Skimmianine

Skimmianine

Names
Preferred IUPAC name 4,7,8-Trimethoxyfuro[2,3-b]quinoline
Other names Skimmianin; β-Fagarine; Chloroxylonine
Identifiers
CAS Number	83-95-4 Y
3D model (JSmol)	Interactive image
PubChem CID	6760
UNII	4E1KLC380B Y
SMILES COC1=C(C2=C(C=C1)C(=C3C=COC3=N2)OC)OC
Properties
Chemical formula	C14H13NO4
Molar mass	259.261 g·mol−1
Melting point	177 °C (351 °F; 450 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Skimmianine is a furoquinoline alkaloid found in Skimmia japonica, a flowering plant in family Rutaceae that is native to Japan and China. It is also a strong acetylcholinesterase (AChE) inhibitor.^[2]

The biosynthesis of skimmianine starts from anthranilic 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 by Claisen 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.

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