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N1376

Naringin

Name: Naringin
Brand: SIGMA

≥90% (HPLC), from citrus fruit

Synonym(s):

4′,5,7-Trihydroxyflavanone 7-rhamnoglucoside, Naringenin 7-neohesperidoside, Naringenine-7-rhamnosidoglucoside, Naringoside

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₃₂O₁₄

CAS Number:

10236-47-2

Molecular Weight:

580.53

UNSPSC Code:

12352201

NACRES:

NA.25

PubChem Substance ID:

24897483

EC Number:

233-566-4

Beilstein/REAXYS Number:

102012

MDL number:

MFCD00148888

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biological source

citrus fruit

Quality Level

200

assay

≥90% (HPLC)

form

powder

color

white to light yellow

solubility

ethanol: 50 mg/mL, slightly hazy to slightly hazy, light yellow to yellow

storage temp.

room temp

SMILES string

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2Oc3cc(O)c4C(=O)CC(Oc4c3)c5ccc(O)cc5)[C@H](O)[C@H](O)[C@H]1O

InChI

1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16?,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1

InChI key

DFPMSGMNTNDNHN-JJLSSNRUSA-N

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Related Categories

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

General description

Naringin is a flavanone glycoside.

Application

Naringin has been used in a study to assess aldosterone production by a human adrenocortical cell line. Long-term naringin consumption reverses a glucose uptake defect and can be used to improve cognitive deficits of Alzheimer′s disease.

Biochem/physiol Actions

Naringin, a flavanoid in grapefruit and other citrus fruits, potently inhibits intestinal organic anion-transporting polypeptide 1A2 (OATP1A2). Grapefruit juice thereby reduces bioavailability of many pharmacological agents taken at the same time.

Other Notes

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Selective inhibition of aromatase by a dihydroisocoumarin from Xyris pterygoblephara.

Denise C Endringer et al.

Journal of natural products, 71(6), 1082-1084 (2008-05-09)

Aromatase is a well-established target for the chemoprevention of breast cancer. The dihydroisocoumarin (3 R,4 R)-(-)-6-methoxy-1-oxo-3-pentyl-3,4-dihydro-1 H-isochromen-4-yl acetate (1) (IC 50 = 1.6 +/- 0.1 microM), isolated from aerial parts of Xyris pterygoblephara, showed aromatase inhibitory activity. The specificity of

Long-term naringin consumption reverses a glucose uptake defect and improves cognitive deficits in a mouse model of Alzheimer's disease.

Dongmei Wang et al.

Pharmacology, biochemistry, and behavior, 102(1), 13-20 (2012-06-29)

Naringin, a bioflavonoid, has been reported to have potent neuro-protective effects, but its preventive effects on amyloid-β (Aβ) induced, Alzheimer's disease (AD) related, cognitive impairment, and the underlying mechanisms of these effects have not been well characterised. Three-month-old APPswe/PSΔE9 transgenic

Prediction of intestinal absorption and metabolism of pharmacologically active flavones and flavanones.

H Serra et al.

Bioorganic & medicinal chemistry, 16(7), 4009-4018 (2008-02-06)

Three glycosilated flavonoids (diosmin, hesperidin and naringin) and respective aglycones were characterized in terms of their apparent ionisation constants and bidirectional permeability using the cellular model Caco-2 as well as the artificial membrane model PAMPA. Ionisation curves were established by

The potassium channel, Kir3.4 participates in angiotensin II-stimulated aldosterone production by a human adrenocortical cell line.

Kenji Oki et al.

Endocrinology, 153(9), 4328-4335 (2012-07-17)

Angiotensin II (A-II) regulation of aldosterone secretion is initiated by inducing cell membrane depolarization, thereby increasing intracellular calcium and activating the calcium calmodulin/calmodulin kinase cascade. Mutations in the selectivity filter of the KCNJ5 gene coding for inward rectifying potassium channel

Purification of naringin and neohesperidin from Huyou (Citrus changshanensis) fruit and their effects on glucose consumption in human HepG2 cells.

Jiukai Zhang et al.

Food chemistry, 135(3), 1471-1478 (2012-09-08)

Huyou (Citrus changshanensis) is rich in naringin and neohesperidin, which are natural flavanone glycosides with a range of biological activities. Among the different fruit parts, i.e. flavedo, albedo, segment membrane (SM), and juice sacs (JS), albedo showed the highest contents

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Global Trade Item Number

SKU	GTIN
N1376-25G	04061834108641
N1376-100G	04061834108603

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