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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
Structure of BERGENIN

SMILES

COC1=C(O)C=C2C(=O)O[C@@H]3[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]3C2=C1O

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

HIDE SMILES / InChI

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

Description
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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Radical scavenging and angiotensin converting enzyme inhibitory activities of standardized extracts of Ficus racemosa stem bark.
2010-12
[Studies on the chemical constituents from Cissus pteroclada].
2010-10
Comparative in vitro bioactivities of tea extracts from six species of Ardisia and their effect on growth inhibition of HepG2 cells.
2010-08-09
[Comparative studies on content of arbutin, bergenin and catechin in different part of Bergenia purpurascens and B. crassifolia].
2010-08
A new lignan dimer from Mallotus philippensis.
2010-03
Preparation, characterization and in vivo evaluation of bergenin-phospholipid complex.
2010-01
Oral characteristics of bergenin and the effect of absorption enhancers in situ, in vitro and in vivo.
2010
New phenolic glycosides from Securinega virosa and their antioxidant activity.
2009-12
How to easily replace the independent atom model - the example of bergenin, a potential anti-HIV agent of traditional Asian medicine.
2009-12
Antiviral activity of some plants used in Nepalese traditional medicine.
2009-12
Differential free radical scavenging activity and radioprotection of caesalpinia digyna extracts and its active constituent.
2009-09
Ficus racemosa Stem Bark Extract: A Potent Antioxidant and a Probable Natural Radioprotector.
2009-09
Reactions of hydroxyl radical with bergenin, a natural poly phenol studied by pulse radiolysis.
2009-08-15
Two new megastigmane sulphonoglucosides from Mallotus anisopodus.
2009-07
[Studies on the chemical constituents from Cissus assamica].
2009-02
Peltophorum africanum, a traditional South African medicinal plant, contains an anti HIV-1 constituent, betulinic acid.
2009-02
Determination of bergenin in human plasma after oral administration by HPLC-MS/MS method and its pharmacokinetic study.
2009-02
Quantitation of bergenin in human plasma by liquid chromatography/tandem mass spectrometry.
2009-01-01
Electrochemical sensors based on carbon nanotubes.
2009
Antioxidant activity of (+)-bergenin: a phytoconstituent isolated from the bark of Sacoglottis uchi Huber (Humireaceae).
2008-08-07
Physicochemical properties of bergenin.
2008-05
Improving activity of salt-lyophilized enzymes in organic media.
2008-03
Studies on the chemical constituents and anticancer activity of Saxifraga stolonifera (L) Meeb.
2008-02-01
Syzygium cumini inhibits growth and induces apoptosis in cervical cancer cell lines: a primary study.
2008
[Kinetics study on intestinal absorption of bergenin in rats].
2007-11
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.
2007-10
Antioxidant activity of Caesalpinia digyna root.
2007-09-05
Electrochemical study of bergenin on a poly(4-(2-pyridylazo)-resorcinol) modified glassy carbon electrode and its determination in tablets and urine.
2007-07-31
Characterization of interaction between bergenin and human serum albumin in membrane mimetic environments.
2007-07-15
Immunomodulatory effect of bergenin and norbergenin against adjuvant-induced arthritis--a flow cytometric study.
2007-06-13
Determination of bergenin in rat plasma by high-performance liquid chromatography.
2007-05
[Content determination of bergenin in Ardisia pusilla by HPLC].
2007-04
Effects of Astilbe thunbergii rhizomes on wound healing Part 1. Isolation of promotional effectors from Astilbe thunbergii rhizomes on burn wound healing.
2007-01-03
Pharmacognostical and physicochemical characteristics of roots of lesser known medicinal plant caesalpinia digyna rottl.
2007-01
Determination and pharmacokinetic study of bergenin in rat plasma by RP-HPLC method.
2006-10
Three new flavonol glycosides from the aerial parts of Rodgersia podophylla.
2006-02
A carbon-carbon-coupled dimeric bergenin derivative biotransformed by Pleurotus ostreatus.
2005-09-15
Anti-platelet aggregating and anti-oxidative activities of 11-O-(4'-O-methylgalloyl)-bergenin, a new compound isolated from Crassula cv. 'Himaturi'.
2005-08
Chemical constituents and antioxidant activity of Mallotus roxburghianus leaves.
2005-06
Evaluation of selected South African medicinal plants for inhibitory properties against human immunodeficiency virus type 1 reverse transcriptase and integrase.
2005-05-13
PTP1B inhibitors from Ardisia japonica.
2005-02
The genus Ardisia: a novel source of health-promoting compounds and phytopharmaceuticals.
2005-01-15
In vitro anti-HCV activities of Saxifraga melanocentra and its related polyphenolic compounds.
2005
[Study on constituents in rhizome of Astilbe chinensis].
2004-07
Trypanocidal activity of bergenin, the major constituent of Flueggea virosa, on Trypanosoma brucei.
2004-06
A new anti-inflammatory glucoside from Ficus racemosa L.
2004-05
Antitumor effect of stilbenoids from Vateria indica against allografted sarcoma S-180 in animal model.
2003-12-31
In vitro inhibitory effects of bergenin and norbergenin on bovine adrenal tyrosine hydroxylase.
2003-09
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.
2002-12
Constituents of Ardisia japonica and their in vitro anti-HIV activity.
1996-06
Patents

Sample Use Guides

In Vivo Use Guide
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
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 Mon Mar 31 18:23:14 GMT 2025
Edited
by admin
on Mon Mar 31 18:23:14 GMT 2025
Record UNII
L84RBE4IDC
Record Status Validated (UNII)
Record Version
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Name Type Language
BERGENIN
INCI   JAN   MI   WHO-DD  
INCI  
Official Name English
BERGENINUM
CHP  
Preferred Name English
YANBAICAISU
Common Name English
PYRANO(3,2-C)(2)BENZOPYRAN-6(2H)-ONE, 3,4,4A,10B-TETRAHYDRO-3,4,8,10-TETRAHYDROXY-2-(HYDROXYMETHYL)-9-METHOXY-(2R,3S,4S,4AR,10BS)-
Common Name English
3,4,4A,10B-TETRAHYDRO-3,4,8,10-TETRAHYDROXY-2-(HYDROXYMETHYL)-9-METHOXYPYRANO(3,2-C)(2)BENZOPYRAN-6(H)-ONE
Common Name English
Bergenin [WHO-DD]
Common Name English
BERGENINUM [CHP]
Common Name English
BERGENIN [JAN]
Common Name English
NSC-757796
Code English
NSC-661749
Code English
BERGENIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C275
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
Code System Code Type Description
NSC
757796
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
ChEMBL
CHEMBL273019
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
MERCK INDEX
m76
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C79897
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
MESH
C006741
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
SMS_ID
300000048273
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
CAS
477-90-7
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
PUBCHEM
66065
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID4048141
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
FDA UNII
L84RBE4IDC
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
NSC
661749
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY
WIKIPEDIA
BERGENIN
Created by admin on Mon Mar 31 18:23:14 GMT 2025 , Edited by admin on Mon Mar 31 18:23:14 GMT 2025
PRIMARY