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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

[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

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
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
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 Fri Dec 15 16:15:33 GMT 2023
Edited
by admin
on Fri Dec 15 16:15:33 GMT 2023
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
YANBAICAISU
Common Name English
BERGENIN [INCI]
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
BERGENINUM
CHP  
Common Name English
NSC-661749
Code English
BERGENIN [MI]
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
NSC
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
ChEMBL
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
MERCK INDEX
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
NCI_THESAURUS
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
MESH
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
CAS
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
PUBCHEM
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
EPA CompTox
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
FDA UNII
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
NSC
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
WIKIPEDIA
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