Naringin
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MedKoo CAT#: 540311

CAS#: 10236-47-2

Description: Naringin is a SERM(selective estrogen receptor modulator) found in citrus fruits. It exhibits a wide variety of biological activities, including inhibiting the release of VEGF in ER+ breast cancer cells, improving colchicine-induced deficits in cognitive performance, attenuating oxidative damage, and suppressing gentamicin-induced pro-inflammatory cytokine expresion.

Chemical Structure

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Naringin
CAS# 10236-47-2
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540311
Name: Naringin
CAS#: 10236-47-2
Chemical Formula: C27H32O14
Exact Mass: 580.18
Molecular Weight: 580.539
Elemental Analysis: C, 55.86; H, 5.56; O, 38.58

Price and Availability

Size Price Availability Quantity
5g USD 195
10g USD 320
25g USD 415
50g USD 650
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Synonym: Aurantiin; AI3-19008; AI319008; AI3 19008; Naringin; Naringoside

IUPAC/Chemical Name: 7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

InChi Key: DFPMSGMNTNDNHN-JJLSSNRUSA-N

InChi Code: InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16?,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

SMILES Code: O=C1CC(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O[C@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)O)O)O)=C3

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Naringin is a major flavanone glycoside obtained from tomatoes, grapefruits, and many other citrus fruits.
In vitro activity: This study investigated the inhibitory effect of Naringin on human AGS cancer cells. AGS cell proliferation was inhibited by Naringin in a dose- and time-dependent manner. Growth inhibitory role of Naringin was observed by western blot analysis demonstrating downregulation of PI3K/Akt/mTOR cascade with an upregulated p21CIPI/WAFI. Formation of cytoplasmic vacuoles and autophagosomes were observed in Naringin-treated AGS cells, further confirmed by the activation of autophagic proteins Beclin 1 and LC3B with a significant phosphorylation of mitogen activated protein kinases (MAPKs). Collectively, these observed results determined that anti-proliferative activity of Naringin in AGS cancer cells is due to suppression of PI3K/Akt/mTOR cascade via induction of autophagy with activated MAPKs. Reference: Int J Oncol. 2015 Sep;47(3):1061-9. https://pubmed.ncbi.nlm.nih.gov/26201693/
In vivo activity: These results showed that oral administration of naringin significantly improved the learning and memory abilities as evidenced by increasing recognition index by 52.5% in the novel object recognition test and inducing a 1.05-fold increase in the crossing-target number in the probe test, and ameliorated mitochondrial dysfunction in mice caused by HFD consumption. Moreover, naringin significantly enhanced insulin signaling pathway as indicated by a 34.5% increase in the expression levels of IRS-1, a 47.8% decrease in the p-IRS-1, a 1.43-fold increase in the p-Akt, and a 1.89-fold increase in the p-GSK-3β in the hippocampus of the HFDN mice versus HFD mice. Reference: Cell Mol Neurobiol. 2015 Oct;35(7):1061-71. https://pubmed.ncbi.nlm.nih.gov/25939427/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 20.0 34.45
DMF:PBS (pH 7.2) (1:1) 0.5 0.86
DMSO 78.3 134.93
Ethanol 23.5 40.48
Water 1.0 1.72

Preparing Stock Solutions

The following data is based on the product molecular weight 580.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. 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. 2. 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. 3. Wei Y, Sun L, Liu C, Li L. Naringin regulates endoplasmic reticulum stress and mitophagy through the ATF3/PINK1 signaling axis to alleviate pulmonary fibrosis. Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan 23. doi: 10.1007/s00210-023-02390-z. Epub ahead of print. PMID: 36688958. 4. 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.
In vitro protocol: 1. 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. 2. 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.
In vivo protocol: 1. Wei Y, Sun L, Liu C, Li L. Naringin regulates endoplasmic reticulum stress and mitophagy through the ATF3/PINK1 signaling axis to alleviate pulmonary fibrosis. Naunyn Schmiedebergs Arch Pharmacol. 2023 Jan 23. doi: 10.1007/s00210-023-02390-z. Epub ahead of print. PMID: 36688958. 2. 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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1: Bharti S, Rani N, Krishnamurthy B, Arya DS. Preclinical evidence for the pharmacological actions of naringin: a review. Planta Med. 2014 Apr;80(6):437-51. doi: 10.1055/s-0034-1368351. Epub 2014 Apr 7. Review. PubMed PMID: 24710903.

2: Li NH, Xu ZW. [Naringin reduced polymethylmethacrylate-induced osteolysis in the mouse air sacs model]. Zhongguo Gu Shang. 2015 Apr;28(4):345-9. Chinese. PubMed PMID: 26072618.

3: 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. eCollection 2015. PubMed PMID: 26619044; PubMed Central PMCID: PMC4664292.

4: Yin FM, Xiao LB, Zhang Y. [Research progress on Drynaria fortunei naringin on inflammation and bone activity]. Zhongguo Gu Shang. 2015 Feb;28(2):182-6. Review. Chinese. PubMed PMID: 25924506.

5: 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. PubMed PMID: 26280522.

