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
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26634046Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26634046
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22261024 |
2.7 µM [IC50] | ||
Target ID: CHEMBL2276 |
0.41 µM [IC50] | ||
Target ID: CHEMBL1907606 |
0.54 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Inhibitory effects of naturally occurring compounds on aflatoxin B(1) biotransformation. | 2001 Nov |
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Characterization of flavonoid--biomembrane interactions. | 2002 Mar 1 |
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Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity. | 2003 May |
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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 |
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On-line characterisation of apple polyphenols by liquid chromatography coupled with mass spectrometry and ultraviolet absorbance detection. | 2004 Aug 13 |
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Molecular characterization and functional expression of flavonol 6-hydroxylase. | 2004 Dec 13 |
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Isolation of flavonol rhamnosides from Loranthus tanakae and cytotoxic effect of them on human tumor cell lines. | 2004 Jan |
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Flavonoids from shoots and roots of Trifolium repens (white clover) grown in presence or absence of the arbuscular mycorrhizal fungus Glomus intraradices. | 2004 Jul |
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Novel flavonol glycoside, 7-O-methyl mearnsitrin, from Sageretia theezans and its antioxidant effect. | 2004 Jul 28 |
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Structural requirements of flavonoids for increment of ocular blood flow in the rabbit and retinal function recovery in rat eyes. | 2004 Jun |
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Allelochemicals of Polygonella myriophylla: chemistry and soil degradation. | 2004 May |
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Screening of mango (Mangifera indica L.) cultivars for their contents of flavonol O- and xanthone C-glycosides, anthocyanins, and pectin. | 2005 Mar 9 |
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Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid. | 2005 Nov 2 |
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[Studies on flavonoid constituents from herbs of Artemisia ordosica II]. | 2006 Dec |
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[Studies on chemical constituents in herb of Myricaria bracteata]. | 2006 Mar |
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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 |
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[Studies on flavonoids of Eupatorium odoratum L]. | 2007 Jun |
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[A new flavonoid from heartwood of Caesalpinia sappan]. | 2008 Apr |
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Chemical composition and botanical origin of red propolis, a new type of brazilian propolis. | 2008 Sep |
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Cytotoxic constituents of chinese propolis. | 2009 Apr |
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Flavonoids inhibit the AU-rich element binding of HuC. | 2009 Jan 31 |
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In vitro anti-influenza viral activities of constituents from Caesalpinia sappan. | 2009 Mar |
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Influence of Honey on the Suppression of Human Low Density Lipoprotein (LDL) Peroxidation (In vitro). | 2009 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27091611
Mice: 200 mkg/kg/day for 20 days
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26634046
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
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RHAMNETIN
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m9564
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90-19-7
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5281691
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DTXSID40237979
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C063423
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71803L5F4S
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SUBSTANCE RECORD