491-54-3 Usage
Description
ARTEMISININ is a naturally occurring sesquiterpene lactone endoperoxide with potent antimalarial properties. It is derived from the plant Artemisia annua, also known as sweet wormwood, and has been used in traditional Chinese medicine for centuries. ARTEMISININ is characterized by its unique chemical structure, which includes a peroxide bridge that is crucial for its therapeutic effects. It is known for its rapid action in treating malaria, particularly when used in combination with other antimalarial drugs.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 491-54-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 1 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 491-54:
(5*4)+(4*9)+(3*1)+(2*5)+(1*4)=73
73 % 10 = 3
So 491-54-3 is a valid CAS Registry Number.
491-54-3Relevant articles and documents
Flavonol glycosides from Costus spicatus
Da Silva, Bernadete P.,Bernardo, Robson R.,Parente, Jose P.
, p. 87 - 92 (2000)
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 of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone
Xiong, Wei,Wang, Xiaohong,Shen, Xianyan,Hu, Cuifang,Wang, Xin,Wang, Fei,Zhang, Guolin,Wang, Chun
, p. 13160 - 13176 (2020/11/23)
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.
Selective methylation of kaempferol via benzylation and deacetylation of kaempferol acetates
Mei, Qinggang,Wang, Chun,Yuan, Weicheng,Zhang, Guolin
, p. 288 - 293 (2015/03/31)
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.