Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C15H8O6 |
| Molecular Weight | 284.2204 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC2=C(C(O)=C1)C(=O)C3=C(C=CC=C3O)C2=O
InChI
InChIKey=FCDLCPWAQCPTKC-UHFFFAOYSA-N
InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
| Molecular Formula | C15H8O6 |
| Molecular Weight | 284.2204 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24699148 | https://www.ncbi.nlm.nih.gov/pubmed/14402302 | https://www.ncbi.nlm.nih.gov/pubmed/9010651 | https://www.ncbi.nlm.nih.gov/pubmed/18123056 | https://www.ncbi.nlm.nih.gov/pubmed/2512175 | https://www.ncbi.nlm.nih.gov/pubmed/25435889
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24699148 | https://www.ncbi.nlm.nih.gov/pubmed/14402302 | https://www.ncbi.nlm.nih.gov/pubmed/9010651 | https://www.ncbi.nlm.nih.gov/pubmed/18123056 | https://www.ncbi.nlm.nih.gov/pubmed/2512175 | https://www.ncbi.nlm.nih.gov/pubmed/25435889
Rhein, also known as cassic acid, is a substance in the anthraquinone group obtained from rhubarb species like Rheum undulatum and Rheum palmatum as well as in Cassia reticulata. Rhein, a metabolite of Diacerein and sennosides, alleviates pain and fever, inhibits inflammation, and has weak laxative. Rhein dose-dependently inhibits superoxide anion production, chemotaxis and phagocytic activity of neutrophils, and macrophage migration and phagocytosis. In addition, rhein exerts its anticancer effects via the modulation of processes of cellular proliferation, apoptosis, migration, and invasion. The pharmacokinetics of rhein have not been intensively studied in humans, but at least one study in healthy male volunteers found that rhein was better absorbed from oral administration of rhubarb than from a retention enema. Rhein (at an oral dose of 50 mg twice per day) was shown to be safe when administered for five days to elderly patients with chronic congestive heart failure.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of the antiviral activity of anthraquinones, anthrones and anthraquinone derivatives against human cytomegalovirus. | 1992 Jan |
|
| Analgesic effect of meloxicam in canine acute dermatitis--a pilot study. | 2002 |
|
| [Study on the quantitative change of anthraquinonoids of Rhei in the preparation of dachengqi]. | 2002 Jan |
|
| Rhein inhibits interleukin-1 beta-induced activation of MEK/ERK pathway and DNA binding of NF-kappa B and AP-1 in chondrocytes cultured in hypoxia: a potential mechanism for its disease-modifying effect in osteoarthritis. | 2003 Aug |
|
| Simultaneous determination of hydroxyanthraquinones in rhubarb and experimental animal bodies by high-performance liquid chromatography. | 2003 Aug |
|
| Molecular and biochemical characterization of an enzyme responsible for the formation of hypericin in St. John's wort (Hypericum perforatum L.). | 2003 Aug 22 |
|
| Solvent effects in permeation assessed in vivo by skin surface biopsy. | 2003 Dec 18 |
|
| [Studies on the chemical constituents of Dendrobium fimbriatum]. | 2003 Jul |
|
| The lead extractor's toolbox: a review of current endovascular pacemaker and ICD lead extraction techniques. | 2003 Jul 1 |
|
| Differential modulation of the TRAIL receptors and the CD95 receptor in colon carcinoma cell lines. | 2003 Jul 21 |
|
| Relapsing fever-like spirochetes infecting European vector tick of Lyme disease agent. | 2003 Jun |
|
| Polyacylated neohesperidosides from Geranium caespitosum: bacterial multidrug resistance pump inhibitors. | 2003 Jun 2 |
|
| Diacerein reduces the level of cartilage chondrocyte DNA fragmentation and death in experimental dog osteoarthritic cartilage at the same time that it inhibits caspase-3 and inducible nitric oxide synthase. | 2003 Mar-Apr |
|
| Pharmacokinetics of rhein from Onpi-to, an Oriental herbal medicine, in rats. | 2003 May |
|
| Pulmonary tuberculosis due to Mycobacterium bovis subsp. caprae in captive Siberian tiger. | 2003 Nov |
|
| [Precipitation reaction between berberine and rheinic acid by capillary electrophoresis]. | 2003 Oct |
|
| Rhein induces apoptosis in HL-60 cells via reactive oxygen species-independent mitochondrial death pathway. | 2003 Oct 15 |
|
| Preparative separation of rhein from Chinese traditional herb by repeated high-speed counter-current chromatography. | 2003 Oct 31 |
|
| Articular chondrocytes cultured in hypoxia: their response to interleukin-1beta and rhein, the active metabolite of diacerhein. | 2004 |
|
| Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones. | 2004 Apr |
|
| Expedient total syntheses of rhein and diacerhein via Fries rearrangement. | 2004 Dec 10 |
|
| Inhibition of human tumor cell proliferation by novel anthraquinones from daylilies. | 2004 Feb 20 |
|
| Determination of rhein, baicalin and berberine in traditional Chinese medicinal preparations by capillary electrophoresis with two-marker technique. | 2004 Jun |
|
