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berberine
9,10-dimethoxy-5,6-dihydro-7?5-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline

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CAS Number: 2086-83-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:218-229-1
FDA UNII: 0I8Y3P32UF
Nikkaji Web:J7.320B
Beilstein Number:3570374
XlogP3-AA:3.60 (est)
Molecular Weight:336.36726000
Formula:C20 H18 N O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:yellow crystals (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 145.00 °C. @ 760.00 mm Hg
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w): -0.990 (est)
Soluble in:
 water, 9.623 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Berberine 98%
BOC Sciences
For experimental / research use only.
Berberine >98%
Coompo
For experimental / research use only.
Berberine from Plants ≥96%
Odor: characteristic
Use: Berberine has shown some activity against fungal infections, Candida albicans, yeast, parasites, and bacterial/viral infections. Berberine seems to exert synergistic effects with fluconazole even in drug-resistant C. albicans infections. Some research has been undertaken into possible use against MRSA infection. Berberine is considered antibiotic. Berberine is a component of some eye drop formulations. There is some evidence it is useful in the treatment of trachoma, and it has been a standard treatment for leishmaniasis. Berberine prevents and suppresses proinflammatory cytokines, E-selectin, and genes, and increases adiponectin expression which partly explains its versatile health effects.
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 329 mg/kg
Yakugaku Zasshi. Journal of Pharmacy. Vol. 82, Pg. 726, 1962.

Dermal Toxicity:
subcutaneous-mouse LD50 18 mg/kg
Russian Pharmacology and Toxicology Vol. 31, Pg. 129, 1968.

subcutaneous-rabbit LDLo 100 mg/kg
"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for berberine usage levels up to:
 not for fragrance use.
 
Recommendation for berberine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :2353
National Institute of Allergy and Infectious Diseases:Data
Chemidplus:0002086831
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):2353
Pubchem (sid):134981728
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C00757
HMDB (The Human Metabolome Database):HMDB03409
FooDB:FDB023165
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-
 benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy- (9CI)
1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium, 5,6-dihydro-9,10-dimethoxy-
 berberal
 berbericine
 berberin
 berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-
5,6-dihydro-9,10-dimethoxy-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
5,6-dihydro-9,10-dimethoxybenzo[g]1,3-benzodioxolo[5,6-a]quinolizinium
9,10-dimethoxy-2,3-(methylene dioxy)-7,8,13,13a-tetrahydroberbinium
9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium
9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium
9,10-dimethoxy-5,6-dihydro-7?5-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium
9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
16,17-dimethoxy-5,7-dioxa-13?5-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium
16,17-dimethoxy-5,7-dioxa-13?5-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium
 majarine
7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-berbinium
7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium
7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium
7,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-(methylene dioxy) berbinium
7,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium
 umbellatin
 umbellatine (6CI)
 

Articles:

