Bergenin

Names

[ CAS No. ]:
477-90-7

[ Name ]:
Bergenin

[Synonym ]:
Vakerin
Ai Cha Su
Bergenitol
Bergenit
Peltophorin
CORYLOPSIN
(+)-Bergenin
3,4,8,10-Tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
4-Methoxy-2-[tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)pyran-2-yl]-a-resorcylic Acid d-Lactone
Pyrano[3,2-c][2]benzopyran-6(2H)-one, 3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-
3,4,4a,10b-Tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxypyrano[3,2-c][2]benzopyran-6(2H)-one
BERGENIN
Bergenin:Pyrano[3,2-c][2]benzopyran-6(2H)-one,3,4,4a,10b-tetrahydro-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-, [2R-(2,3,4,4a, 10b)]-,
CUSCUTIN
Ardisic Acid B
MFCD00133120

Biological Activity

[Description]:

Bergenin, a polyphenol, is a potent antinarcotic agent with antioxidant action. IC50 value: < 2.5 μM (antiplasmodial) [3]Target:In vitro: The naloxone-precipitated withdrawal symptom (jumping frequency) was significantly ameliorated (50% of control group) by administration of bergenin (20 mg/kg) in morphine-treated mice. Furthermore, morphine-induced down-regulation of glutathione (GSH) contents was reversed by bergenin administration in the frontal cortex and liver [2].In vivo: Bergenin attenuated inflammatory cell infiltration and decreased the concentration of NO, TNF-α, IL-1β, and IL-6, which were increased in LPS-induced mouse mastitis [1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Others

Natural Products >> Phenylpropanoids

[References]

[1]. Gao XJ, et al. Bergenin Plays an Anti-Inflammatory Role via the Modulation of MAPK and NF-κB Signaling Pathways in a Mouse Model of LPS-Induced Mastitis. Inflammation. 2015 Jun;38(3):1142-50.

[2]. Yun J, et al. Bergenin decreases the morphine-induced physical dependence via antioxidative activity in mice. Arch Pharm Res. 2015 Jun;38(6):1248-54.

[3]. Uddin G, et al. Comparative antioxidant and antiplasmodial activities of 11-O-galloylbergenin and bergenin isolated from Bergenia ligulata. Trop Biomed. 2014 Mar;31(1):143-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
658.9±55.0 °C at 760 mmHg

[ Melting Point ]:
237-240 °C(lit.)

[ Molecular Formula ]:
C₁₄H₁₆O₉

[ Molecular Weight ]:
328.271

[ Flash Point ]:
250.7±25.0 °C

[ Exact Mass ]:
328.079437

[ PSA ]:
145.91000

[ LogP ]:
0.05

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.655

[ Storage condition ]:
?20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UQ0337200

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb.

Bioorg. Med. Chem. 16 , 1337-44, (2008)

Saxifraga stolonifera, an evergreen dicotyledon, has been identified as an important resource in Chinese medicine due to its anticancer activity. In the present report, chemical components of S. stolo...

Simultaneous quantification of biomarkers bergenin and menisdaurin in the methanol extract of aerial parts of Flueggea virosa by validated HPTLC densitometric method.

J. Chromatogr. Sci. 53 , 824-9, (2015)

A simple, sensitive high-performance thin-layer chromatography (HPTLC) method was developed for the simultaneous quantification of biomarker bergenin and menisdaurin in the methanol extracts of aerial...

A novel lactone from Tripterospermum chinense.

Yao Xue Xue Bao 47(11) , 1517-20, (2012)

A novel lactone, tripterospermumcins E (1), along with four known compounds, sweroside (2), loganic acid (3), 8-epi-kingiside (4) and bergenin (5), were isolated from the aerial parts of Tripterosperm...