(2S)-Narirutin

• CAT Number: R042058
• CAS Number: 14259-46-2
• Molecular Formula: C27H32O14
• Molecular Weight: 580.539
• Purity: ≥95%
• Synonyms: (2S)-7-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Narirutin; Isonaringenin; Isonaringin; Naringenin 7-O-Rutinoside; Naringenin 7-Rutinoside; Naringenin 7β-Rutinoside
• Storage: -20°C
• IUPAC Name: (2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• InChI: InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1
• InChIKey: HXTFHSYLYXVTHC-AJHDJQPGSA-N
• SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)O)O)O)O)O)O

(2S)-Narirutin (CAS 14259-46-2) is a flavanone originally isolated from C. paradisi that has anti-inflammatory and antidepressant-like activities. It reduces airway sensitivity, eosinophil counts and IL-4 levels in bronchoalveolar lavage fluid (BALF), and serum IgE levels in an ovalbumin mouse model of allergic eosinophilic airway inflammation when administered at a dose of 10 mg/kg. Narirutin decreases immobility in the forced swim test and latency to feeding in the novelty-suppressed feeding test, indicating antidepressant-like activity in a mouse model of chronic mild stress-induced depression.

Reference

1.Mizelle, J. W., et al. "Isolation and identification of some flavanone rutinosides of the grapefruit." Analytical biochemistry 12.2 (1965): 316-324.
2.Funaguchi, Norihiko, et al. "Narirutin inhibits airway inflammation in an allergic mouse model." Clinical and experimental pharmacology & physiology 34.8 (2007): 766-770.
3.Li, Yan, et al. "Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model." Neuroreport 29.15 (2018): 1264-1268.