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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O12
Molecular Weight 464.3771
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOQUERCETIN

SMILES

c1cc(c(cc1-c2c(c(=O)c3c(cc(cc3o2)O)O)O[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O4)O)O)O)O)O

InChI

InChIKey=OVSQVDMCBVZWGM-QSOFNFLRSA-N
InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H20O12
Molecular Weight 464.3771
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Isoquercetin is a flavonoid, derivative of quercetin. It was isolated from various plant species including Ammothamnus Lehmanii, Caragana alaica, Cicer baldshuanicum, C. macroconthum, C. pungens, Euphorbia cyparissias, E. helioscapia, E. lathyris, E. lucida, E. purporata and others. It demonstrated radical scavenging activity, inhibitory effects on Na+/K+-ATPase and positive inotropic activity. It is protein disulfide isomerase (PDI) inhibitor. As a PDI inhibitor, this agent blocks PDI-mediated platelet activation, and fibrin generation, which prevents thrombus formation after vascular injury. Isoquercetin inhibited the replication of both influenza A and B viruses at the lowest effective concentration. Isoquercetin activates the ERK1/2-Nrf2 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. It is being investigated for prevention of thromboembolism in selected cancer patients and as an anti-fatigue agent in kidney cancer patients treated with sunitinib.

Originator

Sources: DOI: 10.1007/978-1-4614-0535-1_485

Approval Year

PubMed

PubMed

TitleDatePubMed
Inhibition of HIV infection by flavanoids.
1993 Oct
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.
1995 Apr
[HPLC investigation of antioxidant components in Solidago herba].
2004
[Study on chemical constituents of Lagotis yunnanensis].
2005 Sep
[Studies on chemical constituents from flowers of Apocynum venetum].
2005 Sep
Quantitative determination of major active components in Ginkgo biloba dietary supplements by liquid chromatography/mass spectrometry.
2006
Inhibition of human cytochrome CYP 1 enzymes by flavonoids of St. John's wort.
2006 Jan 16
Constituents from the leaves of Phellodendron amurense and their antioxidant activity.
2006 Sep
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.
2006 Sep-Oct
Simultaneous determination of seven flavonoids in Potentilla multifida by HPLC.
2007 Apr
[Studies on antiproliferative effect of flavones compounds isolated from Yao herb medicines].
2007 Aug
An unusual C6-C6" linked flavonoid from Miconia cabucu (Melastomataceae).
2007 Jul
The anti-thrombotic active constituents from Centella asiatica.
2007 May
Three new 3-benzylbenzofuran-2-one derivatives from Homalium brachybotrys (Flacourtiaceae/Salicaceae s. l.).
2007 Nov
[Isolation and preparation of flavones from the leaves of Lindera aggregata using high speed counter-current chromatography].
2007 Sep
[Study on antioxidant activity of constituents from mulberry leaf].
2008 Apr
[Studies on chemical constituents of Primula sikkmensis].
2008 Jan
Quercetin 3-glucoside protects neuroblastoma (SH-SY5Y) cells in vitro against oxidative damage by inducing sterol regulatory element-binding protein-2-mediated cholesterol biosynthesis.
2008 Jan 25
[Chemical constituents from Polygonum capitatum and their antioxidation activities in vitro].
2008 Jul
Soil quality effects on Chenopodium album flavonoid content and antioxidant potential.
2008 Jul 9
Determination of quercetin and its glucosides in onion by electrochemical methods.
2008 Jun 9
[Studies on chemical constituents of Arachniodes rhomboidea].
2008 Mar
Deconjugation and degradation of flavonol glycosides by pig cecal microbiota characterized by Fluorescence in situ hybridization (FISH).
2008 Mar 26
Camellia japonica suppresses immunoglobulin E-mediated allergic response by the inhibition of Syk kinase activation in mast cells.
2008 May
Pharmacological basis for use of Pistacia integerrima leaves in hyperuricemia and gout.
2008 May 22
Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods.
2008 May 28
Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.).
2008 May-Jun
[Flavones from flowers of Paulownia fortunei].
2008 Nov
Phytochemicals of apple peels: isolation, structure elucidation, and their antiproliferative and antioxidant activities.
2008 Nov 12
Flavonoid glycosides isolated from Salicornia herbacea inhibit matrix metalloproteinase in HT1080 cells.
2008 Oct
Light filtering by epidermal flavonoids during the resistant response of cotton to Xanthomonas protects leaf tissue from light-dependent phytoalexin toxicity.
2008 Sep
Deep supercooling xylem parenchyma cells of katsura tree (Cercidiphyllum japonicum) contain flavonol glycosides exhibiting high anti-ice nucleation activity.
2008 Sep
Chemical composition of the stem bark and leaves of Ficus pandurata Hance.
2009
[Chemical constituents from Neo-Taraxacum siphonathum].
2009 Apr
[Chemical study on ethyl acetate soluble portion of Kadsura oblongifolia].
2009 Apr
[Chemical constituents in Buddleja albiflora].
2009 Dec
[Flavonoid constituents from herbs of Sarcopyramis bodinieri var. delicata].
2009 Jan
[Flavones from Helichrysi flos syn].
2009 Jun
[Chemical constituents of Galium verum].
2009 Nov
Nondigestible saccharides suppress the bacterial degradation of quercetin aglycone in the large intestine and enhance the bioavailability of quercetin glucoside in rats.
2009 Oct 28
Phenolic compounds in leaves of Alchornea triplinervia: anatomical localization, mutagenicity, and antibacterial activity.
2010 Aug
Antioxidant enzymatically modified isoquercitrin or melatonin supplementation reduces oxidative stress-mediated hepatocellular tumor promotion of oxfendazole in rats.
2010 Feb
Antioxidant enzymatically modified isoquercitrin suppresses the development of liver preneoplastic lesions in rats induced by beta-naphthoflavone.
2010 Feb 9
[Flavonoids of Lysimachia paridiformis var. stenophylla].
2010 Jul
[Glycosides from Periploca forrestii].
2010 Mar
[Flavonoids and phenolic acid derivatives from flos farfarae].
2010 May
Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography.
2010 May-Jun
Concomitant apoptosis and regeneration of liver cells as a mechanism of liver-tumor promotion by β-naphthoflavone involving TNFα-signaling due to oxidative cellular stress in rats.
2011 Apr 28
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
Effect of enzymatically modified isoquercitrin on preneoplastic liver cell lesions induced by thioacetamide promotion in a two-stage hepatocarcinogenesis model using rats.
2013 Mar 8
Patents

