520-34-3

Usage

Uses

Used in Pharmaceutical Industry:
Diosmetin is used as an active pharmaceutical ingredient for its antibacterial properties. It can be employed in the development of drugs targeting bacterial infections, contributing to the treatment and prevention of various diseases caused by bacteria.
Used in Cosmetics Industry:
In the cosmetics industry, Diosmetin can be used as an ingredient in skincare products due to its potential antibacterial and anti-inflammatory properties. It may help in the development of products that promote skin health and prevent skin infections.
Used in Research and Development:
Diosmetin's antibacterial properties make it a valuable compound for research and development in the field of microbiology and pharmaceuticals. It can be used in laboratory settings to study its effects on different types of bacteria and to develop new drugs or treatments for bacterial infections.
Used in Agricultural Industry:
Diosmetin's antibacterial properties can also be applied in the agricultural industry, where it can be used as a natural alternative to synthetic chemicals for controlling bacterial infections in crops and livestock. This can contribute to sustainable farming practices and reduce the reliance on harmful chemicals.

Flammability and Explosibility

Notclassified

Biological Activity

diosmetin (dio) is an agonist of the aryl hydrocarbon receptor (ahr). it potently inhibited the enzyme activity of cytochrome p450 1a1 (cyp1a1) in a dose-dependent manner with an ic50 value of approximately 30 nm, in microsomes from mcf-7 cells [1].ahr belongs to the per, arnt, sim/basic-helix-loop-helix superfamily of ligand-activated transcription factors. ahr mediates the toxic effects of polycyclic aromatic hydrocarbons, 2,3,7,8-tetrachlorodibenzo-p-dioxin (tcdd) and polychlorinated biphenyls. these chemicals all bind to ahr, and result in the activation of a battery of genes, including the cytochromes p450 cyp1a1, cyp1a2, and cyp1b1 [2].in mcf-7 cells, at 24 h after the incubation of diosmetin, cyp1a1 mrna was increased in a dose-dependent manner. in mcf-7 cells, diosmetin at 2.5 μm modestly increased cyp1a1 enzyme activity, with an activity increase in cells, while diosmetin at 5 μm did not increase the enzyme activity compared to controls in cells. compared with controls, diosmetin dose-dependently increased the capacity of nuclear extracts to bind an oligonucleotide containing the ahr-binding sequence of cyp1a1 [1].in the presence of cyp1a inhibitor, the concentration of diosmetin ranged from 25 μm at 0 h to 22 μm. in the absence of cyp1a inhibitor, the concentration of diosmetin ranged from 25 μm at 0 h to 15 μm [3].no in vivo result from the administration of diosmetin had been found.

references

[1]. ciolino hp, wang tt and yeh gc. diosmin and diosmetin are agonists of the aryl hydrocarbon receptor that differentially affect cytochrome p450 1a1 activity. cancer res, 1998, 58(13):2754-60.[2]. gonzalez fj and fernandez-salguero p. the aryl hydrocarbon rreceptor studies using the ahr-null mice. drug metabolism and disposition, 1998, 26(12): 1194-1198.[3]. androutsopoulos vp and spandidos da. the flavonoids diosmetin and luteolin exert synergistic cytostatic effects in human hepatoma hepg2 cells via cyp1a-catalyzed metabolism, activation of jnk and erk and p53/p21 up-regulation. j nutr biochem, 2013, 24(2):496-504.

InChI:InChI=1/C16H12O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-7,17-19H,1H3

Upstream product

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• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
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Downstream Products

• 23367-08-0 2-(3,4-dimethoxy-phenyl)-5-hydroxy-7-methoxy-6-methyl-chromen-4-one 
• 70412-86-1 3',5-dihydroxy-4'-methoxy-7-(sulfopropoxy)flavone potassium salt 
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• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 172805-73-1 7-benzyloxy-2-(3-benzyloxy-4-methoxyphenyl)-5-hydroxy-4H-chromen-4-one 
• 172805-77-5 3',7-di-O-(β-hydroxyethyl)diosmetin 
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• 1217077-67-2 6'-nitrodiosmetin 
• 1217077-51-4 2'-nitrodiosmetin 
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• 1563176-82-8 6-C-prenyldiosmetin 
• 1638743-78-8 6-(N,N-dimethylaminomethyl)-5-hydroxy-7,3',4'-trimethoxyflavone 
• 1638743-79-9 6-(N,N-diethylaminomethyl)-5-hydroxy-7,3',4'-trimethoxyflavone 

