (Prunus cerasus) . Journal of Agricultural and Food Chemistry . 47 . 3 . 840–844 . March 1999 . 10552377 . 10.1021/jf980936f .
  10. Vallverdú Queralt A, Odriozola Serrano I, Oms Oliu G, Lamuela Raventós RM, Elez Martínez P, Martín Belloso O . Changes in the polyphenol profile of tomato juices processed by pulsed electric fields . Journal of Agricultural and Food Chemistry . 60 . 38 . 9667–9672 . September 2012 . 22957841 . 10.1021/jf302791k . Olga Martín-Belloso .
  11. Sánchez Rabaneda F, Jáuregui O, Casals I, Andrés Lacueva C, Izquierdo Pulido M, Lamuela Raventós RM . Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao) . Journal of Mass Spectrometry . 38 . 1 . 35–42 . January 2003 . 12526004 . 10.1002/jms.395 . 2003JMSp...38...35S .
  12. Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J . LC-UV-solid-phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano . Analytical Chemistry . 75 . 22 . 6288–6294 . November 2003 . 14616013 . 10.1021/ac0347819 .
  13. Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger AK . Isolation of the MAO-inhibitor naringenin from Mentha aquatica L . Journal of Ethnopharmacology . 117 . 3 . 500–502 . May 2008 . 18372132 . 10.1016/j.jep.2008.02.015 .
  14. Hungria M, Johnston AW, Phillips DA . Effects of flavonoids released naturally from bean (Phaseolus vulgaris) on nodD-regulated gene transcription in Rhizobium leguminosarum bv. phaseoli . Molecular Plant-Microbe Interactions . 5 . 3 . 199–203 . 1992-05-01 . 1421508 . 10.1094/mpmi-5-199 .
  15. Choudhury R, Chowrimootoo G, Srai K, Debnam E, Rice-Evans CA . Interactions of the flavonoid naringenin in the gastrointestinal tract and the influence of glycosylation . Biochemical and Biophysical Research Communications . 265 . 2 . 410–415 . November 1999 . 10558881 . 10.1006/bbrc.1999.1695 .
  16. Erlund I, Meririnne E, Alfthan G, Aro A . Plasma kinetics and urinary excretion of the flavanones naringenin and hesperetin in humans after ingestion of orange juice and grapefruit juice . The Journal of Nutrition . 131 . 2 . 235–241 . February 2001 . 11160539 . 10.1093/jn/131.2.235 . free .
  17. Bugianesi R, Catasta G, Spigno P, D'Uva A, Maiani G . Naringenin from cooked tomato paste is bioavailable in men . The Journal of Nutrition . 132 . 11 . 3349–3352 . November 2002 . 12421849 . 10.1093/jn/132.11.3349 . free .
  18. Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, Ren Y, Li Z, Yu M . 6 . Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol in Escherichia coli . Journal of Agricultural and Food Chemistry . 65 . 8 . 1659–1668 . March 2017 . 28168876 . 10.1021/acs.jafc.6b05212 .
  19. Ibrahim AR . Sulfation of naringenin by Cunninghamella elegans . Phytochemistry . 53 . 2 . 209–212 . January 2000 . 10680173 . 10.1016/S0031-9422(99)00487-2 . 2000PChem..53..209I .
  20. Rothwell JA, Urpi-Sarda M, Boto-Ordoñez M, Llorach R, Farran-Codina A, Barupal DK, Neveu V, Manach C, Andres-Lacueva C, Scalbert A . Systematic analysis of the polyphenol metabolome using the Phenol-Explorer database . Molecular Nutrition & Food Research . 60 . 1 . 203–11 . January 2016 . 26310602 . 5057353 . 10.1002/mnfr.201500435.

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