From Wikipedia, the free encyclopedia
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
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
Y Key: YUSWMAULDXZHPY-UHFFFAOYSA-N
Y 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
C 30 H 18 O 10
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).
Chemical compound
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 (K e = 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
^ 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 )
^
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 .
^ 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 .
^ 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 .
^
"Inhibitors of Plasmodium falciparum M1- Family Alanyl Aminopeptidase (M1AAP)" .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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
Aglycones
Monohydroxyflavone Dihydroxyflavones Trihydroxyflavones Tetrahydroxyflavones Pentahydroxyflavones O-methylated flavones
Glycosides
of apigenin of baicalein of hypolaetin of luteolin
Acetylated Sulfated glycosides Polymers Drugs
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see
here for a full list):
α-EMTBL
Alcohols (e.g.,
drinking alcohol ,
2M2B )
Anabolic steroids
Avermectins (e.g.,
ivermectin )
Barbiturates (e.g.,
phenobarbital )
Benzodiazepines (e.g.,
diazepam )
Bromide compounds (e.g.,
potassium bromide )
Carbamates (e.g.,
meprobamate )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,
ergoloid (dihydroergotoxine) )
Etazepine
Etifoxine
Fenamates (e.g.,
mefenamic acid )
Flavonoids (e.g.,
apigenin ,
hispidulin )
Fluoxetine
Flupirtine
Imidazoles (e.g.,
etomidate )
Kava constituents (e.g.,
kavain )
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,
allopregnanolone ,
cholesterol ,
THDOC )
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,
β-carbolines (e.g.,
abecarnil ),
cyclopyrrolones (e.g.,
zopiclone ),
imidazopyridines (e.g.,
zolpidem ),
pyrazolopyrimidines (e.g.,
zaleplon ))
Norfluoxetine
Petrichloral
Phenols (e.g.,
propofol )
Phenytoin
Piperidinediones (e.g.,
glutethimide )
Propanidid
Pyrazolopyridines (e.g.,
etazolate )
Quinazolinones (e.g.,
methaqualone )
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,
baicalin )
Stiripentol
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal) )
Topiramate
Valerian constituents (e.g.,
valerenic acid )
Volatiles /
gases (e.g.,
chloral hydrate ,
chloroform ,
diethyl ether ,
paraldehyde ,
sevoflurane )
Negative modulators:
1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g.,
penicillins ,
cephalosporins ,
carbapenems )
Basmisanil
Bemegride
Bicyclic phosphates (
TBPS ,
TBPO ,
IPTBO )
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g.,
fipronil )
Flavonoids (e.g.,
amentoflavone ,
oroxylin A )
Flumazenil
Fluoroquinolones (e.g.,
ciprofloxacin )
Flurothyl
Furosemide
Golexanolone
Iomazenil (123 I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g.,
apalutamide ,
bicalutamide ,
enzalutamide ,
flutamide ,
nilutamide )
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e.,
picrotin ,
picrotoxinin and
dihydropicrotoxinin )
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor