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Sigma-Aldrich

Amentoflavon

≥98.0% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C30H18O10
CAS-Nummer:
1617-53-4
Molekulargewicht:
538.46
Beilstein:
380244
MDL-Nummer:
MFCD00017470
UNSPSC-Code:
12352200
PubChem Substanz-ID:
57650005
NACRES:
NA.47

Assay

≥98.0% (HPLC)

Form

solid

Anwendung(en)

metabolomics
vitamins, nutraceuticals, and natural products

Lagertemp.

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

InChIKey

YUSWMAULDXZHPY-UHFFFAOYSA-N

Angaben zum Gen

human ... GABRA1(2554)

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Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

Biflavonoid mit entzündungshemmender, anti-viraler und chemopreventiver Wirkung. Es hemmt die Vaskularisation von Tumoren durch die Blockierung der Aktivität von angiogenen VEGFs. Blockiert die Induktion von COX-2 und reguliert PPAR-γ. Ein negativer Modulator ders GABAA-Rezeptors an der Benzodiazepin-Bindungsstelle.
Amentoflavone has various pharmacological properties such as antioxidant, anti-diabetic, anti-tumor, anti-senescence, neuroprotective, and cardioprotective activities.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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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
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)
Hans Michler et al.
Phytochemical analysis : PCA, 22(1), 42-50 (2010-09-08)
Biflavones of Hypericum perforatum L. are bioactive compounds used in the treatment of inflammation and depression. Determination of amentoflavone and biapigenin from blood is challenging owing to their similar structures and low concentrations. To develop a rapid, sensitive and accurate
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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