Berberine

Berberine is a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs (goldenseal, barberry and Oregon grape)It has a role as an antilipemic drug, a hypoglycemic agent, an antioxidant, a potassium channel blocker, an antineoplastic agent. It inhibits enzymes including: aldehyde reductase; [15-hydroxyprostaglandin dehydrogenase (NAD(+))]; indoleamine 2,3-dioxygenase; reticuline oxidase; [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase]; phospholipase A2; prolyl oligopeptidase; dipeptidyl-peptidase IV; protein-tyrosine-phosphatase; acetylcholinesterase; butyrylcholinesterase; IkappaB kinase. || . IC50 human-ACHE 0.1 muM eleel 0.374 human-BCHE 1.09 muM.

General

Type : Natural, Alkaloid, Not A\/B H target, Isoquinoline, Benzodioxo

Chemical_Nomenclature : 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene

Canonical SMILES : COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC

InChI : InChI=1S\/C20H18NO4\/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\/h3-4,7-10H,5-6,11H2,1-2H3\/q+1

InChIKey : YBHILYKTIRIUTE-UHFFFAOYSA-N

Other name(s) : Umbellatine  ||  Berberin  ||  Berbericine  ||  CHEBI:16118  ||  Berberal  ||  CHEMBL12089  ||  ZINC3779067  ||  CHEMBL295124  ||  DB-050153  ||  Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-  ||  9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium


MW : 336.4

Formula : C20H18NO4+

CAS_number : 2086-83-1

PubChem : 2353

UniChem : YBHILYKTIRIUTE-UHFFFAOYSA-N

Target

Families : Berberine ligand of proteins in family
ACHE BCHE

References (45)

Title : Binding interaction of protoberberine alkaloids against acetylcholinesterase (AChE) using molecular dynamics simulations and QM\/MM calculations - Honorio_2021_Chem.Biol.Interact__109523
Author(s) : Honorio P , Sainimnuan S , Hannongbua S , Saparpakorn P
Ref : Chemico-Biological Interactions , :109523 , 2021
Abstract :
PubMedSearch : Honorio_2021_Chem.Biol.Interact__109523
PubMedID: 34033838

Title : Plant isoquinoline alkaloids as potential neurodrugs: A comparative study of the effects of benzo[c]phenanthridine and berberine-based compounds on beta-amyloid aggregation - Marasco_2021_Chem.Biol.Interact_334_109300
Author(s) : Marasco D , Vicidomini C , Krupa P , Cioffi F , Huy PDQ , Li MS , Florio D , Broersen K , De Pandis MF , Roviello GN
Ref : Chemico-Biological Interactions , 334 :109300 , 2021
Abstract :
PubMedSearch : Marasco_2021_Chem.Biol.Interact_334_109300
PubMedID: 33098838

Title : Molecular dynamics investigation of the interaction between Colletotrichum capsici cutinase and berberine suggested a mechanism for reduced enzyme activity - Li_2021_PLoS.One_16_e0247236
Author(s) : Li Y , Wei J , Yang H , Dai J , Ge X
Ref : PLoS ONE , 16 :e0247236 , 2021
Abstract :
PubMedSearch : Li_2021_PLoS.One_16_e0247236
PubMedID: 33606796

Title : Berberine modulates crucial erectogenic biomolecules and alters histological architecture in penile tissues of diabetic rats - Adefegha_2021_Andrologia__e14074
Author(s) : Adefegha SA , Oboh G , Dada FA , Oyeleye SI , Okeke BM
Ref : Andrologia , :e14074 , 2021
Abstract :
PubMedSearch : Adefegha_2021_Andrologia__e14074
PubMedID: 33930193

Title : Effects of berberine on cholinesterases and monoamine oxidase activities, and antioxidant status in the brain of streptozotocin (STZ)-induced diabetic rats - Adefegha_2021_J.Basic.Clin.Physiol.Pharmacol__
Author(s) : Adefegha SA , Dada FA , Oyeleye SI , Oboh G
Ref : J Basic Clin Physiol Pharmacol , : , 2021
Abstract :
PubMedSearch : Adefegha_2021_J.Basic.Clin.Physiol.Pharmacol__
PubMedID: 33725758

