Coptisine

Chemical compound From Wikipedia, the free encyclopedia

Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis),[1] greater celandine, and opium.[2] 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.[3]

Quick facts Names, Identifiers ...
Coptisine
Names
IUPAC name
7,8,13,13a-Tetradehydro-2′H,2′′H-bis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:9,10]berbin-7-ium
Systematic IUPAC name
6,7-Dihydro-2H,10H-5λ5-[1,3]dioxolo[4,5-g][1,3]dioxolo[4′,5′:7,8]isoquinolino[3,2-a]isoquinolin-5-ylium
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • 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 checkY
    Key: XYHOBCMEDLZUMP-UHFFFAOYSA-N checkY
  • O1c3c(OC1)c2c[n+]6c(cc2cc3)c5cc4OCOc4cc5CC6
Properties
C19H14NO4+
Molar mass 320.319
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Close

Biosynthesis

Coptisine is produced from tetrahydrocoptisine by an oxidation reaction catalysed by the enzyme tetrahydroberberine oxidase.[4][5]

+ H+
 
 
2 O2
2 H2O2
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 

References

Related Articles

Wikiwand AI