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Berberine (PC000871)

Record Information
Version1.0
Creation date2015-10-09 22:33:10 UTC
Update date2017-01-19 02:36:39 UTC
FoodComEx IDPC000871
FoodDB RecordFDB023165
Chemical Information
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 berberine’s 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. Berberine is a bitter tasting compound.
CAS Number2086-83-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbiniumChEBI
9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbiniumChEBI
Berberinhmdb
Coptis rhizomehmdb
Umbellatinehmdb
Chemical FormulaC20H18NO4
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
InChI IdentifierInChI=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
Isomeric SMILESCOC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC
Average Molecular Weight336.3612
Monoisotopic Molecular Weight336.123583069
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 Parents
Substituents
  • Protoberberine skeleton
  • Isoquinoline
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Pyridine
  • Pyridinium
  • Benzenoid
  • Heteroaromatic compound
  • Acetal
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 1 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available