Analytical and in silico study of the inclusion complexes between tropane alkaloids atropine and scopolamine with cyclodextrins

Abstract

Datura stramonium L. (Solanaceae) possesses a rich tropane alkaloids (TAs) spectrum. The plant contains, in particular, the allelopathic compounds scopolamine and atropine, which are poorly soluble in water, thus limiting their use in agrochemical formulations as biocidal and deterrent agents against herbivore insects. The efficacy of the hydrophobic TAs extracts could be increased with the improvement of their dissolution/leaching properties. This is important for improving screening and test performance and for elucidating the activity of environmentally friendly agricultural approaches, with new perspectives for the production and use of those biodegradable insecticidal products. The present study explores the aspects of atropine and scopolamine complexation with cyclodextrin (CDs) through FT-IR and UV–Vis spectroscopies. In addition, the structures of the inclusion complex of atropine, scopolamine and β-CD have been investigated by molecular modeling techniques. The results obtained indicate that β-CDs are a promising carriers for improving the properties of TAs, therefore increasing their application potential in agrochemical formulations. Graphic abstract

Synthesis and Characterization of an Inclusion Complex of dl-Aminoglutethimide with β-Cyclodextrin and Its Innovative Application in a Biological System: Computational and Experimental Investigations

“… 12 Cyclodextrins are able to modify the pharmacological properties of the encapsulated active substances such as solubility, bioavailability, chemical stability, dispersibility, and toxicity; thus, by the preparation of inclusion complexes with cyclodextrin molecules it can be possible to enhance or improve such properties of the active compounds. 13 − 16 …”

“…The most widely accepted host for complex formation is β-CD due to its suitable cavity diameter and low production cost. , β-Cyclodextrin consists of seven α- d -glucopyranose units joined by α-1,4-linkages . Cyclodextrins are able to modify the pharmacological properties of the encapsulated active substances such as solubility, bioavailability, chemical stability, dispersibility, and toxicity; thus, by the preparation of inclusion complexes with cyclodextrin molecules it can be possible to enhance or improve such properties of the active compounds. − …”

Technologies for Solubility, Dissolution and Permeation Enhancement of Natural Compounds

“…The author stated that directly proportional behavior of solubility and beta cyclodextrins was observed. Analytical and in silico study was of the inclusion complexes between tropane alkaloids atropine and scopolamine with cyclodextrins [87]. The most recent study by Ko et al (2021) also highlighted the use of steviol glycosides for the conversion of poorly water soluble curcumin into water soluble curcuminoids (Curcumin-steviol glycosides complex) for antiviral theapy.…”

Spectroscopic investigation and chemical fingerprint of Datura innoxia dry biomass

“…The IR characteristic wave numbers range and bending vibrations (Table 1) were compared with literature data [2,6,[24][25][26][27][28]. Referring to the literature [25], the IR characteristic fingerprint peaks region for Datura innoxia biomass samples are in the range of 1800-600 cm −1 .…”

“…Referring to the literature, the FTIR spectrum of tropane alkaloids is characterized by absorption peaks for the stretching vibrations of various functional groups; 3700-3000 cm −1 (O-H alcohol, N-H amine), 3104 cm −1 (aromatic C-H), 1738 cm −1 (C=O ester), 1650 cm −1 (N-H bending), 1496 cm −1 (C=C aromatic), 1600-1300 cm −1 (C-H bending alkane), 1200 cm −1 (C-O ester), 1050 cm −1 (C-O primary alcohol), 900-700 cm −1 (C-H aromatic bending vibrations) [28].…”