A disaccharide derivative that is (S)-naringenin substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.

Identification

IUPAC Names

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside

Molecular Formula
C27H32O14
Mass
580.53458
Monoisotopic Mass
580.17921
Charge
0
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
C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3cc(O)c4C(=O)C[C@H](Oc4c3)c3ccc(O)cc3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Synonyms

Isonaringenin

Isonaringin

Naringenin 7-O-rutinoside

Narirutin

Species

Europe PubMed Central results


Factors Influencing Visual Improvement after Phacoemulsification Surgery among Malaysian Cataract Patients.

Author: Sa'at N, Ghazali AK, Yaacob NM, Salowi MA.

Abstract: Blindness and visual impairment are part of the global burden of eye disease, with cataract being one of the leading causes of blindness. This study aimed to determine the factors affecting visual acuity (VA) improvement among cataract patients after phacoemulsification surgery in Malaysia. Cataract patients aged over 18 who underwent phacoemulsification surgery between January 2014 and December 2018 were included in this retrospective cohort study. Patients' sociodemographic, comorbidities, surgical, and related complication factors were extracted from the National Eye Database. The outcome was measured by the difference in visual acuity before and after the operation and was categorized as "improved", "no change", and "worse". A total of 180,776 patients were included in the final analysis. Multinomial logistic regression analysis showed "no changes in VA" was significantly higher in patients aged less than 40 years old (OR: 1.66; 95% CI: 1.22, 2.26), patients with ocular comorbidities (OR: 1.65; 95% CI: 1.53, 1.77), patients who had undergone surgery lasting more than 60 min (OR: 1.39; 95% CI: 1.14, 1.69), patients who had surgery without an intraocular lens (IOL) (OR: 1.64; 95% CI: 1.20, 2.26), and patients with postoperative complications (OR: 8.76; 95% CI: 8.13, 9.45). Worsening VA was significantly higher among male patients (OR: 1.11; 95% CI: 1.01, 1.22), patients who had ocular comorbidities (OR: 1.76; 95% CI: 1.59, 1.96), patients who had undergone surgery lasting more than 60 min (OR: 1.94; 95% CI: 1.57, 2.41), patients who had surgery without an IOL (OR: 2.03; 95% CI: 1.48, 2.80), and patients with postoperative complications (OR: 21.46; 95% CI: 19.35, 23.80). The factors impacting "no changes" in and "worsening" of VA after cataract surgery were the following: older age, male gender, ethnicity, ocular comorbidities, surgeon grade, absence of IOL, intraoperative complication, and postoperative problems.

Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-κB and MAPKs activation.

Author: Ha SK, Park HY, Eom H, Kim Y, Choi I.

Abstract: In this study, we examined the regulatory activity of narirutin fraction from citrus peels on the production of inflammatory mediators managing acute or chronic inflammatory diseases in macrophages. Narirutin fraction inhibited the release, by lipopolysaccharide (LPS)-stimulated macrophages, of nitric oxide (NO) and prostaglandin E2 (PGE2) through suppressing the expression of inducible NO synthase (iNOS) and cyclooxygenase-2 (COX-2), respectively. The release, by LPS stimulated macrophages, of interleukin-1β (IL-1β) and tumor necrosis factor-α (TNF-α) was also reduced by narirutin fraction in a dose-dependent manner. Furthermore, narirutin fraction inhibited the LPS-mediated activation of nuclear factor-κB (NF-κB) and mitogen-activated protein kinases (MAPKs), which are signaling molecules involved in production of pro-inflammatory factors. As a result of these properties, narirutin fraction has the potential to be used as a functional dietary supplement and effective anti-inflammatory agent.

Anti-degranulating activity in rat basophil leukemia RBL-2H3 cells of flavanone glycosides and their aglycones in citrus fruits.

Author: Murata K, Takano S, Masuda M, Iinuma M, Matsuda H.

Abstract: The anti-degranulating activity of flavonoids present in Citrus fruits was comprehensively evaluated. Among these, hesperetin and naringenin, respectively aglycones of hesperidin and narirutin, showed significant activity. The targets of hesperetin and naringenin were found: hesperetin inhibited phosphorylation of Syk and Akt, while naringenin suppressed the expression of Lyn and inhibited the phosphorylation of Akt. These results suggest that hesperetin and naringenin inhibit degranulation by suppression of pathway signals and reduce the symptoms of allergy by inhibiting phosphorylation of Akt, which leads to the suppression of cytokines. In addition, hesperetin showed inhibitory activity against the degranulation induced by calcium ionophores, indicating that hesperetin exerts its inhibitory activity by stabilizing the membrane structure.

Phytochemical profile and antioxidant activity of physiological drop of citrus fruits.

Author: Sun Y, Qiao L, Shen Y, Jiang P, Chen J, Ye X.

Abstract: <h4>Unlabelled</h4>The phytochemical content and the antioxidant activity (AA) of physiological drop of the main citrus species grown in China were investigated. Among the flavonoids, hesperidin was found mostly in mandarin and sweet orange, naringin was found mostly in sour orange, pummelo, grapefruit and a hybrid (Gaocheng), narirutin was found in most varieties, neohesperidin was found in Gaocheng and Huyou, and nobiletin and tangeretin were found in most varieties. Hydroxycinnamic acids were the main phenolic acids present, ferulic acid and caffeic acid were the dominant in most cases. There was a greater amount of free (extractable) than bound (insoluble) phenolic acids. Levels of limonoids were higher in Foyou, Eureka lemon, and Gaocheng than those in the other cultivars. The highest level of synephrine was found in Ponkan and Weizhang Satsuma. AA was highest in Ponkan and Weizhang Satsuma and lowest in Huyou, pummel, and lemon. These results suggest that physiological drop of citrus fruits have good potential as sources of different bioactive compounds and antioxidants.<h4>Practical application</h4>Physiological drop of citrus fruits may be a good resource of bioactive compounds including flavonoids, phenolic acids, limonoids, synephrine, and a good material of nutraceuticals.