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Record Information
Version1.0
Created at2006-08-12 20:17:34 UTC
Updated at2021-08-19 20:22:28 UTC
NP-MRD IDNP0000008
Secondary Accession NumbersNone
Natural Product Identification
Common NameBerberine
DescriptionBerberine is a quaternary ammonium salt that belongs to the protoberberine group of benzylisoquinoline alkaloids. Chemically, berberine is classified as an isoquinoline alkaloid. More specifically, berberine is a plant alkaloid derived from tyrosine through a complex 8 step biosynthetic process. Berberine is found in plants such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal). Two other known berberine-containing plants are Phellodendron chinense and Phellodendron amurense. Berberine is usually found in the roots, rhizomes, stems, and bark of Berberis plants. Due to berberine's intense yellow color, plants that contain berberine were traditionally used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence, making it useful in histology for staining heparin in mast cells. Berberine is a bioactive plant compound that has been frequently used in traditional medicine. Among the known physiological effects or bioactivities are: 1) Antimicrobial action against bacteria, fungi, protozoa, viruses, helminthes, and Chlamydia; 2) Antagonism against the effects of cholera and E coli heat-stable enterotoxin; 3) Inhibition of intestinal ion secretion and of smooth muscle contraction; 4) Reduction of inflammation and 5) Stimulation of bile secretion and bilirubin discharge (PMID: 32335802 ). Berberine can inhibit bacterial growth in the gut, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury. Currently, berberine is sold as an Over-the-Counter (OTC) drug for treating gastrointestinal infections in China (PMID: 18442638 ). Berberine also inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis (PMID: 32335802 ). Recent evidence has also confirmed that berberine improves the efficacy and safety of both chemo and radiotherapies for cancer treatment (PMID: 32335802 ). Berberine has also been shown to regulate glucose and lipid metabolism in vitro and in vivo (PMID: 18442638 ). In fact, berberine is the main active component of an ancient Chinese herb Coptis chinensis French, which has been used to treat diabetes for thousands of years. As an anti-diabetic, berberine increases glucose uptake by muscle fibers independent of insulin levels. It triggers AMPK activation and increases glycolysis, leading to decreased insulin resistance and decreased oxygen respiration. The same mechanism leads to a reduction in gluconeogenesis in the liver. AMPK activation by berberine also leads to an antiatherosclerotic effect in mice. Berberine's AMPK activation may also underlie berberines' anti-obesity effects and favorable influence on weight loss (PMID: 18442638 ). While its use as a medication is widely touted, it is important to remember that berberine inhibits CYP2D6 and CYP3A4 enzymes, both of which are involved in the metabolism of many endogenous substances and xenobiotics, including a number of prescription drugs.
Structure
Data?1622842756
Synonyms
ValueSource
7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbiniumChEBI
9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbiniumChEBI
BerberinChEBI
Coptis rhizomeHMDB
Chemical FormulaC20H18NO4
Average Mass336.3612 Da
Monoisotopic Mass336.12358 Da
IUPAC Name16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium
Traditional Name16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium
CAS Registry Number2086-83-1
SMILES
COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC
InChI Identifier
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