Title : Comparative effects of berberine and piperine on the neuroprotective potential of neostigmine - Adefegha_2021_J.Complement.Integr.Med__
Author(s) : Adefegha SA , Oboh G , Okeke BM
Ref : J Complement Integr Med , : , 2021
Abstract :
PubMedSearch : Adefegha_2021_J.Complement.Integr.Med__
PubMedID: 33544523

Title : Berberine Nanoencapsulation Attenuates Hallmarks of Scoplomine Induced Alzheimer's-Like Disease in Rats - Saleh_2021_Curr.Rev.Clin.Exp.Pharmacol_16_139
Author(s) : Saleh SR , Abady MM , Nofal M , Yassa NW , Abdel-Latif MS , Nounou MI , Ghareeb DA , Abdel-Monaem N
Ref : Curr Rev Clin Exp Pharmacol , 16 :139 , 2021
Abstract :
PubMedSearch : Saleh_2021_Curr.Rev.Clin.Exp.Pharmacol_16_139
PubMedID: 32598269

Title : Berberine Ameliorates Glucose Metabolism in Diabetic Rats through the alpha7 Nicotinic Acetylcholine Receptor-Related Cholinergic Anti-Inflammatory Pathway - Wang_2021_Planta.Med__
Author(s) : Wang D , Ren Y , Sun W , Gong J , Zou X , Dong H , Xu L , Wang K , Lu F
Ref : Planta Med , : , 2021
Abstract :
PubMedSearch : Wang_2021_Planta.Med__
PubMedID: 33682914

Title : A review on pain-relieving activity of berberine - Hashemzaei_2020_Phytother.Res__
Author(s) : Hashemzaei M , Rezaee R
Ref : Phytother Res , : , 2020
Abstract :
PubMedSearch : Hashemzaei_2020_Phytother.Res__
PubMedID: 33340158

Title : Discovery of novel berberine derivatives with balanced cholinesterase and prolyl oligopeptidase inhibition profile - Sobolova_2020_Eur.J.Med.Chem_203_112593
Author(s) : Sobolova K , Hrabinova M , Hepnarova V , Kucera T , Kobrlova T , Benkova M , Janockova J , Dolezal R , Prchal L , Benek O , Mezeiova E , Jun D , Soukup O , Korabecny J
Ref : Eur Journal of Medicinal Chemistry , 203 :112593 , 2020
Abstract :
PubMedSearch : Sobolova_2020_Eur.J.Med.Chem_203_112593
PubMedID: 32688201

Title : In vitro and in silico studies of the larvicidal and anticholinesterase activities of berberine and piperine alkaloids on Rhipicephalus microplus - da Silva_2020_Ticks.Tick.Borne.Dis_12_101643
Author(s) : da Silva GD , de Lima HG , de Freitas HF , da Rocha Pita SS , Dos Santos Luz Y , de Figueiredo MP , Uzeda RS , Branco A , Costa SL , Batatinha MJM , Botura MB
Ref : Ticks Tick Borne Dis , 12 :101643 , 2020
Abstract :
PubMedSearch : da Silva_2020_Ticks.Tick.Borne.Dis_12_101643
PubMedID: 33388555

Title : Neuroprotective effects of berberine in animal models of Alzheimer's disease: a systematic review of pre-clinical studies - Yuan_2019_BMC.Complement.Altern.Med_19_109
Author(s) : Yuan NN , Cai CZ , Wu MY , Su HX , Li M , Lu JH
Ref : BMC Complement Altern Med , 19 :109 , 2019
Abstract :
PubMedSearch : Yuan_2019_BMC.Complement.Altern.Med_19_109
PubMedID: 31122236

