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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

Molecular Formula C16H12O7
Molecular Weight 316.2623
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.7 µM [IC50]
0.41 µM [IC50]
0.54 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Mice: 200 mkg/kg/day for 20 days
Route of Administration: Intraperitoneal
In Vitro Use Guide
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
Record UNII
71803L5F4S
Record Status Validated (UNII)
Record Version