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 |
---|---|---|
Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors. | 1996 Dec |
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Characterization of flavonoid--biomembrane interactions. | 2002 Mar 1 |
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Comparative study on the free flavonoid aglycones in herbs of different species of Polygonum L. | 2002 Mar-Apr |
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Detection of isorhamnetin glycosides in extracts of apples (Malus domestica cv. "Brettacher") by HPLC-PDA and HPLC-APCI-MS/MS. | 2002 Mar-Apr |
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Sesquiterpene lactones from Anthemis altissima and their anti-Helicobacter pylori activity. | 2003 May |
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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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Effects of naturally occurring compounds on fibril formation and oxidative stress of beta-amyloid. | 2005 Nov 2 |
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Evaluation of behavioural and antioxidant activity of Cytisus scoparius Link in rats exposed to chronic unpredictable mild stress. | 2008 Apr 24 |
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Interaction of flavonoids, the naturally occurring antioxidants with different media: a UV-visible spectroscopic study. | 2010 Apr |
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