Relevant academic research and scientific papers

New Compounds from Flowers of Phlojodicarpus sibiricus

Chromatographic separation of the MeOH extract from flowers of Phlojodicarpus sibiricus (Fisch.) Koso.-Pol. (Apiaceae) isolated 27 compounds including three new glycosides, the structures of which were established by UV, IR, and NMR spectroscopy and mass

Two flavonoid triglycosides from Buddleja madagascariensis

The structures of two new flavonoid triglycosides isolated from leaves of Buddleja madagascariensis have been established as hesperetin and diosmetin 7-O (2,6-di-O-α-L-rhamnopyranosyl)-β-D-glucopyranosides using mass and NMR spectroscopy. Scutellarein 7-glucoside is reported from this plant for the first time.

NEW GLYCOSIDES FROM PLANTS OF THE GENUS Phlojodicarpus

From plants of the genus Phlojodicarpus have been isolated the new coumarins umbelliferone β-D-apiosyl(16)-β-D-glucopyranoside (I) and 8-(2'-3'-dihydroxy-3'-methylbutyl)umbelliferone 7-O-β-D-glucopyranoside (II) and also the flavone glycoside diosmetin 7-O-β-D-glucopyranoside (III).The result of IR, UV, PMR, and 13C spectroscopy are given.

Continuous flow microchannel synthesis process of flavonoid compounds

The invention provides a continuous flow microchannel synthesis process of flavonoid compounds. According to the process, hesperidin and iodine elementary substance are used as raw materials and react in a continuous flow microchannel reactor in the presence of a reaction solvent to synthesize the flavonoid compound as shown in a formula A. Compared with a traditional kettle-type preparation process, the process disclosed by the invention has the advantages that the preparation time is obviously shortened, and the conversion rate of raw materials and the yield of products are obviously improved; and especially, when the diosmin is prepared under optimal process conditions of continuous flow microchannel synthesis, the conversion rate of the raw material hesperidin is as high as 96.48%, and the yield of the product diosmin is as high as 81.96%. The continuous flow micro-channel synthesis process provided by the invention is beneficial to realizing safe, efficient and rapid industrial production of flavonoid compounds, and has a wide application prospect.

Preparation method of genistein (by machine translation)

The process of the invention is simple, raw material supply is rich, the product purity is high, and the product quality qualified, is suitable for large-scale industrial production, after the reaction, is complete and, filtration; is performed . filtering, is carried out after reaction . The crude product, is filtered, through a mixed solution of an acidic compound and a dimethyl sulfoxide to obtain the geranyin crude oil, after reaction is complete and then reacted; is carried out after the reaction, is complete and then the reaction is carried out, after reaction is completed . through the reaction of, the solvent, and; the solvent . The invention provides a method, for preparing the white leaf ligninoid. (by machine translation)

Synthesis, in Silico and in vitro evaluation of some flavone derivatives for Acetylcholinesterase and BACE-1 inhibitory activity

Acetylcholinesterase (AChE) and β-secretase (BACE-1) have become attractive therapeutic targets for Alzheimer’s disease (AD). Flavones are flavonoid derivatives with various bioactive effects, including AChE and BACE-1 inhibition. In the present work, a series of 14 flavone derivatives was synthesized in relatively high yields (35–85%). Six of the synthetic flavones (B4, B5, B6, B8, D6 and D7) had completely new structures. The AChE and BACE-1 inhibitory activities were tested, giving pIC50 3.47–4.59 (AChE) and 4.15–5.80 (BACE-1). Three compounds (B3, D5 and D6) exhibited the highest biological effects on both AChE and BACE-1. A molecular docking investigation was conducted to explain the experimental results. These molecules could be employed for further studies to discover new structures with dual action on both AChE and BACE-1 that could serve as novel therapies for AD.

Synthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance

3′,4′,7-Trimethoxyflavone (TMF) has been reported to show a potent reversal effect on drug resistance mediated by breast cancer resistance protein (BCRP)/ATP-binding cassette subfamily G member 2 (ABCG2). In this study, we designed and synthesized five derivatives with either a hydroxy group or a fluorine atom at C-5 and several kinds of capping moiety at the C-7 hydroxy group, on the same 3′,4′-dimethoxy-substituted flavone skeleton. We subsequently evaluated the efficacies of these compounds against BCRP-expressing human leukaemia K562/BCRP cells. Reversal of drug resistance was expressed as the concentration of compound causing a twofold reduction in drug sensitivity (RI50). Of the synthesized compounds, the reversal effect of 5-hydroxy-3′,4′,7-trimethoxyflavone (HTMF, RI50 7.2 nm) towards 7-ethyl-10-hydroxycamptothecin (SN-38) was stronger than that of TMF (RI50 18 nm). Fluoro-substituted 5-fluoro-3′,4′,7-trimethoxyflavone (FTMF, RI50 25 nm) and monoglycosylated 7-(β-glucosyloxy)-5-hydroxy-3′,4′-dimethoxyflavone (GOHDMF, 91 nm) also exhibited reversal effects, whereas the di- and triglycoside derivatives did not. TMF, HTMF and FTMF at 0.01–10 μm upregulated the K562/BCRP cellular accumulation of Hoechst 33342 nuclear staining dye. In addition, western blotting revealed that treatment of K562/BCRP cells with 0.1 μm TMF, HTMF or FTMT suppressed the expression of BCRP. HTMF showed the strongest inhibition of BCRP-mediated efflux and suppression of BCRP expression of the three effective synthesized flavones.

Semi-synthesis method of diosmetin

The invention provides a semi-synthesis method of diosmetin. A purpose of the present invention is to solve the problems of high production cost and low synthesis efficiency of the existing synthesismethod. According to the present invention, neohesperidin, pyridine and iodine are heated and react to prepare neodiosmin, and the neodiosmin is hydrolyzed with a sodium hydroxide solution to preparediosmetin; and the semi-synthesis method has characteristics of short process time, simple post-treatment, low production cost, high product purity and high yield, and is suitable for the industrial production of diosmetin.

Synthesizing method of diosmetin

The invention provides a synthesizing method of diosmetin. The problems that an existing chemical synthesizing method is high in production cost and low in synthesizing efficiency are solved. The synthesizing method comprises the steps: firstly, ethyl acetoacetate and 2-hydroxyl-3-methoxy-benzoyl chloride react under an alkaline condition to prepare 2-hydroxyl-3-methoxy-ethyl benzoylacetate; thenthe prepared 2-hydroxyl-3-methoxy-ethyl benzoylacetate and phloroglucinol are mixed to generate a condensation reaction under high-temperature and high-vacuum conditions, so that a crude diosmetin product is generated; and finally, the crude diosmetin product is subjected to ethyl alcohol refining, and then a fine diosmetin product with the liquid phase content being 98% or above is obtained. Thesynthesizing route is simple, the crude product is obtained only through two steps and then refined through conventional means, and operating is easy and convenient; and the synthesizing cost is low,the synthesizing efficiency is high, the product yield is high, thus the synthesizing method is suitable for industrial production, and the whole synthesizing route is economical and practical.

Structure-activity relationship of the inhibitory effects of flavonoids on nitric oxide production in RAW264.7 cells

We isolated flavonoids from herbal specimens from the Tibetan region (Sophora yunnanensis and Rhodiola sacra) that suppress nitric oxide (NO) production in macrophages stimulated by lipopolysaccharide and interferon-γ. The isolated flavonoids carry symmetric substitutions in the B ring (R3′= R5′). We analyzed the quantitative structure-activity relationship of the inhibitory activity by comparative molecular field analysis (CoMFA) using this series of flavonoids. Use of flavonoids with symmetrical substitutions in the B ring made it simpler to align molecules because it was not necessary to consider a huge number of combinations due to the B-ring conformation. The CoMFA model, whose cross-validated q2value was 0.705, suggested the existence of a hydroxy group at the 5-position, the choice of the A/C-ring scaffold (chromane or chromene) and electrostatic field around the B ring are important for NO inhibitory activity. Flavonoids synthesized based on the CoMFA model exhibited significant inhibitory potential against NO production, validating the predictive capability of the CoMFA model.