Naringenin
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MedKoo CAT#: 527706

CAS#: 480-41-1

Description: Naringenin is a bioflavonoid drug potentially for the treatment of HCV infection. has antioxidant and chelating effects in the liver. Naringenin significantly suppressed UVB-induced extracellular signal-regulated kinase 2 (ERK2) activity and subsequently attenuated UVB-induced phosphorylation of p90(RSK) by competitively binding with ATP. Naringenin exerts potent anti-photoaging effects by suppressing ERK2 activity and decreasing FRA1 stability, followed by down-regulation of AP-1 transactivation and MMP-1 expression. Naringenin blocks TGF-β1 trafficking from the trans-Golgi network by suppressing PKC activity, resulting in a reduction of TGF-β1 secretion from breast cancer cells.


Price and Availability

Size Price Shipping out time Quantity
25g USD 375 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-09-22. Prices are subject to change without notice.

Naringenin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 527706
Name: Naringenin
CAS#: 480-41-1
Chemical Formula: C15H12O5
Exact Mass: 272.0685
Molecular Weight: 272.256
Elemental Analysis: C, 66.17; H, 4.44; O, 29.38


Synonym: Naringenin; NSC 11855; NSC-11855; NSC11855

IUPAC/Chemical Name: (S)-5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

InChi Key: FTVWIRXFELQLPI-ZDUSSCGKSA-N

InChi Code: InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

SMILES Code: O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O)=CC(O)=C13


Technical Data

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


References

1: Tang JY, Jin P, He Q, Lu LH, Ma JP, Gao WL, Bai HP, Yang J. Naringenin ameliorates hypoxia/reoxygenation-induced endoplasmic reticulum stress-mediated apoptosis in H9c2 myocardial cells: involvement in ATF6, IRE1α and PERK signaling activation. Mol Cell Biochem. 2017 Jan;424(1-2):111-122. doi: 10.1007/s11010-016-2848-1. PubMed PMID: 27785700.

2: Ozkaya A, Sahin Z, Dag U, Ozkaraca M. Effects of Naringenin on Oxidative Stress and Histopathological Changes in the Liver of Lead Acetate Administered Rats. J Biochem Mol Toxicol. 2016 May;30(5):243-8. doi: 10.1002/jbt.21785. PubMed PMID: 26929248.

3: Jung SK, Ha SJ, Jung CH, Kim YT, Lee HK, Kim MO, Lee MH, Mottamal M, Bode AM, Lee KW, Dong Z. Naringenin targets ERK2 and suppresses UVB-induced photoaging. J Cell Mol Med. 2016 May;20(5):909-19. doi: 10.1111/jcmm.12780. PubMed PMID: 26861188; PubMed Central PMCID: PMC4831363.

4: Chattopadhyay D, Sen S, Chatterjee R, Roy D, James J, Thirumurugan K. Context- and dose-dependent modulatory effects of naringenin on survival and development of Drosophila melanogaster. Biogerontology. 2016 Apr;17(2):383-93. doi: 10.1007/s10522-015-9624-6. PubMed PMID: 26520643.

5: Zhang F, Dong W, Zeng W, Zhang L, Zhang C, Qiu Y, Wang L, Yin X, Zhang C, Liang W. Naringenin prevents TGF-β1 secretion from breast cancer and suppresses pulmonary metastasis by inhibiting PKC activation. Breast Cancer Res. 2016 Apr 1;18(1):38. doi: 10.1186/s13058-016-0698-0. PubMed PMID: 27036297; PubMed Central PMCID: PMC4818388.

6: Wu LH, Lin C, Lin HY, Liu YS, Wu CY, Tsai CF, Chang PC, Yeh WL, Lu DY. Naringenin Suppresses Neuroinflammatory Responses Through Inducing Suppressor of Cytokine Signaling 3 Expression. Mol Neurobiol. 2016 Mar;53(2):1080-91. doi: 10.1007/s12035-014-9042-9. PubMed PMID: 25579382.

7: Ren B, Qin W, Wu F, Wang S, Pan C, Wang L, Zeng B, Ma S, Liang J. Apigenin and naringenin regulate glucose and lipid metabolism, and ameliorate vascular dysfunction in type 2 diabetic rats. Eur J Pharmacol. 2016 Feb 15;773:13-23. doi: 10.1016/j.ejphar.2016.01.002. PubMed PMID: 26801071.

8: Ke JY, Cole RM, Hamad EM, Hsiao YH, Cotten BM, Powell KA, Belury MA. Citrus flavonoid, naringenin, increases locomotor activity and reduces diacylglycerol accumulation in skeletal muscle of obese ovariectomized mice. Mol Nutr Food Res. 2016 Feb;60(2):313-24. doi: 10.1002/mnfr.201500379. PubMed PMID: 26573879; PubMed Central PMCID: PMC4789085.

