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40584

Sigma-Aldrich

Amentoflavone

≥98.0% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C30H18O10
Número de CAS:
1617-53-4
Peso molecular:
538.46
Beilstein/REAXYS Number:
380244
MDL number:
MFCD00017470
UNSPSC Code:
12352200
PubChem Substance ID:
57650005
NACRES:
NA.47

Quality Level

100

assay

≥98.0% (HPLC)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

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

InChI key

YUSWMAULDXZHPY-UHFFFAOYSA-N

Gene Information

human ... GABRA1(2554)

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General description

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)

Biochem/physiol Actions

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
In vitro enzyme inhibitory properties, antioxidant activities, and phytochemical studies on Juniperus drupacea
Orhan DD, et al.,
journal of research in pharmacy, 23(1), 83-92 (2019)
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
Ismail O Ishola et al.
Journal of ethnopharmacology, 142(2), 383-389 (2012-05-23)
Cnestis ferruginea (CF) Vahl ex DC (Connaraceae) is a shrub widely used in Traditional African Medicine (TAM) for the treatment of various painful and inflammatory conditions. To isolate the active pharmacological constituents responsible for the anti-inflammatory and antinociceptive properties of
Chan-Woo Lee et al.
Bioorganic & medicinal chemistry, 16(2), 732-738 (2007-11-22)
The methanol extract from Selaginella tamariscina significantly inhibited UV irradiation induced activity of matrix metalloproteinase-1 (MMP-1) in primary fibroblasts from human skin. Using the technique of bioassay-directed chromatographic separation, five biflavonoids were isolated from the ethyl acetate soluble fraction of
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