(S)-Naringenin

• CAT Number: R063662
• CAS Number: 480-41-1
• Molecular Formula: C15H12O5
• Molecular Weight: 272.25
• Purity: ≥95%
• Storage: 3 years -20C powder
• InChI: 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
• InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
• SMILES: O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O)=CC(O)=C13

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.

Reference

1:Naringenin improves the healing process of thermally-induced skin damage in rats. Al-Roujayee AS.J Int Med Res. 2017 Apr;45(2):570-582. doi: 10.1177/0300060517692483. Epub 2017 Mar 16. PMID: 28415935 2:Enantioselective Modulatory Effects of Naringenin  Enantiomers on the Expression Levels of miR-17-3p  Involved in Endogenous Antioxidant Defenses. Curti V, Di Lorenzo A, Rossi D, Martino E, Capelli E, Collina S, Daglia M.Nutrients. 2017 Feb 28;9(3). pii: E215. doi: 10.3390/nu9030215. PMID: 28264488 Free PMC Article3:Absorption and disposition of naringenin and quercetin after simultaneous administration via intestinal perfusion in mice. Orrego-Lagarón N, Martínez-Huélamo M, Quifer-Rada P, Lamuela-Raventos RM, Escribano-Ferrer E.Food Funct. 2016 Sep 14;7(9):3880-9. doi: 10.1039/c6fo00633g. Epub 2016 Aug 12. PMID: 27515345 4:Hydroxylation of diverse flavonoids by CYP450 BM3 variants: biosynthesis of eriodictyol from naringenin in whole cells and its biological activities. Chu LL, Pandey RP, Jung N, Jung HJ, Kim EH, Sohng JK.Microb Cell Fact. 2016 Aug 5;15(1):135. doi: 10.1186/s12934-016-0533-4. PMID: 27495155 Free PMC Article5:Naringenin Alleviates Cadmium-Induced Toxicity through the Abrogation of Oxidative Stress in Swiss Albino Mice. Das A, Roy A, Das R, Bhattacharya S, Haldar PK.J Environ Pathol Toxicol Oncol. 2016;35(2):161-9. doi: 10.1615/JEnvironPatholToxicolOncol.2016015892. PMID: 27481493 6:Naringenin ameliorates pathological changes in liver and kidney of diabetic mice: a preliminary study. Sirovina D, Oršolić N, Gregorović G, Končić MZ.Arh Hig Rada Toksikol. 2016 Mar;67(1):19-24. doi: 10.1515/aiht-2016-67-2708. PMID: 27092635 7:Naringenin Inhibits Superoxide Anion-Induced Inflammatory Pain: Role of Oxidative Stress, Cytokines, Nrf-2 and the NO-cGMP-PKG-KATP Channel Signaling Pathway. Manchope MF, Calixto-Campos C, Coelho-Silva L, Zarpelon AC, Pinho-Ribeiro FA, Georgetti SR, Baracat MM, Casagrande R, Verri WA Jr.PLoS One. 2016 Apr 5;11(4):e0153015. doi: 10.1371/journal.pone.0153015. eCollection 2016. PMID: 27045367 Free PMC Article8:Naringenin prevents TGF-β1 secretion from breast cancer and suppresses pulmonary metastasis by inhibiting PKC activation. Zhang F, Dong W, Zeng W, Zhang L, Zhang C, Qiu Y, Wang L, Yin X, Zhang C, Liang W.Breast Cancer Res. 2016 Apr 1;18(1):38. doi: 10.1186/s13058-016-0698-0. PMID: 27036297 Free PMC Article9:Naringenin-induced migration of embrynoic trophectoderm cells is mediated via PI3K/AKT and ERK1/2 MAPK signaling cascades. Lim W, Song G.Mol Cell Endocrinol. 2016 Jun 15;428:28-37. doi: 10.1016/j.mce.2016.03.018. Epub 2016 Mar 17. PMID: 26994515 10:Biochemical and Molecular Mechanisms of Radioprotective Effects of Naringenin, a Phytochemical from Citrus Fruits. Kumar S, Tiku AB.J Agric Food Chem. 2016 Mar 2;64(8):1676-85. doi: 10.1021/acs.jafc.5b05067. Epub 2016 Feb 16. PMID: 26881453