7785-53-7Relevant articles and documents
Synthesis of Aristoquinoline Enantiomers and Their Evaluation at the α3β4 Nicotinic Acetylcholine Receptor
Argade, Malaika D.,Straub, Carolyn J.,Rusali, Lisa E.,Santarsiero, Bernard D.,Riley, Andrew P.
supporting information, p. 7693 - 7697 (2021/08/16)
The first synthesis of aristoquinoline (1), a naturally occurring nicotinic acetylcholine receptor (nAChR) antagonist, was accomplished using two different approaches. Comparison of the synthetic material's spectroscopic data to that of the isolated alkaloid identified a previously misassigned stereogenic center. An evaluation of each enantiomer's activity at the α3β4 nAChR revealed that (+)-1 is significantly more potent than (-)-1. This unexpected finding suggests that naturally occurring 1 possesses the opposite absolute configuration from indole-containing Aristotelia alkaloids.
Stolonidiol: Synthesis, Target Identification, and Mechanism for Choline Acetyltransferase Activation
Mason, Jeremy W.,Schmid, Cullen L.,Bohn, Laura M.,Roush, William R.
supporting information, p. 5865 - 5869 (2017/05/04)
Stolonidiol, a marine natural product, has been reported to potentiate the activity of choline acetyltransferase (ChAT), the enzyme that produces the neurotransmitter acetylcholine. Here we report the total synthesis of stolonidiol starting from (R)-(+)-limonene. To identify the mechanism by which ChAT activity is increased, we sought to identify the biological target of stolonidiol. We show that stolonidiol binds to the phorbol ester binding site of protein kinase C (PKC), induces translocation of PKC to the cell membrane, and activates kinase activity. Furthermore, we confirmed the increase in ChAT activity observed upon treatment of cells with stolonidiol and show that this effect is mediated by PKC. Collectively, our data strongly suggest that PKC activation by stolonidiol is responsible for the resulting potentiation of ChAT activity.
Enantioselective synthesis of α-terpineol and nephthenol by intramolecular acyloxazolidinone enolate alkylations
Jin, Yinghua,Coates, Robert M.
, p. 2902 - 2904 (2008/09/18)
Enolate anions generated from norterpenyl bromides bearing oxazolidinone chiral auxiliaries at the chain termini underwent efficient, stereo-biased cyclizations to form 6- and 14-membered rings in novel synthetic routes to α-terpineol and nephthenol enantiomers. The Royal Society of Chemistry 2006.
