Tetrahydrocoptisine
Chemical compound
From Wikipedia, the free encyclopedia
Tetrahydrocoptisine (also known as stylopine) is an alkaloid isolated from Corydalis species.[1][2]
(S)-tetrahydrocoptisine | |
| Names | |
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| IUPAC name
5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-2,4(8),9,15(23),16(20),21-hexaene | |
| Other names
Stylopine | |
| Identifiers | |
3D model (JSmol) |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C19H17NO4 | |
| Molar mass | 323.348 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
The (S)-isomer of tetrahydrocoptisine is produced when the enzyme (S)-stylopine synthase acts on (S)-cheilanthifoline to form a second methylenedioxy ring:[2][3]
-(S)-Cheilanthifoline.svg)
Metabolism
Tetrahydrocoptisine is converted to coptisine by an oxidation reaction catalysed by the enzyme tetrahydroberberine oxidase.[2][4]
Alternatively, it can be converted into protopine in two steps. The first is a methylation reaction by the enzyme (S)-tetrahydroprotoberberine N-methyltransferase using the cofactor, S-adenosyl methionine (SAM). This transfers a methyl group, giving S-adenosyl-L-homocysteine (SAH).[2][5]
-cis-N-methylstylopine.svg)
Then the product, (S)-cis-N-methylstylopine, is oxidised by the enzyme methyltetrahydroprotoberberine 14-monooxygenase:[2][6]