9: Hashimoto T, Ide T. Activity and mRNA Levels of Enzymes Involved in Hepatic Fatty Acid Synthesis in Rats Fed Naringenin. J Agric Food Chem. 2015 Nov 4;63(43):9536-42. doi: 10.1021/acs.jafc.5b03734. PubMed PMID: 26466635.

10: Roy S, Ahmed F, Banerjee S, Saha U. Naringenin ameliorates streptozotocin-induced diabetic rat renal impairment by downregulation of TGF-β1 and IL-1 via modulation of oxidative stress correlates with decreased apoptotic events. Pharm Biol. 2016 Sep;54(9):1616-27. doi: 10.3109/13880209.2015.1110599. PubMed PMID: 26928632.

11: Orrego-Lagarón N, Martínez-Huélamo M, Vallverdú-Queralt A, Lamuela-Raventos RM, Escribano-Ferrer E. High gastrointestinal permeability and local metabolism of naringenin: influence of antibiotic treatment on absorption and metabolism. Br J Nutr. 2015 Jul;114(2):169-80. doi: 10.1017/S0007114515001671. PubMed PMID: 26083965.

12: Manchope MF, Calixto-Campos C, Coelho-Silva L, Zarpelon AC, Pinho-Ribeiro FA, Georgetti SR, Baracat MM, Casagrande R, Verri WA Jr. Naringenin Inhibits Superoxide Anion-Induced Inflammatory Pain: Role of Oxidative Stress, Cytokines, Nrf-2 and the NO-cGMP-PKG-KATP Channel Signaling Pathway. PLoS One. 2016 Apr 5;11(4):e0153015. doi: 10.1371/journal.pone.0153015. PubMed PMID: 27045367; PubMed Central PMCID: PMC4821586.

13: Kumar S, Tiku AB. Biochemical and Molecular Mechanisms of Radioprotective Effects of Naringenin, a Phytochemical from Citrus Fruits. J Agric Food Chem. 2016 Mar 2;64(8):1676-85. doi: 10.1021/acs.jafc.5b05067. PubMed PMID: 26881453.

14: Fouad AA, Albuali WH, Jresat I. Protective Effect of Naringenin against Lipopolysaccharide-Induced Acute Lung Injury in Rats. Pharmacology. 2016;97(5-6):224-32. doi: 10.1159/000444262. PubMed PMID: 26872264.

15: Demirdag R, Comakli V, Ozkaya A, Sahin Z, Dag U, Yerlikaya E, Kuzu M. Examination of changes in enzyme activities of erythrocyte glucose 6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase in rats given Naringenin and Lead acetate. J Biochem Mol Toxicol. 2015 Jan;29(1):43-7. doi: 10.1002/jbt.21606. PubMed PMID: 25228019.

16: Park HJ, Choi YJ, Lee JH, Nam MJ. Naringenin causes ASK1-induced apoptosis via reactive oxygen species in human pancreatic cancer cells. Food Chem Toxicol. 2017 Jan;99:1-8. doi: 10.1016/j.fct.2016.11.008. PubMed PMID: 27838343.

17: Shi D, Xu Y, Du X, Chen X, Zhang X, Lou J, Li M, Zhuo J. Co-treatment of THP-1 cells with naringenin and curcumin induces cell cycle arrest and apoptosis via numerous pathways. Mol Med Rep. 2015 Dec;12(6):8223-8. doi: 10.3892/mmr.2015.4480. PubMed PMID: 26496980.

18: Li YR, Chen DY, Chu CL, Li S, Chen YK, Wu CL, Lin CC. Naringenin inhibits dendritic cell maturation and has therapeutic effects in a murine model of collagen-induced arthritis. J Nutr Biochem. 2015 Dec;26(12):1467-78. doi: 10.1016/j.jnutbio.2015.07.016. PubMed PMID: 26350255.

19: Yoshida H, Tsuhako R, Atsumi T, Narumi K, Watanabe W, Sugita C, Kurokawa M. Naringenin interferes with the anti-diabetic actions of pioglitazone via pharmacodynamic interactions. J Nat Med. 2016 Dec 3. [Epub ahead of print] PubMed PMID: 27915399.

20: Álvarez-Álvarez R, Botas A, Albillos SM, Rumbero A, Martín JF, Liras P. Molecular genetics of naringenin biosynthesis, a typical plant secondary metabolite produced by Streptomyces clavuligerus. Microb Cell Fact. 2015 Nov 9;14:178. doi: 10.1186/s12934-015-0373-7. PubMed PMID: 26553209; PubMed Central PMCID: PMC4640377.