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Structure Database (LMSD)

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Common Name

Rhamnetin

Systematic Name

3,5,3',4'-Tetrahydroxy-7-methoxyflavone

Synonyms

7-Methoxyquercetin

LM ID

LMPK12112624

Formula

C₁₆H₁₂O₇

Exact Mass

Calculate m/z

316.058305

Status

Curated

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View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category

Main Class

Sub Class

Polyketides [PK]

Flavonoids [PK12]

Flavones and Flavonols [PK1211]

Biological Context

Rhamnetin is a flavonoid that has been found in O. falcate and has diverse biological activities.^1,2,3,4 It reduces production of reactive oxygen species (ROS) and apoptosis induced by miconazole in H9c2 cardiomyocytes.² Rhamnetin inhibits LPS-induced TNF-α and nitric oxide (NO) production in rat neonatal organotypic hippocampal slice cultures (OHSCs) under control conditions and during ethanol withdrawal, as well as NMDA-induced neurotoxicity in OHSCs undergoing ethanol withdrawal.³ Dietary administration of rhamnetin (0.1 and 0.2% w/w) reduces serum levels of malondialdehyde (MDA) and liver and erythrocyte levels of thiobarbituric acid reactive substances (TBARS) in rats fed a cholesterol-free diet.⁴ Rhamnetin increases time spent in the target quadrant in the Morris water maze in a rat model of traumatic brain injury.⁵

This information has been provided by Cayman Chemical

References

1. Jiang, H., Zhan, W.Q., and Jiang, S.X. Antioxidant activities of extracts and flavonoid compounds from Oxytropis falcate Bunge. Nat. Prod. Res. 22(18), 1650-1656 (2008).

2. Zhang, W., Li, B., Guo, Y., et al. Rhamnetin attenuates cognitive deficit and inhibits hippocampal inflammatory response and oxidative stress in rats with traumatic brain injury. Cent. Eur. J. Immunol. 40(1), 35-41 (2015).

3. Lutz, J.A., Carter, M., Fields, L., et al. The dietary flavonoid rhamnetin inhibits both inflammation and excitotoxicity during ethanol withdrawal in rat organotypic hippocampal slice cultures. Alcohol Clin. Exp. Res. 39(12), 2345-2353 (2015).

4. Lee, K.P., Kim, J.-E., and Park, W.-H. Cytoprotective effect of rhamnetin on miconazole-induced H9c2 cell damage. Nutr. Res. Pract. 9(6), 586-591 (2015).

5. Igarashi, K., and Ohmuma, M. Effects of isorhamnetin, rhamnetin, and quercetin on the concentrations of cholesterol and lipoperoxide in the serum and liver and on the blood and liver antioxidative enzyme activities of rats. Biosci. Biotechnol. Biochem. 59(4), 595-601 (1995).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Viridiplantae (#33090)

Flavonoid imported from http://metabolomics.jp/

String Representations

InChiKey (Click to copy)

JGUZGNYPMHHYRK-UHFFFAOYSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1(OC)=CC2OC(C3C=C(O)C(O)=CC=3)=C(O)C(=O)C=2C(O)=C1

Other Databases

Wikipedia

KEGG ID

HMDB ID

CHEBI ID

METABOLOMICS ID

PubChem CID

Cayman ID

PDB ID

Calculated Physicochemical Properties

Heavy Atoms 23

Rings 3

Aromatic Rings 3

Rotatable Bonds 2

Van der Waals Molecular Volume 255.99

Topological Polar Surface Area 120.36

Hydrogen Bond Donors 4

Hydrogen Bond Acceptors 7

logP 3.19

Molar Refractivity 81.24

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