Columbamine

Columbamine
Names
IUPAC name
3,9,10-Trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol
Other names
Dehydroisocorypalmine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
SMILES
  • COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC(=C(C=C4CC3)OC)O)OC
Properties
Chemical formula
 C20H20NO4+
Molar mass 338.382 g·mol−1
Melting point 280–282 °C (536–540 °F; 553–555 K) (chloride salt)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[2] It has usually been isolated and characterised as its chloride salt.[1]

Occurrence

Columbamine has been found in several Berberis species, Coptis chinensis[3] and Jateorhiza palmata.[1]

Biosynthesis

The biosynthesis of columbamine starts with tyrosine and proceeds via (S)-reticuline in a pathway leading to benzylisoquinoline alkaloids.[4][5] The final step is catalysed by the enzyme tetrahydroberberine oxidase, which oxidises (S)-isocorypalmine:[1][6]

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

References

  1. ^ a b c d 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.
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