Bengenin Chemical Properties

Melting point:

237-240 °C(lit.)

alpha 

D18 -37.7° (c = 1.96 in ethanol); D24 -45.3° (c = 0.51 for anhydr in water)

Boiling point:

386.03°C (rough estimate)

Density 

1.3901 (rough estimate)

refractive index 

1.6550 (estimate)

storage temp. 

-20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

8.26±0.70(Predicted)

color 

White to Off-White

λmax

277nm(EtOH)(lit.)

LogP

-1.398 (est)

CAS DataBase Reference

477-90-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UQ0337200

HS Code 

29329990

Bengenin Usage And Synthesis

Description

The plant resources of bergenin are rich, mainly from Rock cabbage (Bergenia purpurascens) and thick leafy rock cabbage (Astilbe macroflora) from Saxifragaceae and the roots, stems, and leaves of bai liang jin (Ardisia crispa) from Ardisia japonica (Thunb.) Blume. In Chinese medicine Rock cabbage (Bergenia purpurascens) is the common folk medicine, with nourishing, stanching bleeding, relieving a cough, and other effects. Its earliest record is contained in the classified herbal in Qing Dynasty .
There are ten kinds of Rock cabbage (Bergenia purpurascens) in Asia, mainly growing in East Asia, north of South Asia, and southeastern Central Asia. There are seven species (including three endemic species) in China, mainly distributed in Shaanxi (Qinling), Xinjiang, Sichuan, Yunnan, and Tibet .

Chemical Properties

White powder

Physical properties

Appearance: white, loose needle-like crystal or crystalline powder with light odor and bitter taste and discolored when encountered with light or heat. Solubility: dissolved in methanol and slightly soluble in water or ethanol. Melting point: 232– 240?°C. Specific optical rotation: ?38° to ?45°.

History

In 1958, Hay and Haynes first reported the complete synthesis of bergenin, using 4-methoxy gallate and A-D-bromo-2, 3, 4, 6-tetraacetylglucose as raw materials to synthesize bergenin successfully .
In 1987, Chen Wendou determined the content of bergenin as 5.8% in the alcohol extract of Astilbe chinensis (Maxim.), Franch. et Savat.(Luoxinfu), and Rock cabbage (Bergenia purpurascens) by using high-performance liquid chromatography. In 1991, Wang Junping determined the content of bergenin in the alcohol extract of Rodgersia podophylla as 19.17% with spectrophotometry.
By doing thin layer qualitative analysis, Liu Nunian discovered that bergenin could be found in seven kinds of plants including sour moss (Ardisia solanacea), Luosan tree (Ardisia quinquegona Bl.), Cinnabar root (Ardisia crenata Sims), Zijinniu (Ardisia japonica), Lianzuozijinniu (Ardisia primulaefolia), Jiujielong (Ardisia pusilla), and Xinyezijinniu (Ardisia maclurei) from Ardisia. In addition, Zhang Yi determined the content of bergenin in the medicinal plants from Ardisiawith high-performance liquid chromatography, and results showed that there were four species of plants with the content of bergenin of more than 1%, having great resource utilization value. There are 11 species of plants with the content of bergenin less than 1%, such as Xiaoqiaomuzijinniu (Ardisia arborescens), twist fruit, fine umbrella (Ardisia affinis Hemsl.), and so on. They had some useful value as well .
In recent years, it has been found that both 8, 10-dimethylca bergenin and 11-0-gallate betaine had weak inhibitory effects on the tumor in mice, and their effects were stronger than that of bergenin. The effect of acetylated bergenin was stronger than that of bergenin on liver injury induced by chloroform in mice. The new bergenin derivatives from the Ardisia gigantifolia stapf had a certain degree of free radical-scavenging effect and anti-HIV viral activity .

Uses

A herbal remedy with antioxidant, antimicrobial and antiinflammatory properties.

Definition

ChEBI: A natural product found in Cenostigma gardnerianum.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

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.

Pharmacology

1. Cough-relieving effect Bergenin had a significant relieving effect on coughs caused by electrical stimulation of the laryngeal nerve and ammonia spray. The dose of its cough-relieving effect was equivalent to 1/7–1/4 dose of codeine. No tolerance was found after a 23-day consecutive administration of bergenin due to its selective inhibition on cough center .
2. Expectorant effect Dwarf tea (Japanese Ardisia Herb) decoction was found to have a clear expectorant effect after intragastric administration to mice at the dose of 25?g/kg, and its effect strength is equivalent to that of Platycodon grandiflorum at the same dose.
3. Anti-inflammatory and anti-ulcer effect In the model of chronic bronchitis caused by sulfur dioxide fumigation in rats, 80 mg/kg/day of bergenin was given once a day for 10?days. The results showed that the tracheal goblet cell number from the rats in the treatment group decreased, suggesting that the amount of sputum reduced. Inflammatory cell infiltration was found to alleviate, and the degree of emphysema and lung collapse were also reduced. Okada found that bergenin had a therapeutic effect on experimental gastric ulcer rats, consistent with the clinical application of bergenin in the treatment of gastric ulcer, duodenal ulcer, and chronic gastritis .
Recent studies have shown that bergenin had certain analgesic and antiinflammatory properties and had the potential to control inflammatory pain through inhibiting the production of IL-β and TNF-α . Bergenin preparations have been widely used clinically for the treatment of chronic bronchitis, gastritis, and gastric and duodenal ulcers.
4. Antipyretic effect The alcohol extracts of Ardisia crispa had a strong antipyretic effect on the fever caused by the injection of cholera typhoid, paratyphoid, TAB vaccine, and tetanus toxin in the ear of rabbit.
5. Antiviral effect Rodgersia podophylla alcohol extract at the dose of 0.017–0.034?mg/ml cannot only inhibit the replication of DNA virus but also the replication of RNA virus. The cells with inactivated virus can continue to split and proliferate, indicating that the treatment is effective and with no obvious cell toxicity .
6. Liver protection Bergenin was found to improve the liver injury induced by carbon tetrachloride in mice. It cannot only reduce the release of glutamate acetyltransferase and sorbitol dehydrogenase from mice liver but also reduce the glutathione reductase and increase the glutathione content, indicating that bergenin protected the liver through the regulation of glutathione and inhibiting the release of free radicals .
7. Cardiovascular system effects Bergenin had some therapeutic effects on the arrhythmia in mice.
8. Toxicity test Mice were intraperitoneally injected with bergenin; the minimum lethal dose is 10?g/kg; no toxic reaction was found after intragastric administration of bergenin at the dose of 12?g/kg. No effects were found in the growth and development, liver function, and ECG of young rats after the intragastric administration with bergenin at the dose of 2.5?g/kg for consecutive 60?days, and no toxic performance was found in the heart, liver, kidney, lung, spleen, stomach, intestine, brain, and other organs by pathological biopsy

Clinical Use

Bergenin was recorded in People’s Republic of China Pharmacopoeia as an antitussive expectorant, used for the treatment of chronic bronchitis, emphysema, bronchial asthma, and other respiratory diseases. Used alone, or in compound preparation, such as compound bergenin tablets, Qingjin syrup, Compound Hu ear tablets, Qingfei antitussive syrup, liver poison net particles, Kechuanping oral solution, and silicone lung oral solution, it is mainly used for the treatment of chronic bronchitis. Its efficacy was proven to be relatively stable and improved in the compound preparations after a wide range of clinical validation.

target

Nrf2 | HO-1 | NO | TNF-α | NF-kB | IL Receptor | MAPK

Bengenin(477-90-7)Related Product Information

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