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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=CC2=C(C(=O)C(O)=C(O2)C3=CC(O)=C(O)C=C3)C(O)=C1

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

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
Inhibitory effects of naturally occurring compounds on aflatoxin B(1) biotransformation.
2001 Nov
Characterization of flavonoid--biomembrane interactions.
2002 Mar 1
Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity.
2003 May
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 Sep 9
On-line characterisation of apple polyphenols by liquid chromatography coupled with mass spectrometry and ultraviolet absorbance detection.
2004 Aug 13
Molecular characterization and functional expression of flavonol 6-hydroxylase.
2004 Dec 13
Isolation of flavonol rhamnosides from Loranthus tanakae and cytotoxic effect of them on human tumor cell lines.
2004 Jan
Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices.
2004 Jul
Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans and its antioxidant effect.
2004 Jul 28
Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes.
2004 Jun
Allelochemicals of Polygonella myriophylla: chemistry and soil degradation.
2004 May
Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O- and xanthone C-glycosides, anthocyanins, and pectin.
2005 Mar 9
Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid.
2005 Nov 2
[Studies on flavonoid constituents from herbs of Artemisia ordosica II].
2006 Dec
[Studies on chemical constituents in herb of Myricaria bracteata].
2006 Mar
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 flavonoids of Eupatorium odoratum L].
2007 Jun
[A new flavonoid from heartwood of Caesalpinia sappan].
2008 Apr
Chemical composition and botanical origin of red propolis, a new type of brazilian propolis.
2008 Sep
Cytotoxic constituents of chinese propolis.
2009 Apr
Flavonoids inhibit the AU-rich element binding of HuC.
2009 Jan 31
In vitro anti-influenza viral activities of constituents from Caesalpinia sappan.
2009 Mar
Influence of Honey on the Suppression of Human Low Density Lipoprotein (LDL) Peroxidation (In vitro).
2009 Mar
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
Name Type Language
RHAMNETIN
MI  
Common 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
NSC-19802
Code 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 Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
PRIMARY
MERCK INDEX
m9564
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
PRIMARY Merck Index
CAS
90-19-7
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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PUBCHEM
5281691
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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ECHA (EC/EINECS)
201-974-1
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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NSC
19802
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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CHEBI
74992
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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EPA CompTox
DTXSID40237979
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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MESH
C063423
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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FDA UNII
71803L5F4S
Created by admin on Fri Dec 15 22:05:55 GMT 2023 , Edited by admin on Fri Dec 15 22:05:55 GMT 2023
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