Title : Berberine ameliorates lipopolysaccharide-induced learning and memory deficit in the rat: insights into underlying molecular mechanisms - Sadraie_2019_Metab.Brain.Dis_34_245
Author(s) : Sadraie S , Kiasalari Z , Razavian M , Azimi S , Sedighnejad L , Afshin-Majd S , Baluchnejadmojarad T , Roghani M
Ref : Metabolic Brain Disease , 34 :245 , 2019
Abstract :
PubMedSearch : Sadraie_2019_Metab.Brain.Dis_34_245
PubMedID: 30456649

Title : Synthesis and Inhibition Evaluation of New Benzyltetrahydroprotoberberine Alkaloids Designed as Acetylcholinesterase Inhibitors - de Lima_2019_Front.Chem_7_629
Author(s) : de Lima BR , Lima JM , Maciel JB , Valentim CQ , Nunomura RCS , Lima ES , Koolen HHF , de Souza ADL , Pinheiro MLB , Cass QB , da Silva FMA
Ref : Front Chem , 7 :629 , 2019
Abstract :
PubMedSearch : de Lima_2019_Front.Chem_7_629
PubMedID: 31620424

Title : Berberine Ameliorates Spatial Learning Memory Impairment and Modulates Cholinergic Anti-Inflammatory Pathway in Diabetic Rats - Wang_2019_Front.Pharmacol_10_1003
Author(s) : Wang K , Chen Q , Wu N , Li Y , Zhang R , Wang J , Gong D , Zou X , Liu C , Chen J
Ref : Front Pharmacol , 10 :1003 , 2019
Abstract :
PubMedSearch : Wang_2019_Front.Pharmacol_10_1003
PubMedID: 31551793

Title : Neuroprotective effect of berberine agonist against impairment of learning and memory skills in severe traumatic brain injury via Sirt1\/p38 MAPK expression - Wang_2018_Mol.Med.Rep_17_6881
Author(s) : Wang J , Zhang Y
Ref : Mol Med Rep , 17 :6881 , 2018
Abstract :
PubMedSearch : Wang_2018_Mol.Med.Rep_17_6881
PubMedID: 29512719

Title : Molecular Modeling on Berberine Derivatives toward BuChE: An Integrated Study with Quantitative Structure-Activity Relationships Models, Molecular Docking, and Molecular Dynamics Simulations - Fang_2016_Chem.Biol.Drug.Des_87_649
Author(s) : Fang J , Pang X , Wu P , Yan R , Gao L , Li C , Lian W , Wang Q , Liu AL , Du GH
Ref : Chemical Biology Drug Des , 87 :649 , 2016
Abstract :
PubMedSearch : Fang_2016_Chem.Biol.Drug.Des_87_649
PubMedID: 26648584

Title : Berberine relieves insulin resistance via the cholinergic anti-inflammatory pathway in HepG2 cells - Li_2016_J.Huazhong.Univ.Sci.Technolog.Med.Sci_36_64
Author(s) : Li F , Zhao YB , Wang DK , Zou X , Fang K , Wang KF
Ref : J Huazhong Univ Sci Technolog Med Sci , 36 :64 , 2016
Abstract :
PubMedSearch : Li_2016_J.Huazhong.Univ.Sci.Technolog.Med.Sci_36_64
PubMedID: 26838742

Title : Berberine protects against memory impairment and anxiogenic-like behavior in rats submitted to sporadic Alzheimer's-like dementia: Involvement of acetylcholinesterase and cell death - de Oliveira_2016_Neurotoxicol_57_241
Author(s) : de Oliveira JS , Abdalla FH , Dornelles GL , Adefegha SA , Palma TV , Signor C , da Silva Bernardi J , Baldissarelli J , Lenz LS , Magni LP , Rubin MA , Pillat MM , de Andrade CM
Ref : Neurotoxicology , 57 :241 , 2016
Abstract :
PubMedSearch : de Oliveira_2016_Neurotoxicol_57_241
PubMedID: 27746125

