Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H16O9 |
Molecular Weight | 328.2714 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12OC(=O)C3=C(C(O)=C(OC)C(O)=C3)[C@]1([H])O[C@H](CO)[C@@H](O)[C@@H]2O
InChI
InChIKey=YWJXCIXBAKGUKZ-HJJNZUOJSA-N
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
Molecular Formula | C14H16O9 |
Molecular Weight | 328.2714 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27717728Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17408893
http://www.alternative-medicine.mobi/bergenin.html
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27717728
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/17408893
http://www.alternative-medicine.mobi/bergenin.html
Bergenin, isolated from Bergenia ligulata is a potent antioxidant and antilithiatic agent. Bergenin is an effective and broad-spectrum antifungal and antiviral Chinese medicine. Bergenin was reported to possess anti-microbial properties against filamentous fungi, yeast and HIV, but not against bacteria. Bergenin also exhibits anti-inflammatory activity through the inhibition of cyclo-oxygenase-2 or by means of affecting the Th1- or Th2-skewed cytokine production. Bergenin also exerts an anti-oxidant effect by scavenging free radicals, such as H, OH and CH3. In addition, bergenin was reported to possess hepatoprotective, neuroprotective and gastroprotective properties. R. aesculifolia Batal containing bergenin was used to treat protozoal infection and fever in rural China. Also was evaluated the antimalarial activity of bergenin in vitro and in vivo trials. Bergenin effectively inhibited Plasmodium falciparum growth in vitro (IC50, 14.1 µg̸ml, with ~100% inhibition at 50 µg/ml), without apparent cytotoxicity to erythrocytes or to mammalian HeLa and HepG2 cells. Bergenin exhibited less cytotoxic activity and the selectivity index (SI) was 887 and 1,355 for HeLa and HepG2 cells, respectively. The administration of bergenin to Plasmodium berghei infected mice for 6 days significantly inhibited the growth of the parasites. These findings provide evidence that bergenin may be a promising novel drug for antimalarial treatment. Antioxidant potential of bergenin was shown based on decreasing in lipid peroxides and increasing in superoxide dismutase (SOD) and catalase (CAT). Histopathological studies demonstrated the regenerative effect of bergenin on pancreatic β cells. Was shown, that bergenin isolated from C. digyna possesses significant antidiabetic, hypolipidemic and antioxidant activity in Type 2 diabetic rats.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Constituents of Ardisia japonica and their in vitro anti-HIV activity. | 1996 Jun |
|
The influence of Sacoglottis gabonensis stem bark extract and its isolate bergenin, Nigerian alcoholic beverage additives, on the metabolic and haematological side effects of 2,4-dinitrophenyl hydrazine-induced tissue damage. | 2002 Dec |
|
In vitro inhibitory effects of bergenin and norbergenin on bovine adrenal tyrosine hydroxylase. | 2003 Sep |
|
Antitumor effect of stilbenoids from Vateria indica against allografted sarcoma S-180 in animal model. | 2003 Sep-Oct |
|
[Study on constituents in rhizome of Astilbe chinensis]. | 2004 Jul |
|
Trypanocidal activity of bergenin, the major constituent of Flueggea virosa, on Trypanosoma brucei. | 2004 Jun |
|
A new anti-inflammatory glucoside from Ficus racemosa L. | 2004 May |
|
In vitro anti-HCV activities of Saxifraga melanocentra and its related polyphenolic compounds. | 2005 |
|
Anti-platelet aggregating and anti-oxidative activities of 11-O-(4'-O-methylgalloyl)-bergenin, a new compound isolated from Crassula cv. 'Himaturi'. | 2005 Aug |
|
PTP1B inhibitors from Ardisia japonica. | 2005 Feb |
|
The genus Ardisia: a novel source of health-promoting compounds and phytopharmaceuticals. | 2005 Jan 15 |
|
Chemical constituents and antioxidant activity of Mallotus roxburghianus leaves. | 2005 Jun |
|
Evaluation of selected South African medicinal plants for inhibitory properties against human immunodeficiency virus type 1 reverse transcriptase and integrase. | 2005 May 13 |
|
A carbon-carbon-coupled dimeric bergenin derivative biotransformed by Pleurotus ostreatus. | 2005 Sep 15 |
|
Three new flavonol glycosides from the aerial parts of Rodgersia podophylla. | 2006 Feb |
|
Determination and pharmacokinetic study of bergenin in rat plasma by RP-HPLC method. | 2006 Oct |
|
[Content determination of bergenin in Ardisia pusilla by HPLC]. | 2007 Apr |
|
Pharmacognostical and physicochemical characteristics of roots of lesser known medicinal plant caesalpinia digyna rottl. | 2007 Jan |
|
Effects of Astilbe thunbergii rhizomes on wound healing Part 1. Isolation of promotional effectors from Astilbe thunbergii rhizomes on burn wound healing. | 2007 Jan 3 |
|
Electrochemical study of bergenin on a poly(4-(2-pyridylazo)-resorcinol) modified glassy carbon electrode and its determination in tablets and urine. | 2007 Jul 31 |
|
Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis--a flow cytometric study. | 2007 Jun 13 |
|
Determination of bergenin in rat plasma by high-performance liquid chromatography. | 2007 May |
|
[Kinetics study on intestinal absorption of bergenin in rats]. | 2007 Nov |
|
