Amentoflavone

Amentoflavone

IUPAC name 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Other names Didemethyl-ginkgetin 3',8-Biapigenin
Identifiers
CAS number	1617-53-4
PubChem	5281600
ChemSpider	4444919^Y
ChEMBL	CHEMBL63354^Y
Jmol-3D images	Image 1
SMILES O=C1\C=C(/Oc2cc(O)cc(O)c12)c6cc(c5c(O)cc(O)c3c5O/C(=C\C3=O)c4ccc(O)cc4)c(O)cc6
InChI InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H^Y Key: YUSWMAULDXZHPY-UHFFFAOYSA-N^Y InChI=1/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H Key: YUSWMAULDXZHPY-UHFFFAOYAB
Properties
Molecular formula	C₃₀H₁₈O₁₀
Molar mass	538.45 g/mol
Exact mass	538.089997
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Amentoflavone is a constituent of a number of plants with medicinal properties, including Ginkgo biloba and Hypericum perforatum (St. John’s Wort).^[1]

It is a biflavonoid (bis-apigenin coupled at 8 and 3' positions).

Amentoflavone can interact with many other medications by being a potent inhibitor of CYP3A4 and CYP2C9, which are proteins used for drug metabolism in the body.^[2]

References

^ Pan X, Tan N, Zeng G, Zhang Y, Jia R (October 2005). "Amentoflavone and its derivatives as novel natural inhibitors of human Cathepsin B". Bioorg. Med. Chem. 13 (20): 5819–25. doi:10.1016/j.bmc.2005.05.071. PMID 16084098.
^ Kimura Y, Ito H, Ohnishi R, Hatano T (January 2010). "Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity". Food Chem. Toxicol. 48 (1): 429–35. doi:10.1016/j.fct.2009.10.041. PMID 19883715.