Casticin

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Casticin
Casticin.svg
Names
Preferred IUPAC name
5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-1-benzopyran-4-one
Other names
Vitexicarpin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C19H18O8/c1-23-11-6-5-9(7-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
    Key: PJQLSMYMOKWUJG-UHFFFAOYSA-N
  • InChI=1/C19H18O8/c1-23-11-6-5-9(7-10(11)20)17-19(26-4)16(22)14-12(27-17)8-13(24-2)18(25-3)15(14)21/h5-8,20-21H,1-4H3
    Key: PJQLSMYMOKWUJG-UHFFFAOYAH
  • COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC)OC)O)OC)O
Properties
C19H18O8
Molar mass 374.34 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Casticin is a methoxylated flavonol, meaning the core flavonoid structure has methyl groups attached. Found in Artemisia annua , the flavonoid has been shown to enhance the antimalarial activity of artemisinin though casticin itself has no direct antimalarial effects. [1] [2] It has been shown to have anti-mitotic activity. It is also found in Vitex agnus-castus . [3]

Related Research Articles

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<span class="mw-page-title-main">Secondary metabolite</span> Type of organic compound

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<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

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<i>Artemisia</i> (plant) Genus of flowering plants in the daisy family Asteraceae

Artemisia is a large, diverse genus of plants with between 200 and 400 species belonging to the daisy family Asteraceae. Common names for various species in the genus include mugwort, wormwood, and sagebrush.

<i>Artemisia annua</i> Herb known as sweet wormwood used to treat malaria

Artemisia annua, also known as sweet wormwood, sweet annie, sweet sagewort, annual mugwort or annual wormwood, is a common type of wormwood native to temperate Asia, but naturalized in many countries including scattered parts of North America.

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Artemisinin and its semisynthetic derivatives are a group of drugs used in the treatment of malaria due to Plasmodium falciparum. It was discovered in 1972 by Tu Youyou, who shared the 2015 Nobel Prize in Physiology or Medicine for her discovery. Artemisinin-based combination therapies (ACTs) are now standard treatment worldwide for P. falciparum malaria as well as malaria due to other species of Plasmodium. Artemisinin is extracted from the plant Artemisia annua, sweet wormwood, a herb employed in Chinese traditional medicine. A precursor compound can be produced using a genetically engineered yeast, which is much more efficient than using the plant.

<span class="mw-page-title-main">Naringenin</span> Chemical compound

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1,2,4-Trioxane is one of the isomers of trioxane. It has the molecular formula C3H6O3 and consists of a six membered ring with three carbon atoms and three oxygen atoms. The two adjacent oxygen atoms form a peroxide functional group and the other forms an ether functional group. It is like a cyclic acetal but with one of the oxygen atoms in the acetal group being replaced by a peroxide group.

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<span class="mw-page-title-main">Baicalein</span> Chemical compound

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<span class="mw-page-title-main">Fisetin</span> Chemical compound

Fisetin (7,3′,4′-flavon-3-ol) is a plant flavonol from the flavonoid group of polyphenols. It can be found in many plants, where it serves as a yellow/ochre colouring agent. It is also found in many fruits and vegetables, such as strawberries, apples, persimmons, onions and cucumbers. Its chemical formula was first described by Austrian chemist Josef Herzig in 1891.

<i>Artemisia herba-alba</i> Species of plant

Artemisia herba-alba, the white wormwood, is a perennial shrub in the genus Artemisia that grows commonly on the dry steppes of the Mediterranean regions in Northern Africa, Western Asia and Southwestern Europe. It is used as an antiseptic and antispasmodic in herbal medicine.

<span class="mw-page-title-main">Acacetin</span> Chemical compound

Acacetin is a 4′-O-methylated flavone of the parent compound apigenin, found in Robinia pseudoacacia, Turnera diffusa (damiana), shows moderate aromatase inhibition, Betula pendula, and in the fern Asplenium normale.

Project 523 is a code name for a 1967 secret military project of the People's Republic of China to find antimalarial medications. Named after the date the project launched, 23 May, it addressed malaria, an important threat in the Vietnam War. At the behest of Ho Chi Minh, Prime Minister of North Vietnam, Zhou Enlai, the Premier of the People's Republic of China, convinced Mao Zedong, Chairman of the Communist Party of China, to start the mass project "to keep [the] allies' troops combat-ready", as the meeting minutes put it. More than 500 Chinese scientists were recruited. The project was divided into three streams. The one for investigating traditional Chinese medicine discovered and led to the development of a class of new antimalarial drugs called artemisinins. Launched during and lasting throughout the Cultural Revolution, Project 523 was officially terminated in 1981.

Pregnancy-associated malaria (PAM) or placental malaria is a presentation of the common illness that is particularly life-threatening to both mother and developing fetus. PAM is caused primarily by infection with Plasmodium falciparum, the most dangerous of the four species of malaria-causing parasites that infect humans. During pregnancy, a woman faces a much higher risk of contracting malaria and of associated complications. Prevention and treatment of malaria are essential components of prenatal care in areas where the parasite is endemic – tropical and subtropical geographic areas. Placental malaria has also been demonstrated to occur in animal models, including in rodent and non-human primate models.

<span class="mw-page-title-main">Ian A. Graham</span>

Ian Alexander Graham is a professor of Biochemical Genetics in the Centre for Novel Agricultural Products (CNAP) at the University of York.

<span class="mw-page-title-main">Moroidin</span> Chemical compound

Moroidin is a biologically active compound found in the plants Dendrocnide moroides and Celosia argentea. It is a peptide composed of eight amino acids, with unusual leucine-tryptophan and tryptophan-histidine cross-links that form its two rings. Moroidin has been shown to be at least one of several bioactive compounds responsible for the painful sting of the Dendrocnide moroides plant. It also has demonstrated anti-mitotic properties, specifically by inhibition of tubulin polymerization. Anti-mitotic activity gives moroidin potential as a chemotherapy drug, and this property combined with its unusual chemical structure has made it a target for organic synthesis.

<span class="mw-page-title-main">Blumeatin</span> Chemical compound

Blumeatin is a flavanone found in Blumea balsamifera, and has been reported to be present in Artemisia annua.

References

  1. Elford BC; Roberts MF; Phillipson JD; Wilson RJ (1987). "Potentiation of the antimalarial activity of qinghaosu by methoxylated flavones". Trans R Soc Trop Med Hyg. 81 (3): 434–436. doi:10.1016/0035-9203(87)90161-1. PMID   3318019.
  2. Liu KC; Yang SL; Roberts MF; Elford BC; Phillipson JD (1992). "Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures". Plant Cell Rep. 11 (12): 537–640. doi:10.1007/bf00236389. PMID   24213368. S2CID   9405266.
  3. Hoberg, Eva; Meier, Beat; Sticher, Otto (2000). "An analytical high performance liquid chromatographic method for the determination of agnuside and p-hydroxybenzoic acid contents in Agni-casti fructus". Phytochemical Analysis. 11 (5): 327–329. doi:10.1002/1099-1565(200009/10)11:5<327::AID-PCA523>3.0.CO;2-0.