1.0 2011-09-21 00:25:37 UTC 2025-11-19 02:43:23 UTC FDB023165 Berberine Berberine 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. 7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium Berberin Coptis rhizome Umbellatine C20H18NO4 336.3612 336.123583069 16,17-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 16,17-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 2086-83-1 COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC 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 YBHILYKTIRIUTE-UHFFFAOYSA-N 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. Protoberberine alkaloids and derivatives Organic compounds Alkaloids and derivatives Protoberberine alkaloids and derivatives Aromatic heteropolycyclic compounds Acetals Alkyl aryl ethers Anisoles Azacyclic compounds Benzodioxoles Heteroaromatic compounds Hydrocarbon derivatives Isoquinolines and derivatives Organic cations Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Pyridinium derivatives Acetal Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Azacycle Benzenoid Benzodioxole Ether Heteroaromatic compound Hydrocarbon derivative Isoquinoline Organic cation Organic nitrogen compound Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Protoberberine skeleton Pyridine Pyridinium Alkaloids Isoquinoline alkaloids a small molecule alkaloid antibiotic berberine alkaloid botanical anti-fungal agent organic heteropentacyclic compound Solid logp -0.18 ALOGPS logs -6.02 ALOGPS solubility 3.54e-04 g/l ALOGPS logp -1.3 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac 16,17-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 ChemAxon average_mass 336.3612 ChemAxon mono_mass 336.123583069 ChemAxon smiles COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC ChemAxon formula C20H18NO4 ChemAxon 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 ChemAxon inchikey YBHILYKTIRIUTE-UHFFFAOYSA-N ChemAxon polar_surface_area 40.8 ChemAxon refractivity 93.52 ChemAxon polarizability 36.92 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 1 ChemAxon formal_charge 1 ChemAxon Specdb::CMs 7778 Specdb::CMs 152588 Specdb::NmrTwoD 1899 Specdb::MsMs 2289 Specdb::MsMs 2290 Specdb::MsMs 2291 Specdb::MsMs 5925 Specdb::MsMs 5926 Specdb::MsMs 5927 Specdb::MsMs 5928 Specdb::MsMs 5929 Specdb::MsMs 5930 Specdb::MsMs 5931 Specdb::MsMs 5932 Specdb::MsMs 5933 Specdb::MsMs 5934 Specdb::MsMs 255885 Specdb::MsMs 255886 Specdb::MsMs 255887 Specdb::MsMs 275826 Specdb::MsMs 275827 Specdb::MsMs 275828 Specdb::MsMs 445340 Specdb::MsMs 445341 Specdb::MsMs 445432 Specdb::MsMs 445433 Specdb::MsMs 445434 Specdb::MsMs 445435 Specdb::NmrOneD 1964 Specdb::NmrOneD 21702 Specdb::NmrOneD 21703 Specdb::NmrOneD 21704 Specdb::NmrOneD 21705 Specdb::NmrOneD 21706 Specdb::NmrOneD 21707 Specdb::NmrOneD 21708 Specdb::NmrOneD 21709 Specdb::NmrOneD 21710 Specdb::NmrOneD 21711 Specdb::NmrOneD 21712 Specdb::NmrOneD 21713 Specdb::NmrOneD 21714 Specdb::NmrOneD 21715 Specdb::NmrOneD 21716 Specdb::NmrOneD 21717 Specdb::NmrOneD 21718 Specdb::NmrOneD 21719 Specdb::NmrOneD 21720 Specdb::NmrOneD 21721 Specdb::NmrOneD 166379 Specdb::NmrOneD 166533 Specdb::NmrOneD 166658 HMDB03409 16118 BER #<Reference:0x000055ce3203c590> #<Reference:0x000055ce3203c338> #<Reference:0x000055ce3203c0e0> #<Reference:0x000055ce3203d490> #<Reference:0x000055ce3203bf28> #<Reference:0x000055ce3203bd70> #<Reference:0x000055ce3203bbb8> bitter