| Determination of active ingredients in Huangdan Yinchen Keli by CZE with amperometric detection. | 2004 Jun 29 |
|
| [Effects of rhein on the function of human mesangial cells in high glucose environment]. | 2004 Nov |
|
| [Simultaneous determination of 4 anthraquinones in Kuhuang injection by RP-HPLC]. | 2004 Nov |
|
| [Effects of combination therapy of rehin and tetramethylpyrazine on experimental hepatic fibrosis induced by tetrachloride]. | 2004 Nov |
|
| Antigenotoxic properties of Cassia tea (Cassia tora L.): mechanism of action and the influence of roasting process. | 2004 Nov 19 |
|
| Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography. | 2004 Oct 15 |
|
| Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi. | 2004 Oct 6 |
|
| [Determination of active anthraquinones in Rheum and its tea preparations by micellar electrokinetic capillary electrophoresis]. | 2004 Sep |
|
| Screening procedure for detection of stimulant laxatives and/or their metabolites in human urine using gas chromatography-mass spectrometry after enzymatic cleavage of conjugates and extractive methylation. | 2005 Apr |
|
| [A new isoflavone from Huoxue Yiqi Tang]. | 2005 Aug |
|
| Habitat characterization and spatial distribution of Anopheles sp. mosquito larvae in Dar es Salaam (Tanzania) during an extended dry period. | 2005 Jan 14 |
|
| Peptide-based approaches to treat asthma, arthritis, other autoimmune diseases and pathologies of the central nervous system. | 2005 Jul-Aug |
|
| [Influence of processing rhubarb on it's anthraquinone contents]. | 2005 Jun |
|
| [Progress in study on mechanisms of rhubarb in treating chronic renal failure]. | 2005 May |
|
| Simultaneous determination of anthraquinones, their 8-beta-D-glucosides, and sennosides of Rhei Rhizoma by capillary electrophoresis. | 2005 May |
|
| Simultaneous determination of anthraquinones in Rhubarb by pressurized liquid extraction and capillary zone electrophoresis. | 2005 May |
|
| Effects and wavelet spectral entropy analysis of rhubarb extracts rhein on synaptic transmission in rat hippocampal ca1 area in vitro. | 2005 May 20 |
|
| Separation and determination of anthraquinones in Cassia obtusifolia (Leguminosae) by micellar electrokinetic capillary electrophoresis. | 2005 Nov |
|
| The influence of the sennosides on absorption of glycyrrhetic acid in rats. | 2005 Oct |
|
| IL-1beta synthesis by chondrocyte analyzed by 3D microscopy and flow cytometry: effect of Rhein. | 2006 |
|
| Inhibition of interleukin-1beta-induced activation of MEK/ERK pathway and DNA binding of NF-kappaB and AP-1: potential mechanism for Diacerein effects in osteoarthritis. | 2006 |
|
| [Study on the selection of crude drugs of rhubarb dispensing granule]. | 2006 Apr |
|
| Determination of five anthraquinones in medicinal plants by capillary zone electrophoresis with beta-cyclodextrin addition. | 2006 Aug 4 |
|
| Insulin sensitizing and alpha-glucoamylase inhibitory action of sennosides, rheins and rhaponticin in Rhei Rhizoma. | 2006 Jan 25 |
|
| Rapid separation and determination of structurally related anthraquinones in Rhubarb by pressurized capillary electrochromatography. | 2007 Jan 4 |
|
| Simultaneous determination of eight active components in Chinese medicine 'YIQING' capsule using high-performance liquid chromatography. | 2007 Jan 4 |
|
| Study on the electrochemical behavior and differential pulse voltammetric determination of rhein using a nanoparticle composite film-modified electrode. | 2007 May |
Patents
Sample Use Guides
SKOV3-PM4 cells were allowed to grow in 96-well plates at 5,000 cells/well for 24 h and then treated with different concentrations of rhein, respectively. Forty-eight hours later, 20 μl of 5 mg/ml MTT solution was added to each well. The plates were incubated at 37˚C in 5% CO2 for 4 h, then the supernatant was discarded and 150 μl DMSO was added to dissolve the formazan. The absorbance at a wavelength of 490 nm was measured using a microplate reader
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 01:56:09 UTC 2023
by
admin
on
Thu Jul 06 01:56:09 UTC 2023
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| Record UNII |
YM64C2P6UX
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| Record Status |
Validated (UNII)
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| Record Version |
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10168
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DB13174
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C020491
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207-521-4
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Rhein (molecule)
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DTXSID4026000
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M9569
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38629
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| Related Record | Type | Details | ||
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