Cheilanthifoline
Chemical compound
From Wikipedia, the free encyclopedia
(S)-Cheilanthifoline is a benzylisoquinoline alkaloid (BIA) which has been isolated from Corydalis cheilanthifolia and Argemone mexicana.[1][2] It is derived from (S)-reticuline, a pivotal intermediate in the biosynthesis of numerous BIAs. (S)-cheilanthifoline is the immediate precursor of the BIA (S)-stylopine ((S)-stylopine synthase/CYP719A20), which is the precursor for the alkaloids protopine and sanguinarine.[3][4]
-(S)-Cheilanthifoline.svg)
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| Names | |
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| IUPAC name
2-Methoxy-2′H-[1,3]dioxolo[4′,5′:9,10]berbin-3-ol | |
| Systematic IUPAC name
(6aS)-9-Methoxy-6,6a,11,14-tetrahydro-2H,12H-[1,3]dioxolo[4,5-h]isoquinolino[2,1-b]isoquinolin-8-ol | |
| Other names
(S)-Cheilanthifoline | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
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| KEGG | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C19H19NO4 | |
| Molar mass | 325.364 g·mol−1 |
| Melting point | 184 °C (363 °F; 457 K)[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
Cheilanthifoline is produced from the benzylisoquinoline alkaloid, scoulerine, by the enzyme (S)-cheilanthifoline synthase.[4][5]
Scoulerine is one of the products derived from (S)-reticuline.[1]
Metabolism
Cheilanthifoline is the precursor to other alkaloids.[4][6] For example, (S)-stylopine (also known as tetrahydrocoptisine) is produced when the enzyme (S)-stylopine synthase forms a second methylenedioxy ring:[7]
