Centaureidin

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	17313-52-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:69356^N
ChemSpider	4474997^N
PubChem CID	5315773
UNII	548R7290J9^Y
CompTox Dashboard (EPA)	DTXSID50169530
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,1-3H3^N Key: BZXULYMZYPRZOG-UHFFFAOYSA-N^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,1-3H3 Key: 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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Centaureidin is an O-methylated flavonol. It can be isolated from Tanacetum microphyllum,^[1] Achillea millefolium,^[2] Brickellia veronicaefolia, Bidens pilosa^[3] and Polymnia fruticosa.^[4]

References

^ 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.
^ "Assessment Report on Achillea Millefolium L., Herba" (PDF). European Medicines Agency. 15 September 2010. Retrieved 15 October 2018.
^ 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.
^ 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	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)