Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | 2C20H18NO4.O4S.3H2O |
| Molecular Weight | 822.831 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[O-]S([O-])(=O)=O.COC1=C(OC)C2=C(C=C1)C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=C2.COC6=C(OC)C7=C(C=C6)C=C8C9=CC%10=C(OCO%10)C=C9CC[N+]8=C7
InChI
InChIKey=FYBWCLKVKGHJKS-UHFFFAOYSA-L
InChI=1S/2C20H18NO4.H2O4S.3H2O/c2*1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;1-5(2,3)4;;;/h2*3-4,7-10H,5-6,11H2,1-2H3;(H2,1,2,3,4);3*1H2/q2*+1;;;;/p-2
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C20H18NO4 |
| Molecular Weight | 336.3612 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | O4S |
| Molecular Weight | 96.063 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://examine.com/supplements/berberine/ | https://www.ncbi.nlm.nih.gov/pubmed/19686830 | https://www.ncbi.nlm.nih.gov/pubmed/25610485
Curator's Comment: description was created based on several sources, including:
https://examine.com/supplements/berberine/ | https://www.ncbi.nlm.nih.gov/pubmed/19686830 | https://www.ncbi.nlm.nih.gov/pubmed/25610485
Berberine, an alkaloid isolated from Rhizoma Coptidis, is known to have a wide array of therapeutic effects including antimicrobial, antineoplastic, and hepatoprotective effects. It is found in several plants including European barberry, goldenseal, goldthread, Oregon grape, phellodendron, and tree tumeric. Berberine seems to slightly reduce blood sugar levels in people with diabetes. Berberine might lower blood pressure. Berberine is possibly safe for most adults for short-term use when taken by mouth or applied to the skin.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. | 1992 May 29 |
|
| [Determination of berberine in human serum by reversed-phase high performance liquid chromatography]. | 1997 Sep |
|
| Screening of compounds for antimicrosporidial activity in vitro. | 1998 |
|
| The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan. | 1998 Dec |
|
| Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2. | 1998 Oct |
|
| Differential inhibitory effects of protoberberines on sterol and chitin biosyntheses in Candida albicans. | 1999 May |
|
| Protective effect of berberine on cyclophosphamide-induced haemorrhagic cystitis in rats. | 2001 May |
|
| Potential antimutagenic activity of berberine, a constituent of Mahonia aquifolium. | 2002 Feb 19 |
|
| Identification of three sulfate-conjugated metabolites of berberine chloride in healthy volunteers' urine after oral administration. | 2002 Jan |
|
| Search of chemical scaffolds for novel antituberculosis agents. | 2005 Apr |
|
| Effect of artemisinin/artesunate as inhibitors of hepatitis B virus production in an "in vitro" replicative system. | 2005 Nov |
|
| Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. | 2005 Winter |
|
| Berberine enhances inhibition of glioma tumor cell migration and invasiveness mediated by arsenic trioxide. | 2008 Feb 25 |
|
| Anti-diabetic effects of cinnamaldehyde and berberine and their impacts on retinol-binding protein 4 expression in rats with type 2 diabetes mellitus. | 2008 Nov 5 |
|
| Berberine suppresses intestinal disaccharidases with beneficial metabolic effects in diabetic states, evidences from in vivo and in vitro study. | 2010 Apr |
|
| [Controlling effect of berberine on in vitro synthesis and metabolism of steroid hormones in insulin resistant ovary]. | 2010 Feb |
|
| Berberine attenuates lipopolysaccharide-induced impairments of intestinal glutamine transport and glutaminase activity in rat. | 2011 Apr |
|
| Characterization of protoberberine analogs employed as novel human P2X7 receptor antagonists. | 2011 Apr 15 |
|
| Berberine down-regulates the Th1/Th2 cytokine gene expression ratio in mouse primary splenocytes in the absence or presence of lipopolysaccharide in a preventive manner. | 2011 Dec |
|
| Protective effect of berberine on antioxidant enzymes and positive transcription elongation factor b expression in diabetic rat liver. | 2011 Mar |
|
| Berberine protects against lipopolysaccharide-induced intestinal injury in mice via alpha 2 adrenoceptor-independent mechanisms. | 2011 Nov |
|
| The formation and stabilization of a novel G-quadruplex in the 5'-flanking region of the relaxin gene. | 2012 |
|
| Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii. | 2012 Apr 15 |
|
| Alteration of hepatic glutathione peroxidase and superoxide dismutase expression in streptozotocin-induced diabetic mice by berberine. | 2012 Aug |
|
| Modulations of cytochrome P450 expression in diabetic mice by berberine. | 2012 Mar 5 |
|
| Mechanism study of goldenseal-associated DNA damage. | 2013 Jul 31 |
|
| Berberine, a natural antidiabetes drug, attenuates glucose neurotoxicity and promotes Nrf2-related neurite outgrowth. | 2013 Nov 1 |
|
| The potential effect of berberine in mercury-induced hepatorenal toxicity in albino rats. | 2014 Jul |
|
| Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line. | 2014 Nov 5 |
|
| Berberine promotes bone marrow-derived mesenchymal stem cells osteogenic differentiation via canonical Wnt/β-catenin signaling pathway. | 2016 Jan 5 |
Sample Use Guides
500 mg of berberine 2-3 times daily for up to 3 months
Route of Administration:
Oral
Berberine acted cytotoxically on both tumour cell lines. The melanoma B16 cells were much more sensitive to berberine treatment than the U937 cells. The value of IC(100) was below 100 ug/ml for the U937 cells and below 1 ug/ml for the B16 cells. As for both cell lines under the long-term influence the values of IC(50) were found to be less than 4 ug/ml.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
T3MQ0UO932
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| Record Status |
Validated (UNII)
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| Record Version |
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ACTIVE MOIETY |