Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C76H51O46.C20H18NO4 |
| Molecular Weight | 2036.5518 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(OCO5)C=C4CC3.OC6=CC(=CC(O)=C6O)C(=O)OC7=CC(=CC(O)=C7O)C(=O)OC[C@H]8O[C@@H](OC(=O)C9=CC(O)=C(O)C(OC(=O)C%10=CC(O)=C(O)C(O)=C%10)=C9)[C@H](OC(=O)C%11=CC(O)=C(O)C(OC(=O)C%12=CC(O)=C(O)C(O)=C%12)=C%11)[C@@H](OC(=O)C%13=CC(O)=C(O)C(OC(=O)C%14=CC(O)=C(O)C(O)=C%14)=C%13)[C@@H]8OC(=O)C%15=CC(O)=C(O)C(OC(=O)C%16=CC(O)=C([O-])C(O)=C%16)=C%15
InChI
InChIKey=ASLOQCPXFXCORP-HBNMXAOGSA-M
InChI=1S/C76H52O46.C20H18NO4/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;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/h1-20,52,63-65,76-101H,21H2;3-4,7-10H,5-6,11H2,1-2H3/q;+1/p-1/t52-,63-,64+,65-,76+;/m1./s1
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 |
|
| HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. | 1992 May 29 |
|
| Effect of long-term administration of berberine on scopolamine-induced amnesia in rats. | 1997 Jul |
|
| [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 |
|
| Analysis of coptisine, berberine and palmatine in adulterated Chinese medicine by capillary electrophoresis-electrospray ion trap mass spectrometry. | 2000 Jan 14 |
|
| Protective effect of berberine on cyclophosphamide-induced haemorrhagic cystitis in rats. | 2001 May |
|
| Antimicrobial activity of berberine--a constituent of Mahonia aquifolium. | 2002 |
|
| 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 |
|
| Inhibitory effect of berberine on tert-butyl hydroperoxide-induced oxidative damage in rat liver. | 2002 Nov |
|
| Fluorescence assay based on preconcentration by a self-ordered ring using berberine as a model analyte. | 2002 Nov 1 |
|
| [Inhibitory action of berberine on glucose absorption]. | 2003 Dec |
|
| [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 |
|
| Berberine enhances inhibition of glioma tumor cell migration and invasiveness mediated by arsenic trioxide. | 2008 Feb 25 |
|
| Protection by and anti-oxidant mechanism of berberine against rat liver fibrosis induced by multiple hepatotoxic factors. | 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 |
|
| Synthesis of 9-substituted derivatives of berberine as anti-HIV agents. | 2011 Apr |
|
| Hepatoprotective activity of berberine is mediated by inhibition of TNF-α, COX-2, and iNOS expression in CCl(4)-intoxicated mice. | 2011 Feb 4 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Palmatine activates AhR and upregulates CYP1A activity in HepG2 cells but not in human hepatocytes. | 2014 Jun |
|
| 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.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
CHEMBL2109102
Created by
admin on Sat Dec 16 05:50:51 GMT 2023 , Edited by admin on Sat Dec 16 05:50:51 GMT 2023
|
PRIMARY | |||
|
165411863
Created by
admin on Sat Dec 16 05:50:51 GMT 2023 , Edited by admin on Sat Dec 16 05:50:51 GMT 2023
|
PRIMARY | |||
|
3JT0W0GL7J
Created by
admin on Sat Dec 16 05:50:51 GMT 2023 , Edited by admin on Sat Dec 16 05:50:51 GMT 2023
|
PRIMARY | |||
|
SUB13047MIG
Created by
admin on Sat Dec 16 05:50:51 GMT 2023 , Edited by admin on Sat Dec 16 05:50:51 GMT 2023
|
PRIMARY | |||
|
100000077168
Created by
admin on Sat Dec 16 05:50:51 GMT 2023 , Edited by admin on Sat Dec 16 05:50:51 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
