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]
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 disaccharideneohesperidose 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]
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]
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]
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 DNAin 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]
Wistuba, Dorothee; Trapp, Oliver; Gel-Moreto, Nuria; Galensa, Rudolf; Schurig, Volker (2006-05-01). "Stereoisomeric Separation of Flavanones and Flavanone-7-O-glycosides by Capillary Electrophoresis and Determination of Interconversion Barriers". Analytical Chemistry. 78 (10): 3424–3433. doi:10.1021/ac0600499. ISSN0003-2700. PMID16689546.
Krause, Martin; Galensa, Rudolf (1991). "High-performance liquid chromatography of diastereomeric flavanone glycosides in Citrus on a β-cyclodextrin-bonded stationary phase (Cyclobond I)". Journal of Chromatography A. 588 (1–2): 41–45. doi:10.1016/0021-9673(91)85005-z.
Gaggeri, Raffaella; Rossi, Daniela; Collina, Simona; Mannucci, Barbara; Baierl, Marcel; Juza, Markus (2011-08-12). "Quick development of an analytical enantioselective high performance liquid chromatography separation and preparative scale-up for the flavonoid Naringenin". Journal of Chromatography A. 1218 (32): 5414–5422. doi:10.1016/j.chroma.2011.02.038. PMID21397238.
Naringenin also produces BDNF-dependent antidepressant-like effects in mice.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. PMID24121063. S2CID24620048.
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. PMID16111881.
Naringenin has been reported to induce apoptosis in preadipocytes.Hsu, Chin-Lin; Huang, Shih-Li; Yen, Gow-Chin (2006-06-01). "Inhibitory Effect of Phenolic Acids on the Proliferation of 3T3-L1 Preadipocytes in Relation to Their Antioxidant Activity". Journal of Agricultural and Food Chemistry. 54 (12): 4191–4197. doi:10.1021/jf0609882. ISSN0021-8561. PMID16756346.
Naringenin lowers the plasma and hepatic cholesterol concentrations by suppressing HMG-CoA reductase and ACAT in rats fed a high-cholesterol diet.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. PMID10545673. S2CID5685548.
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