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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 RHAMNETIN

SMILES

COC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C3=CC=C(O)C(O)=C3

InChI

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

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28858248 | https://www.ncbi.nlm.nih.gov/pubmed/27091611 | https://www.ncbi.nlm.nih.gov/pubmed/26155182

Rhamnetin is phenolic flavonoid compound and methylated derivatives of quercetin commonly found in fruits and vegetables that possess antioxidant and anti-inflammatory properties. Rhamnetin can be found in cloves, sweet wormwood, and green vegetables such as coriander leaves and seeds Cloves and coriander are common elements in many types of cuisine. Similar amounts of rhamnetin are found in apple pomace, peanuts, sour cherries, and radishes.8 It is generally considered that a regular intake of small amounts of the above-mentioned fruits and vegetables, which are commonly available, serves a protective role in preventing various diseases. Rhamnetin suppressed the mouse macrophage inflammatory protein (MIP-1, MIP-2), and mouse TNF-α cytokine production in LPS-stimulated macrophages. A nontoxic dose of rhamnetin also suppressed NO production. Rhamnetin acts as a promising sensitizer to chemotherapy and may be a novel approach to overcome the multi-drug resistance process of hepatocellular carcinoma.

Originator

Sources: Justus Liebig's Annalen der Chemie 196, 299, 338. From: J. Am. Chem. Soc. 2(1), 62-5 1880.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones.
2012-06
3-Hydroxymethylglutaryl flavonol glycosides from a Mongolian and Tibetan medicine, Oxytropis racemosa.
2010-12
Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative.
2010-07-06
Flavonoids from the aerial parts of Diplomorpha canescens.
2010-06
Interaction of flavonoids, the naturally occurring antioxidants with different media: a UV-visible spectroscopic study.
2010-04
Polyphenolic profile and bioactivity study of Oenothera speciosa Nutt. aerial parts.
2009-04-07
Cytotoxic constituents of chinese propolis.
2009-04
In vitro anti-influenza viral activities of constituents from Caesalpinia sappan.
2009-03
Influence of Honey on the Suppression of Human Low Density Lipoprotein (LDL) Peroxidation (In vitro).
2009-03
Flavonoids inhibit the AU-rich element binding of HuC.
2009-01-31
Screening for fractions of Oxytropis falcata Bunge with antibacterial activity.
2009
Flavonoid-induced morphological modifications of endothelial cells through microtubule stabilization.
2009
Antioxidant activities of extracts and flavonoid compounds from Oxytropis falcate Bunge.
2008-12
Chemical composition and botanical origin of red propolis, a new type of brazilian propolis.
2008-09
Evaluation of behavioural and antioxidant activity of Cytisus scoparius Link in rats exposed to chronic unpredictable mild stress.
2008-04-24
[A new flavonoid from heartwood of Caesalpinia sappan].
2008-04
Online RP-HPLC-DPPH screening method for detection of radical-scavenging phytochemicals from flowers of Acacia confusa.
2008-01-23
[Studies on flavonoids of Eupatorium odoratum L].
2007-06
Anti-inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-kappaB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-kappaB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages.
2007
[Studies on flavonoid constituents from herbs of Artemisia ordosica II].
2006-12
Ethnopharmacological evaluation of radal (leaves of Lomatia hirsuta) and isolation of 2-methoxyjuglone.
2006-08-31
New flavonol glycosides and new xanthone from Polygala japonica.
2006-07-26
Antioxidant activity of coumarins and flavonols from the resinous exudate of Haplopappus multifolius.
2006-05
[Studies on chemical constituents in herb of Myricaria bracteata].
2006-03
Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid.
2005-11-02
Arbuscular mycorrhizal colonization of tomato by Gigaspora and Glomus species in the presence of root flavonoids.
2005-06
[Study on flavonoids from leaf of Ipomoea batatas].
2005-04
Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O- and xanthone C-glycosides, anthocyanins, and pectin.
2005-03-09
Molecular characterization and functional expression of flavonol 6-hydroxylase.
2004-12-13
On-line characterisation of apple polyphenols by liquid chromatography coupled with mass spectrometry and ultraviolet absorbance detection.
2004-08-13
Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans and its antioxidant effect.
2004-07-28
Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices.
2004-07
Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.
2004-06
Allelochemicals of Polygonella myriophylla: chemistry and soil degradation.
2004-05
Isolation of flavonol rhamnosides from Loranthus tanakae and cytotoxic effect of them on human tumor cell lines.
2004-01
Inhibitory effects of plant-derived flavonoids and phenolic acids on malonaldehyde formation from ethyl arachidonate.
2003-11-19
Investigation of natural dyes occurring in historical Coptic textiles by high-performance liquid chromatography with UV-Vis and mass spectrometric detection.
2003-09-19
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
2003-09-09
Identification of flavonol and xanthone glycosides from mango (Mangifera indica L. Cv. "Tommy Atkins") peels by high-performance liquid chromatography-electrospray ionization mass spectrometry.
2003-08-13
Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
2003-05
Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L.
2002-10-09
Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. "Brettacher") by HPLC-PDA and HPLC-APCI-MS/MS.
2002-05-23
Characterization of flavonoid--biomembrane interactions.
2002-03-01
Inhibitory effects of naturally occurring compounds on aflatoxin B(1) biotransformation.
2001-11
Inhibitory activity of flavonoids and tannins against HIV-1 protease.
2000-09
Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors.
1996-12
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.
1994-08-03
Inhibition of reverse transcriptases by flavonoids.
1989-09
Patents

