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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O7
Molecular Weight 316.2623
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISORHAMNETIN

SMILES

COC1=C(O)C=CC(=C1)C2=C(O)C(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=IZQSVPBOUDKVDZ-UHFFFAOYSA-N
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

HIDE SMILES / InChI

Molecular Formula C16H12O7
Molecular Weight 316.2623
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Isorhamnetin, a flavonol aglycone, isolated from the traditional Chinese medicine H. rhamnoides L., was frequently used in traditional medicine to prevent and treat diverse diseases. Isorhamnetin has been shown to play a variety of roles in anti-oxidation, anti-inflammation, anti-tumor, anti-viral, and neurodegenerative injury protection. Isorhamnetin could inhibit the H2O2-induced activation of the intrinsic apoptotic pathway by scavenging free ROS and extracellular signal-regulated kinase 1/2 (ERK1/2) inactivation. In the type 2 diabetic rat model, isorhamnetin was found to be able to inhibit the NF-κB signaling activity, attenuate oxidative stress, and decrease the production of inflammatory mediators. Isorhamnetin can suppress skin cancer, breast cancer, colon cancer and atherosclerosis by inhibiting PI3K/AKT activation. Isorhamnetin shows inhibitory activity toward CYP1B1 expression and function.

Originator

Sources: DOI: 10.1021/ja02229a015
Curator's Comment: glucoside

Approval Year

PubMed

PubMed

TitleDatePubMed
The flavonoids, quercetin and isorhamnetin 3-O-acylglucosides diminish neutrophil oxidative metabolism and lipid peroxidation.
2001
Coumaroyl flavonol glycosides from the leaves of Ginkgo biloba.
2001 Dec
Two flavonol 5-O-glycosides from the roots of Leuzea carthamoides.
2001 Dec
Kaempferol, isorhamnetin and their glycosides in the flowers of Asclepias syriaca L.
2001 Jul-Aug
[Comparison of photometric, electrochemical and post-column fluorescence detection for the determination of flavonoids by HPLC].
2001 Jun
Alkaloids and flavonoids from peanut skins.
2001 Jun
Antiprotozoal activity of the constituents of Conyza filaginoides.
2001 May
Flavonol glycosides from the flowers of Bellis perennis.
2001 Nov
Contrasting influences of glucuronidation and O-methylation of epicatechin on hydrogen peroxide-induced cell death in neurons and fibroblasts.
2001 Nov 1
The impact of different flavonoid classes on colonic CI- secretion in rats.
2001 Oct 15
Effects of intrinsic fluorescence and quenching on fluorescence-based screening of natural products.
2002 Apr
Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch).
2002 Apr 10
Chemical analysis of Ginkgo biloba leaves and extracts.
2002 Aug 16
Effect of five flavonoid compounds isolated from leaves of Diospyros kaki on stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophils.
2002 Dec
[Studies on chemical constituents of Cuscuta chinensis].
2002 Feb
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.
2002 Feb
Endothelium-independent vasodilator effects of the flavonoid quercetin and its methylated metabolites in rat conductance and resistance arteries.
2002 Jul
Quercetin metabolism in the lens: role in inhibition of hydrogen peroxide induced cataract.
2002 Jul 1
Characterisation of new oligoglycosidic compounds in two Chinese medicinal herbs.
2002 Jul-Aug
Flavonoid glycosides from Rhazya orientalis.
2002 Mar
Evaluation of the release profiles of flavonoids from topical formulations of the crude extract of the leaves of Dodonea viscosa (Sapindaceae).
2002 May
Further isolation of peroxynitrite and 1,1-diphenyl-2-picrylhydrazyl radical scavenging isorhamnetin 7-O-glucoside from the leaves of Brassica juncea L.
2002 Oct
Flavonol triglycosides from the leaves of Hammada scoparia (POMEL) ILJIN.
2002 Sep
Varietal differences among the polyphenol profiles of seven table grape cultivars studied by LC-DAD-MS-MS.
2002 Sep 25
Chemical composition of shallot (Allium ascalonicum Hort.).
2002 Sep 25
Chemical characterization and biological effects of Sicilian Opuntia ficus indica (L.) mill. Fruit juice: antioxidant and antiulcerogenic activity.
2003 Aug 13
Enhancing effect of lipids and emulsifiers on the accumulation of quercetin metabolites in blood plasma after the short-term ingestion of onion by rats.
2003 Dec
Flavonol and drimane-type sesquiterpene glycosides of Warburgia stuhlmannii leaves.
2003 Jun
Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages.
2003 Jun 15
Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
2003 May
Effects of the flavonoid quercetin and its methylated metabolite isorhamnetin in isolated arteries from spontaneously hypertensive rats.
2003 Nov
Phenols and flavonoids in Aleppo pine needles as bioindicators of air pollution.
2003 Nov-Dec
Mechanisms involved in the antiplatelet activity of rutin, a glycoside of the flavonol quercetin, in human platelets.
2004 Jul 14
Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.
2004 Jun
Phytochemical analysis of ethyl acetate extract from Astragalus corniculatus Bieb. and brain antihypoxic activity.
2004 Jun
Flavonoid-rich dark chocolate improves endothelial function and increases plasma epicatechin concentrations in healthy adults.
2004 Jun
The type of sugar moiety is a major determinant of the small intestinal uptake and subsequent biliary excretion of dietary quercetin glycosides.
2004 Jun
Structural investigations of flavonol glycosides from sea buckthorn (Hippophaë rhamnoides) pomace by NMR spectroscopy and HPLC-ESI-MS(n).
2004 Jun 30
The protozoan Tetrahymena as a bioindicator to screen bioactive substances.
2004 Nov
Characterisation of flavonols in broccoli (Brassica oleracea L. var. italica) by liquid chromatography-uV diode-array detection-electrospray ionisation mass spectrometry.
2004 Oct 29
Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity.
2004 Sep 13
Investigation of the bioavailability of hypericin, pseudohypericin, hyperforin and the flavonoids quercetin and isorhamnetin following single and multiple oral dosing of a hypericum extract containing tablet.
2005
Antiinflammatory constituents from the roots of Smilax bockii warb.
2005 Apr
Inhibitory activity of isorhamnetin from Persicaria thunbergii on Farnesyl Protein Transferase.
2005 Feb
[Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts].
2005 Jan
Breast cancer resistance protein (Bcrp1/Abcg2) limits net intestinal uptake of quercetin in rats by facilitating apical efflux of glucuronides.
2005 Jun
The influence of Calendulae officinalis flos extracts on cell cultures, and the chromatographic analysis of extracts.
2005 Jun 15
Quercetin metabolism in vital and apoptotic human leukaemia cells.
2005 Mar
Synergistic effects of flavonoids and ascorbate on enhancement in DNA degradation induced by a bleomycin-Fe complex.
2005 Mar
Simultaneous determination of quercetin, kaempferol and isorhamnetin accumulated human breast cancer cells, by high-performance liquid chromatography.
2005 Sep 1
Patents

