10.1016/j.phytochem.2012.09.009
The research aimed to determine if Erythroxylum coca, the plant from which cocaine is derived, uses hydroxycinnamoyl quinate esters to store tropane alkaloids like cocaine and cinnamoyl cocaine. The study established a correlation between the levels of these alkaloids and two hydroxycinnamoyl esters of quinic acid, chlorogenic acid, and 4-coumaroyl quinate. The researchers isolated and characterized the BAHD acyltransferase enzyme responsible for the final step in hydroxycinnamoyl quinate biosynthesis and found its gene expression to correlate with tropane alkaloid accumulation. They also observed and quantified the physical interaction between chlorogenic acid and cocaine in vitro using UV and NMR spectroscopic methods. The study concluded that hydroxycinnamoyl quinate esters likely serve as complexation partners for the storage of cocaine and other coca alkaloids in E. coca.
10.1080/00397910802281429
The research develop an efficient synthetic route for creating three new polyhydroxylated amino cyclohexane derivatives (aminocyclitols) from D-(-)-quinic acid, with the potential for significant biological activities, particularly as glycosidase inhibitors. The key steps involved the highly stereoselective dihydroxylation of protected azido cyclohexene derivatives (5, 9, and 15), which were derived from D-(-)-quinic acid. The subsequent hydrogenation under acidic conditions yielded the target aminocyclitols (1, 2, and 3) with high overall yields. The study successfully demonstrated a general and efficient route for synthesizing these compounds, which are expected to be valuable for future biological studies and as intermediates in the synthesis of antibiotics. Key chemicals used in the research include D-(-)-quinic acid, KMnO4, MgSO4, trichloroacetonitrile, DBU, and various protecting and deprotecting agents such as methanesulfonyl chloride and lithium hydroxide. The conclusions highlight the high diastereoselectivity of the dihydroxylation process and the feasibility of the synthetic route, paving the way for further exploration of the biological potential of these new aminocyclitols.
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