Title : Isolation of cholinesterase and beta-secretase 1 inhibiting compounds from Lycopodiella cernua - Nguyen_2015_Bioorg.Med.Chem_23_3126
Author(s) : Nguyen VT , To DC , Tran MH , Oh SH , Kim JA , Ali MY , Woo MH , Choi JS , Min BS
Ref : Bioorganic & Medicinal Chemistry , 23 :3126 , 2015
Abstract :
PubMedSearch : Nguyen_2015_Bioorg.Med.Chem_23_3126
PubMedID: 26003344

Title : The therapeutic potential of berberine against the altered intrinsic properties of the CA1 neurons induced by Abeta neurotoxicity - Haghani_2015_Eur.J.Pharmacol_758_82
Author(s) : Haghani M , Shabani M , Tondar M
Ref : European Journal of Pharmacology , 758 :82 , 2015
Abstract :
PubMedSearch : Haghani_2015_Eur.J.Pharmacol_758_82
PubMedID: 25861937

Title : Protective effect of berberine, an isoquinoline alkaloid ameliorates ethanol-induced oxidative stress and memory dysfunction in rats - Patil_2015_Pharmacol.Biochem.Behav_136_13
Author(s) : Patil S , Tawari S , Mundhada D , Nadeem S
Ref : Pharmacol Biochem Behav , 136 :13 , 2015
Abstract :
PubMedSearch : Patil_2015_Pharmacol.Biochem.Behav_136_13
PubMedID: 26159088

Title : Synergistic inhibition on acetylcholinesterase by the combination of berberine and palmatine originally isolated from chinese medicinal herbs - Mak_2014_J.Mol.Neurosci_53_511
Author(s) : Mak SH , Luk WW , Cui W , Hu S , Tsim KWK , Han Y
Ref : Journal of Molecular Neuroscience , 53 :511 , 2014
Abstract :
PubMedSearch : Mak_2014_J.Mol.Neurosci_53_511
PubMedID: 24793543

Title : In vitro biological assessment of berberis vulgaris and its active constituent, berberine: antioxidants, anti-acetylcholinesterase, anti-diabetic and anticancer effects - Abd_2013_BMC.Complement.Altern.Med_13_218
Author(s) : Abd El-Wahab AE , Ghareeb DA , Sarhan EE , Abu-Serie MM , El Demellawy MA
Ref : BMC Complement Altern Med , 13 :218 , 2013
Abstract :
PubMedSearch : Abd_2013_BMC.Complement.Altern.Med_13_218
PubMedID: 24007270

Title : Verapamil augments the neuroprotectant action of berberine in rat model of transient global cerebral ischemia - Singh_2013_Eur.J.Pharmacol_720_98
Author(s) : Singh DP , Chopra K
Ref : European Journal of Pharmacology , 720 :98 , 2013
Abstract :
PubMedSearch : Singh_2013_Eur.J.Pharmacol_720_98
PubMedID: 24177287

Title : Molecular basis of inhibitory activities of berberine against pathogenic enzymes in Alzheimer's disease - Ji_2012_ScientificWorldJournal_2012_823201
Author(s) : Ji HF , Shen L
Ref : ScientificWorldJournal , 2012 :823201 , 2012
Abstract :
PubMedSearch : Ji_2012_ScientificWorldJournal_2012_823201
PubMedID: 22262957

Title : Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids - Huang_2012_Bioorg.Med.Chem_20_3038
Author(s) : Huang L , Su T , Shan W , Luo Z , Sun Y , He F , Li X
Ref : Bioorganic & Medicinal Chemistry , 20 :3038 , 2012
Abstract :
PubMedSearch : Huang_2012_Bioorg.Med.Chem_20_3038
PubMedID: 22472046

Title : The therapeutic potential of Berberis darwinii stem-bark: quantification of berberine and in vitro evidence for Alzheimer's disease therapy - Habtemariam_2011_Nat.Prod.Commun_6_1089
Author(s) : Habtemariam S
Ref : Nat Prod Commun , 6 :1089 , 2011
Abstract :
PubMedSearch : Habtemariam_2011_Nat.Prod.Commun_6_1089
PubMedID: 21922905

