Narirutin

CAS# 14259-46-2

Narirutin

Catalog No. BCN6300----Order now to get a substantial discount!

Product Name & Size Price Stock
Narirutin: 5mg $81 In Stock
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Quality Control of Narirutin

Number of papers citing our products

Chemical structure

Narirutin

3D structure

Chemical Properties of Narirutin

Cas No. 14259-46-2 SDF Download SDF
PubChem ID 442431 Appearance White powder
Formula C27H32O14 M.Wt 580.53
Type of Compound Flavonoids Storage Desiccate at -20°C
Synonyms Isonaringin; Naringenin 7-rutinoside; 4',5,7-Trihydroxyflavanone 7-rutinoside
Solubility DMSO : 125 mg/mL (215.32 mM; Need ultrasonic)
Chemical 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
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
Standard InChIKey HXTFHSYLYXVTHC-AJHDJQPGSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Narirutin

1 Monarda sp.

Biological Activity of Narirutin

DescriptionCitrus narirutin fraction (CNF), contained 75% of narirutin, co-administration of CNF with alcohol can alleviate alcohol induced liver damage through preventing lipid formation, protecting antioxidant system and suppressing productions of pro-inflammatory cytokines. Narirutin has anti-inflammatory effect in a murine model of allergic eosinophilic airway inflammation, the mechanism is likely to be associated with a reduction in the OVA-induced increases of IL-4 and IgE.
TargetsNO | NOS | PGE | COX | TNF-α | NF-kB | MAPK | IL Receptor
In vitro

Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-κB and MAPKs activation.[Pubmed: 22813871]

Food Chem Toxicol. 2012 Oct;50(10):3498-504.


METHODS AND RESULTS:
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.
CONCLUSIONS:
As a result of these properties, Narirutin fraction has the potential to be used as a functional dietary supplement and effective anti-inflammatory agent.

In vivo

Narirutin fraction from citrus peels attenuates alcoholic liver disease in mice.[Pubmed: 23416143]

Food Chem Toxicol. 2013 May;55:637-44.


METHODS AND RESULTS:
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 purification. ICR mice were divided into four groups; normaldiet control, ethanol control (6.5g ethanol/kg), low-CNF (ethanol+150mg CNF/kg) and high-CNF (ethanol+300mg CNF/kg) groups. Consumption of alcohol for 8weeks induced severe liver damage with increases in prognostic indicators such as aspartate transaminase, alanine transaminase in serum whereas co-administration of CNF suppressed their increases. Excessive accumulations in liver TG and TC in ethanol control group were also suppressed by co-administration of CNF. Co-administration of CNF maintained SOD activity, GSH and malondialdehyde levels close to those of the normal diet group. Chronic consumption of alcohol also stimulated abrupt increases in pro-inflammatory cytokines such as nuclear factor (NF)-κB, tumor necrosis factor (TNF)-α and interleukin (IL)-1β in liver otherwise co-administration of CNF effectively suppressed production of these cytokines dose-dependently.
CONCLUSIONS:
These results indicate that co-administration of CNF with alcohol can alleviate alcohol induced liver damage through preventing lipid formation, protecting antioxidant system and suppressing productions of pro-inflammatory cytokines.

Protocol of Narirutin

Animal Research

Narirutin inhibits airway inflammation in an allergic mouse model.[Pubmed: 17600554]

Clin Exp Pharmacol Physiol. 2007 Aug;34(8):766-70.

1. Flavonoids are naturally occurring compounds that possess anti-allergic, anti-inflammatory, antiproliferative and anti-oxidant properties.
METHODS AND RESULTS:
In the present study, we investigated whether the flavonoid Narirutin could reduce airway inflammation in ovalbumin (OVA)-sensitized/challenged NC/Nga mice, a model of allergic eosinophilic airway inflammation. 2. Mice were initially immunized intraperitoneally with OVA on Days 0 and 7 and then challenged with inhaled OVA on Days 14, 15 and 16. In addition, some mice received Narirutin orally at doses of 0.1, 1 or 10 mg/kg bodyweight daily on Days 7-16. 3. At 10 mg/kg, but not 0.1 or 1 mg/kg, Narirutin significantly diminished OVA-induced airway inflammation caused by infiltration of lung tissue with inflammatory and mucus-producing cells, as well as reduced eosinophil counts in the peripheral blood and bronchoalveolar lavage fluid (BALF), interleukin (IL)-4 levels in BALF and IgE levels in serum. 4. The mechanism of the anti-inflammatory effect of Narirutin are likely to be associated with a reduction in the OVA-induced increases of IL-4 and IgE in a murine model of allergic eosinophilic airway inflammation.
CONCLUSIONS:
These findings suggest that Narirutin may be an effective new tool in the treatment of bronchial asthma.

Structure Identification
J AOAC Int. 2009 May-Jun;92(3):789-96.

Liquid chromatographic determination of narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the raw herb and of the dried aqueous extract.[Pubmed: 19610369]

A validated analytical method is reported for the analysis of Narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the dried raw herb and of the commercially prepared dried aqueous extract.
METHODS AND RESULTS:
The samples were extracted by sonication in methanol and the extract was analyzed by liquid chromatography-photodiode array (PDA) detection with identity confirmation by negative electrospray ionization-tandem mass spectrometry (MS). A C18 column was used with a methanol-water gradient mobile phase. Narirutin and hesperidin were quantified at 284 nm using the PDA detector. Using the MS detector, the Narirutin precursor ion with m/z 579 produced daughter ions with m/z 271 and 151. For hesperidin, the precursor ion with m/z 609 produced the m/z 301, 285, and 164 ions. The amounts of Narirutin and hesperidin found in the certified raw herb were 14.2 and 147.9 mg/g, respectively, and in the dried aqueous extract the amounts were 9.2 and 8.6 mg/g, respectively. For the raw herb, the average recovery across the three spike levels (50, 100, and 150%) for Narirutin and hesperidin were 110.7 and 94.5%, respectively.
CONCLUSIONS:
For the dried aqueous extract, the average recovery across the three spike levels for Narirutin and hesperidin were 85.8 and 98.9%, respectively.

