The fate and biological functions of naringeninin vivo are unknown, remaining under preliminary research, as of 2024.[2] High consumption of dietary naringenin is generally regarded as safe, mainly due to its low bioavailability.[2] Takingdietary supplements or consuming grapefruit excessively may impair the action ofanticoagulants and increase the toxicity of variousprescription drugs.[2]
Similar tofuranocoumarins present in citrus fruits, naringenin may evokeCYP3A4 suppression in the liver and intestines, possibly resulting in adverseinteractions with common medications.[2][3][4][5]
Like the majority of flavanones, naringenin has a single chiral center at carbon 2, although the optical purity is variable.[6][7]Racemization of (S)-(−)-naringenin has been shown to occur fairly quickly.[8]
Naringenin can be produced from naringin by the hydrolytic action of the liver enzyme naringinase.[2] Naringenin is derived frommalonyl-CoA and4-coumaroyl-CoA.[2] The latter is derived fromphenylalanine. The resulting tetraketide is acted on bychalcone synthase to give the chalcone that then undergoes ring-closure to naringenin.[19]
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.[2][21] The biological activities of naringenin metabolites are unknown, and likely to be different in structure and function from those of the parent compound.[2][21]Naringenin has been proposed as a potential nephroprotective agent in diabetic kidney disease.[22]
^abcdefghijklm"Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2024. Retrieved9 May 2024.
^Lohezic-Le Devehat, F.; Marigny, K.; Doucet, M.; Javaudin, L. (2002). "[Grapefruit juice and drugs: a hazardous combination?]".Therapie.57 (5):432–445.ISSN0040-5957.PMID12611197.
^Yáñez JA, Andrews PK, Davies NM (April 2007). "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.PMID17113835.
^abYáñez JA, Remsberg CM, Miranda ND, Vega-Villa KR, Andrews PK, Davies NM (March 2008). "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.PMID18058792.S2CID24051610.
^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.32 (1–2):69–72.doi:10.1007/BF02262470.ISSN0009-5893.S2CID95215634.
^Gel-Moreto N, Streich R, Galensa R (August 2003). "Chiral separation of diastereomeric flavanone-7-O-glycosides in citrus by capillary electrophoresis".Electrophoresis.24 (15):2716–2722.doi:10.1002/elps.200305486.PMID12900888.S2CID40261445.
^Wang H, Nair MG, Strasburg GM, Booren AM, Gray JI (March 1999). "Antioxidant polyphenols from tart cherries (Prunus cerasus)".Journal of Agricultural and Food Chemistry.47 (3):840–844.Bibcode:1999JAFC...47..840W.doi:10.1021/jf980936f.PMID10552377.
^Vallverdú Queralt A, Odriozola Serrano I, Oms Oliu G, Lamuela Raventós RM, Elez Martínez P,Martín Belloso O (September 2012). "Changes in the polyphenol profile of tomato juices processed by pulsed electric fields".Journal of Agricultural and Food Chemistry.60 (38):9667–9672.Bibcode:2012JAFC...60.9667V.doi:10.1021/jf302791k.PMID22957841.
^Sánchez Rabaneda F, Jáuregui O, Casals I, Andrés Lacueva C, Izquierdo Pulido M, Lamuela Raventós RM (January 2003). "Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao)".Journal of Mass Spectrometry.38 (1):35–42.Bibcode:2003JMSp...38...35S.doi:10.1002/jms.395.PMID12526004.
^Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J (November 2003). "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.doi:10.1021/ac0347819.PMID14616013.
^Olsen HT, Stafford GI, van Staden J, Christensen SB, Jäger AK (May 2008). "Isolation of the MAO-inhibitor naringenin from Mentha aquatica L".Journal of Ethnopharmacology.117 (3):500–502.doi:10.1016/j.jep.2008.02.015.PMID18372132.
^Hungria M, Johnston AW, Phillips DA (1992-05-01). "Effects of flavonoids released naturally from bean (Phaseolus vulgaris) on nodD-regulated gene transcription inRhizobium leguminosarum bv.phaseoli".Molecular Plant-Microbe Interactions.5 (3):199–203.Bibcode:1992MPMI....5..199H.doi:10.1094/mpmi-5-199.PMID1421508.
^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".Biochemical and Biophysical Research Communications.265 (2):410–415.Bibcode:1999BBRC..265..410C.doi:10.1006/bbrc.1999.1695.PMID10558881.
^Wang C, Zhi S, Liu C, Xu F, Zhao A, Wang X, et al. (March 2017). "Characterization of Stilbene Synthase Genes in Mulberry (Morus atropurpurea) and Metabolic Engineering for the Production of Resveratrol inEscherichia coli".Journal of Agricultural and Food Chemistry.65 (8):1659–1668.Bibcode:2017JAFC...65.1659W.doi:10.1021/acs.jafc.6b05212.PMID28168876.
