Casticin

Casticin
Names

IUPAC name 3′,5-Dihydroxy-3,4′,6,7-tetramethoxyflavone
Systematic IUPAC name 5-Hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxy-4H-1-benzopyran-4-one
Other names Vitexicarpin
Identifiers
CAS Number	479-91-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:69355
ChEMBL	ChEMBL452767
ChemSpider	4474632
PubChem CID	5315263
UNII	753GT729OU^Y
CompTox Dashboard (EPA)	DTXSID80197326
InChI 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
SMILES COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C(=C(C=C3O2)OC)OC)O)OC)O
Properties
Chemical formula	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). Infobox references

Chemical compound

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]

References

^ 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.
^ 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.
^ 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.

External links

Liu, Enyu; Kuang, Yongqin; He, Weiqi; Xing, Xuemin; Gu, Jianwen (2013). "Casticin induces human glioma cell death through apoptosis and mitotic arrest". Cell. Physiol. Biochem. 31 (6): 805–14. doi:10.1159/000350098. PMID 23816816.

Flavones and their conjugates

Aglycones

Monohydroxyflavone	3-Hydroxyflavone 6-Hydroxyflavone
Dihydroxyflavones	Chrysin 4',7-Dihydroxyflavone 7,8-Dihydroxyflavone
Trihydroxyflavones	Apigenin Baicalein Galangin Norwogonin 7,8,3'-Trihydroxyflavone 6,7,4'-Trihydroxyflavone
Tetrahydroxyflavones	Fisetin Kaempferol Isoscutellarein Luteolin Norartocarpetin Scutellarein
Pentahydroxyflavones	Herbacetin Morin Quercetin Nortangeretin 6-Hydroxyluteolin Norwightin Hypolaetin Tricetin
O-methylated flavones	4',7-Dihydroxy-6-methoxyflavone Acacetin Alnetin Artocarpetin Chrysoeriol Cirsilineol Cirsiliol Cirsimaritin Diosmetin Eupatilin Genkwanin Hispidulin Nepetin Nobiletin Oroxylin A Pratol Salvigenin Sinensetin Tangeretin Techtochrysin Tricin Wogonin Zapotin

Glycosides

of apigenin	Apiin Apigetrin Isovitexin Rhoifolin Saponarin Schaftoside Vicenin-2 Vitexin
of baicalein	Baicalin Tetuin
of hypolaetin	Hypolaetin 8-glucoside Hypolaetin 8-glucuronide
of luteolin	Cynaroside Isoorientin Orientin Veronicastroside Luteolin-7-O-glucuronide