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Synthesis of 1-O-methylchlorogenic acid: Reassignment of structure for MCGA3 isolated from bamboo (Phyllostachys edulis) leaves

Permanent URL:
http://handle.nal.usda.gov/10113/58569
File:
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Abstract:
The first synthesis of 1-O-methylchlorogenic acid is described. The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involved C-1 alkylation of the known (-)-4,5-cyclohexylidenequinic acid lactone followed by methoxide opening to the hydroxyl ester. Acylation of the C-5 hydroxyl group followed by sequential removal of protecting groups afforded 1-O-methylchlorogenic acid. The NMR spectroscopic characteristics of this compound did not coincide with those reported for the original isolation from bamboo (Phyllostachys edulis) leaves of the compound designated MCGA3. Comparison of the published spectroscopic data reported for MCGA3, with both reported literature values and spectroscopic data obtained from an authentic sample, lead to the conclusion that the compound isolated from bamboo (Phyllostachys edulis) leaves is instead methyl chlorogenate.
Author(s):
Wayne E. Zeller
Subject(s):
Phyllostachys edulis , acylation , alkylation , bioactive properties , chemical structure , chlorogenic acid , leaf extracts , leaves , nuclear magnetic resonance spectroscopy
Source:
Journal of Agricultural and Food Chemistry 2014 v.62
Language:
English
Year:
2014
Collection:
Journal Articles, USDA Authors, Peer-Reviewed
Rights:
Works produced by employees of the U.S. Government as part of their official duties are not copyrighted within the U.S. The content of this document is not copyrighted.