Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H18NO4.HO4S |
| Molecular Weight | 433.432 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS([O-])(=O)=O.COC1=C(OC)C2=C(C=C1)C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=C2
InChI
InChIKey=JISRTQBQFQMSLG-UHFFFAOYSA-M
InChI=1S/C20H18NO4.H2O4S/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;1-5(2,3)4/h3-4,7-10H,5-6,11H2,1-2H3;(H2,1,2,3,4)/q+1;/p-1
| 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 | HO4S |
| Molecular Weight | 97.071 |
| Charge | -1 |
| 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 |
|---|---|---|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| Effect of long-term administration of berberine on scopolamine-induced amnesia in rats. | 1997 Jul |
|
| 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 |
|
| [The interaction of berberine and human serum albumin]. | 2004 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 |
|
| Activation of the aryl hydrocarbon receptor by berberine in HepG2 and H4IIE cells: Biphasic effect on CYP1A1. | 2005 Sep 15 |
|
| Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. | 2005 Winter |
|
| Effect of berberine on interleukin 8 and monocyte chemotactic protein 1 expression in a human retinal pigment epithelial cell line. | 2006 |
|
| Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells. | 2006 Feb |
|
| Combination of simvastatin with berberine improves the lipid-lowering efficacy. | 2008 Aug |
|
| Berberine enhances inhibition of glioma tumor cell migration and invasiveness mediated by arsenic trioxide. | 2008 Feb 25 |
|
| Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula. | 2008 Jul 23 |
|
| Effect of berberine on expression of hepatocyte nuclear factor-4alpha in rats with fructose-induced insulin resistance. | 2008 Jun |
|
| Protection by and anti-oxidant mechanism of berberine against rat liver fibrosis induced by multiple hepatotoxic factors. | 2008 Mar |
|
| Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry. | 2008 Mar |
|
| 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 |
|
| Effect of berberine on the antioxidant status, ultrastructural modifications and protein bound carbohydrates in azoxymethane-induced colon cancer in rats. | 2009 Feb 12 |
|
| Berberine suppresses intestinal disaccharidases with beneficial metabolic effects in diabetic states, evidences from in vivo and in vitro study. | 2010 Apr |
|
| Anti-herpes simplex virus effects of berberine from Coptidis rhizoma, a major component of a Chinese herbal medicine, Ching-Wei-San. | 2010 Dec |
|
| Berberine inhibits SREBP-1-related clozapine and risperidone induced adipogenesis in 3T3-L1 cells. | 2010 Dec |
|
| [Controlling effect of berberine on in vitro synthesis and metabolism of steroid hormones in insulin resistant ovary]. | 2010 Feb |
|
| Cytotoxicity of berberine on human cervical carcinoma HeLa cells through mitochondria, death receptor and MAPK pathways, and in-silico drug-target prediction. | 2010 Sep |
|
| Effect of traditional Chinese medicinal herbs on Candida spp. from patients with HIV/AIDS. | 2011 Apr |
|
| Synthesis of 9-substituted derivatives of berberine as anti-HIV agents. | 2011 Apr |
|
| 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 |
|
| Hepatoprotective activity of berberine is mediated by inhibition of TNF-α, COX-2, and iNOS expression in CCl(4)-intoxicated mice. | 2011 Feb 4 |
|
| Antitumor effects of the combination of cholesterol reducing drugs. | 2011 Jul |
|
| 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 |
|
| Potential anti-aging agents suppress the level of constitutive mTOR- and DNA damage- signaling. | 2012 Dec |
|
| Modulations of cytochrome P450 expression in diabetic mice by berberine. | 2012 Mar 5 |
|
| Mechanism study of goldenseal-associated DNA damage. | 2013 Jul 31 |
|
| Berberine attenuates bleomycin induced pulmonary toxicity and fibrosis via suppressing NF-κB dependant TGF-β activation: a biphasic experimental study. | 2013 May 23 |
|
| Berberine, a natural antidiabetes drug, attenuates glucose neurotoxicity and promotes Nrf2-related neurite outgrowth. | 2013 Nov 1 |
|
| Berberine protects liver from ethanol-induced oxidative stress and steatosis in mice. | 2014 Dec |
|
| The potential effect of berberine in mercury-induced hepatorenal toxicity in albino rats. | 2014 Jul |
|
| Palmatine activates AhR and upregulates CYP1A activity in HepG2 cells but not in human hepatocytes. | 2014 Jun |
|
| Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line. | 2014 Nov 5 |
|
| The neuroprotective effect of berberine in mercury-induced neurotoxicity in rats. | 2015 Aug |
|
| Kinetics and molecular docking studies of cholinesterase inhibitors derived from water layer of Lycopodiella cernua (L.) Pic. Serm. (II). | 2015 Oct 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
by
admin
on
Edited
Fri Dec 15 17:23:00 GMT 2023
by
admin
on
Fri Dec 15 17:23:00 GMT 2023
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| Record UNII |
69A4M9800W
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| Record Status |
Validated (UNII)
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| Record Version |
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