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Rhamnetin

(Synonyms: 鼠李素) 目录号 : GC41004

A flavonoid with diverse biological activities

Rhamnetin Chemical Structure

Cas No.:90-19-7

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500μg
¥496.00
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1mg
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5mg
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产品描述

Rhamnetin is a natural flavonoid that has been isolated from a variety of plants. Like other flavonoids, rhamnetin has antioxidant activity. Rhamnetin has cytoprotective and anti-inflammatory actions, both in cells and in animal models of disease.

Chemical Properties

Cas No. 90-19-7 SDF
别名 鼠李素
Canonical SMILES OC1=CC(OC)=CC2=C1C(C(O)=C(C3=CC=C(O)C(O)=C3)O2)=O
分子式 C16H12O7 分子量 316.3
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Research Update

Rhamnetin: a review of its pharmacology and toxicity

J Pharm Pharmacol 2022 Jun 9;74(6):793-799.PMID:34931654DOI:10.1093/jpp/rgab163.

Objectives: Numerous natural products, including Rhamnetin, have been studied in recent years owing to the need for new herbal remedies to treat different illnesses. This study aimed to review the salient properties of Rhamnetin and its pharmacological potential and possible toxicological effects. Key findings: A search carried out in the ScienceDirect database using the term 'Rhamnetin' yielded 573 articles published between 1977 and 2021. However, only those studies that mentioned pharmacological activity of Rhamnetin were included in this study. As a result of this selection process, this study included reports that describe Rhamnetin as a secondary metabolite with several pharmacological properties. Summary: Rhamnetin (2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxychromen-4-one) is a secondary metabolite, belonging to the flavonoid class, present in various plants and fruits; it has different pharmacological properties, including antioxidant, anticancer, anti-inflammatory, antiviral and antibacterial activity. However, conclusive results on the toxicology of Rhamnetin have not been reported yet. Therefore, further research is needed to gather detailed information about the effects of Rhamnetin.

Rhamnetin ameliorates macrophage-mediated inflammation and pro-atherosclerosis pathways in apolipoprotein E-deficient mice

J Physiol Pharmacol 2021 Apr;72(2).PMID:34374661DOI:10.26402/jpp.2021.2.10.

The present study was performed to examine the protective effects of Rhamnetin against the development of atherosclerosis and its effects on the regulation of several pathways. The anti-atherosclerosis effect of Rhamnetin was examined in cells stimulated with oxidized low-density lipoprotein (ox-LDL) by estimating the percentages of foam cell formation and apoptotic cells and determining the expression of specific proteins. As an in vivo model of atherosclerosis, apolipoprotein E-deficient (ApoE-/-) mice were treated with intragastric Rhamnetin at 100 or 200 mg/kg for 8 weeks. The levels of inflammatory cytokines and oxidative stress parameters were determined in the aortic tissue of rhamnetin-treated ApoE-/- mice. The effects of Rhamnetin on the Toll-like receptor 4 (TLR-4) pathway were assessed by quantitative reverse transcription polymerase chain reaction. The results of this study suggest that Rhamnetin reduces the percentages of foam cells and apoptotic cells and the expression of CD36 and TLR-4 protein in ox-LDL-stimulated macrophages. The Rhamnetin treatment group showed reductions in the lipid profile and levels of parameters of liver function compared to ApoE-/- mice. The levels of inflammatory cytokines and oxidative stress were reduced in the aortic tissue of the Rhamnetin treatment group compared to ApoE-/- mice. Treatment with Rhamnetin ameliorated the expression of TLR-4 mRNA and components of the TLR-4 pathway in the aortic tissue of ApoE-/- mice. In conclusion, the results of this study suggest that Rhamnetin treatment inhibits the inflammatory and pro-atherosclerosis pathways in ApoE-/- mice.

Rhamnetin ameliorates non-alcoholic steatosis and hepatocellular carcinoma in vitro

Mol Cell Biochem 2022 Dec 10.PMID:36495373DOI:10.1007/s11010-022-04619-6.

