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Amentoflavone

From Wikipedia, the free encyclopedia

Amentoflavone
Skeletal formula
Ball-and-stick model of amentoflavone
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
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 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
  • 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 mass538.464 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Amentoflavone is a biflavonoid (bis-apigenin coupled at 8 and 3 positions, or 3,8″-biapigenin) constituent of a number of plants includingGinkgo biloba,Chamaecyparis obtusa (hinoki),Biophytum sensitivum,Selaginella tamariscina,[1]Hypericum perforatum (St. John's Wort)[2] andXerophyta plicata.[3]

Amentoflavone can interact with many medications by being a potent inhibitor ofCYP3A4 andCYP2C9, which areenzymes responsible for themetabolism of some drugs in the body.[4] It is also an inhibitor of humancathepsin B.[2]

Amentoflavone has a variety ofin vitro activities including antimalarial activity,[5] anticancer activity (which may, at least in part, be mediated by its inhibition offatty acid synthase),[6][7][8] andantagonist activity at theκ-opioid receptor (Ke = 490 nmol L−1)[9] as well as activity at theallostericbenzodiazepine site of theGABAA receptor as anegative allosteric modulator.[10]

See also

[edit]

References

[edit]
  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.
  2. ^abPan 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)". Archived fromthe original on December 14, 2012.
  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.

External links

[edit]
Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
Sulfated glycosides
Polymers
Drugs
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAATooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
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