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 |
| HXTFHSYLYXVTHC-AJHDJQPGSA-N |
| 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 |
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antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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anti-inflammatory agent
Any compound that has anti-inflammatory effects.
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View more via ChEBI Ontology
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(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside
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Isonaringenin
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ChemIDplus
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Isonaringin
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ChemIDplus
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Naringenin 7-O-rutinoside
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KEGG COMPOUND
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Narirutin
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KEGG COMPOUND
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1361182
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Reaxys Registry Number
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Reaxys
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14259-46-2
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CAS Registry Number
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KEGG COMPOUND
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14259-46-2
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CAS Registry Number
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ChemIDplus
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Sun Y, Qiao L, Shen Y, Jiang P, Chen J, Ye X (2013)
Phytochemical profile and antioxidant activity of physiological drop of citrus fruits.
Journal of food science 78, C37-42 [PubMed:23301602]
[show Abstract]
UnlabelledThe 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.Practical applicationPhysiological drop of citrus fruits may be a good resource of bioactive compounds including flavonoids, phenolic acids, limonoids, synephrine, and a good material of nutraceuticals. | Murata K, Takano S, Masuda M, Iinuma M, Matsuda H (2013)
Anti-degranulating activity in rat basophil leukemia RBL-2H3 cells of flavanone glycosides and their aglycones in citrus fruits.
Journal of natural medicines 67, 643-646 [PubMed:22903244]
[show 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. | Ha SK, Park HY, Eom H, Kim Y, Choi I (2012)
Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-κB and MAPKs activation.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 50, 3498-3504 [PubMed:22813871]
[show 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. | Ramful D, Bahorun T, Bourdon E, Tarnus E, Aruoma OI (2010)
Bioactive phenolics and antioxidant propensity of flavedo extracts of Mauritian citrus fruits: potential prophylactic ingredients for functional foods application.
Toxicology 278, 75-87 [PubMed:20100535]
[show Abstract]
The flavedo extracts of twenty-one varieties of citrus fruits (oranges, satsumah, clementine, mandarins, tangor, bergamot, lemon, tangelos, kumquat, calamondin and pamplemousses) grown in Mauritius were examined for their total phenolic, flavonoid and vitamin C contents and antioxidant activities. Total phenolics correlated strongly with the trolox equivalent antioxidant capacity (TEAC), ferric reducing antioxidant capacity (FRAP) and hypochlorous acid (HOCl) scavenging activity assays (r > 0.85). Based on their antioxidant activities in these three assays nine citrus fruits namely, one orange, clementine, tangor and pamplemousse variety, two tangelo varieties and three mandarin varieties, were further characterized for their flavanone, flavonol and flavone levels by HPLC and their antioxidant activities were assessed by the copper-phenanthroline and iron chelation assays. The flavanone, hesperidin, was present at the highest concentrations in all flavedo extracts except for pamplemousses where it was not detected. Contents in hesperidin ranged from 83 ± 0.06 to 234 ± 1.73 mg/g FW. Poncirin, didymin, diosmin, isorhoifolin and narirutin were also present in all extracts whereas naringin was present only in one mandarin variety. The nine flavedo extracts exhibited good DNA protecting ability in the cuphen assay with IC₅₀ values ranging from 6.3 ± 0.46 to 23.0 ± 0.48 mg FW/mL. Essentially the flavedos were able to chelate metal ions however, tangor was most effective with an IC₅₀ value of 9.1 ± 0.08 mg FW/mL. The flavedo extracts of citrus fruits represent a significant source of phenolic antioxidants with potential prophylactic properties for the development of functional foods. |
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