Non-alcoholic fatty liver (NAFLD) is a widespread disease with various complications including Non-alcoholic steatohepatitis (NASH) that could lead to cirrhosis and ultimately hepatocellular carcinoma (HCC). Up till now there is no FDA approved drug for treatment of NAFLD. Flavonoids such as Rhamnetin (Rhm) have been ascribed effective anti-inflammatory and anti-oxidative properties. Thus, Rhm as a potent flavonoid could target multiple pathological cascades causing NAFLD to prevent its progression into HCC. NAFLD is a multifactorial disease and its pathophysiology is complex and is currently challenged by the 'Multiple-hit hypothesis' that includes wider range of comorbidities rather than previously established theory of 'Two-hit hypothesis'. Herein, we aimed at establishing reliable in vitro NASH models using different mixtures of variable ratios and concentrations of oleic acid (OA) and palmitic acid (PA) combinations using HepG2 cell lines. Moreover, we compared those models in the context of oil red staining, triglyceride levels and their altered downstream molecular signatures for genes involved in de novo lipogenesis, inflammation, oxidative stress and apoptotic machineries as well. Lastly, the effect of Rhm on NASH and HCC models was deeply investigated. Over the 10 NASH models tested, PA 500 µM concentration was the best model to mimic the molecular events of steatosis induced NAFLD. Rhm successfully ameliorated the dysregulated molecular events caused by the PA-induced NASH. Additionally, Rhm regulated inflammatory and oxidative machinery in the HepG2 cancerous cell lines. In conclusion, PA 500 µM concentration is considered an effective in vitro model to mimic NASH. Rhm could be used as a promising therapeutic modality against both NASH and HCC pathogenesis.

Rhamnetin, a Natural Flavonoid, Ameliorates Organ Damage in a Mouse Model of Carbapenem-Resistant Acinetobacter baumannii-Induced Sepsis

Int J Mol Sci 2022 Oct 25;23(21):12895.PMID:36361685DOI:10.3390/ijms232112895.

In sepsis, the persistence of uncontrolled inflammatory response of infected host cells eventually leads to severe lung and organ failure and, ultimately, death. Carbapenem-resistant Acinetobacter baumannii (CRAB), causative bacteria of sepsis and lung failure in acute cases, belongs to a group of critical pathogens that cannot be eradicated using the currently available antibiotics. This underlines the necessity of developing new modes of therapeutics that can control sepsis at the initial stages. In this study, we investigated the anti-inflammatory activities in vitro and in vivo and the antiseptic effects of Rhamnetin, a naturally occurring flavonoid. We found that among its isoforms, the potency of Rhamnetin was less explored but Rhamnetin possessed superior anti-inflammatory activity with least cytotoxicity. Rhamnetin showed significant anti-inflammatory effects in lipopolysaccharide-, CRAB-, and Escherichia coli (E. coli)-stimulated mouse macrophages by inhibiting the release of interleukin-6 and nitric oxide. In a mouse model of sepsis infected with clinically isolated CRAB or E. coli, Rhamnetin significantly reduced the bacterial burden in the organs. In addition, normalized pro-inflammatory cytokine levels in lung lysates and histological analysis of lung tissue indicated alleviation of lung damage. This study implies that a potent natural product such as Rhamnetin could be a future therapeutic for treating carbapenem-resistant gram-negative sepsis.

Rhamnetin IS A BETTER INHIBITOR OF SARS-COV-2 2'-O-METHYLTRANSFERASE THAN DOLUTEGRAVIR: A COMPUTATIONAL PREDICTION

Afr J Infect Dis 2022 May 6;16(2):80-96.PMID:35582066DOI:10.21010/Ajid.v16i2.9.

Background: The 2'-O-methyltransferase is responsible for the capping of SARS-CoV-2 mRNA and consequently the evasion of the host's immune system. This study aims at identifying prospective natural inhibitors of the active site of SARS-CoV-2 2'O-methyltransferase (2'-OMT) through an in silico approach. Materials and methods: The target was docked against a library of natural compounds obtained from edible African plants using PyRx - virtual screening software. The antiviral agent, Dolutegravir which has a binding affinity score of -8.5 kcal mol-1 with the SARS-CoV-2 2'-OMT was used as a standard. Compounds were screened for bioavailability through the SWISSADME web server using their molecular descriptors. Screenings for pharmacokinetic properties and bioactivity were performed with PKCSM and Molinspiration web servers respectively. The PLIP and Fpocket webservers were used for the binding site analyses. The Galaxy webserver was used for simulating the time-resolved motions of the apo and holo forms of the target while the MDWeb web server was used for the analyses of the trajectory data. Results: The Root-Mean-Square-Deviation (RMSD) induced by Rhamnetin is 1.656A0 compared to Dolutegravir (1.579A0). The average B-factor induced by Rhamnetin is 113.75 while for Dolutegravir is 78.87; the Root-Mean-Square-Fluctuation (RMSF) for Rhamnetin is 0.75 and for Dolutegravir is 0.67. Also, at the active site, Rhamnetin also has a binding affinity score of -9.5 kcal mol-1 and forms 7 hydrogen bonds compared to Dolutegravir which has -8.5 kcal mol-1 and forms 4 hydrogen bonds respectively. Conclusion: Rhamnetin showed better inhibitory activity at the target's active site than Dolutegravir.