Sample Use Guides

500 mg or 1000 mg, Once daily, 28 days
Route of Administration: Oral
The protein expression of Nrf2 in rat hippocampal neurons in the 100 ug/ml group increased by 200% compared with the OGD/R (oxygen-glucose deprivation followed by reoxygenation) group.
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:16:24 UTC 2021
Edited
by admin
on Sat Jun 26 06:16:24 UTC 2021
Record UNII
6HN2PC637T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOQUERCETIN
INCI  
Official Name English
QUERCETIN-3-O-.BETA.-D-GLUCOSIDE
Systematic Name English
QUERCETIN 3.BETA.-GLUCOSIDE
Common Name English
ISOQUERCETIN [INCI]
Common Name English
QUERCETIN-3-O-GLUCOSIDE
Common Name English
3',4',5,7-TETRAHYDROXYFLAVONE-3-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-
Common Name English
ISOQUERCITRIN [MI]
Common Name English
NSC-115918
Code English
QUERCETIN-3-.BETA.-GLUCOPYRANOSIDE
Common Name English
QUERCETIN 3-O-GLUCOSIDE
Common Name English
GLUCOSYL-3-QUERCETIN
Common Name English
QUERCETIN 3-O-GLUCOPYRANOSIDE [WHO-DD]
Common Name English
QUERCETIN GLUCOSIDE
Common Name English
3-GLUCOSYLQUERCETIN
Common Name English
QUERCETIN 3-D-GLUCOSIDE
Common Name English
QUERCETIN 3-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
3-O-.BETA.-D-GLUCOPYRANOSYLQUERCETIN
Common Name English
QUERCETOL 3-MONOGLUCOSIDE
Common Name English
QUERCETIN 3-O-GLUCOPYRANOSIDE
WHO-DD  
Common Name English
CONTIGOSIDE B
Common Name English
QUERCETIN-3-GLUCOSE
Common Name English
ISOQUERCETIN, (-)-
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2- (3,4-DIHYDROXYPHENYL)-3- (SS-D-GLUCOFURANOSYLOXY)-5,7-DIHYDROXY-
Systematic Name English
QUERCETIN 3-O-GLUCOSIDE (CONSTITUENT OF GINKGO) [DSC]
Common Name English
HIRSUTRIN
Common Name English
RONACARE ISOQUERCETIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C68457
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
Code System Code Type Description
PUBCHEM
5280804
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
EPA CompTox
482-35-9
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
FDA UNII
6HN2PC637T
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
MESH
C110309
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
CAS
482-35-9
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
NCI_THESAURUS
C117288
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
WIKIPEDIA
ISOQUERCETIN
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
MERCK INDEX
M6537
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB12665
Created by admin on Sat Jun 26 06:16:24 UTC 2021 , Edited by admin on Sat Jun 26 06:16:24 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER Flavonoid
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Repeated chromatography of the n-BuOH soluble fraction yielded this flavonoid glucoside. Has shown antimicrobial activiral activity in other studies.
PARENT -> CONSTITUENT ALWAYS PRESENT
Secondary metabolite detected in developing cacao seeds.