491-54-3

Usage

Uses

Used in Pharmaceutical Industry:
ARTEMISININ is used as an antimalarial drug for its ability to rapidly reduce parasite levels in the blood of patients suffering from Plasmodium falciparum malaria. It is particularly effective against drug-resistant strains of the parasite, making it a crucial component in the global fight against malaria.
Used in Anticancer Applications:
ARTEMISININ has shown potential as an anticancer agent, with research indicating that it may have cytotoxic effects on various cancer cell lines. It is believed to work by generating reactive oxygen species, which can damage cancer cells and inhibit their growth.
Used in Drug Delivery Systems:
ARTEMISININ has been explored for its potential use in drug delivery systems, particularly in the development of novel formulations that can improve its solubility, stability, and bioavailability. This includes the use of nanoparticles, liposomes, and other advanced drug delivery technologies to enhance the therapeutic potential of ARTEMISININ and its derivatives.
Used in Cosmetics Industry:
Due to its potent antioxidant and anti-inflammatory properties, ARTEMISININ has found applications in the cosmetics industry, where it is used in various skincare products to promote skin health and protect against environmental stressors.
Used in Agricultural Industry:
ARTEMISININ has also been investigated for its potential use in the agricultural industry as a natural pesticide or insect repellent, leveraging its antimicrobial and insecticidal properties to protect crops from pests and diseases.

Biological Activity

the effects of phytoestrogens have been studied in the hypothalamic-pituitary-gonadal axis and various non-gonadal targets. epidemiologic and experimental evidence indicates a protective effect of phytoestrogens also in colorectal cancer. the mechanism through which estrogenic molecules control colorectal cancer tumorigenesis could possibly involve estrogen receptor β, which is the predominantly expressed estrogen receptor subtype in colon mucosa.

in vitro

kaempferide triglycoside proved to inhibit the proliferation of native and estrogen receptor β overexpressing colon cancer cells via a mechanism not mediated by ligand binding dependent estrogen receptor activation. it affected hct8 cell cycle progression through increasing the g0/g1 cell fraction and in estrogen receptor β overexpressing cells increased two antioxidant enzymes [1].

in vivo

the aim of one previous study was to evaluate the effect of kaempferol on tissue lipid peroxidation and antioxidant status in 1,2-dimethyl hydrazine induced colorectal cancer in male wistar rats and to compare its efficacy with irinotecan. this study revealed that kaempferol could be safely used as a chemopreventive agent in colorectal cancer [2].

references

[1] martineti v, tognarini i, azzari c, carbonell sala s, clematis f, dolci m, lanzotti v, tonelli f, brandi ml, curir p. inhibition of in vitro growth and arrest in the g0/g1 phase of hct8 line human colon cancer cells by kaempferide triglycoside from dianthus caryophyllus. phytother res. 2010 sep;24(9):1302-8. [2] nirmala p, ramanathan m. effect of kaempferol on lipid peroxidation and antioxidant status in 1,2-dimethyl hydrazine induced colorectal carcinoma in rats. eur j pharmacol. 2011 mar 1;654(1):75-9.

Upstream product

• 20869-95-8 ermanin 
• 65982-77-6 2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone 
• 794-94-5 p-Methoxybenzoic anhydride 
• 520-18-3 kaempferol 
• 108-73-6 3,5-dihydroxyphenol 
• 1258963-38-0 kaempferide, 7-O-(4-O-acethyl-α-L-rhamnopyranosyl) 
• 3570-69-2 3,5,7-trihydroxy-2-(4′-methoxyphenyl)chroman-4-one 
• 689260-84-2 C₂₂H₂₆O₉ 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 16274-11-6 3,5,7-triacetoxy-2-(4-acetoxy-phenyl)-chromen-4-one 
• 100-09-4 4-methoxybenzoic acid 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 18065-05-9 1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone 

Downstream Products

• 144-62-7 oxalic acid 
• 100-09-4 4-methoxybenzoic acid 
• 1246764-75-9 7-O-labda-8⁽¹⁷⁾,13E-dienyl-4'-O-methylkaempferol 
• 1246764-76-0 3-O-labda-8⁽¹⁷⁾,13E-dienyl-4'-O-methylkaempferol 
• 1046759-43-6 8-C-labda-8⁽¹⁷⁾,13E-dienyl-4'-O-methylkaempferol 
• 1246764-74-8 3,7-O-di(labda-8⁽¹⁷⁾,13E-dienyl)-4'-O-methylkaempferol 
• 554453-86-0 8,8'-bi-kaempferide 
• 118525-40-9 icaritin 
• 1219698-82-4 C₂₅H₁₈O₁₀ 

Relevant academic research and scientific papers

Flavonol glycosides from Costus spicatus

Two flavonol diglycosides, tamarixetin 3-O-neohesperidoside, kaempferide 3-O-neohesperidoside and the known quercetin 3-O-neohesperidoside, together with six other known flavonoids were isolated from the leaves of Costus spicatus and their structures were elucidated by a combination of spectroscopic and chemical methods. The flavonol diglycosides were evaluated for inhibitory activity of nitric oxide production by activated macrophages (Fig. 1).

