Amentoflavone

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Amentoflavone
Skeletal formula
Ball-and-stick model of amentoflavone
Names
IUPAC name
(4′,5,7-Trihydroxyflavone)-(3′→8)-(4′,5,7-trihydroxyflavone)
Preferred IUPAC name
8-[5-(5,7-Dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names
Didemethyl-ginkgetin
3′,8′′-Biapigenin
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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 checkY
    Key: YUSWMAULDXZHPY-UHFFFAOYSA-N checkY
  • 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
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
Properties
Chemical formula
 C30H18O10
Molar mass 538.464 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY  (what is checkY☒N ?)
Infobox references

Amentoflavone is a biflavonoid (bis-apigenin coupled at 8 and 3' positions, or 3′,8′′-biapigenin) constituent of a number of plants including Ginkgo biloba, Chamaecyparis obtusa (hinoki), Hypericum perforatum (St. John's Wort)[1] and Xerophyta plicata.[2]

Amentoflavone can interact with many medications by being a potent inhibitor of CYP3A4 and CYP2C9, which are enzymes responsible for the metabolism of some drugs in the body.[3] It is also an inhibitor of human cathepsin B.[1]

Amentoflavone has a variety of in vitro activities including antimalarial activity,[4] anticancer activity (which may, at least in part, be mediated by its inhibition of fatty acid synthase),[5][6][7] and antagonist activity at the κ-opioid receptor (Ke = 490 nmol L−1)[8] as well as activity at the allosteric benzodiazepine site of the GABAA receptor as a negative allosteric modulator.[9]

See also[]

  • Apigenin

References[]

  1. ^ a b Pan X, Tan N, Zeng G, Zhang Y, Jia R (2005). "Amentoflavone and its derivatives as novel natural inhibitors of human Cathepsin B". Bioorg. Med. Chem. 13 (20): 5819–5825. doi:10.1016/j.bmc.2005.05.071. PMID 16084098.
  2. ^ Williams, Christine A.; Harborne, Jeffrey B.; Tomas-Barberan A., Francisco (1987). "Biflavonoids in the primitive monocots Isophysis tasmanica and Xerophyta plicata". Phytochemistry. 26 (9): 2553. doi:10.1016/S0031-9422(00)83875-3.
  3. ^ Kimura, Y; Ito, H; Ohnishi, R; Hatano, T (2010). "Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity". Food Chem. Toxicol. 48 (1): 429–435. doi:10.1016/j.fct.2009.10.041. PMID 19883715.
  4. ^ "Inhibitors of Plasmodium falciparum M1- Family Alanyl Aminopeptidase (M1AAP)".
  5. ^ Lee, JS; Lee, MS; Oh, WK; Sul, JY (2009). "Fatty acid synthase inhibition by amentoflavone induces apoptosis and antiproliferation in human breast cancer cells" (PDF). Biol. Pharm. Bull. 32 (8): 1427–1432. doi:10.1248/bpb.32.1427. PMID 19652385.
  6. ^ Wilsky, S; Sobotta, K; Wiesener, N; Pilas, J; Althof, N; Munder, T; Wutzler, P; Henke, A (2012). "Inhibition of fatty acid synthase by amentoflavone reduces coxsackievirus B3 replication". Arch. Virol. 157 (2): 259–269. doi:10.1007/s00705-011-1164-z. PMID 22075919.
  7. ^ Lee, JS; Sul, JY; Park, JB; Lee, MS; Cha, EY; Song, IS; Kim, JR; Chang, ES (2013). "Fatty Acid Synthase Inhibition by Amentoflavone Suppresses HER2/neu(erbB2) Oncogene in SKBR3 Human Breast Cancer Cells". Phytother. Res. 27 (5): 713–720. doi:10.1002/ptr.4778. PMID 22767439.
  8. ^ Katavic PL, Lamb K, Navarro H, Prisinzano TE (2007). "Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships". J. Nat. Prod. 70 (8): 1278–1282. doi:10.1021/np070194x. PMC 2265593. PMID 17685652.
  9. ^ Hanrahan, JR; Chebib, M; Davucheron, NL; Hall, BJ; Johnston, GA (2003). "Semisynthetic preparation of amentoflavone: A negative modulator at GABA(A) receptors". Bioorg. Med. Chem. Lett. 13 (14): 2281–2284. doi:10.1016/s0960-894x(03)00434-7. PMID 12824018.
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