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Narirutin

$142

  • Brand : BIOFRON

  • Catalogue Number : BF-N1002

  • Specification : 98%

  • CAS number : 14259-46-2

  • Formula : C27H32O14

  • Molecular Weight : 580.53

  • PUBCHEM ID : 442431

  • Volume : 20mg

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Catalogue Number

BF-N1002

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

580.53

Appearance

White powder

Botanical Source

young fruit of Citrus grandis (L.) Osbeck.

Structure Type

Flavonoids

Category

Standards;Natural Pytochemical;API

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

Synonyms

(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/(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranoside/ISONARINGIN/Isonaringenin/Naringenin 7-O-rutinoside/4H-1-Benzopyran-4-one, 7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-/Naringenin-7-rutinoside/(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-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-one/Narirutin/(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/(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-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-one/Naringenin 7-rutinoside/(S)-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/naringenin-7-O-rutinoside/Apigenin-7-rutinosid/(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-methyltetrahydro-2H-pyran-2-yl]oxy}methyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-on

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

Density

1.7±0.1 g/cm3

Solubility

Flash Point

307.3±27.8 °C

Boiling Point

924.3±65.0 °C at 760 mmHg

Melting Point

152-190ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:14259-46-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

30028378

Abstract

Depression is a highly debilitating and life-threatening mental disorder, which is accompanied by dysregulation of the peripheral and central immune system. Narirutin (NR), which has antioxidant and anti-inflammatory activities, is one of the active constituents isolated from Citrus unshiu. However, its potential antidepressant-like and anxiolytic-like effects are poorly understood. The present study was aimed to investigate whether NR confers an antidepressant-like effect in mice exposed to a chronic mild stress (CMS) model of depression. The results showed that NR treatment for 1 week significantly alleviated the depressive-like behaviours of CMS-exposed mice, as indicated by restored decreased sucrose preference and shortened floating time in the forced swimming test. Moreover, NR treatment significantly blocked the CMS-induced anxiety-like behaviors, including increased time spent in the central zone in the open field test, and shortened the latency to feeding in the novelty suppressed feeding test. Taken together, our findings suggested that NR exerted potential antidepressant-like and anxiolytic-like effects in CMS mice model of depression, which support further exploration into developing NR as a novel agent to treat depression and even other stress-related disorders.

Title

Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model.

Author

Li Y1, Du Y2, Yang J3, Xiu Z2, Yang N2, Zhang J2, Gao Y2,4, Li B5, Shi H2,4,6,7.

Publish date

2018 Oct 17;

PMID

31654517

Abstract

BACKGROUND:
Shikimate pathway is essential for tubercular bacillus but it is absent in mammals. Therefore, shikimate kinase and other enzymes in the pathway are potential targets for the development of novel anti-tuberculosis drugs.

OBJECTIVE:
In the present study shikimate kinase is selected as the target for in silico screening of phytochemicals with an aim to discover a novel herbal drug against Mycobacterium tuberculosis(Mtb).

METHODS:
A structure based drug discovery approach has been undertaken for the execution of the objective. Virtual screening of phytochemical database NPACT against the target, shikimate kinase (PDB ID 3BAF),is carried out followed by toxicity and drug-likeness filtration. Finally, a lead, narirutin was selected for in vitro anti-tubercular study.

RESULTS:
Narirutin, present in citrus fruits, emerges as the lead. It isconsideredto be non-toxic with predicted high LD50 value, 12000 mg/kg body weight. The phytochemical is tested for its anti-tubercular activity in vitro. It has MIC9962.5μg/mL against the MtbH37Rv strain.

CONCLUSIONS:
This is the first ever report to show anti-tuberculosis potency of narirutin.

Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.net.

KEYWORDS

Drug-likeness; Molecular docking; Mycobacterium tuberculosis; Narirutin; Shikimate kinase; Toxicity

Title

Structure-based Discovery of Narirutin as a Shikimate Kinase Inhibitor with Anti-tubercular Potency.

Author

Sahu PK1, Mohapatra PK2, P Rajani D3, Raval MK1.

Publish date

2019 Oct 25

PMID

17600554

Abstract

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.

Title

Narirutin inhibits airway inflammation in an allergic mouse model.

Author

Funaguchi N1, Ohno Y, La BL, Asai T, Yuhgetsu H, Sawada M, Takemura G, Minatoguchi S, Fujiwara T, Fujiwara H.

Publish date

2007 Aug


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