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SMB00321

Sigma-Aldrich

Narirutin

≥98% (HPLC)

Synonyme(s) :

Narirutin, (2S)-7-((6-O-(6-Deoxy-a-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, Isonaringenin, Isonaringin, Naringenin rutinoside

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About This Item

Formule empirique (notation de Hill):
C27H32O14
Numéro CAS:
14259-46-2
Poids moléculaire :
580.53
Numéro MDL:
MFCD00017316
Code UNSPSC :
12352205
ID de substance PubChem :
329824953
Nomenclature NACRES :
NA.25

Pureté

≥98% (HPLC)

Forme

powder

Pf

180 °C

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Chaîne SMILES 

OC1=CC=C([C@@H]2CC(C(C(O)=CC(O[C@@H]3O[C@H](CO[C@H]4[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O4)[C@@H](O)[C@H](O)[C@H]3O)=C5)=C5O2)=O)C=C1

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

Clé InChI

HXTFHSYLYXVTHC-AJHDJQPGSA-N

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Catégories apparentées

Description générale

Narirutin is a flavanone that constitutes the major flavonoids found in citrus fruits like oranges, grapefruits, and tangerines. It is a multi-potent phytochemical.

Application

Narirutin has been used as a flavonoid supplement to study its effect on the prevention of depression-like behavior and modulatory effect on the inflammatory profile in rat female offspring.

Actions biochimiques/physiologiques

Narirutin is known to possess anti-allergic, anti-inflammatory, antioxidant, and anti-proliferative properties. It inhibits allergic eosinophilic airway inflammation in the mouse model. Narirutin also inhibits lipopolysaccharide (LPS)-induced inflammatory response by inhibiting nuclear factor-κB (NF-κB) and mitogen-activated protein kinases (MAPKs). It displays antioxidant and protective effects on attenuating alcohol-induced liver damage while co-consumed with alcohol in mice model, and can be useful in Alzheimer′s disease (AD) therapeutics.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Bing Zhang et al.
Molecules (Basel, Switzerland), 24(11) (2019-05-31)
A UHPLC-QQQ-MS/MS method was developed to quantify the significant constituents in Wen-Dan Decoction (WDD), a traditional Chinese medicine. Analysis of 19 compounds was conducted on an ACQUITY UPLC® BEH C18 Column (2.1 × 50 mm, 1.7 μm) using elution with
Sang Keun Ha et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(10), 3498-3504 (2012-07-21)
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
Sandipan Chakraborty et al.
International journal of biological macromolecules, 103, 733-743 (2017-05-23)
Alzheimer's disease (AD) is a complex disorder and the disease mechanism is yet to be properly characterized. Over the years, "amyloid cascade" emerges as principal pathogenic event in AD. β-Secretase 1 (BACE1) controls the rate-limiting step in amyloid beta (Aβ)
Ho-Young Park et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 55, 637-644 (2013-02-19)
This study aimed to demonstrate protective activities of the narirutin fraction from peels of Citrus unshiu against ethanol-induced hepatic damage through an animal study. Citrus narirutin fraction (CNF), contained 75% of narirutin, was obtained by an ultra-sonicated extraction and further
Xiu-Min Chen et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 105, 398-406 (2017-04-17)
Dry citrus peels, also known as "chenpi", have been traditionally used to treat and relieve intestinal inflammation. Recently we have reported that orange peel extracts (OPE) which contain relatively greater polymethoxylated flavone (PMF) content exhibit superior antioxidant and anti-inflammatory activities
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