Prunin

Names

[ CAS No. ]:
529-55-5

[ Name ]:
Prunin

[Synonym ]:
5-Hydroxy-2-(4-hydroxyphényl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromén-4-one
4H-1-Benzopyran-4-one, 7-(β-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-
4',5-DIHYDROXY-7-GLUCOSYLOXYFLAVANONE
5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-on
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl-β-D-glucopyranoside
naringenin 7-O-beta-D-glucoside
5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl β-D-glucopyranoside
NARINGENIN-7-O-GLUCOSIDE
5-Hydroxy-2-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2,3-dihydro-4H-chromen-4-one
Naringenin-7-glucoside
PRUNIN

Biological Activity

[Description]:

Prunin is a potent inhibitor of human enterovirus A71 (HEVA71). Prunin shows strong inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), with an IC50 of 5.5 µM[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphatase

Research Areas >> Infection

Research Areas >> Metabolic Disease

[In Vitro]

Prunin exhibited dose-dependent inhibitory activity against ONOO--mediated tyrosine nitration and stimulated glucose uptake by decreasing PTP1B expression level in insulin-resistant HepG2 cells. Prunin shows significant inhibitory activity against α-glucosidase, with an IC50 of 317 ± 2.12 µM[2].

[References]

[1]. Gunaseelan S, et al. Prunin suppresses viral IRES activity and is a potential candidate for treating enterovirus A71 infection. Sci Transl Med. 2019 Oct 30;11(516). pii: eaar5759.

[2]. Jung HA, et al. Prunin is a highly potent flavonoid from Prunus davidiana stems that inhibits protein tyrosine phosphatase 1B and stimulates glucose uptake in insulin-resistant HepG2 cells. Arch Pharm Res. 2017 Jan;40(1):37-48.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
802.4±65.0 °C at 760 mmHg

[ Melting Point ]:
222-224ºC

[ Molecular Formula ]:
C₂₁H₂₂O₁₀

[ Molecular Weight ]:
434.393

[ Flash Point ]:
284.6±27.8 °C

[ Exact Mass ]:
434.121307

[ PSA ]:
166.14000

[ LogP ]:
0.82

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.691

[ Storage condition ]:
?20°C

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
N

[ Risk Phrases ]:
22

[ Safety Phrases ]:
22-45

[ RIDADR ]:
UN 3077 9 / PGIII

Articles

A rapid method for the determination of naringin, prunin, and naringenin applied to the assay of naringinase.

Anal. Biochem. 134(2) , 393-7, (1983)

A naringinase assay capable of distinguishing between the content of naringin, prunin, and naringenin present in the incubation mixture, is described. The amount of these compounds can be estimated by...

Antihyperlipidemic effect of flavonoids from Prunus davidiana.

J. Nat. Prod. 54(1) , 218-24, (1991)

Blood lipid levels in rats with hyperlipidemia resulting from high-fat feeding were determined after ip administration of an MeOH extract of Prunus davidiana stems and its flavonoid components, (+)-ca...

Crystal structure of prunin-1, a major component of the almond (Prunus dulcis) allergen amandin.

J. Agric. Food Chem. 57(18) , 8643-51, (2009)

Seed storage proteins are accumulated during seed development and act as a reserve of nutrition for seed germination and young sprout growth. Plant seeds play an important role in human nutrition by p...