Coptisine

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).

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]

Biosynthesis

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

2D representation of the chemical structure of Q27102969.
tetrahydrocoptisine
+ H+
 
 
2 O2
2 H2O2
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of coptisine .
coptisine


References

  1. ^ Chen J, Wang F, Liu J, Lee FS, Wang X, Yang H (April 2008). "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". Analytica Chimica Acta. 613 (2): 184–95. doi:10.1016/j.aca.2008.02.060. PMID 18395058.
  2. ^ Hakim, Sohrab A. E.; Mijović, Valerie; Walker, James (1961). "Distribution of Certain Poppy-Fumaria Alkaloids and a Possible Link with the Incidence of Glaucoma". Nature. 189 (4760): 198–201. doi:10.1038/189198a0. PMID 13710637.
  3. ^ Tang J, Feng Y, Tsao S, Wang N, Curtain R, Wang Y (October 2009). "Berberine and Coptidis rhizoma as novel antineoplastic agents: a review of traditional use and biomedical investigations". Journal of Ethnopharmacology. 126 (1): 5–17. doi:10.1016/j.jep.2009.08.009. hdl:10722/127599. PMID 19686830.
  4. ^ Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia; Duan, Baozhong; Sun, Wei; Gao, Ranran; Chen, Shilin; Xu, Zhichao (2024). "Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids". Natural Product Reports. 41 (11): 1787–1810. doi:10.1039/D4NP00029C. PMID 39360417.
  5. ^ "Coptisine biosynthesis". PubChem. Retrieved 2026-02-06.
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