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40584

Sigma-Aldrich

Amentoflavone

≥98.0% (HPLC)

Synonyme(s) :

Didemethyl-ginkgetin, I3′,II8-Biapigenin, Tridemethylsciadopitysin

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About This Item

Formule empirique (notation de Hill):
C30H18O10
Numéro CAS:
1617-53-4
Poids moléculaire :
538.46
Numéro Beilstein :
380244
Numéro MDL:
MFCD00017470
Code UNSPSC :
12352200
ID de substance PubChem :
57650005
Nomenclature NACRES :
NA.47

Pureté

≥98.0% (HPLC)

Forme

solid

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

2-8°C

Chaîne SMILES 

Oc1ccc(cc1)C2=CC(=O)c3c(O)cc(O)c(c3O2)-c4cc(ccc4O)C5=CC(=O)c6c(O)cc(O)cc6O5

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

Clé InChI

YUSWMAULDXZHPY-UHFFFAOYSA-N

Informations sur le gène

human ... GABRA1(2554)

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Description générale

Amentoflavone is a naturally occurring polyphenolic biflavonoid found in many plants. Structurally, it has an apigenin dimer which is linked by a C3′-C8′′ covalent bond.

Application

Amentoflavone has been used:
  • as a chemical inhibitor to determine the selective attenuation of p-Cresol glucuronidation in HepaRG cells
  • as a reference standard for qualitative and quantitative analyses of phenolic compounds of Juniperus foetidissima Willd. and Juniperus sabina L. using reverse phase- high-performance liquid chromatography- diode array detector (RP-HPLC-DAD)
  • as a reference standard to analyze and standardize the methanol extract process of Juniperus drupacea Labill. phenolic compounds using reverse phase- high-performance liquid chromatography - diode array detector (RP-HPLC-DAD)

Actions biochimiques/physiologiques

Amentoflavone has various pharmacological properties such as antioxidant, anti-diabetic, anti-tumor, anti-senescence, neuroprotective, and cardioprotective activities.
Biflavonoid with anti-inflammatory, anti-viral and cancer chemopreventive activity. It inhibits vascularization of tumors by blocking the activity of angiogenic VEGFs. Blocks the induction of COX-2 and up-regulates PPAR-γ. It is a negative modulator of the GABAA receptor at the benzodiazepine binding site.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Scott Baggett et al.
Journal of natural products, 68(3), 354-360 (2005-03-25)
A MeOH extract of Garcinia xanthochymus fruits was subjected to activity-guided fractionation, yielding two new benzophenones, guttiferone H (1) and gambogenone (2). Compound 1 contains a seven-membered ring attached to the bicyclo[3.3.1]nonane system at positions 7 and 8 and displayed
Sheng Yu et al.
Molecules (Basel, Switzerland), 22(2) (2017-02-18)
Amentoflavone (C30H18O10) is a well-known biflavonoid occurring in many natural plants. This polyphenolic compound has been discovered to have some important bioactivities, including anti-inflammation, anti-oxidation, anti-diabetes, and anti-senescence effects on many important reactions in the cardiovascular and central nervous system
Hiroaki Sasaki et al.
Bioorganic & medicinal chemistry letters, 20(15), 4558-4560 (2010-07-06)
Here, we describe amentoflavone-type biflavonoids, which were isolated from natural sources and were found to inhibit beta-secretase (BACE-1). The structure-activity relationship was studied, and compounds 1-8, 10, 17, and 18 showed BACE-1 inhibitory activity. Among these compounds, 2,3-dihydroamentoflavone 17 and
A A Kaikabo et al.
Journal of ethnopharmacology, 138(1), 253-255 (2011-09-17)
Amentoflavone and 4' monomethoxy amentoflavone were previously isolated from Garcinia livingstonei leaves. These compounds had good activities (MIC 6 and 8 μg/ml) against some nosocomial bacteria. In this study, the activity of these purified compounds were tested against fast-growing non-pathogenic
Ismail O Ishola et al.
Pharmacology, biochemistry, and behavior, 103(2), 322-331 (2012-09-05)
The root decoction of Cnestis ferruginea (CF) Vahl DC (Connaraceae) is used in traditional African medicine in the management of psychiatric disorders. This study presents the antidepressant and anxiolytic effects of amentoflavone (CF-2) isolated from the root extract of C.
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