Isoquercitrin

Names

[ Name ]:
Isoquercitrin

[Synonym ]:
Quercetin 3-O-β-glucoside
trifoliin
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucofuranoside
quercetin 3-O-β-D-glucopyranoside
Quercetin 3β-O-glucoside
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(β-D-glucofuranosyloxy)-5,7-dihydroxy-
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxy-phenyl)-3-(β-D-glucofuranosyloxy)-5,7-dihydroxy-
Quercetin 3-β-glucoside
Quercetin 3-O-glucofuranoside
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl β-D-glucopyranoside
Isopseudopsoralen
isopseudopsoralene
Quercetin 3-β-D-glucoside
quercetin-3-glucoside
3-O-β-D-Glucopyranosylquercetin
Quercetin glucoside
Isoquercitroside
Quercetin-3-O-β-D-glucoside
isopseudosporalen
Quercetin-3-O-β-glucopyranoside
Isoquercetrin
Quercetin 3-O-glucoside
Quercetin 3-D-glucoside
Isoquercitrin
isoquercetin
quercetin 3-O-β-D-glucoside
Hirsutrin
isotrifoliin
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-
3,3',4',5,7-Pentahydroxyflavone 3-b-D-glucofuranoside
Quercetin-3-β-glucopyranoside
quercetin 3-O-beta-D-glucofuranoside
Quercetin-3-O-glucoside
Quercetin 3-β-O-glucoside
2-(3,4-Dihydroxyphenyl)-3-(b-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
Quercetin 3-O-glucopyranoside

Biological Activity

[Description]:

Isoquercitrin is an effective antioxidant and an eosinophilic inflammation suppressor.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Natural Products >> Flavonoids

Research Areas >> Inflammation/Immunology

[In Vitro]

Isoquercitrin occurs widely in plants.10 μM of Isoquercitrin of the seven compounds partially but significantly blunt the negative effect of H2O2 on RGC-5 cells, as the viability of cells in the presence of H2O2 is increased from approximately 63% to 83% and 90% at 10 and 50 μM, respectively. Indeed, 50 μM Isoquercitrin is more effective as a neuroprotectant than the same concentration of EGCG[1].

[In Vivo]

In animals receiving Isoquercitrin or quercetin, eosinophil counts are lower in the BALF, blood and lung parenchyma. Neutrophil counts in blood and IL-5 levels in lung homogenate are lower only in Isoquercitrin-treated mice. No alterations in mononuclear cell numbers were observed[2].

[Animal admin]

Mice[2] BALB/c mice are immunized (ovalbumin/aluminum hydroxide, s.c.), followed by two intranasal ovalbumin challenges. From day 18 to day 22 after the first immunization, the mice receive daily gavages of Isoquercitrin (15 mg/kg) or quercetin (10 mg/kg). Dexamethasone (1 mg/kg, s. c.) is administered as a positive control. Leucocytes are analyzed in bronchoalveolar lavage fluid (BALF), blood and pulmonary parenchyma at 24 h after the last ovalbumin challenge. Interleukin-5 (IL-5) is analyzed in BALF and lung homogenates[2].

[References]

[1]. Jung SH, et al. Isoquercitrin is the most effective antioxidant in the plant Thuja orientalis and able to counteract oxidative-induced damage to a transformed cell line (RGC-5 cells). Neurochem Int. 2010 Dec;57(7):713-21.

[2]. Rogerio AP, et al. Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma. Inflamm Res. 2007 Oct;56(10):402-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
872.6±65.0 °C at 760 mmHg

[ Melting Point ]:
225-227°

[ Molecular Formula ]:
C₂₁H₂₀O₁₂

[ Molecular Weight ]:
464.376

[ Flash Point ]:
307.5±27.8 °C

[ Exact Mass ]:
464.095490

[ PSA ]:
210.51000

[ LogP ]:
1.75

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.803

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LK8960000

CHEMICAL NAME :: Flavone, 3,3',4',5,7-pentahydroxy-, 3-beta-D-glucofuranoside

CAS REGISTRY NUMBER :: 21637-25-2

LAST UPDATED :: 199410

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C21-H20-O12

MOLECULAR WEIGHT :: 464.41

WISWESSER LINE NOTATION :: T66 BO EVJ CR CQ DQ& DO- BT5OTJ CQ DQ EYQ1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 40 ug/plate

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 3,401,1981

Safety Information

[ Safety Phrases ]:
24/25

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ RTECS ]:
LK8960000

Precursor & DownStream

Precursor

DownStream

Articles

Isoquercitrin provides better bioavailability than quercetin: comparison of quercetin metabolites in body tissue and brain sections after six days administration of isoquercitrin and quercetin.

Pharmazie 67(12) , 991-6, (2012)

In the present study, over a period of 8 days 12 mg/kg/d quercetin aglycone and 18 mg/kg/d isoquercitrin were orally given to rats, respectively. Four hours after administration, plasma samples were t...

A sensitive LC-MS/MS method for simultaneous determination of six flavonoids in rat plasma: application to a pharmacokinetic study of total flavonoids from mulberry leaves.

J. Pharm. Biomed. Anal. 84 , 189-95, (2013)

A simple and sensitive LC-MS/MS method has been developed and validated for the determination of rutin, isoquercitrin, astragalin, quercetin, kaempferol and isorhamnetin in rat plasma using naringin a...

Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba.

Magn. Reson. Chem. 50(8) , 569-75, (2012)

The complete and unambiguous (1)H NMR assignments of ten marker constituents of Ginkgo biloba are described. The comprehensive (1)H NMR profiles (fingerprints) of ginkgolide A, ginkgolide B, ginkgolid...