| Record Information |
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| Version | 1.0 |
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| Created at | 2006-08-12 20:17:34 UTC |
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| Updated at | 2020-09-11 01:33:48 UTC |
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| NP-MRD ID | NP0000008 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Berberine |
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| Description | Berberine, also known as coptis rhizome, 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. Oxidation of the tertiary amine then occurs and an iminium ion is formed. 2. Dopamine 1 then reacts with 4-hydroxy-phenylacetaldehyde 2 to form (S)-norcolaurine 3 in a reaction similar to the Mannich reaction. The alkaloid berberine has a tetracyclic skeleton derived from a benzyltetrahydroisoquinoline system with the incorporation of an extra carbon atom provided by S-adenosyl methionine via an N-methyl group. 8 (S)-canadine is then oxidized to give the quaternary isoquinolinium system of berberine. Berberine is an extremely weak basic (essentially neutral) compound (based on its pKa). Berberine is a bitter tasting compound. Outside of the human body,. Reticuline is known as the immediate precursor of protoberberine alkaloids in plants. Its potential for causing adverse effects is high, including untoward interactions with prescription drugs, reducing the intended effect of established therapies. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium | ChEBI | | 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium | ChEBI | | Berberin | ChEBI | | Coptis rhizome | HMDB |
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| Chemical Formula | C20H18NO4 |
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| Average Molecular Weight | 336.3612 |
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| Monoisotopic Molecular Weight | 336.123583069 |
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| IUPAC Name | 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 |
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| Traditional Name | 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 |
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| CAS Registry Number | 2086-83-1 |
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| SMILES | COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC |
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| 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 |
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| InChI Key | YBHILYKTIRIUTE-UHFFFAOYSA-N |
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| Spectra |
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| | | Species of Origin |
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| Species | Plantae |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Protoberberine alkaloids and derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Protoberberine alkaloids and derivatives |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 145 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
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