Synthesis and Biological Evaluation of 4-Substituted Kaempfer-3-ols

The synthesis of two series of five kaempfer-3-ols was described. The first set all have a C-3 hydroxyl group and the second has a carboxymethoxy ether at the C-3 position. Both series have variable substitution at the C-4 position (i.e., OH, Cl, F, H, OMe). Both kaempferols and carboxymethoxy ethers were evaluated for their ability to inhibit ribosomal s6 kinase (RSK) activity and cancer cell proliferation.

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

Method for preparing icaritin intermediate

The invention provides a method for preparing an icaritin intermediate. The method includes the steps of a, enabling phloroglucinol to react with one of a 2-benzyloxy acetylation reagent and 2-benzyloxy acetonitrile to obtain 2-benzyloxy-1-(2,4,6-trihydroxyphenyl)ethanone; b. subjecting a reaction product obtained from the step a and p-methoxybenzoyl halide to Baker-Venkataraman reaction so as toobtain 3-(benzyloxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-benzopyran-4-one; c. subjecting the reaction product obtained in the step b to hydrogenation so as to obtain the icaritin intermediate, namely 3,5,7-trihydroxy-2-(4-methoxyphenyl)-4H-benzopyran-4-one.

Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates

A strategy for selective mono-, di- and tri-O-methylation of kaempferol, predominantly on the basis of selective benzylation and controllable deacetylation of kaempferol acetates, was developed. From the selective deacetylation and benzylation of kaempferol tetraacetate (1), 3,4′,5,-tri-O-acetylkaempferol (2) and 7-O-benzyl-3,4′5,-tri-O-acetylkaempferol (8) were obtained, respectively. By controllable deacetylation and followed selective or direct methylation of these two intermediates, eight O-methylated kaempferols were prepared with 51-77% total yields from kaempferol.

Total synthesis of icaritin via microwave-assistance Claisen rearrangement

The novel total synthesis of icaritin (1), naturally occurring with important bioactive 8-prenylflavonoid, was performed via a reaction sequence of 8 steps including Baker-Venkataraman reaction, chemoselective benzyl or methoxymethyl protection, dimethyldioxirane (DMDO) oxidation, O-prenylation, Claisen rearrangement and deprotection, starting from 2,4,6-trihydroxyacetophenone and 4-hydroxybenzoic acid in overall yields of 23%. The key step was Claisen rearrangement under microwave irradiation. MS, 1H and 13C NMR techniques have been used to confirm the structures of all synthetic compounds.

Synthesis and antioxygenic activities of seabuckthorn flavone-3-ols and analogs

A practical synthesis of polyhydroxy- and regiospecifically methylated flavone-3-ols which are components of commercial 'seabuckthorn flavone' has been achieved by modified Algar-Flynn-Oyamada method. Antioxidant activities of seabuckthorn extracts, isolated products and a number of flavone-3-ols have been determined. Structure-activity relationships have been discussed. Amongst the compounds tested, gallic acid, which is also present in seabuckthorn, was found to be the most effective antioxidant and radioprotectant.

7-O-Arylmethylgalangin as a novel scaffold for anti-HCV agents

In spite of potent antiviral activity, suboptimal physicochemical properties of aryl diketo acids (ADKs) necessitates modification of the core 1,3-diketo acid functionality into a novel scaffold. As the metal-binding affinity of the diketo acid is the key to the antiviral activity of ADKs, we anticipated 3,5-dihydroxy-4-oxo arrangement of galangin scaffold would serve as an excellent mimic for the diketo acid functionality. In this study, through synthesis and biological evaluation of various galangin derivatives, we have shown that the diketo acid functionality can be successfully replaced with the galangin scaffold by specific combination of the substituents to result in identification of a novel galangin derivative (3s) with anti-HCV activity (EC50 = 0.9 μM) comparable to the ADK counterpart.

Flavonoids from the leaves of actinidia kolomikta

One new acetylated flavonoid, kaempferide-7-O-(4'-O-acetyl)-α-L- rhamnoside, and six known flavonoids were isolated from the EtOAc fraction of the leaves of Actinidia kolomikta (Rupr. et Maxim.) Planch. The chemical structures of the isolated compounds we

A rare flavonol glycoside from Aerva tomentosa Forsk as antimicrobial and hepatoprotective agent

From the perianth lobes of A. tomentosa, kaempferide 3-0-(6″O-acetyl-4?-O-α-methylsinapyl)neohesperidoside has been isolated which has shown marked antimicrobial and hepatoprotective activities.