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Chemical Structure| 10236-47-2 Chemical Structure| 10236-47-2

Structure of Naringin
CAS No.: 10236-47-2

Chemical Structure| 10236-47-2

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Naringin is a flavanone glycoside, which exerts a variety of pharmacological effects such as antioxidant activity, blood lipid lowering, anticancer activity, and inhibition of cytochrome P450 enzymes.

Synonyms: Naringoside; NSC 5548; AI3-19008

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Product Citations

Product Citations

Tonduru, Arun Kumar ; Maljaei, Seyed Hamed ; Adla, Santosh Kumar ; Anamea, Landry ; Tampio, Janne ; Kralova, Adela , et al.

Abstract: OATP1C1 (organic anion-transporting polypeptide 1C1) transports thyroid hormones, particularly thyroxine (T4), into human astrocytes. In this study, we investigated the potential of utilizing OATP1C1 to improve the delivery of anti-inflammatory drugs into glial cells. We designed and synthesized eight novel prodrugs by incorporating T4 and 3,5-diiodo-L-tyrosine (DIT) as promoieties to selected anti-inflammatory drugs. The prodrug uptake in OATP1C1-expressing human U-87MG glioma cells demonstrated higher accumulation with T4 promoiety compared to those with DIT promoiety or the parent drugs themselves. In silico models of OATP1C1 suggested dynamic binding for the prodrugs, wherein the pose changed from vertical to horizontal. The predicted binding energies correlated with the transport profiles, with T4 derivatives exhibiting higher binding energies when compared to prodrugs with a DIT promoiety. Interestingly, the prodrugs also showed utilization of oatp1a4/1a5/1a6 in mouse primary astrocytes, which was further supported by docking studies and a great potential for improved brain drug delivery.

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Product Details of Naringin

CAS No. :10236-47-2
Formula : C27H32O14
M.W : 580.53
SMILES Code : O=C1C2=C(C=C(O[C@H](O[C@H](CO)[C@@H](O)[C@@H]3O)[C@@H]3O[C@H]4[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)C=C2O)O[C@H](C5=CC=C(O)C=C5)C1
Synonyms :
Naringoside; NSC 5548; AI3-19008
MDL No. :MFCD00148888
InChI Key :DFPMSGMNTNDNHN-ZPHOTFPESA-N
Pubchem ID :442428

Safety of Naringin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

In Vitro:

Cell Line
Concentration Treated Time Description References
3T3-L1 cells 6.25–25 μM 48 h increased UCP1 and PGC-1α gene expression Curr Res Food Sci. 2024 Jan 18;8:100683.
MC3T3-E1 cells 80 μg/mL 72 h CS@MSNs-Naringin showed low cytotoxicity to MC3T3-E1 cells. Int J Nanomedicine. 2024 Jun 24;19:6337-6358.
Bone marrow-derived macrophages (BMMs) 80 μg/mL 7 days CS@MSNs-Naringin significantly inhibited osteoclast formation and bone resorption activity, accompanied by decreased phosphorylation of key factors in the NF-κB and MAPK signaling pathways, increased apoptosis levels, and a reduction in the production of osteoclast-specific genes and proteins. Int J Nanomedicine. 2024 Jun 24;19:6337-6358.
HUVECs 60-100 µM 24 h To evaluate the effect of naringin on HUVECs migration and tube formation. The results showed that naringin significantly inhibited the migration and tube formation capacity of HUVECs. Antioxidants (Basel). 2025 Feb 18;14(2):236.
ARPE-19 cells 60-100 µM 24 h To evaluate the protective effect of naringin on CoCl2-induced damage in ARPE-19 cells. The results showed that naringin pretreatment significantly increased the viability of ARPE-19 cells and reduced CoCl2-induced cytotoxicity. Antioxidants (Basel). 2025 Feb 18;14(2):236.
Bone marrow-derived macrophages (BMDMs) 50, 100, 200 µM 24 h To investigate the effect of naringin on LPS-stimulated macrophage polarization, results showed that naringin significantly reduced the expression of inflammatory cytokines IL-1β, IL-6, and TNF-α, and promoted M2 macrophage polarization. Mol Ther Nucleic Acids. 2021 Jul 16;25:502-514.
Xenopus oocytes 30 μM To investigate the inhibitory effect of naringin on capsaicin-induced TRPV1 currents, results showed that naringin reversibly inhibited TRPV1 currents. Antioxidants (Basel). 2021 Dec 28;11(1):64.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Rats Bilateral calvarial bone defect model In situ drug delivery 1 mg/mL Single dose, lasting 8 weeks CS@MSNs-Naringin promoted new bone formation while significantly inhibiting osteoclast activity in vivo. Int J Nanomedicine. 2024 Jun 24;19:6337-6358.
C57BL/6J mice High-fat diet-induced obesity model Oral gavage 100 mg/kg Daily for 12 weeks Naringin significantly inhibited gain, reduced liver and epididymal white adipose tissue (eWAT) weight, improved glucose tolerance, and promoted brown adipose tissue (BAT) thermogenesis and white adipose tissue (WAT) browning. Additionally, Naringin altered gut microbiota composition, increasing the abundance of Bifidobacterium and Lachnospiraceae_bacterium_28-4, while reducing the abundance of Lachnospiraceae_bacterium_DW59 and Dubosiella_newyorkensis. Curr Res Food Sci. 2024 Jan 18;8:100683.
C57BL/6 mice Cecal ligation and puncture (CLP)-induced sepsis model Intraperitoneal injection 10, 30, 60 mg/kg Single dose, monitored for 72 hours To investigate the protective effect of naringin on sepsis-induced intestinal injury, results showed that naringin significantly improved the survival rate of septic mice, alleviated inflammatory response and intestinal damage, and promoted M2 macrophage polarization. Mol Ther Nucleic Acids. 2021 Jul 16;25:502-514.
Mice Balb C white laboratory mice Intragastric administration 500 mg/kg Once daily for 21 days To evaluate the effects of naringin and grapefruit extract on oxidative stress biomarkers, results showed naringin significantly restored GSH levels and CAT activity, while grapefruit extract significantly reduced MDA levels Antioxidants (Basel). 2025 Jan 28;14(2):157