PubMed:Neuraminidase inhibitory activities of quaternary isoquinoline alkaloids from Corydalis turtschaninovii rhizome.
PubMed:The Rhizome Mixture of Anemarrhena asphodeloides and Coptidis chinensis Ameliorates Acute and Chronic Colitis in Mice by Inhibiting the Binding of Lipopolysaccharide to TLR4 and IRAK1 Phosphorylation.
PubMed:Bitter stimuli modulate the feeding decision of a blood-sucking insect via two sensory inputs.
PubMed:Berberine and limonin suppress IgE production by human B cells and peripheral blood mononuclear cells from food-allergic patients.
PubMed:Coptis chinensis alkaloids exert anti-adipogenic activity on 3T3-L1 adipocytes by downregulating C/EBP-α and PPAR-γ.
PubMed:Synergistic Inhibitory Effect of Berberine and d-Limonene on Human Gastric Carcinoma Cell Line MGC803.
PubMed:Beyond androgen deprivation: ancillary integrative strategies for targeting the androgen receptor addiction of prostate cancer.
PubMed:Inhibitory Activities of Palmatine from Coptis chinensis Against Helicobactor pylori and Gastric Damage.
PubMed:The potential effect of berberine in mercury-induced hepatorenal toxicity in albino rats.
PubMed:Simultaneous determination of matrine and berberine in fruits, vegetables, and soil using ultra-performance liquid chromatography/tandem mass spectrometry.
PubMed:Metformin and berberine prevent olanzapine-induced weight gain in rats.
PubMed:O-hexadecyl-dextran entrapped berberine nanoparticles abrogate high glucose stress induced apoptosis in primary rat hepatocytes.
PubMed:Berberine prevents nigrostriatal dopaminergic neuronal loss and suppresses hippocampal apoptosis in mice with Parkinson's disease.
PubMed:New aspects of Saccharomyces cerevisiae as a novel carrier for berberine.
PubMed:Application of quantitative 1H NMR for the calibration of protoberberine alkaloid reference standards.
PubMed:Ameliorative effect of Pracparatum mungo extract on high cholesterol diets in hamsters.
PubMed:Verapamil augments the neuroprotectant action of berberine in rat model of transient global cerebral ischemia.
PubMed:Selective extraction of berberine and palmatine from Huangbai powder.
PubMed:Berberine exerts nephroprotective effect against cisplatin-induced kidney damage through inhibition of oxidative/nitrosative stress, inflammation, autophagy and apoptosis.
PubMed:Optimization of ultrasonic-assisted extraction of bioactive alkaloid compounds from rhizoma coptidis (Coptis chinensis Franch.) using response surface methodology.
PubMed:Resolution of liver fibrosis by isoquinoline alkaloid berberine in CCl₄-intoxicated mice is mediated by suppression of oxidative stress and upregulation of MMP-2 expression.
PubMed:Berberine ameliorates cold and mechanical allodynia in a rat model of diabetic neuropathy.
PubMed:Identification of novel dietary phytochemicals inhibiting the efflux transporter breast cancer resistance protein (BCRP/ABCG2).
PubMed:Antihyperglycemic effect of the traditional Chinese scutellaria-coptis herb couple and its main components in streptozotocin-induced diabetic rats.
PubMed:Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives: a lipophilic substitute role.
PubMed:Anti-hyperglycemic effects and mechanism of traditional Chinese medicine Huanglian Wan in streptozocin-induced diabetic rats.
PubMed:Use of a lipid-lowering food supplement in patients on hormone therapy following breast cancer.
PubMed:A novel fluorescent biosensor for detection of target DNA fragment from the transgene cauliflower mosaic virus 35S promoter.
PubMed:Berberine, an isoquinoline alkaloid, inhibits the metastatic potential of breast cancer cells via Akt pathway modulation.
PubMed:Sodium caprate augments the hypoglycemic effect of berberine via AMPK in inhibiting hepatic gluconeogenesis.
PubMed:Anti-diabetic effect of a traditional Chinese medicine formula.
PubMed:Structural changes of gut microbiota during berberine-mediated prevention of obesity and insulin resistance in high-fat diet-fed rats.
PubMed:Coptis chinensis inflorescence extract protection against ultraviolet-B-induced phototoxicity, and HPLC-MS analysis of its chemical composition.
PubMed:Berberine promotes axonal regeneration in injured nerves of the peripheral nervous system.