Sample Use Guides

Mice: 200 mkg/kg/day for 20 days
Route of Administration: Intraperitoneal
To determine cell viability, a 2,3-bis [2-methyloxy-4-nitro-5-sulfophenyl]-2H-tetrazolium-5-carboxanilide (XTT) assay was employed using the WelCountTM cell proliferation assay kit (WELLGENE, Daegu, South Korea). H9c2 cells were harvested with trypsin-EDTA and resuspended in culture medium. H9c2 cells (5 × 103 cells/well) were then seeded in 96-well plates and cultivated in DMEM containing 10% FBS for 24 h. Cells were then cultivated in serum-free DMEM for 6 h, followed by incubation in serum-free medium containing rhamnetin or miconazole for 24 h. XTT dye was added to each well and incubated for 3 h. Formazan dye formation was quantitated with an enzymelinked immunosorbent assay reader at 450 nm. Morphological changes in the cells were observed, and images were captured under an inverted microscope connected to a digital camera
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:23:33 GMT 2025
Edited
by admin
on Mon Mar 31 20:23:33 GMT 2025
Record UNII
71803L5F4S
Record Status Validated (UNII)
Record Version
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Name Type Language
RHAMNETIN
MI  
Common Name English
NSC-19802
Preferred Name English
QUERCETIN 7-METHYL ETHER
Common Name English
2-(3,4-DIHYDROXYPHENYL)-3,5-DIHYDROXY-7-METHOXY-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
RHAMNETIN [MI]
Common Name English
3,5,3',4'-TETRAHYDROXY-7-METHOXYFLAONE
Common Name English
FLAVONE, 3,3',4',5-TETRAHYDROXY-7-METHOXY-
Systematic Name English
3,3',4',5-TETRAHYDROXY-7-METHOXYFLAVONE
Systematic Name English
7-METHYLQUERCETIN
Common Name English
7-METHOXYQUERCETIN
Common Name English
7-O-METHYLQUERCETIN
Common Name English
FLAVONE, 7-METHOXY-3,3',4',5-TETRAHYDROXY-
Systematic Name English
.BETA.-RHAMNOCITRIN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-3,5-DIHYDROXY-7-METHOXY-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
RHAMNETIN
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
MERCK INDEX
m9564
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY Merck Index
CAS
90-19-7
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
PUBCHEM
5281691
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-974-1
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
NSC
19802
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
CHEBI
74992
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID40237979
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
MESH
C063423
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY
FDA UNII
71803L5F4S
Created by admin on Mon Mar 31 20:23:33 GMT 2025 , Edited by admin on Mon Mar 31 20:23:33 GMT 2025
PRIMARY