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Skimmianine is a furoquinoline alkaloid found in '' Skimmia japonica'', a flowering plant in family
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Rutaceae
The Rutaceae () is a family (biology), family, commonly known as the rueRUTACEAE
in Bo ...
that is native to Japan and China. It is a known in Bo ...
acetylcholinesterase inhibitor
Acetylcholinesterase inhibitors (AChEIs) also often called cholinesterase inhibitors, inhibit the enzyme acetylcholinesterase from breaking down the neurotransmitter acetylcholine into choline and acetate, thereby increasing both the level an ...
.
Biosynthesis
The biosynthesis of skimmianine starts fromanthranilic acid
Anthranilic acid is an aromatic acid with the formula C6H4(NH2)(CO2H) and has a sweetish taste. The molecule consists of a benzene ring, ''ortho''-substituted with a carboxylic acid and an amine. As a result of containing both acidic and basic f ...
, 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
The Claisen condensation is a carbon–carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base. The reaction produces a β-keto ester or a β- diketone. It is named ...
. 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. Platydesmine is then forming an intermediate through the oxidative cleavage reaction by losing an isopropyl group to form dictamine. Finally, skimmianine is formed through the hydroxylation of dictamine.
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References