PubMed:Activity of isoflavones and berberine on vasomotor symptoms and lipid profile in menopausal women.
PubMed:Determination of benzimidazole residues in animal tissue samples by combination of magnetic solid-phase extraction with capillary zone electrophoresis.
PubMed:Protective effect of berberine on serum glucose levels in non-obese diabetic mice.
PubMed:Anti-diabetic effects of TongGuanWan, a Chinese traditional herbal formula, in C57BL/KsJ-db/db mice.
PubMed: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.
PubMed:Growth suppression of HER2-overexpressing breast cancer cells by berberine via modulation of the HER2/PI3K/Akt signaling pathway.
PubMed:Berberine, an isoquinoline alkaloid in herbal plants, protects pancreatic islets and serum lipids in nonobese diabetic mice.
PubMed:[Antidiabetic activity of berberin and extract, obtained from the bark of Phellodendron lavalei, introduced in subtropic regions of Georgia, in streptozotocin induced diabetic rats].
PubMed:Oral administration of levo-tetrahydropalmatine attenuates reinstatement of extinguished cocaine seeking by cocaine, stress or drug-associated cues in rats.
PubMed:Consumption of bitter alkaloids in Drosophila melanogaster in multiple-choice test conditions.
PubMed:Pigment identification, antioxidant activity, and nutrient composition of Tinospora cordifolia (willd.) Miers ex Hook. f & Thoms fruit.
PubMed:Five bitter compounds display different anti-inflammatory effects through modulating cytokine secretion using mouse primary splenocytes in vitro.
PubMed:Food allergy herbal formula 2 protection against peanut anaphylactic reaction is via inhibition of mast cells and basophils.
PubMed:Antioxidant and antiproliferative properties of water extract from Mahonia bealei (Fort.) Carr. leaves.
PubMed:Preventive effect of Coptis chinensis and berberine on intestinal injury in rats challenged with lipopolysaccharides.
PubMed:Tetrahydropalmatine inhibits pro-inflammatory mediators in lipopolysaccharide-stimulated THP-1 cells.
PubMed:Levo-tetrahydropalmatine attenuates cocaine self-administration under a progressive-ratio schedule and cocaine discrimination in rats.
PubMed:Regulation of survival, proliferation, invasion, angiogenesis, and metastasis of tumor cells through modulation of inflammatory pathways by nutraceuticals.
PubMed:Limited taste discrimination in Drosophila.
PubMed:Effects of berberine against radiation-induced intestinal injury in mice.
PubMed:Berberine reduces methylation of the MTTP promoter and alleviates fatty liver induced by a high-fat diet in rats.
PubMed:Seasonal variation of biomass and bioactive alkaloid content of goldenseal, Hydrastis canadensis.
PubMed:Hypoglycemic and insulin-sensitizing effects of berberine in high-fat diet- and streptozotocin-induced diabetic rats.
PubMed:Acute toxicity of berberine and its correlation with the blood concentration in mice.
PubMed:Evaluation of genotoxicity of Yanhuanglian dehydrocavidine (YHL-DC) in vitro and in vivo.
PubMed:Berberine inhibits adipogenesis in high-fat diet-induced obesity mice.
PubMed:Palmatine attenuates D-galactosamine/lipopolysaccharide-induced fulminant hepatic failure in mice.
PubMed:AMP-activated protein kinase: a potential target for the diseases prevention by natural occurring polyphenols.
PubMed:Berberine improves free-fatty-acid-induced insulin resistance in L6 myotubes through inhibiting peroxisome proliferator-activated receptor gamma and fatty acid transferase expressions.
PubMed:Determination of protoberberine alkaloids in medicinal plants based on acidic potassium permanganate chemiluminescence system.
PubMed:Anti-Alzheimer and antioxidant activities of Coptidis Rhizoma alkaloids.
PubMed:Feminization and alteration of Drosophila taste neurons induce reciprocal effects on male avoidance behavior.
PubMed:Palmatine from Coptidis rhizoma reduces ischemia-reperfusion-mediated acute myocardial injury in the rat.
PubMed:[Effect of additives on absorption of Coptis chinensis total alkaloids and pharmacokinetics in mice].
PubMed:Investigation of the anti-fungal activity of coptisine on Candida albicans growth by microcalorimetry combined with principal component analysis.
