NDLI: Inclusion complexes with cyclodextrin and usnic acid

Content Provider	Springer Nature Link
Author	Nikolić, Vesna Stanković, Mihajlo Nikolić, Ljubiša Nikolić, Goran Ilić Stojavić, Snežana Popsavin, Mirjana Zlatković, Saša Kundaković, Tatjana
Copyright Year	2012
Abstract	Molecular inclusion complexes of usnic acid (UA) with β-cyclodextrin (β-CD) and 2-hydroxypropyl β-cyclodextrin (HP β-CD) were prepared by the co-precipitation method in the solid state in the molar ratio of 1:1. Structural complexes characterization was based on different methods, FTIR, $^{1}$H NMR, XRD and DSC. Parallel to the complex by the above methods, corresponding physical mixtures of UA with cyclodextrins and complexing agents (β-CD, HP β-CD and UA) were analyzed. The results of DSC analysis showed that, at around 200 °C, the endothermal peak in the complexes with cyclodextrins originating from the UA melting has disappeared. Complex diffractogram patterns do not contain peaks characteristic for the pure UA. They are more appropriate to cyclodextrin diffractogram. This fact points to the molecular encapsulation of UA in the cyclodextrin cavity. Chemical shifts in $^{1}$H NMR spectra after the inclusion of UA into the cyclodextrin cavity, especially H-3 protons (0.0012 and 0.0102 ppm in the β-CD and HP β-CD, respectively) and H-5 and H-6 (0.0134 ppm) and hydrogen from CH$_{3}$ (0.0073 ppm) HP β-CD also points to the formation of molecular inclusion complexes. The improved solubility of UA in water was achieved by molecular incapsulation. In the complex with β-CD the solubility is 0.3 mg/cm$^{3}$, with HP β-CD 4.2 mg/cm$^{3}$ while the uncomplexed UA solubility is 0.06 mg/cm$^{3}$. The microbial activity of UA and both complexes was tested against eight bacteria and two fungi and during the test no reduced activity of UA in the complexes was observed.
Starting Page	173
Ending Page	182
Page Count	10
File Format	PDF
ISSN	09230750
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume Number	76
Issue Number	1-2
e-ISSN	15731111
Language	English
Publisher	Springer Netherlands
Publisher Date	2012-06-20
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Usnic acid β-cyclodextrin 2-hydroxypropyl β-cyclodextrin Inclusion complex Solubility Antimicrobial activity Organic Chemistry Food Science Crystallography
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Food Science

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