Discrimination of Solanaceae Taxa and Quantification of Scopolamine and Hyoscyamine by ATR-FTIR Spectroscopy

Abstract

Plant species of the Solanaceae family (nightshades) contain pharmacologically active anticholinergic tropane alkaloids, e.g., scopolamine and hyoscyamine. Tropane alkaloids are of special interest, either as active principles or as starting materials for semisynthetic production of other substances. For genetic evaluation, domestication, cultivation, harvest and post-harvest treatments, quantification of the individual active principles is necessary to monitor industrial processes and the resulting finished products. Up to now, frequently applied methods for quantification are based on high performance liquid chromatography and gas chromatography optionally combined with mass spectrometry. However, alternative analytical methods have the potential to replace the established standard methods partly. In this context, attenuated total reflection-Fourier transform infrared spectroscopy enabled chemotaxonomical classification of the Solanaceae Atropa belladonna, Datura stramonium, Hyoscyamus niger, Solanum dulcamara, and Duboisia in combination with cluster analysis. Also discrimination of genotypes within species was achieved to some extent. The most characteristic scopolamine bands could be identified in attenuated total reflection-Fourier transform infrared spectra of Solanaceae leaves, which allow a fast characterisation of plants with high scopolamine content. Applying a partial least square algorithm, very good calibration statistics were obtained for the prediction of the scopolamine content (residual prediction deviation = 7.67), and moderate prediction quality could be achieved for the hyoscyamine content (residual prediction deviation = 2.48).

Key words

Solanaceae - scopolamine - hyoscyamine - ATR-FTIR spectroscopy - chemotaxonomy - PLS prediction

• References

• 1 El Bazaoui A, Bellimam MA, Soulaymani A. Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS. Fitoterapia 2011; 82: 193-197
• 2 Berkov S, Zayed R, Doncheva T. Alkaloid patterns in some varieties of Datura stramonium . Fitoterapia 2006; 77: 179-182
• 3 Berkov S, Doncheva T, Philipov S, Alexandrov K. Ontogenetic variation of the tropane alkaloids in Datura stramonium . Biochem Syst Ecol 2005; 33: 1017-1029
• 4 EFSA Panel on Contaminants in the Food Chain CONTAM. Scientific opinion on tropane alkaloids in food and feed. EFSA Journal 2013; 11: 1-113
• 5 Baranska M, Schulz H. Determination of alkaloids through infrared and Raman spectroscopy. In: Cordell GA, editor The alkaloids: Chemistry and biology. Amsterdam: The Academic Press; 2009: 217-255
• 6 Schulz H, Baranska M. Identification and quantification of valuable plant substances by IR and Raman spectroscopy. Vib Spectrosc 2007; 43: 13-25
• 7 Günzler H, Gremlich HU. IR Spectroscopy. An Introduction. 1st ed.. Weinheim: Wiley-VCH; 2002
• 8 Chalmers JM, Griffiths PR. Applications in life, pharmaceutical and natural sciences, 5th edition. Chichester: John Wiley & Sons; 2004
• 9 Movasaghi Z, Rehman S, Rehman IU. Fourier transform infrared (FTIR) spectroscopy of biological tissues. Appl Spectrosc Rev 2008; 43: 134-179
• 10 Naumann D. Infrared spectroscopy in microbiology. In: Meyers RA, editor Encyclopedia of analytical chemistry. Chichester: John Wiley & Sons; 2000: 102-131
• 11 Wilson RH, Smith AC, Kačuráková M, Saunders PK, Wellner N, Waldron KW. The mechanical properties and molecular dynamics of plant cell wall polysaccharides studied by Fourier-transform infrared spectroscopy. Plant Physiol 2000; 124: 397-405
• 12 Schulz H, Baranska M, Quilitzsch R, Schütze W. Determination of alkaloids in capsules, milk and ethanolic extracts of poppy (Papaver somniferum L.) by ATR-FT-IR and FT-Raman spectroscopy. Analyst 2004; 129: 917-920
• 13 Rana R, Müller G, Naumann A, Polle A. FTIR spectroscopy in combination with principal component analysis or cluster analysis as a tool to distinguish beech (Fagus sylvatica L.) trees grown at different sites. Holzforschung 2008; 62: 530-538
• 14 Krähmer A, Gudi G, Weiher N, Gierus M, Schütze W, Schulz H. Characterization and quantification of secondary metabolite profiles in leaves of red and white clover species by NIR and ATR-IR spectroscopy. Vib Spectrosc 2013; 68: 96-103
• 15 Sauer O, Weilemann S. Scopolamin, Hyoscyamin und Atropin – Nachtschattengewächse (Solanaceae species). In: Sauer O, Weilemann S, eds. Drogen: Eigenschaften, Wirkungen, Intoxikation. Hannover: Schlütersche GmbH & Co. KG; 2000: 46-47
• 16 ICH Expert Working Group. Validation of analytical procedures: Text and methodology Q2(R1). In: ICH Guidelines. European Union, Japan, USA. Geneva: ICH; 1994: 1-13 Available online: www.ich.org
• 17 Lill NA, Rupprecht H. ATR-IR spectroscopy for the identification of Transdermal Therapeutic Systems (TTS). Pharm Ztg 1989; 134: 139-143
• 18 Schrader B. Infrared and Raman spectroscopy methods and applications. Weinheim: Wiley-VCH Verlagsgesellschaft mbH; 1995
• 19 Schrader B. Raman/infrared atlas of organic compounds. In: Ebel HF, editor. Weinheim: Wiley-VCH; 1989