Canadine
Chemical compound
From Wikipedia, the free encyclopedia
Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.
(S)-(-)-canadine | |
| Names | |
|---|---|
| IUPAC name
9,10-Dimethoxy-2′H-[1,3]dioxolo[4′,5′:2,3]berbine | |
| Systematic IUPAC name
(13aS)-9,10-Dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline | |
| Other names
(S)-Tetrahydroberberine; Xanthopuccine | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.023.468 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C20H21NO4 | |
| Molar mass | 339.391 g·mol−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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Biosynthesis
Metabolically, (S)-canadine is derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIA structural subgroups, through three enzymatic steps: 1) berberine bridge enzyme to (S)-scoulerine; 2) (S)-scoulerine 9-O-methyltransferase to (S)-tetrahydrocolumbamine; and 3) (S)-canadine synthase/CYP719A21 to (S)-canadine.[1]
(S)-Canadine is the immediate metabolic precursor of berberine, which is produced through the action of the enzyme tetrahydroberberine oxidase.[1]
It is also an intermediate in the biosynthesis of noscapine, which is likewise a benzylisoquinoline alkaloid, but of the phthalideisoquinoline structural subgroup.[2][3]
(S)-Canadine, berberine, palmatine, and hydrastine are the major alkaloids present in goldenseal.[4] In Corydalis cava, the enzyme berberine reductase converts berberine back to canadine but as the (R) enantiomer of the product.[5]
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This type of inversion of stereochemistry allows both enantiomers of some alkaloids to be present in this species.[6]
Effects
A number of in vitro effects of (S)-canadine have been reported. It stimulates myogenesis and inhibits muscle protein degradation.[7] (S)-Canadine blocks K(ATP) channels in dopamine neurons.[8][9] (S)-Canadine has displayed antioxidant activity: though it lacked any demonstrable cytotoxic effect in three unique cell cultures, it was observed to possess antioxidant activity against free radical-induced oxidative injury.[10][11] (S)-Canadine can block voltage-dependent calcium channels, but at a level significantly lower than that of verapamil.[12]