InChI KeyYBHILYKTIRIUTE-UHFFFAOYSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)V.dorna832021-08-15View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)V.dorna832021-07-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, simulated)V.dorna832021-09-06View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)V.dorna832021-09-06View Spectrum
Species
Species of Origin
Species NameSourceReference
Argemone mexicanaKNApSAcK Database
Argemone spp.KNApSAcK Database
Argemone subfusiformiaKNApSAcK Database
Argemone subfusiformis var.subinermisKNApSAcK Database
Asteropyrum cavalerieiKNApSAcK Database
Berberis aemulansKNApSAcK Database
Berberis aquifoliumKNApSAcK Database
Berberis aristataKNApSAcK Database
Berberis brandisianaKNApSAcK Database
Berberis candidulaKNApSAcK Database
Berberis croaticaKNApSAcK Database
Berberis darwiniiKNApSAcK Database
Berberis densifloraKNApSAcK Database
Berberis diaphanaKNApSAcK Database
Berberis dubiaKNApSAcK Database
Berberis heterobotrysKNApSAcK Database
Berberis iliensisKNApSAcK Database
Berberis integerrimaKNApSAcK Database
Berberis julianaeKNApSAcK Database
Berberis nervosaKNApSAcK Database
Berberis numularisKNApSAcK Database
Berberis oblongaKNApSAcK Database
Berberis poirettiiKNApSAcK Database
Berberis potaniniiKNApSAcK Database
Berberis pruinosaKNApSAcK Database
Berberis pseudanubalataKNApSAcK Database
Berberis rigidifoliaKNApSAcK Database
Berberis spp.KNApSAcK Database
Berberis stenophyllaKNApSAcK Database
Berberis thunbergiiKNApSAcK Database
Berberis turcomanicaKNApSAcK Database
Berberis vulgarisKNApSAcK Database
Berberis wilsonaeKNApSAcK Database
Berberis wilsoniaeKNApSAcK Database
Chelidonium majus L.KNApSAcK Database
Chelidonium spp.KNApSAcK Database
Coptis chinensisKNApSAcK Database
Coptis deltoideaKNApSAcK Database
Coptis deltoidesKNApSAcK Database
Coptis gulinensisKNApSAcK Database
Coptis japonicaKNApSAcK Database
Coptis linearisepalaKNApSAcK Database
Coptis omeiensisKNApSAcK Database
Coptis spp.KNApSAcK Database
Coptis teetoidesKNApSAcK Database
Corydalis amuncaKNApSAcK Database
Corydalis intermediaKNApSAcK Database
Corydalis ledebourianaKNApSAcK Database
Corydalis longicalcarataKNApSAcK Database
Corydalis ophiocarpaKNApSAcK Database
Corydalis remotaKNApSAcK Database
Corydalis solidaKNApSAcK Database
Corydalis spp.KNApSAcK Database
Corydalis yanhusuoKNApSAcK Database
Coscinium fenestratumKNApSAcK Database
Eschscholtzia californiaKNApSAcK Database
Evodia mellifoliaKNApSAcK Database
Evodia spp.KNApSAcK Database
Glaucium arabicumKNApSAcK Database
Hydrastis canadensisKNApSAcK Database
Macleaya cordataKNApSAcK Database
Magnolia biondiiKNApSAcK Database
Mahonia aquifoliumKNApSAcK Database
Mahonia bealeiKNApSAcK Database
Mahonia bodinieriKNApSAcK Database
Mahonia confusaKNApSAcK Database
Mahonia eurybracteataKNApSAcK Database
Mahonia fortuneiKNApSAcK Database
Mahonia gracilipesKNApSAcK Database
Mahonia japonicaKNApSAcK Database
Mahonia spp.KNApSAcK Database
Mahonia veitchiorumKNApSAcK Database
Nandina domesticaKNApSAcK Database
Nandina spp.KNApSAcK Database
Naravelia zeylandicaKNApSAcK Database
Papaver albifloraKNApSAcK Database
Papaver bracteatumKNApSAcK Database
Papaver confineKNApSAcK Database
Papaver pinnatifidumKNApSAcK Database
Papaver radicatumKNApSAcK Database
Papaver rhoeas chelidonidesKNApSAcK Database
Papaver rhopalotheceKNApSAcK Database
Papaver somniferumKNApSAcK Database
Phellodendron amurenseKNApSAcK Database
Phellodendron chinenseKNApSAcK Database
Phellodendron chinensisKNApSAcK Database
Phellodendron lavalleiKNApSAcK Database
Phellodendron wilsoniiKNApSAcK Database
Ranunculus serbicusKNApSAcK Database
Stephania cepharanthaKNApSAcK Database
Stephania tetrandraKNApSAcK Database
Stylophorum lasiocarpumKNApSAcK Database