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

1.72mL

0.34mL

0.17mL

8.61mL

1.72mL

0.86mL

17.23mL

3.45mL

1.72mL

References

[1]Schindler R, Mentlein R. Flavonoids and vitamin E reduce the release of the angiogenic peptide vascular endothelial growth factor from human tumor cells. J Nutr. 2006 Jun;136(6):1477-82.

[2]Ueng YF, Chang YL, et al. In vitro and in vivo effects of naringin on cytochrome P450-dependent monooxygenase in mouse liver. Life Sci. 1999;65(24):2591-602.

[3]de Castro WV, Mertens-Talcott S, et al. Effect of grapefruit juice, naringin, naringenin, and bergamottin on the intestinal carrier-mediated transport of talinolol in rats. J Agric Food Chem. 2008 Jun 25;56(12):4840-5.

[4]Punithavathi VR, Anuthama R, et al. Combined treatment with naringin and vitamin C ameliorates streptozotocin-induced diabetes in male Wistar rats. J Appl Toxicol. 2008 Aug;28(6):806-13.

[5]Li F, Sun X, et al. Naringin prevents ovariectomy-induced osteoporosis and promotes osteoclasts apoptosis through the mitochondria-mediated apoptosis pathway. Biochem Biophys Res Commun. 2014 Sep 26;452(3):629-35.

[6]Chen F, Zhang N, Ma X, Huang T, Shao Y, Wu C, Wang Q. Naringin Alleviates Diabetic Kidney Disease through Inhibiting Oxidative Stress and Inflammatory Reaction. PLoS One. 2015 Nov 30;10(11):e0143868. doi: 10.1371/journal.pone.0143868. Retraction in: PLoS One. 2018 Feb 1;13(2):e0192465. PMID: 26619044; PMCID: PMC4664292.

[7]Ueng YF, Chang YL, Oda Y, Park SS, Liao JF, Lin MF, Chen CF. In vitro and in vivo effects of naringin on cytochrome P450-dependent monooxygenase in mouse liver. Life Sci. 1999;65(24):2591-602. doi: 10.1016/s0024-3205(99)00528-7. PMID: 10619367.

[8]Raha S, Yumnam S, Hong GE, Lee HJ, Saralamma VV, Park HS, Heo JD, Lee SJ, Kim EH, Kim JA, Kim GS. Naringin induces autophagy-mediated growth inhibition by downregulating the PI3K/Akt/mTOR cascade via activation of MAPK pathways in AGS cancer cells. Int J Oncol. 2015 Sep;47(3):1061-9. doi: 10.3892/ijo.2015.3095. Epub 2015 Jul 20. PMID: 26201693.

[9]Kulasekaran G, Ganapasam S. Neuroprotective efficacy of naringin on 3-nitropropionic acid-induced mitochondrial dysfunction through the modulation of Nrf2 signaling pathway in PC12 cells. Mol Cell Biochem. 2015 Nov;409(1-2):199-211. doi: 10.1007/s11010-015-2525-9. Epub 2015 Aug 18. PMID: 26280522.

[10]Wang D, Yan J, Chen J, Wu W, Zhu X, Wang Y. Naringin Improves Neuronal Insulin Signaling, Brain Mitochondrial Function, and Cognitive Function in High-Fat Diet-Induced Obese Mice. Cell Mol Neurobiol. 2015 Oct;35(7):1061-71. doi: 10.1007/s10571-015-0201-y. Epub 2015 May 5. PMID: 25939427.

 

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