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
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 |
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Effects of bergenin, the major constituent of Mallotus japonicus against D-galactosamine-induced hepatotoxicity in rats. | 2001 |
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Protective effects of acetylbergenin against carbon tetrachloride-induced hepatotoxicity in rats. | 2001 Apr |
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Hopeafuran and a C-glucosyl resveratrol isolated from stem wood of Hopea utilis. | 2001 Jun |
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Ardisiphenols and other antioxidant principles from the fruits of Ardisia colorata. | 2002 Nov |
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Antitumor effect of stilbenoids from Vateria indica against allografted sarcoma S-180 in animal model. | 2003 Sep-Oct |
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[Study on constituents in rhizome of Astilbe chinensis]. | 2004 Jul |
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PTP1B inhibitors from Ardisia japonica. | 2005 Feb |
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Evaluation of selected South African medicinal plants for inhibitory properties against human immunodeficiency virus type 1 reverse transcriptase and integrase. | 2005 May 13 |
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Pharmacognostical and physicochemical characteristics of roots of lesser known medicinal plant caesalpinia digyna rottl. | 2007 Jan |
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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 |
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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 |
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Physicochemical properties of bergenin. | 2008 May |
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Characterization of interaction between bergenin and human serum albumin in membrane mimetic environments. | 2008 May-Jul |
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Peltophorum africanum, a traditional South African medicinal plant, contains an anti HIV-1 constituent, betulinic acid. | 2009 Feb |
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Ficus racemosa Stem Bark Extract: A Potent Antioxidant and a Probable Natural Radioprotector. | 2009 Sep |
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[Comparative studies on content of arbutin, bergenin and catechin in different part of Bergenia purpurascens and B. crassifolia]. | 2010 Aug |
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A new lignan dimer from Mallotus philippensis. | 2010 Mar |
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.
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NCI_THESAURUS |
C275
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757796
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CHEMBL273019
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m76
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C79897
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C006741
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477-90-7
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L84RBE4IDC
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661749
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BERGENIN
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SUBSTANCE RECORD