Thalictrum atriplexKNApSAcK Database
Thalictrum faberiKNApSAcK Database
Thalictrum flavumKNApSAcK Database
Thalictrum foetidumKNApSAcK Database
Thalictrum foliolosumKNApSAcK Database
Thalictrum foliosumKNApSAcK Database
Thalictrum glandulosissimumKNApSAcK Database
Thalictrum honanenseKNApSAcK Database
Thalictrum longipedunculatumKNApSAcK Database
Thalictrum microgynumKNApSAcK Database
Thalictrum minusKNApSAcK Database
Thalictrum orientaleKNApSAcK Database
Thalictrum petaloidumKNApSAcK Database
Thalictrum przewalskiiKNApSAcK Database
Thalictrum purpurescensKNApSAcK Database
Thalictrum simplexKNApSAcK Database
Thalictrum spp.KNApSAcK Database
Thalictrum symplexKNApSAcK Database
Thalictrum thunbergiiKNApSAcK Database
Thalictrum wanqiiKNApSAcK Database
Toddalia aculeata Pers.KNApSAcK Database
Toddalia spp.KNApSAcK Database
Xanthorhiza simplicissimaKNApSAcK Database
Zanthoxylum spp.KNApSAcK Database
Ziziphus jujubaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Acangelisia gusanlungKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtoberberine alkaloids and derivatives
Sub ClassNot Available
Direct ParentProtoberberine alkaloids and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point145 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.62 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.990 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility0.00035 g/LALOGPS
logP-0.18ALOGPS
logP-1.3ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.8 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.52 m³·mol⁻¹ChemAxon
Polarizability36.92 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External Links
HMDB IDHMDB0003409
DrugBank IDDB04115
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023165
KNApSAcK IDC00001819
Chemspider ID2263
KEGG Compound IDC00757
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBerberine
METLIN ID3471
PubChem Compound2353
PDB IDNot Available
ChEBI ID16118
Good Scents IDrw1070241
References
General References
  1. Pan GY, Wang GJ, Sun JG, Huang ZJ, Zhao XC, Gu Y, Liu XD: [Inhibitory action of berberine on glucose absorption]. Yao Xue Xue Bao. 2003 Dec;38(12):911-4. [PubMed:15040083 ]
  2. Yu HH, Kim KJ, Cha JD, Kim HK, Lee YE, Choi NY, You YO: Antimicrobial activity of berberine alone and in combination with ampicillin or oxacillin against methicillin-resistant Staphylococcus aureus. J Med Food. 2005 Winter;8(4):454-61. [PubMed:16379555 ]
  3. Zhao CC, Zheng WF, Li MQ: [The interaction of berberine and human serum albumin]. Guang Pu Xue Yu Guang Pu Fen Xi. 2004 Jan;24(1):111-3. [PubMed:15768991 ]
  4. Pan JF, Yu C, Zhu DY, Zhang H, Zeng JF, Jiang SH, Ren JY: Identification of three sulfate-conjugated metabolites of berberine chloride in healthy volunteers' urine after oral administration. Acta Pharmacol Sin. 2002 Jan;23(1):77-82. [PubMed:11860742 ]
  5. Zhang H, Shao Z, Sun Y: [Determination of berberine in human serum by reversed-phase high performance liquid chromatography]. Se Pu. 1997 Sep;15(5):454-5. [PubMed:15739507 ]
  6. Liu Y, Huang CZ, Li YF: Fluorescence assay based on preconcentration by a self-ordered ring using berberine as a model analyte. Anal Chem. 2002 Nov 1;74(21):5564-8. [PubMed:12433089 ]
  7. Mantena SK, Sharma SD, Katiyar SK: Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells. Mol Cancer Ther. 2006 Feb;5(2):296-308. [PubMed:16505103 ]
  8. Song D, Hao J, Fan D: Biological properties and clinical applications of berberine. Front Med. 2020 Oct;14(5):564-582. doi: 10.1007/s11684-019-0724-6. Epub 2020 Apr 25. [PubMed:32335802 ]
  9. Yin J, Xing H, Ye J: Efficacy of berberine in patients with type 2 diabetes mellitus. Metabolism. 2008 May;57(5):712-7. doi: 10.1016/j.metabol.2008.01.013. [PubMed:18442638 ]