Title : Synthesis, biological evaluation and molecular modeling of novel triazole-containing berberine derivatives as acetylcholinesterase and beta-amyloid aggregation inhibitors - Shi_2011_Bioorg.Med.Chem_19_2298
Author(s) : Shi A , Huang L , Lu C , He F , Li X
Ref : Bioorganic & Medicinal Chemistry , 19 :2298 , 2011
Abstract :
PubMedSearch : Shi_2011_Bioorg.Med.Chem_19_2298
PubMedID: 21397508

Title : Decrease in the production of beta-amyloid by berberine inhibition of the expression of beta-secretase in HEK293 cells - Zhu_2011_BMC.Neurosci_12_125
Author(s) : Zhu F , Wu F , Ma Y , Liu G , Li Z , Sun Y , Pei Z
Ref : BMC Neurosci , 12 :125 , 2011
Abstract :
PubMedSearch : Zhu_2011_BMC.Neurosci_12_125
PubMedID: 22152059

Title : Protection of cholinergic and antioxidant system contributes to the effect of berberine ameliorating memory dysfunction in rat model of streptozotocin-induced diabetes - Bhutada_2011_Behav.Brain.Res_220_30
Author(s) : Bhutada P , Mundhada Y , Bansod K , Tawari S , Patil S , Dixit P , Umathe S , Mundhada D
Ref : Behavioural Brain Research , 220 :30 , 2011
Abstract :
PubMedSearch : Bhutada_2011_Behav.Brain.Res_220_30
PubMedID: 21262264

Title : Benzenediol-berberine hybrids: multifunctional agents for Alzheimer's disease - Jiang_2011_Bioorg.Med.Chem_19_7228
Author(s) : Jiang H , Wang X , Huang L , Luo Z , Su T , Ding K , Li X
Ref : Bioorganic & Medicinal Chemistry , 19 :7228 , 2011
Abstract :
PubMedSearch : Jiang_2011_Bioorg.Med.Chem_19_7228
PubMedID: 22041172

Title : Synthesis, biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant, inhibitors of acetylcholinesterase, butyrylcholinesterase and amyloid-beta aggregation - Shan_2011_Eur.J.Med.Chem_46_5885
Author(s) : Shan WJ , Huang L , Zhou Q , Meng FC , Li XS
Ref : Eur Journal of Medicinal Chemistry , 46 :5885 , 2011
Abstract :
PubMedSearch : Shan_2011_Eur.J.Med.Chem_46_5885
PubMedID: 22019228

Title : Modulation of glucagon-like peptide-1 release by berberine: in vivo and in vitro studies - Yu_2010_Biochem.Pharmacol_79_1000
Author(s) : Yu Y , Liu L , Wang X , Liu X , Xie L , Wang G
Ref : Biochemical Pharmacology , 79 :1000 , 2010
Abstract :
PubMedSearch : Yu_2010_Biochem.Pharmacol_79_1000
PubMedID: 19945441

Title : A new and weakly antispasmodic protoberberine alkaloid from Rhizoma Coptidis - Zhao_2010_Phytother.Res_24_1414
Author(s) : Zhao M , Xian YF , Ip SP , Fong HH , Che CT
Ref : Phytother Res , 24 :1414 , 2010
Abstract :
PubMedSearch : Zhao_2010_Phytother.Res_24_1414
PubMedID: 20564546

Title : Berberine derivatives, with substituted amino groups linked at the 9-position, as inhibitors of acetylcholinesterase\/butyrylcholinesterase - Huang_2010_Bioorg.Med.Chem.Lett_20_6649
Author(s) : Huang L , Luo Z , He F , Shi A , Qin F , Li X
Ref : Bioorganic & Medicinal Chemistry Lett , 20 :6649 , 2010
Abstract :
PubMedSearch : Huang_2010_Bioorg.Med.Chem.Lett_20_6649
PubMedID: 20880702

