Determination Of The Enantiomeric Purity Of Scopolamine Isolated From Plant Extract Using Achiral/chiral Coupled Column Chromatography

Abstract

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 β‐cyclodextrin columns in series which were used to resolve the scopolamine enantiomers. A single acetylated β‐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 acemization. Both the salt and the extract were found to be susceptible to racemization under basic conditions (≥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. Copyright © 1991 John Wiley & Sons, Ltd.

Department(s)

Chemistry

International Standard Serial Number (ISSN)

1099-0801; 0269-3879

Document Type

Article - Journal

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2023 Wiley, All rights reserved.

Publication Date

01 Jan 1991

PubMed ID

2032020

Link to Full Text

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