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Merck
CN

SMB00073

Bergenin

≥95% (LC/MS-ELSD)

Synonym(s):

Cuscutin, Ardisic acid B, Vakerin

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About This Item

Empirical Formula (Hill Notation):
C14H16O9
CAS Number:
477-90-7
Molecular Weight:
328.27
MDL number:
MFCD00133120
UNSPSC Code:
12352205
PubChem Substance ID:
329824752
NACRES:
NA.25

Key Documents

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Assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

O1[C@@H]2[C@H](OC(=O)c3c2c(c(c(c3)O)OC)O)[C@H]([C@@H]([C@H]1CO)O)O

InChI

1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1

InChI key

YWJXCIXBAKGUKZ-HJJNZUOJSA-N

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General description

Natural product derived from plant source.

Biochem/physiol Actions

Bergenin displays antinociceptive and anti-inflammatory properties, in addition to its use in folk medicines as a potent hepatoprotective agent. Bergenin acts by inhibiting the formation of interleukin 1beta and TNF-α, which suggests its potential use for controling inflammatory pain.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
122228211V
122228-211V

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B Nyasse et al.
Die Pharmazie, 59(6), 492-494 (2004-07-14)
The presence of bergenin in substantial amounts in the methanol leaves extract of Flueggea virosa (Euphorbiaceae) was established as a strong chemotaxomic point of differentiation between Flueggea virosa and Securinega virosa. Bergenin showed an inhibitory effect on the growth of
Dong Wang et al.
Bioorganic & medicinal chemistry letters, 15(18), 4073-4075 (2005-07-05)
A novel C-C-coupled dimer derivative of bergenin was produced by the biotransformation of cultured mycelia of white rot fungus Pleurotus ostreatus. Its structure was elucidated by detailed spectroscopic analysis.
Heitor A De Abreu et al.
Organic & biomolecular chemistry, 6(15), 2713-2718 (2008-07-18)
(+)-Bergenin (1) was isolated from Sacoglottis uchi, a species of vegetable found in the Amazon region and popularly used for the treatment of several hepatic problems. The structure of 1 was fully characterized using IR, GC-MS and NMR (1D and
Faiyaz Ahmed et al.
Phytotherapy research : PTR, 24(12), 1839-1843 (2010-06-22)
The present study evaluated the radical scavenging and angiotensin converting enzyme (ACE) inhibitory activity of cold and hot aqueous extracts of Ficus racemosa (Moraceae) stem bark. The extracts were standardized using HPLC. Radical scavenging activity was determined using 1,1-diphenyl-2-picrylhydrazyl radical
Yusei Kashima et al.
Journal of oleo science, 62(6), 391-401 (2013-06-04)
Here we evaluated the inhibitory effects of bergenin analogues (2-10), prepared from naturally occurring bergenin, (1) on β-secretase (BACE1) activity. All the bergenin analogues that were analyzed inhibited BACE1 in a dose-dependent manner. 11-O-protocatechuoylbergenin (5) was the most potent inhibitor
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