Amentoflavone

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Contents

Amentoflavone
Amentoflavone.svg
Amentoflavone molecule ball.png
Names
IUPAC name
(4′,5,7-Trihydroxyflavone)-(3′→8)-(4′,5,7-trihydroxyflavone)
Systematic 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
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: YUSWMAULDXZHPY-UHFFFAOYSA-N Yes check.svgY
  • 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
  • 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
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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), Biophytum sensitivum , Selaginella tamariscina , [1] Hypericum perforatum (St. John's Wort) [2] and Xerophyta plicata . [3]

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. [4] It is also an inhibitor of human cathepsin B. [2]

Amentoflavone has a variety of in vitro activities including antimalarial activity, [5] anticancer activity (which may, at least in part, be mediated by its inhibition of fatty acid synthase), [6] [7] [8] and antagonist activity at the κ-opioid receptor (Ke = 490  nmol L−1) [9] as well as activity at the allosteric benzodiazepine site of the GABAA receptor as a negative allosteric modulator. [10]

See also

References

  1. ↑ Xiong X (22 December 2021). "Insights Into Amentoflavone: A Natural Multifunctional Biflavonoid". Frontiers in Pharmacology . 12. doi: 10.3389/fphar.2021.768708 . PMC   8727548 . PMID   35002708.{{cite journal}}: CS1 maint: date and year (link)
  2. 1 2 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.
  3. ↑ Williams CA, Harborne JB, Tomas-Barberan A F (1987). "Biflavonoids in the primitive monocots Isophysis tasmanica and Xerophyta plicata". Phytochemistry . 26 (9): 2553. Bibcode:1987PChem..26.2553W. doi:10.1016/S0031-9422(00)83875-3.
  4. ↑ 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.
  5. ↑ "Inhibitors of Plasmodium falciparum M1- Family Alanyl Aminopeptidase (M1AAP)".
  6. ↑ 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.
  7. ↑ 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. S2CID   254054659.
  8. ↑ 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. S2CID   26035868.
  9. ↑ 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.
  10. ↑ 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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