6: Takumi S, Ikema S, Hanyu T, Shima Y, Kurimoto T, Shiozaki K, Sugiyama Y, Park HD, Ando S, Furukawa T, Komatsu M. Naringin attenuates the cytotoxicity of hepatotoxin microcystin-LR by the curious mechanisms to OATP1B1- and OATP1B3-expressing cells. Environ Toxicol Pharmacol. 2015 Mar;39(2):974-81. doi: 10.1016/j.etap.2015.02.021. Epub 2015 Mar 7. PubMed PMID: 25818985.

7: Jiao HY, Su WW, Li PB, Liao Y, Zhou Q, Zhu N, He LL. Therapeutic effects of naringin in a guinea pig model of ovalbumin-induced cough-variant asthma. Pulm Pharmacol Ther. 2015 Aug;33:59-65. doi: 10.1016/j.pupt.2015.07.002. Epub 2015 Jul 10. PubMed PMID: 26169899.

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. PubMed PMID: 26201693.

9: Ahmad SF, Attia SM, Bakheet SA, Zoheir KM, Ansari MA, Korashy HM, Abdel-Hamied HE, Ashour AE, Abd-Allah AR. Naringin attenuates the development of carrageenan-induced acute lung inflammation through inhibition of NF-κb, STAT3 and pro-inflammatory mediators and enhancement of IκBα and anti-inflammatory cytokines. Inflammation. 2015 Apr;38(2):846-57. doi: 10.1007/s10753-014-9994-y. PubMed PMID: 25117567.

10: Wang L, Zhang YG, Wang XM, Ma LF, Zhang YM. Naringin protects human adipose-derived mesenchymal stem cells against hydrogen peroxide-induced inhibition of osteogenic differentiation. Chem Biol Interact. 2015 Dec 5;242:255-61. doi: 10.1016/j.cbi.2015.10.010. Epub 2015 Oct 19. PubMed PMID: 26482937.

11: Qi Z, Xu Y, Liang Z, Li S, Wang J, Wei Y, Dong B. Naringin ameliorates cognitive deficits via oxidative stress, proinflammatory factors and the PPARγ signaling pathway in a type 2 diabetic rat model. Mol Med Rep. 2015 Nov;12(5):7093-101. doi: 10.3892/mmr.2015.4232. Epub 2015 Aug 20. PubMed PMID: 26300349.

12: Fan J, Li J, Fan Q. Naringin promotes differentiation of bone marrow stem cells into osteoblasts by upregulating the expression levels of microRNA-20a and downregulating the expression levels of PPARγ. Mol Med Rep. 2015 Sep;12(3):4759-65. doi: 10.3892/mmr.2015.3996. Epub 2015 Jun 24. PubMed PMID: 26126997.

13: Surampalli G, K Nanjwade B, Patil PA. Corroboration of naringin effects on the intestinal absorption and pharmacokinetic behavior of candesartan cilexetil solid dispersions using in-situ rat models. Drug Dev Ind Pharm. 2015;41(7):1057-65. doi: 10.3109/03639045.2014.925918. Epub 2014 Jun 11. PubMed PMID: 24918161.

14: Wang D, Ma W, Wang F, Dong J, Wang D, Sun B, Wang B. Stimulation of Wnt/β-Catenin Signaling to Improve Bone Development by Naringin via Interacting with AMPK and Akt. Cell Physiol Biochem. 2015;36(4):1563-76. doi: 10.1159/000430319. Epub 2015 Jul 10. PubMed PMID: 26159568.

15: Li CH, Wang JW, Ho MH, Shih JL, Hsiao SW, Thien DV. Immobilization of naringin onto chitosan substrates by using ozone activation. Colloids Surf B Biointerfaces. 2014 Mar 1;115:1-7. doi: 10.1016/j.colsurfb.2013.11.006. Epub 2013 Nov 15. PubMed PMID: 24317428.

16: Cao X, Lin W, Liang C, Zhang D, Yang F, Zhang Y, Zhang X, Feng J, Chen C. Naringin rescued the TNF-α-induced inhibition of osteogenesis of bone marrow-derived mesenchymal stem cells by depressing the activation of NF-кB signaling pathway. Immunol Res. 2015 Jul;62(3):357-67. doi: 10.1007/s12026-015-8665-x. PubMed PMID: 26032685.

17: 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. PubMed PMID: 25939427.

18: Li F, Sun X, Ma J, Ma X, Zhao B, Zhang Y, Tian P, Li Y, Han Z. 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. doi: 10.1016/j.bbrc.2014.08.117. Epub 2014 Aug 30. PubMed PMID: 25181344.

19: Adil M, Kandhare AD, Visnagri A, Bodhankar SL. Naringin ameliorates sodium arsenite-induced renal and hepatic toxicity in rats: decisive role of KIM-1, Caspase-3, TGF-β, and TNF-α. Ren Fail. 2015;37(8):1396-407. doi: 10.3109/0886022X.2015.1074462. Epub 2015 Sep 3. PubMed PMID: 26337322.

20: Li N, Xu Z, Wooley PH, Zhang J, Yang SY. Therapeutic potentials of naringin on polymethylmethacrylate induced osteoclastogenesis and osteolysis, in vitro and in vivo assessments. Drug Des Devel Ther. 2013 Dec 10;8:1-11. doi: 10.2147/DDDT.S52714. eCollection 2014. PubMed PMID: 24376342; PubMed Central PMCID: PMC3864877.