Columbamine

Columbamine
Names
IUPAC name
3,9,10-Trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol
Other names
Dehydroisocorypalmine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-17(22)19(24-2)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1
    Key: YYFOFDHQVIODOQ-UHFFFAOYSA-O
  • COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)O)OC
Properties
C20H20NO4+
Molar mass 338.382 g·mol−1
Melting point 280–282 °C (536–540 °F; 553–555 K) (chloride salt)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Columbamine is an isoquinoline alkaloid made up of four rings, two of which contain nitrogen. It is related to berberine but without its methylenedioxy group. Columbamine is also called dehydroisocorypalmine. It has usually been isolated and characterised as its chloride salt.

Occurrence

Columbamine has been found in several Berberis species, Coptis chinensis and Jateorhiza palmata.

Biosynthesis

The biosynthesis of columbamine starts with tyrosine and proceeds via (S)-reticuline in a pathway leading to benzylisoquinoline alkaloids. The final step is catalysed by the enzyme tetrahydroberberine oxidase, which oxidises (S)-isocorypalmine:

2D representation of the chemical structure of Q27102599.
(S)-isocorypalmine
+ 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 columbamine .
columbamine

Metabolism

Columbamine is converted to berberine by the enzyme columbamine oxidase:

2 columbamine
 
 
O2
2 H2O
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2
 
2D representation of the chemical structure of berberine .
berberine

A methylation reaction catalysed by columbamine O-methyltransferase produces palmatine. The methyl group comes from the cofactor, S-adenosyl methionine (SAM). This enzyme was characterised from Berberis wilsoniae.

2D representation of the chemical structure of columbamine .
columbamine
+ SAM
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of palmatine .
palmatine
+ SAH
 


References

  1. 1 2 3 4 Mascavage, Linda M.; Jasmin, Serge; Sonnet, Philip E.; Wilson, Michael; Dalton, David R. (2010). "Alkaloids". Ullmann's Encyclopedia of Industrial Chemistry. p. 54. doi:10.1002/14356007.a01_353.pub2. ISBN 978-3-527-30385-4.
  2. ↑ PubChem. "Columbamine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-29.
  3. ↑ Wu-Chang Chuang; Dun-Shyurng Young; Lilian Kao Liu; Shuenn-Jyi Sheu (1996). "Liquid chromatographic-electrospray mass spectrometric analysis of Coptidis Rhizoma". Journal of Chromatography A. 755: 19–26. doi:10.1016/S0021-9673(96)00591-2.
  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. ↑ Begley, Tadhg P. (2009). Encyclopedia of Chemical Biology. Vol. 10. Wiley. pp. 1569–1570. doi:10.1002/cbic.200900262. ISBN 978-0-471-75477-0.
  6. ↑ Enzyme 1.3.3.8 at KEGG Pathway Database.
  7. ↑ Rueffer M, Zenk MH (1985). "Berberine synthesis, the methylenedioxy group forming enzyme in berberine synthesis". Tetrahedron Lett. 26 (2): 201–202. doi:10.1016/S0040-4039(00)61879-8.
  8. ↑ Rueffer M, Amann M, Zenk MH (1986). "S-Adenosyl-L-methionine:columbamine O-methyltransferase, a compartmentalized enzyme in protoberberine biosynthesis". Plant Cell Reports. 5 (3): 182–185. Bibcode:1986PCelR...5..182R. doi:10.1007/BF00269113. PMID 24248127.