.svg) | |
| Names | |
|---|---|
| Preferred IUPAC name 4,7,8-Trimethoxyfuro[2,3-b]quinoline | |
| Other names Skimmianin; β-Fagarine; Chloroxylonine | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| EC Number |
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| KEGG | |
| UNII | |
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| Properties | |
| C14H13NO4 | |
| Molar mass | 259.261 g·mol−1 |
| Melting point | 177 °C (351 °F; 450 K)[1] |
| Hazards | |
| GHS labelling:[1] | |
 | |
| Warning | |
| H302,H315,H319 | |
| P264,P264+P265,P270,P280,P301+P317,P302+P352,P305+P351+P338,P321,P330,P332+P317,P337+P317,P362+P364,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Skimmianine is afuroquinoline alkaloid found inSkimmia japonica, a flowering plant in familyRutaceae that is native to Japan and China. It a knownacetylcholinesterase inhibitor[2]
The biosynthesis of skimmianine starts fromanthranilic acid,[3] which is very abundant in the family Rutaceae. By combining anthranilic acid acetate, anthraniloyl-CoA is formed as a starting unit and able to extend side chain by adding malonyl-CoA byClaisen condensation. Next, lactam is formed through the cyclization and generate a heterocyclic system, leading the dienol tautomer adopt the 4-hydroxy quinolone tautomer, which is 4-hydroxy-2-quinolone.
With the formation of quinolone, alkylation is happening at C-3 position by introducing dimethylallyl diphosphate. Another key step is the cyclization on the dimethylallyl sidechain, forming a new heterocyclic five-member-ring.[4] Platydesmine is then forming an intermediate through the oxidative cleavage reaction[5] by losing an isopropyl group to form dictamine. Finally, skimmianine is formed through the hydroxylation of dictamine.