Separation and evaluation of free radical-scavenging activity of phenol components of green, brown, and black leaves of Bergenia crassifolia by using HPTLC-DPPH* method. | 2007 Oct |
|
Antioxidant activity of Caesalpinia digyna root. | 2007 Sep 5 |
|
Syzygium cumini inhibits growth and induces apoptosis in cervical cancer cell lines: a primary study. | 2008 |
|
Antioxidant activity of (+)-bergenin: a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae). | 2008 Aug 7 |
|
Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb. | 2008 Feb 1 |
|
Improving activity of salt-lyophilized enzymes in organic media. | 2008 Mar |
|
Physicochemical properties of bergenin. | 2008 May |
|
Characterization of interaction between bergenin and human serum albumin in membrane mimetic environments. | 2008 May-Jul |
|
Electrochemical sensors based on carbon nanotubes. | 2009 |
|
Reactions of hydroxyl radical with bergenin, a natural poly phenol studied by pulse radiolysis. | 2009 Aug 15 |
|
New phenolic glycosides from Securinega virosa and their antioxidant activity. | 2009 Dec |
|
How to easily replace the independent atom model - the example of bergenin, a potential anti-HIV agent of traditional Asian medicine. | 2009 Dec |
|
Antiviral activity of some plants used in Nepalese traditional medicine. | 2009 Dec |
|
[Studies on the chemical constituents from Cissus assamica]. | 2009 Feb |
|
Peltophorum africanum, a traditional South African medicinal plant, contains an anti HIV-1 constituent, betulinic acid. | 2009 Feb |
|
Determination of bergenin in human plasma after oral administration by HPLC-MS/MS method and its pharmacokinetic study. | 2009 Feb |
|
Quantitation of bergenin in human plasma by liquid chromatography/tandem mass spectrometry. | 2009 Jan 1 |
|
Two new megastigmane sulphonoglucosides from Mallotus anisopodus. | 2009 Jul |
|
Differential free radical scavenging activity and radioprotection of caesalpinia digyna extracts and its active constituent. | 2009 Sep |
|
Ficus racemosa Stem Bark Extract: A Potent Antioxidant and a Probable Natural Radioprotector. | 2009 Sep |
|
Oral characteristics of bergenin and the effect of absorption enhancers in situ, in vitro and in vivo. | 2010 |
|
[Comparative studies on content of arbutin, bergenin and catechin in different part of Bergenia purpurascens and B. crassifolia]. | 2010 Aug |
|
Comparative in vitro bioactivities of tea extracts from six species of Ardisia and their effect on growth inhibition of HepG2 cells. | 2010 Aug 9 |
|
Radical scavenging and angiotensin converting enzyme inhibitory activities of standardized extracts of Ficus racemosa stem bark. | 2010 Dec |
|
Preparation, characterization and in vivo evaluation of bergenin-phospholipid complex. | 2010 Jan |
|
A new lignan dimer from Mallotus philippensis. | 2010 Mar |
|
[Studies on the chemical constituents from Cissus pteroclada]. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27717728
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/22178680
Bergenin was administrated at a dose of 10mg/kg body wt i.p. from 14th day of establishing the 28 days hyperoxaluria rat model.
Bergenin was administered at doses of 2.5, 5, and 10 mg/kg; p.o. to normal rats which were subjected to oral glucose tolerance test (OGTT). Bergenin at same dose level was given to diabetic rats and fasting blood glucose level was estimated on 0th, 7th and 14th day of treatment while plasma lipids, antioxidant enzymes and liver glycogen level in diabetic rats were estimated on 14th day of treatment followed by histopathological studies of pancreas.
Route of Administration:
Other
In Vitro Use Guide
Sources: http://dx.doi.org/10.1590/S0044-59672009000100019
Curator's Comment: All samples were able to inhibit the growth of the all tested Candida species and clearly the inhibitory effect of the samples is associated with the presence of bergenin. Bergenin had MIC of 14.9, 14.9 and 29.8 µM, respectively for C. albicans, C. tropicalis and C. guilliermondii
Antimicrobial activity of bergenin was evaluated by the agar-well diffusion method. The test microorganisms were seeded into respective medium. The wells were filled with 100 µL of test solution. The tested solutions of bergenin (Berg) was obtained by serial two-fold dilutions in DMSO (dimethyl sulfoxide) of an initial sample at 5.0 mg/mL.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:15:33 GMT 2023
by
admin
on
Fri Dec 15 16:15:33 GMT 2023
|
Record UNII |
L84RBE4IDC
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C275
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
757796
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
CHEMBL273019
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
m76
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | Merck Index | ||
|
C79897
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
C006741
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
477-90-7
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
66065
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
DTXSID4048141
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
L84RBE4IDC
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
661749
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY | |||
|
BERGENIN
Created by
admin on Fri Dec 15 16:15:33 GMT 2023 , Edited by admin on Fri Dec 15 16:15:33 GMT 2023
|
PRIMARY |