Title : Synthesis, biological evaluation, and molecular modeling of berberine derivatives as potent acetylcholinesterase inhibitors - Huang_2010_Bioorg.Med.Chem_18_1244
Author(s) : Huang L , Shi A , He F , Li X
Ref : Bioorganic & Medicinal Chemistry , 18 :1244 , 2010
Abstract :
PubMedSearch : Huang_2010_Bioorg.Med.Chem_18_1244
PubMedID: 20056426

Title : Synthesis and biological evaluation of a new series of berberine derivatives as dual inhibitors of acetylcholinesterase and butyrylcholinesterase - Huang_2010_Bioorg.Med.Chem_18_4475
Author(s) : Huang L , Luo Z , He F , Lu J , Li X
Ref : Bioorganic & Medicinal Chemistry , 18 :4475 , 2010
Abstract :
PubMedSearch : Huang_2010_Bioorg.Med.Chem_18_4475
PubMedID: 20471843

Title : Berberine and total base from rhizoma coptis chinensis attenuate brain injury in an aluminum-induced rat model of neurodegenerative disease - Zhang_2009_Saudi.Med.J_30_760
Author(s) : Zhang J , Yang JQ , He BC , Zhou QX , Yu HR , Tang Y , Liu BZ
Ref : Saudi Med J , 30 :760 , 2009
Abstract :
PubMedSearch : Zhang_2009_Saudi.Med.J_30_760
PubMedID: 19526156

Title : The natural product berberine is a human prolyl oligopeptidase inhibitor - Tarrago_2007_ChemMedChem_2_354
Author(s) : Tarrago T , Kichik N , Segui J , Giralt E
Ref : ChemMedChem , 2 :354 , 2007
Abstract :
PubMedSearch : Tarrago_2007_ChemMedChem_2_354
PubMedID: 17295371

Title : Potentiation of nerve growth factor-induced neurite outgrowth in PC12 cells by a Coptidis Rhizoma extract and protoberberine alkaloids - Shigeta_2002_Biosci.Biotechnol.Biochem_66_2491
Author(s) : Shigeta K , Ootaki K , Tatemoto H , Nakanishi T , Inada A , Muto N
Ref : Biosci Biotechnol Biochem , 66 :2491 , 2002
Abstract :
PubMedSearch : Shigeta_2002_Biosci.Biotechnol.Biochem_66_2491
PubMedID: 12506995

Title : Effect of long-term administration of berberine on scopolamine-induced amnesia in rats - Peng_1997_Jpn.J.Pharmacol_74_261
Author(s) : Peng WH , Hsieh MT , Wu CR
Ref : Japanese Journal of Pharmacology , 74 :261 , 1997
Abstract :
PubMedSearch : Peng_1997_Jpn.J.Pharmacol_74_261
PubMedID: 9268086

Title : Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores - Schmeller_1997_Phytochemistry_44_257
Author(s) : Schmeller T , Latz-Bruning B , Wink M
Ref : Phytochemistry , 44 :257 , 1997
Abstract :
PubMedSearch : Schmeller_1997_Phytochemistry_44_257
PubMedID: 9004542

Title : A paradoxical stimulatory effect of berberine on guinea-pig ileum contractility: possible involvement of acetylcholine release from the postganglionic parasympathetic nerve and cholinesterase inhibition - Shin_1993_Life.Sci_53_1495
Author(s) : Shin DH , Yu H , Hsu WH
Ref : Life Sciences , 53 :1495 , 1993
Abstract :
PubMedSearch : Shin_1993_Life.Sci_53_1495
PubMedID: 8412513

Title : Pharmacological effects of berberine on the longitudinal muscle of the guinea-pig isolated ileum - Tsai_1991_Arch.Int.Pharmacodyn.Ther_310_116
Author(s) : Tsai CS , Ochillo RF
Ref : Archives Internationales de Pharmacodynamie et de Therapie , 310 :116 , 1991
Abstract :
PubMedSearch : Tsai_1991_Arch.Int.Pharmacodyn.Ther_310_116
PubMedID: 1772324