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Centaureidin

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Centaureidin
Chemical structure of centaureidin
Chemical structure of centaureidin
Names
IUPAC name 3′,5,7-Trihydroxy-3,4′,6-trimethoxyflavone
Systematic IUPAC name 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxy-4H-1-benzopyran-4-one
Other names Desmethoxycentaureidine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3Key: BZXULYMZYPRZOG-UHFFFAOYSA-N
  • InChI=1/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3Key: BZXULYMZYPRZOG-UHFFFAOYAN
SMILES
  • O=C1c3c(O)c(OC)c(O)cc3O/C(=C1/OC)c2ccc(OC)c(O)c2
Properties
Chemical formula C18H16O8
Molar mass 360.31 g/mol
Density 1.542 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Centaureidin is an O-methylated flavonol. It can be isolated from Tanacetum microphyllum, Achillea millefolium, Brickellia veronicaefolia, Bidens pilosa and Polymnia fruticosa.

References

  1. Abad, Maria Jose; Bermejo, Paulina; Villar, Angel (1995). "The activity of flavonoids extracted from Tanacetum microphyllum DC. (Compositae) on soybean lipoxygenase and prostaglandin synthetase". General Pharmacology: The Vascular System. 26 (4): 815–9. doi:10.1016/0306-3623(94)00242-F. PMID 7635257.
  2. "Assessment Report on Achillea Millefolium L., Herba" (PDF). European Medicines Agency. 15 September 2010. Retrieved 15 October 2018.
  3. Chang, Shu-Lin; Chiang, Yi-Ming; Chang, Cicero Lee-Tian; Yeh, Hsu-Hua; Shyur, Lie-Fen; Kuo, Yueh-Hsiung; Wu, Tung-Kung; Yang, Wen-Chin (2007). "Flavonoids, centaurein and centaureidin, from Bidens pilosa, stimulate IFN-γ expression". Journal of Ethnopharmacology. 112 (2): 232–6. doi:10.1016/j.jep.2007.03.001. PMID 17408892.
  4. Beutler, John A.; Cardellina, John H.; Lin, Chii M.; Hamel, Ernest; Cragg, Gordon M.; Boyd, Michael R. (1993). "Centaureidin, a cytotoxic flavone from Polymnia fruticosa, inhibits tubulin polymerization". Bioorganic & Medicinal Chemistry Letters. 3 (4): 581–4. doi:10.1016/S0960-894X(01)81233-6.
Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides of herbacetin
Glycosides of kaempferol
Glycosides of myricetin
Conjugates of quercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
other
Derivative flavonols
Aglycones
Glycosides
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Semisynthetic
Glycosides
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