Columbamine
Organic chemical
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| IUPAC name
3,9,10-Trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol | |
| Other names
Dehydroisocorypalmine | |
| Identifiers | |
3D model (JSmol) |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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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]
-Isocorypalmine.svg)
