6601-62-3

Usage

Uses

Used in Pharmaceutical Industry:
Cirsimaritin is used as an anti-inflammatory agent for its ability to reduce inflammation and alleviate pain. Its antioxidant properties also contribute to its potential use in treating conditions associated with oxidative stress.
Used in Cosmetic Industry:
Due to its antioxidant and anti-inflammatory properties, cirsimaritin can be used as an active ingredient in skincare products. It may help protect the skin from environmental stressors, reduce inflammation, and promote a healthier skin appearance.
Used in Nutraceutical Industry:
Cirsimaritin's beneficial properties can be harnessed in the development of dietary supplements and functional foods. Its antioxidant and anti-inflammatory effects may support overall health and well-being when consumed as part of a balanced diet.

InChI:InChI=1/C17H14O6/c1-21-14-8-13-15(16(20)17(14)22-2)11(19)7-12(23-13)9-3-5-10(18)6-4-9/h3-8,18,20H,1-2H3

Upstream product

• 53002-40-7 2-(4-benzyloxy-phenyl)-5,6,7-trimethoxy-chromen-4-one 
• 1402607-46-8 2-(4-(benzyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one 
• 1486-50-6 4-(benzyloxy)benzoic acid chloride 
• 642-71-7 3,4,5-trimethoxyphenol 
• 22248-14-2 6-hydroxy-2,3,4-trimethoxyacetophenone 
• 1486-51-7 p-(benzyloxy)benzoic acid 
• 17742-46-0 acetic acid 3,4,5-trimethoxy-phenyl ester 
• 95868-60-3 6--2,3,4-trimethoxy-acetophenon 
• 95868-61-4 α-(p-Benzyloxy-benzoyl)-6-hydroxy-2,3,4-trimethoxy-acetophenon 
• 99-96-7 4-hydroxy-benzoic acid 
• 27740-01-8 scutellarin 
• 529-53-3 scutellarein 
• 1105056-24-3 9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 
• 1447-88-7 hispidulin 

Downstream Products

• 13020-20-7 C₃₁H₃₂O₁₅ 

Relevant academic research and scientific papers

Flavonoid glycosides from microtea debilis and their cytotoxic and anti-inflammatory effects

Two new 5-O-glucosylflavones, 5-O-β-D-glucopyranosyl cirsimaritin (1) and 5, 4'-O-β-Ddiglucopyranosyl cirsimaritin (2), four known flavonoids, cirsimarin (3), cirsimaritin (4), salvigenin (5), 4', 5-dihydroxy-7- methoxyflavone (6), and a norisoprenoid, vo

Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives

A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.

Design, synthesis and evaluation of scutellarein-O-acetamidoalkylbenzylamines as potential multifunctional agents for the treatment of Alzheimer's disease

A series of scutellarein-O-acetamidoalkylbenzylamines derivatives were designed based on a multitarget-directed ligands strategy for the treatment of Alzheimer's disease. Among these compounds, compound T-22 demonstrated excellent acetylcholinesterase inhibitory, moderate inhibitory effects on self-induced Aβ1-42 aggregation, Cu2+-induced Aβ1-42 aggregation, human AChE-induced Aβ1-40 aggregation and disassembled Cu2+-induced aggregation of the well-structured Aβ1-42 fibrils, and also acted as potential antioxidant and biometals chelator. Both kinetic analysis of AChE inhibition and molecular modeling study suggested that T-22 interacted with both the catalytic active site and peripheral anionic site of AChE. Moreover, compound T-22 showed a good neuroprotective effect against H2O2-induced PC12?cell injury and low toxicity in SH-SY5Y cells. Furthermore, the step-down passive avoidance test indicated T-22 significantly reversed scopolamine-induced memory deficit in mice. Taken together, the data showed that T-22 was an interesting multifunctional lead compound worthy of further study for AD.

Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo

Scutellarin (1) could be hydrolyzed into scutellarein (2) in vivo and then converted into methylated, sulfated and glucuronidated forms. In order to investigate the biological activities of these methylated metabolites, eight methylated analogs of scutellarein (2) were synthesized via semi-synthetic methods. The antithrombotic activities of these compounds were evaluated through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity. Furthermore, the physicochemical properties of these compounds including aqueous solubility and lipophilicity were also investigated. The results showed that 6-O-methylscutellarein (5) demonstrated potent antithrombotic activity, stronger antioxidant activity and balanced solubility and permeability compared with scutellarin (1), which warrants further development of 5 as a promising lead for the treatment of ischemic cerebrovascular disease.

Flavones and triterpenes from the leaves of Vitex peduncularis

A new flavone, 4'-acetoxy-5-hydroxy-6,7-dimethoxyflavone 1 together with four known compounds, cirsimaritin 2, genkwanin 3, 3α-friedelinol 4 and 3β-friedelinol 5 have been isolated from the leaves of Vitex peduncularis Wall. (Verbenaceae). The structure of the new flavone was elucidated by detailed spectral (including 2D-NMR) and chemical studies.

Multifunctional scutellarin-rivastigmine hybrids with cholinergic, antioxidant, biometal chelating and neuroprotective properties for the treatment of Alzheimer's disease

To discover multifunctional agents for the treatment of Alzheimer's disease (AD), a series of scutellarein carbamate derivatives were designed and synthesized based on the multitarget-directed ligand strategy. Their acetylcholinesterase and butyrylcholinesterase inhibitory activities, antioxidant activities, metal-chelating properties and neuroprotective effects against hydrogen peroxide induced PC12 cell injury were evaluated in vitro. The results showed that most of the synthetic compounds exhibited good multifunctional activities. In particular, compound 15c exhibited dual inhibitory potency on acetylcholinesterase and butyrylcholinesterase with IC50 values of 0.57 and 22.6 μM, respectively, and good antioxidative activity, with a value 1.3-fold of Trolox. In addition, 15c acted as a selective biometal chelator and possessed neuroprotective effects. Furthermore, 15c could cross the blood-brain barrier (BBB) in vitro and had significant neuroprotective effects in scopolamine-induced cognitive impairment in mice. Taken together, these results suggest that compound 15c might be a potential multifunctional agent for the treatment of AD.

Design, synthesis and evaluation of scutellarein- O -alkylamines as multifunctional agents for the treatment of Alzheimer's disease

A series of scutellarein-O-alkylamine derivatives were designed, synthesized and tested as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good multifunctional activities. Among them, compound 16d demonstrated significant metal chelating properties, moderate acetylcholinesterase (AChE) inhibitory and anti-oxidative activity, and excellent inhibitory effects on self-induced Aβ21-42 aggregation, Cu2+-induced Aβ21-42 aggregation, human AChE-induced Aβ21-40 aggregation and disassembled Cu2+-induced aggregation of the well-structured Aβ21-42 fibrils. Both kinetic analysis of AChE inhibition and molecular modeling study suggested that 16d binds simultaneously to the catalytic active site and peripheral anionic site of AChE. Moreover, compound 16d showed a good protective effect against H2O2-induced PC12 cell injury, with low toxicity in SH-SY5Y cells. Furthermore, the step-down passive avoidance test showed this compound significantly reversed scopolamine-induced memory deficit in mice. Thus, 16d was shown to be an interesting multifunctional lead compound worthy of further study.

Total synthesis of cirsimarin and evidence of its lipolytic and antilipogenic activities on human adipocytes

A straightforward procedure leading to the flavone cirsimaritin and its 4′-O-β-d-glycosylation to afford cirsimarin, its corresponding flavone glucopyranoside, is described. The biological properties of cirsimarin, measured on human adipocytes, showed potent effects on both lipolysis and lipogenesis. Cirsimarin could therefore be considered as an efficient tool in the struggle against excessive adipose tissue deposition and as a potential candidate in the treatment of obesity.

Synthesis of Cirsimaritin (5,4'-Dihydroxy-6,7-dimethoxyflavone) by Transacylation Method

Cirsimaritin (I) has been synthesised from the readily accessible dinatin (5,7,4'-trihydroxy-6-methoxyflavone).The key step involves transacylation of fully benzoylated dinatin.