COPTISINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H14NO4
Molecular Weight	320.3188
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

C1OC2=C(O1)C=C3C(CC[N+]4=C3C=C5C=CC6=C(OCO6)C5=C4)=C2

InChI

InChIKey=XYHOBCMEDLZUMP-UHFFFAOYSA-N

InChI=1S/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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795 | https://www.ncbi.nlm.nih.gov/pubmed/26228628 | https://www.ncbi.nlm.nih.gov/pubmed/26134304

Coptisine (COP), a protoberberine alkaloid, is widely found in Chinese medicinal plants (family Berberidaceae, Ranunculaceae and Papaveraceae). It is reported that COP has a wide range of pharmacological and biological activities, including antibacterial, hypoglycemic, anti-tumorigenic, and gastric-mucous membrane protection. Considerable attention has been focused on its activity against central nervous system disorders, such as improving the symptoms of Alzheimer’s disease and even preventing its onset, by exerting antidepressant effects as a potent type A monoamine oxidase inhibitor. Coptisine was found to be an efficient uncompetitive Indoleamine 2,3-dioxygenase inhibitor. Coptisine is a potent inhibitor of human organic cation transporters.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Activator 1430
ERK1 and ERK2 cascade 8 Target ID: GO:0070371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Inhibitor 8297
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	0.9 µM [IC50]
Solute carrier family 22 member 2 8 Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	2.3 µM [IC50]
Solute carrier family 22 member 3 6 Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	2.3 µM [IC50]
Indoleamine 2,3-dioxygenase 19 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Inhibitor 8297	6.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25081696	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28351307	Primary	Basic research	Unknown Approved Use Unknown
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24607417	Primary	Preclinical	Unknown Approved Use Unknown
Hepatoma 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14756686	Primary	Basic research	Unknown Approved Use Unknown
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14756686	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.	1992 May 29	1376118
Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.	2001	11504450
Inhibition of type A monoamine oxidase by coptisine in mouse brain.	2001 Dec 28	11833714
[The effects of kampo-formulation and the constituting crude drugs, prescribed for the treatment of peptic ulcer on H,K-ATPase activity].	2001 Feb	11218732
In vitro cytotoxicity of the protoberberine-type alkaloids.	2001 Jul	11473418
Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine.	2001 May-Jul	11482767
Gastric-mucous membrane protection activity of coptisine derivatives.	2001 Nov	11725963
Potentiation of nerve growth factor-induced neurite outgrowth in PC12 cells by a Coptidis Rhizoma extract and protoberberine alkaloids.	2002 Nov	12506995
Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site.	2003 Apr	12709895
[Study on the solubility changes of Rhizoma Coptidis' main chemical constituents influenced by the proportion of Rhizoma Coptidis and Fructus Evodiae].	2003 Jul	15139107
Coptidis Rhizoma: protective effects against peroxynitrite-induced oxidative damage and elucidation of its active components.	2004 Apr	15099450
Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukaemia cell growth.	2004 Jan-Feb	14756686
Study on noncovalent complexes of cytotoxic protoberberine alkaloids with double-stranded DNA by using electrospray ionization mass spectrometry.	2004 Oct 4	15341959
[Quality assessment of Coptis chinensis in China].	2005 Apr	16011089
Sensitivity improvement on detection of Coptidis alkaloids by sweeping in capillary electrophoresis.	2005 Feb 7	15664741
[Studies on the alkaloids from herb of Corydalis adunca].	2005 Nov	16468373
Double blockade of cell cycle progression by coptisine in vascular smooth muscle cells.	2005 Oct 15	16140275
Simultaneous determination of four active alkaloids from a traditional Chinese medicine Corydalis saxicola Bunting. (Yanhuanglian) in plasma and urine samples by LC-MS-MS.	2006 Feb 2	16356790
Proapoptotic activity of Ukrain is based on Chelidonium majus L. alkaloids and mediated via a mitochondrial death pathway.	2006 Jan 17	16417634
Bioavailabilty and pharmacokinetics of four active alkaloids of traditional Chinese medicine Yanhuanglian in rats following intravenous and oral administration.	2006 Jun 16	16644173
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine.	2006 Mar 2	16512916
Selective inhibition of vascular smooth muscle cell proliferation by coptisine isolated from Coptis rhizoma, one of the crude drugs composing Kampo medicines Unsei-in.	2006 May	16635741
Simultaneous analysis of nine active components in Gegen Qinlian preparations by high-performance liquid chromatography with diode array detection.	2006 Sep	17069251
Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry.	2006 Sep 18	16730156
High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.	2007 Apr	17536728
Analysis of Central European Corydalis species by nonaqueous capillary electrophoresis-electrospray ion trap mass spectrometry.	2007 Aug 3	17395190
[Absorption of coptisine chloride and berberrubine across human intestinal epithelial by using human Caco-2 cell monolayers].	2007 Dec	18330249
Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.	2007 Dec	17891749
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008 Apr 24	17804078
[Analysis of the main components of coptis-evodia herb couple by HPLC-DAD-MS].	2008 Mar	18630268
Alkaloids from Corydalis saxicola and their anti-hepatitis B virus activity.	2008 May	18493964
Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species.	2009 Aug 24	19703289
Bear bile: dilemma of traditional medicinal use and animal protection.	2009 Jan 12	19138420
Hydroxyl radical scavenging activities of isoquinoline alkaloids isolated from Coptis chinensis.	2009 Mar	19387576
Inhibitory Effects of Coptidis rhizoma and Berberine on Cocaine-induced Sensitization.	2009 Mar	18955248
Purification of alkaloids from Corydalis yanhusuo W. T. Wang using preparative 2-D HPLC.	2009 May	19347864
Selective regulation of multidrug resistance protein in vascular smooth muscle cells by the isoquinoline alkaloid coptisine.	2010	20410605
[Simultaneous determination of the five alkaloids in Rhizoma Coptidis by nonaqueous capillary electrophoresis].	2010 Apr	20712125
[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].	2010 Dec	21438408
Quality assurance for Chinese herbal formulae: standardization of IBS-20, a 20-herb preparation.	2010 Feb 22	20175906
[Pharmacodyamic material basis of rhizoma coptidis on insulin resistance].	2010 Jul	20939284
[Simultaneous determination of six alkaloids in Coptis chinensis of different regions by RP-HPLC].	2010 Oct	21174768