Sample Use Guides

Mice: 100 mg/kg/day for 8 weeks
Route of Administration: Oral
Isorhamnetin (3-O-methyl quercetin) had no effect on human neuroblastoma SH-SY5Y cells viability even at 100 uM and even in presence of 500 uM ascorbic acid
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:05:49 GMT 2023
Edited
by admin
on Sat Dec 16 20:05:49 GMT 2023
Record UNII
07X3IB4R4Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISORHAMNETIN
INCI   USP-RS  
INCI  
Official Name English
3,4',5,7-TETRAHYDROXY-3'-METHOXYFLAVONE
Systematic Name English
3'-O-METHYLQUERCETIN
Common Name English
METHYLQUERCETIN, 3'-O-
Common Name English
ISORHAMNETIN (CONSTITUENT OF GINKGO) [DSC]
Common Name English
ISORHAMNETIN [USP-RS]
Common Name English
3,5,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-4-BENZOPYRONE
Systematic Name English
ISORHAMNETIN [INCI]
Common Name English
FLAVONE, 3,4',5,7-TETRAHYDROXY-3'-METHOXY-
Systematic Name English
4H-1-BENZOPYRAN-4-ONE, 3,5,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-
Systematic Name English
C.I. 75680
Common Name English
QUERCETIN 3'-METHYL ETHER
Common Name English
Code System Code Type Description
PUBCHEM
5281654
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
RS_ITEM_NUM
1351800
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-545-5
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
WIKIPEDIA
ISORHAMNETIN
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
CHEBI
6052
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
CHEBI
144055
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
FDA UNII
07X3IB4R4Z
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID10197379
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
CAS
480-19-3
Created by admin on Sat Dec 16 20:05:49 GMT 2023 , Edited by admin on Sat Dec 16 20:05:49 GMT 2023
PRIMARY
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