Narirutin Dilution Calculator

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Preparing Stock Solutions of Narirutin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7226 mL 8.6128 mL 17.2256 mL 34.4513 mL 43.0641 mL
5 mM 0.3445 mL 1.7226 mL 3.4451 mL 6.8903 mL 8.6128 mL
10 mM 0.1723 mL 0.8613 mL 1.7226 mL 3.4451 mL 4.3064 mL
50 mM 0.0345 mL 0.1723 mL 0.3445 mL 0.689 mL 0.8613 mL
100 mM 0.0172 mL 0.0861 mL 0.1723 mL 0.3445 mL 0.4306 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Narirutin

Narirutin inhibits airway inflammation in an allergic mouse model.[Pubmed:17600554]

Clin Exp Pharmacol Physiol. 2007 Aug;34(8):766-70.

1. Flavonoids are naturally occurring compounds that possess anti-allergic, anti-inflammatory, antiproliferative and anti-oxidant properties. In the present study, we investigated whether the flavonoid Narirutin could reduce airway inflammation in ovalbumin (OVA)-sensitized/challenged NC/Nga mice, a model of allergic eosinophilic airway inflammation. 2. Mice were initially immunized intraperitoneally with OVA on Days 0 and 7 and then challenged with inhaled OVA on Days 14, 15 and 16. In addition, some mice received Narirutin orally at doses of 0.1, 1 or 10 mg/kg bodyweight daily on Days 7-16. 3. At 10 mg/kg, but not 0.1 or 1 mg/kg, Narirutin significantly diminished OVA-induced airway inflammation caused by infiltration of lung tissue with inflammatory and mucus-producing cells, as well as reduced eosinophil counts in the peripheral blood and bronchoalveolar lavage fluid (BALF), interleukin (IL)-4 levels in BALF and IgE levels in serum. 4. The mechanism of the anti-inflammatory effect of Narirutin are likely to be associated with a reduction in the OVA-induced increases of IL-4 and IgE in a murine model of allergic eosinophilic airway inflammation. These findings suggest that Narirutin may be an effective new tool in the treatment of bronchial asthma.

Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-kappaB and MAPKs activation.[Pubmed:22813871]

Food Chem Toxicol. 2012 Oct;50(10):3498-504.

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-1beta (IL-1beta) and tumor necrosis factor-alpha (TNF-alpha) was also reduced by Narirutin fraction in a dose-dependent manner. Furthermore, Narirutin fraction inhibited the LPS-mediated activation of nuclear factor-kappaB (NF-kappaB) 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.

Narirutin fraction from citrus peels attenuates alcoholic liver disease in mice.[Pubmed:23416143]

Food Chem Toxicol. 2013 May;55:637-44.

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 purification. ICR mice were divided into four groups; normaldiet control, ethanol control (6.5g ethanol/kg), low-CNF (ethanol+150mg CNF/kg) and high-CNF (ethanol+300mg CNF/kg) groups. Consumption of alcohol for 8weeks induced severe liver damage with increases in prognostic indicators such as aspartate transaminase, alanine transaminase in serum whereas co-administration of CNF suppressed their increases. Excessive accumulations in liver TG and TC in ethanol control group were also suppressed by co-administration of CNF. Co-administration of CNF maintained SOD activity, GSH and malondialdehyde levels close to those of the normal diet group. Chronic consumption of alcohol also stimulated abrupt increases in pro-inflammatory cytokines such as nuclear factor (NF)-kappaB, tumor necrosis factor (TNF)-alpha and interleukin (IL)-1beta in liver otherwise co-administration of CNF effectively suppressed production of these cytokines dose-dependently. These results indicate that co-administration of CNF with alcohol can alleviate alcohol induced liver damage through preventing lipid formation, protecting antioxidant system and suppressing productions of pro-inflammatory cytokines.

Liquid chromatographic determination of narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the raw herb and of the dried aqueous extract.[Pubmed:19610369]

J AOAC Int. 2009 May-Jun;92(3):789-96.

A validated analytical method is reported for the analysis of Narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the dried raw herb and of the commercially prepared dried aqueous extract. The samples were extracted by sonication in methanol and the extract was analyzed by liquid chromatography-photodiode array (PDA) detection with identity confirmation by negative electrospray ionization-tandem mass spectrometry (MS). A C18 column was used with a methanol-water gradient mobile phase. Narirutin and hesperidin were quantified at 284 nm using the PDA detector. Using the MS detector, the Narirutin precursor ion with m/z 579 produced daughter ions with m/z 271 and 151. For hesperidin, the precursor ion with m/z 609 produced the m/z 301, 285, and 164 ions. The amounts of Narirutin and hesperidin found in the certified raw herb were 14.2 and 147.9 mg/g, respectively, and in the dried aqueous extract the amounts were 9.2 and 8.6 mg/g, respectively. For the raw herb, the average recovery across the three spike levels (50, 100, and 150%) for Narirutin and hesperidin were 110.7 and 94.5%, respectively. For the dried aqueous extract, the average recovery across the three spike levels for Narirutin and hesperidin were 85.8 and 98.9%, respectively.

Description

Narirutin, one of the active constituents isolated from Citrus unshiu, has antioxidant and anti-inflammatory activities. Narirutin is a shikimate kinase inhibitor with anti-tubercular potency.

Keywords:

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