Amentoflavone

Amentoflavone

Amentoflavone
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
ChEMBL  YesY
Jmol-3D images Image 1
Properties
Molecular formula C30H18O10
Molar mass 538.46 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/N?)
Amentoflavone

Amentoflavone is a biflavonoid (bis-apigenin coupled at 8 and 3' positions) 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 affinities for opioid receptors (as an antagonist)[8] and the allosteric (benzodiazepine) site on the GABAA receptor as a negative allosteric modulator.[9]

References

  1. ^ a b 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.  
  2. ^ Williams, Christine A.;  
  3. ^ Kimura, Y; Ito, H; Ohnishi, R; Hatano, T (January 2010). "Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity". Food Chemistry Toxicology 48 (1): 429–35.  
  4. ^ "Inhibitors of Plasmodium falciparum M1- Family Alanyl Aminopeptidase (M1AAP)". 
  5. ^ Lee, JS; Lee, MS; Oh, WK; Sul, JY (August 2009). "Fatty acid synthase inhibition by amentoflavone induces apoptosis and antiproliferation in human breast cancer cells" (PDF). Biological & Pharmaceutical Bulletin 32 (8): 1427–1432.  
  6. ^ Wilsky, S; Sobotta, K; Wiesener, N; Pilas, J; Althof, N; Munder, T; Wutzler, P; Henke, A (February 2012). "Inhibition of fatty acid synthase by amentoflavone reduces coxsackievirus B3 replication". Archives of Virology 157 (2): 259–269.  
  7. ^ Lee, JS; Sul, JY; Park, JB; Lee, MS; Cha, EY; Song, IS; Kim, JR; Chang, ES (May 2013). "Fatty Acid Synthase Inhibition by Amentoflavone Suppresses HER2/neu(erbB2) Oncogene in SKBR3 Human Breast Cancer Cells". Phytotherapy Research 27 (5): 713–720.  
  8. ^ Katavic PL, Lamb K, Navarro H, Prisinzano TE. (August 2007). "Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships". J Nat Prod. 70 (8): 1278–82.  
  9. ^ Hanrahan, JR; Chebib, M; Davucheron, NL; Hall, BJ; Johnston, GA (2003). "Semisynthetic preparation of amentoflavone: A negative modulator at GABA(A) receptors". Bioorganic & Medicinal Chemistry Letters 13 (14): 2281–4.