Determination of the enantiomeric purity of scopolamine isolated from plant extract using achiral/chiral coupled column chromatography.
The optical purity of scopolamine derived from Datura sanguinea was determined using coupled column chromatography. A C18 column was used to separate scopolamine from the additional alkaloids and other biological material present in the vegetal extract. The C18 column was coupled through a six-port switching valve to two beta-cyclodextrin columns in series which were used to resolve the scopolamine enantiomers. A single acetylated beta-cyclodextrin column gives equivalent results to the native cyclodextrin columns because of slightly higher enantioselectivity for scopolamine. A multistep extraction procedure is used to isolate scopolamine from the vegetal material. 4-6% of the scopolamine in the final extract was found to be the d enantiomer. Sample extracts as well as commercial scopolamine hydrobromide were treated under various conditions commonly encountered during typical commercial extraction procedures and analyzed in order to determine if the d enantiomer was present in the original material or if it was produced during the extraction process and, if so, determine which step and conditions contribute to racemization. Both the salt and the extract were found to be susceptible to racemization under basic conditions (greater than or equal to pH 9) although the extract appeared to be more susceptible than the salt. Tropic acid formed from the hydrolysis of scopolamine seemed to be completely racemized even though the remaining scopolamine was only partially racemized. Within experimental error, no d enantiomer was found in the original fresh plant material.
Stalcup
A M
AM
Department of Chemistry, University of Missouri-Rolla 65401.
Faulkner
J R
JR
Tang
Y
Y
Armstrong
D W
DW
Levy
L W
LW
Regalado
E
E
D000107:Acetylation; D002845:Chromatography / Q000379:methods*; D003505:Cyclodextrins; D006863:Hydrogen-Ion Concentration; D010936:Plant Extracts / Q000032:analysis*; D012601:Scopolamine / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
D003505:Cyclodextrins; D010936:Plant Extracts; D047392:beta-Cyclodextrins; D012601:Scopolamine; C031215:betadex