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50,100 or 150mg/kg body weight daily

Route of Administration: Oral

In Vitro Use Guide

In HCT-116 cells, Coptisine exhibited cell cytotoxicity at a high rate (IC50 was 27.13 μg/mL vs 282.2 μg/mL in human colorectal epithelial cells FHC). Besides, Coptisine (2.5 μg/mL) decreased the survival rate of cells time-dependently .

Name

Type

Language

COPTISINE

Common Name

English

YHL II

Code

English

COPTISINE [MI]

Common Name

English

COPTISIN

Common Name

English

BIS(1,3)BENZODIOXOLO(5,6-A:4',5'-G)QUINOLIZINIUM, 6,7-DIHYDRO-

Systematic Name

English

7,8,13,13A-TETRADEHYDRO-2,3:9,10-BISMETHYLENEDIOXYBERBINIUM

Common Name

English

6,7-DIHYDROBIS(1,3)BENZODIOXOLO(5,6-A:4',5'-G)QUINOLIZINIUM

Systematic Name

English

ALKALOID A, FROM COPTIS GROENLANDICA

Common Name

English

BERBINIUM, 7,8,13,13A-TETRADEHYDRO-2,3:9,10-BIS(METHYLENEDIOXY)-

Common Name

English

BIS(METHYLENEDIOXY)PROTOBERBERINE

Common Name

English

Code System Code Type Description

HSDB

8323