{{cs1 config|name-list-style=vanc}} {{Chembox | Watchedfields = changed | verifiedrevid = 403346640 | ImageFile = Amentoflavone.svg | ImageClass = skin-invert-image | ImageSize = 220 | ImageAlt = Skeletal formula | ImageFile1 = Amentoflavone molecule ball.png | ImageClass1 = bg-transparent | ImageAlt1 = Ball-and-stick model of amentoflavone | IUPACName = (4′,5,7-Trihydroxyflavone)-(3′→8)-(4′,5,7-trihydroxyflavone) | SystematicName = 8-[5-(5,7-Dihydroxy-4-oxo-4''H''-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one | OtherNames = Didemethyl-ginkgetin<br>3{{prime}},8{{pprime}}-Biapigenin |Section1={{Chembox Identifiers | InChIKey = YUSWMAULDXZHPY-UHFFFAOYAB | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YUSWMAULDXZHPY-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 1617-53-4 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 9I1VC79L77 | PubChem = 5281600 | KEGG = C10018 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 63354 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4444919 | 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 = 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 }} |Section2={{Chembox Properties | C=30 | H=18 | O=10 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Amentoflavone''' is a biflavonoid (''bis''-apigenin coupled at 8 and 3{{prime}} positions, or 3{{prime}},8{{pprime}}-biapigenin) constituent of a number of plants including ''Ginkgo biloba'', ''Chamaecyparis obtusa'' (hinoki), ''Biophytum sensitivum'', ''Selaginella tamariscina'',<ref>{{cite journal | doi = 10.3389/fphar.2021.768708 | title = Insights Into Amentoflavone: A Natural Multifunctional Biflavonoid | last1 = Xiong | first1 = Xifeng | journal = Frontiers in Pharmacology | volume = 12 | date = 22 December 2021 | pmid = 35002708 | pmc = 8727548 | doi-access = free }}</ref> ''Hypericum perforatum'' (St. John's Wort)<ref name=Pan>{{cite journal |vauthors=Pan X, Tan N, Zeng G, Zhang Y, Jia R |title=Amentoflavone and its derivatives as novel natural inhibitors of human Cathepsin B |journal=Bioorg. Med. Chem. |volume=13 |issue=20 |pages=5819–5825 |year=2005 |pmid=16084098 |doi=10.1016/j.bmc.2005.05.071 }}</ref> and ''Xerophyta plicata''.<ref>{{cite journal | doi = 10.1016/S0031-9422(00)83875-3 | title = Biflavonoids in the primitive monocots Isophysis tasmanica and Xerophyta plicata | year = 1987 | last1 = Williams | first1 = Christine A. | last2 = Harborne | first2 = Jeffrey B. | last3 = Tomas-Barberan A. | first3 = Francisco | author-link2 = Jeffrey Harborne | journal = Phytochemistry | volume = 26 | issue = 9 | pages = 2553| bibcode = 1987PChem..26.2553W }}</ref>
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.<ref>{{cite journal |author1=Kimura, Y |author2=Ito, H |author3=Ohnishi, R |author4=Hatano, T |title=Inhibitory effects of polyphenols on human cytochrome P450 3A4 and 2C9 activity |journal=Food Chem. Toxicol. |volume=48 |issue=1 |pages=429–435 |year=2010 |pmid=19883715 |doi=10.1016/j.fct.2009.10.041 }}</ref> It is also an inhibitor of human cathepsin B.<ref name=Pan/>
Amentoflavone has a variety of ''in vitro'' activities including antimalarial activity,<ref>{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/assay/assay.cgi?aid=1445 | archive-url = https://archive.today/20121214021845/http://pubchem.ncbi.nlm.nih.gov/assay/assay.cgi?aid=1445 | url-status = dead | archive-date = December 14, 2012 | title = Inhibitors of Plasmodium falciparum M1- Family Alanyl Aminopeptidase (M1AAP)}}</ref> anticancer activity (which may, at least in part, be mediated by its inhibition of fatty acid synthase),<ref>{{cite journal|title=Fatty acid synthase inhibition by amentoflavone induces apoptosis and antiproliferation in human breast cancer cells|journal=Biol. Pharm. Bull.|year=2009|volume=32|issue=8|pages=1427–1432|doi=10.1248/bpb.32.1427|pmid=19652385|author1=Lee, JS |author2=Lee, MS |author3=Oh, WK |author4=Sul, JY |url=https://www.jstage.jst.go.jp/article/bpb/32/8/32_8_1427/_pdf|format=PDF|doi-access=free|url-access=subscription}}</ref><ref>{{cite journal|title=Inhibition of fatty acid synthase by amentoflavone reduces coxsackievirus B3 replication|journal=Arch. Virol.|volume=157|issue=2|pages=259–269|doi=10.1007/s00705-011-1164-z|pmid=22075919|author1=Wilsky, S |author2=Sobotta, K |author3=Wiesener, N |author4=Pilas, J |author5=Althof, N |author6=Munder, T |author7=Wutzler, P |author8=Henke, A |year=2012|s2cid=254054659 }}</ref><ref>{{cite journal|title=Fatty Acid Synthase Inhibition by Amentoflavone Suppresses HER2/neu(erbB2) Oncogene in SKBR3 Human Breast Cancer Cells|journal=Phytother. Res.|year=2013|volume=27|issue=5|pages=713–720|doi=10.1002/ptr.4778|pmid=22767439|author1=Lee, JS |author2=Sul, JY |author3=Park, JB |author4=Lee, MS |author5=Cha, EY |author6=Song, IS |author7=Kim, JR |author8=Chang, ES |s2cid=26035868 }}</ref> and antagonist activity at the κ-opioid receptor (''K''<sub>e</sub> = 490 nmol L<sup>−1</sup>)<ref name = Katavic>{{cite journal |vauthors=Katavic PL, Lamb K, Navarro H, Prisinzano TE |title=Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships |journal=J. Nat. Prod. |volume=70 |issue=8 |pages=1278–1282 |year=2007 |pmid=17685652 |doi=10.1021/np070194x |pmc=2265593}}</ref> as well as activity at the allosteric benzodiazepine site of the GABA<sub>A</sub> receptor as a negative allosteric modulator.<ref>{{cite journal | pmid = 12824018 | year = 2003 | last1 = Hanrahan | first1 = JR | last2 = Chebib | first2 = M | last3 = Davucheron | first3 = NL | last4 = Hall | first4 = BJ | last5 = Johnston | first5 = GA | title = Semisynthetic preparation of amentoflavone: A negative modulator at GABA(A) receptors | volume = 13 | issue = 14 | pages = 2281–2284 | journal = Bioorg. Med. Chem. Lett. | doi=10.1016/s0960-894x(03)00434-7}}</ref>
==See also== * Apigenin
==References== {{Reflist|2}}
==External links== * {{Commons category-inline}}
{{Flavones}} {{GABA receptor modulators}} {{Opioid receptor modulators}}
Category:Flavones Category:Cytochrome P450 inhibitors Category:Natural phenol dimers Category:Resorcinols Category:Kappa-opioid receptor antagonists Category:GABAA receptor negative allosteric modulators Category:Hexols Category:CYP2C9 inhibitors