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40584

Amentoflavone

≥98.0% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C30H18O10
CAS Number:
1617-53-4
Molecular Weight:
538.46
UNSPSC Code:
12352200
NACRES:
NA.47
PubChem Substance ID:
57650005
MDL number:
MFCD00017470
Beilstein/REAXYS Number:
380244

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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

SMILES string

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

InChI key

YUSWMAULDXZHPY-UHFFFAOYSA-N

assay

≥98.0% (HPLC)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

Quality Level

100

Gene Information

human ... GABRA1(2554)

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1 of 4

This Item
1079817827818571
Amentoflavone ≥98.0% (HPLC)

Sigma-Aldrich

40584

Amentoflavone

Apigenin ≥95.0% (HPLC)

Sigma-Aldrich

10798

Apigenin

Apigenin Induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 µM).

Sigma-Aldrich

178278

Apigenin

Amentoflavone analytical standard

Supelco

18571

Amentoflavone

form

solid

form

-

form

crystalline solid

form

-

assay

≥98.0% (HPLC)

assay

≥95.0% (HPLC)

assay

≥98% (HPLC)

assay

≥98.0% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

application(s)

-

application(s)

-

application(s)

food and beverages

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

Gene Information

human ... GABRA1(2554)

Gene Information

human ... ADORA3(140), CDC2(983), CDK5(1020), CDK6(1021), CYP1A2(1544), ESR1(2099), ESR2(2100), GSK3A(2931)
mouse ... Hexa(15211)
rat ... Adora1(29290), Adora2a(25369), Il4(287287), Tnf(24835)

Gene Information

-

Gene Information

-

General description

Amentoflavone is a naturally occurring polyphenolic biflavonoid found in many plants.[1] Structurally, it has an apigenin dimer which is linked by a C3′-C8′′ covalent bond.[1]

Application

Amentoflavone has been used:
  • as a chemical inhibitor to determine the selective attenuation of p-Cresol glucuronidation in HepaRG cells[2]
  • 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)[3]
  • 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.[1]
Biflavonoid with anti-inflammatory, anti-viral and cancer chemopreventive activity. 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.
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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK5038
BCCH1195
BCBZ7532
BCBV6157
BCBQ1550V

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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)
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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