Coptisine: Difference between revisions

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| verifiedrevid = 460107369

|ImageFile=coptisine.png

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|ImageSize=200px

| ImageSize=200px

|IUPACName=6,7-Dihydro-bis(1,3)benzodioxolo (5,6-a:4',5'-g)quinolizinium

| IUPACName=7,8,13,13a-Tetradehydro-2′''H'',2′′''H''-bis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:9,10]berbin-7-ium

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|OtherNames=

| SystematicName=6,7-Dihydro-2''H'',10''H''-5λ5-[1,3]dioxolo[4,5-''g''][1,3]dioxolo[4′,5′:7,8]isoquinolino[3,2-''a'']isoquinolin-5-ylium

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|Section1= {{Chembox Identifiers

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|Section1={{Chembox Identifiers

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 65268

| InChI = 1/C19H14NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8H,3-4,9-10H2/q+1

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| StdInChIKey = XYHOBCMEDLZUMP-UHFFFAOYSA-N

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| CASNo=3486-66-6

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| ChEMBL = 362071

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0GCL71VN14

| ChEMBL_Ref = {{ebicite|correct|EBI}}

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| ChEMBL = 362071

| PubChem=72322

| SMILES = O1c3c(OC1)c2c[n+]6c(cc2cc3)c5cc4OCOc4cc5CC6

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|Section2= {{Chembox Properties

|Section2={{Chembox Properties

| Formula=C19H14NO4+

| MolarMass=320.319

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|Section3= {{Chembox Hazards

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'''Coptisine''' is an [[alkaloid]] found in Chinese goldthread (''[[Coptis chinensis]]''),<ref name="pmid18395058">{{cite journal | vauthors = Chen J, Wang F, Liu J, Lee FS, Wang X, Yang H | title = Analysis of alkaloids in Coptis chinensis Franch by accelerated solvent extraction combined with ultra performance liquid chromatographic analysis with photodiode array and tandem mass spectrometry detections | journal = Analytica Chimica Acta | volume = 613 | issue = 2 | pages = 184–95 | date = April 2008 | pmid = 18395058 | doi = 10.1016/j.aca.2008.02.060 }}</ref> [[Chelidonium|greater celandine]], and opium.<ref>{{cite journal |pages=198–201 |doi=10.1038/189198a0 |title=Distribution of Certain Poppy-Fumaria Alkaloids and a Possible Link with the Incidence of Glaucoma |year=1961 |last1=Hakim |first1=Sohrab A. E. |last2=Mijović |first2=Valerie |last3=Walker |first3=James |journal=Nature |volume=189 |issue=4760 |pmid=13710637}}</ref> Famous for the bitter taste that it produces, it is used in [[Chinese herbal medicine]] along with the related compound [[berberine]] for digestive disorders caused by bacterial infections.<ref name="pmid19686830">{{cite journal | vauthors = Tang J, Feng Y, Tsao S, Wang N, Curtain R, Wang Y | title = Berberine and Coptidis rhizoma as novel antineoplastic agents: a review of traditional use and biomedical investigations | journal = Journal of Ethnopharmacology | volume = 126 | issue = 1 | pages = 5–17 | date = October 2009 | pmid = 19686830 | doi = 10.1016/j.jep.2009.08.009 | hdl = 10722/127599 | hdl-access = free }}</ref>

'''Coptisine''' is an [[alkaloid]] found in Chinese goldthread (''[[Coptis chinensis]]'').<ref>[http://alternativehealing.org/huang_lian.htm Complementary and Alternative Healing University (Chinese Medicine)]</ref> Famous for the bitter taste that it produces, it is used in [[Chinese herbal medicine]] along with the related compound [[berberine]] for treating digestive disorders caused by bacterial infections.

== References==

Also found in [[Chelidonium|Greater Celandine]] and has also been detected in [[Opium]].<ref>Hakim et al., 1961</ref> {{Fact|date=September 2008}}

Coptisine has been found to reversibly inhibit [[Monoamine oxidase A]] in mice, pointing to a potential role as a natural antidepressant<ref>[http://www.ncbi.nlm.nih.gov/pubmed/11833714 "Inhibition of type A monoamine oxidase by coptisine in mouse brain." Ro JS, Lee SS, Lee KS, Lee MK]</ref>. However, this may also imply a hazard for those taking other medications or with a natural functional disorder in Monoamine oxidase A.

Coptisine was found to be toxic to larval [[brine shrimp]] and a variety of human cell lines, potentially implying a therapeutic effect on cancer or alternatively a generally toxic character. The same authors illustrate a four-step process to produce Coptisine from [[Berberine]]<ref>[http://www.ncbi.nlm.nih.gov/pubmed/11482767 "Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine", Colombo et al]</ref>.

==Footnotes==

[[Category:~~Alkaloids~~]]

[[Category:Isoquinoline alkaloids]]

[[Category:Benzodioxoles]]

[[Category:Quaternary ammonium compounds]]