PubMed:Separation and detection of isoquinoline alkaloids using MEEKC coupled with field-amplified sample injection induced by ACN.
PubMed:Inhibitory activities of the alkaloids from Coptidis Rhizoma against aldose reductase.
PubMed:Combination of simvastatin with berberine improves the lipid-lowering efficacy.
PubMed:Protective effects of berberine against low-density lipoprotein (LDL) oxidation and oxidized LDL-induced cytotoxicity on endothelial cells.
PubMed:Berberine activates GLUT1-mediated glucose uptake in 3T3-L1 adipocytes.
PubMed:Effects of herbal products and their constituents on human cytochrome P450(2E1) activity.
PubMed:Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats.
PubMed:Eulipidemic effects of berberine administered alone or in combination with other natural cholesterol-lowering agents. A single-blind clinical investigation.
PubMed:Berberine reduces the expression of adipogenic enzymes and inflammatory molecules of 3T3-L1 adipocyte.
PubMed:Nanostructured electrochemical DNA biosensors for detection of the effect of berberine on DNA from cancer cells.
PubMed:The effect of L-stepholidine, a novel extract of Chinese herb, on the acquisition, expression, maintenance, and re-acquisition of morphine conditioned place preference in rats.
PubMed:Berberine induces apoptosis through a mitochondrial/caspase pathway in human promonocytic U937 cells.
PubMed:Photochemical and phototoxic activity of berberine on murine fibroblast NIH-3T3 and Ehrlich ascites carcinoma cells.
PubMed:Berberine, a natural plant product, activates AMP-activated protein kinase with beneficial metabolic effects in diabetic and insulin-resistant states.
PubMed:Effect of berberine on proliferation, biosynthesis of macromolecules, cell cycle and induction of intercalation with DNA, dsDNA damage and apoptosis in Ehrlich ascites carcinoma cells.
PubMed:Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus.
PubMed:[Chemical constituents from Corydalis humosa].
PubMed:Berberine-antiproliferative activity in vitro and induction of apoptosis/necrosis of the U937 and B16 cells.
PubMed:Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts.
PubMed:A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis.
PubMed:Oxygen activation by photoexcited protoberberinium alkaloids from Mahonia aquifolium.
PubMed:Effect of Alstonia scholaris in enhancing the anticancer activity of berberine in the Ehrlich ascites carcinoma-bearing mice.
PubMed:Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.
PubMed:Effect of berberine on proliferation, cell cycle and apoptosis in HeLa and L1210 cells.
PubMed:Isoflavones as potentiators of antibacterial activity.
PubMed:Variations in alkaloid content of herbal products containing goldenseal.
PubMed:Photostabilization of an entomopathogenic fungus using composite clay matrices.
PubMed:Giardiasis: pathophysiology and management.
PubMed:Rat lens aldose reductase inhibitory activities of Coptis japonica root-derived isoquinoline alkaloids.
PubMed:Anticachectic effects of the natural herb Coptidis rhizoma and berberine on mice bearing colon 26/clone 20 adenocarcinoma.
PubMed:Anticachectic effects of Coptidis rhizoma, an anti-inflammatory herb, on esophageal cancer cells that produce interleukin 6.
PubMed:Cordycepin: selective growth inhibitor derived from liquid culture of Cordyceps militaris against Clostridium spp.
PubMed:Antiphotooxidative activity of protoberberines derived from Coptis japonica makino in the chlorophyll-sensitized photooxidation of oil.
PubMed:Growth-inhibiting effects of Coptis japonica root-derived isoquinoline alkaloids on human intestinal bacteria.
PubMed:Effects of berberine on arylamine N-acetyltransferase activity in human bladder tumour cells.
PubMed:The clinical spectrum of Jin Bu Huan toxicity.
PubMed:Theoretical grounds and experimental confirmation of the antiviral effect of the preparation Ukrain.
PubMed:Control of diarrheal diseases.
 
Notes:
an alkaloid from hydrastis canadensis l., berberidaceae. it is also found in many other plants. it is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [HMDB]
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