Syntheses of chiral 1,8-cineole-metabolites and determination of their enantiomeric composition in human urine after ingestion of 1,8-cineole-containing capsules

Schaffarczyk M, Balaban TS, Rychlik M, Büttner A (2013)

Publication Type: Journal article

Publication year: 2013

Journal

ChemPlusChem Wiley

Publisher: Wiley-VCH Verlag

Book Volume: 78

Pages Range: 77-85

Journal Issue: 1

DOI: 10.1002/cplu.201200253

Abstract

The chiral metabolites in human urine were investigated after ingestion of a 1,8-cineole (eucalyptol)-containing enterocoated capsule (Soledum). For identification of the various enantiomers the enantiomerically pure (-/+)-α2-hydroxy-1,8- cineole, (-/+)-β2-hydroxy-1,8-cineole, (-/+)-9-hydroxy-1,8-cineole, and (-/+)-2-oxo-1,8-cineole were prepared. To achievethis aim, after acetylation of the synthesized racemic 2-and 9-hydroxy-1,8-cineoles, pig liver esterase- or yeast-mediated hydrolysis provided the (-)-alcohols with their antipodal(+)-acetates with enantiomeric excess of 33-100 %. Dess-Martin periodinane oxidation of the alcohol (+)-α2-hydroxy-1,8-cineole, obtained by hydrolysis of the resolved acetate, provided the corresponding (+)-2-oxo-1,8-cineole, meanwhile the oxidation of (-)-α2-hydroxy-1,8-cineole gave (-)-2-oxo-1,8-cineole. Using these standards seven metabolites (+/-)-α2-hydroxy-1,8-cineole, (+/-)-β2-hydroxy-1,8-cineole, (+/-)-α3-hydroxycineole,(+/-)-3-oxo-1, 8-cineole, 4-hydroxy-1,8-cineole, 7-hydroxy-1,8-cineole, and (+/-)-9-hydroxy-1,8-cineole, all liberated from their glucuronides, were identified in urine by GCMS on a chiral stationary phase after consumption of 10 mg of 1,8-cineole. Metabolite screening using 2H3-1,8- cineol as the internal standard revealed (+/-)-α2-hydroxy-1,8-cineole as the predominant metabolite followed by (+/-)-9-hydroxy-1,8-cineole. Furthermore, the results showed that one enantiomer is always formed preferentially. © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Authors with CRIS profile

Andrea Büttner

Involved external institutions

Fraunhofer-Institut für Verfahrenstechnik und Verpackung (IVV) DE Germany (DE) Aix-Marseille University / Aix-Marseille Université FR France (FR) Technische Universität München (TUM) DE Germany (DE)

How to cite

APA:

Schaffarczyk, M., Balaban, T.S., Rychlik, M., & Büttner, A. (2013). Syntheses of chiral 1,8-cineole-metabolites and determination of their enantiomeric composition in human urine after ingestion of 1,8-cineole-containing capsules. ChemPlusChem, 78(1), 77-85. https://doi.org/10.1002/cplu.201200253

MLA:

Schaffarczyk, Monika, et al. "Syntheses of chiral 1,8-cineole-metabolites and determination of their enantiomeric composition in human urine after ingestion of 1,8-cineole-containing capsules." ChemPlusChem 78.1 (2013): 77-85.

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