Methyl-β-cyclodextrin Inclusion Complex with β-Caryophyllene: Preparation, Characterization, and Improvement of Pharmacological Activities

Abstract

β-Caryophyllene (BCP) is a sesquiterpene that shows high potential in pharmacological applications. However, these have been drastically limited by the respective volatility and poor water solubility. The present study investigates the formation of inclusion complexes between BCP and methyl-β-cyclodextrin (MβCD) and shows that these complexes promote a significant improvement of the anti-inflammatory, gastric protection, and antioxidant activities relative to neat BCP. It is shown that the solubility of BCP is significantly increased through complexation in phase solubility studies. Inclusion complexes with MβCD in solid state were prepared by three different methods, kneading, rotary evaporation, and lyophilization, with the latter confirmed by differential scanning calorimetry, Fourier transformed infrared spectroscopy, scanning electron microscopy, 1H NMR spectroscopy, and molecular dynamics studies. This study provides for the first time a full characterization of inclusion complexes between BCP and MβCD and highlights the impact of complex formation upon pharmacological activity.

Inclusion Complexes of Citronella Oil with β-Cyclodextrin for Controlled Release in Biofunctional Textiles

“…On the other hand, from the FTIR spectrum of the inclusion complex it is possible to observe the presence of bands at 1720.77 and 1641.25 cm −1 , the first characterized by the band of the C=O aldehyde carbonyl group and the second by the C=C alkene stretch, groups that are present in the citronella molecule. This result was found in the work of Santos et al [40], in which they performed the inclusion of the essential oil of citronella in cyclodextrin.…”

“…Figure 4a shows that the spectrum corresponding to citronella allows for observation of the presence of the vibrational mode of CH carbonyl bonded aldehyde and C=O carbonyl bonded aldehyde [40], with bands corresponding to 2856.20 and 1720.77 cm −1 , respectively. CH 2 asymmetric stretching and CH 3 asymmetric bending are also observed as bands in the regions 2917.91 and 1446.06 cm −1 .…”

Preparation and Characterization of Liposomal β-Caryophyllene (Rephyll) by Nanofiber Weaving Technology and Its Effects on Delayed Onset Muscle Soreness (DOMS) in Humans: A Randomized, Double-Blinded, Crossover-Designed, and Placebo-Controlled Study

“…The strong band was detected at 885 cm –1 in the BCP spectrum, which is assigned to out-of-plane deformation vibration of =CH distinctive of the BCP molecule. 31 However, this band is not observed in the spectrum of Rephyll ( Figure 4 b), maybe due to the constraint of the vibration because of the encapsulation process. At 858 cm –1 , a band was identified in the spectrum of Rephyll ( Figure 4 b), which characterized the distinctive composition of cellulose, which is presented in the NF.…”

Toxicological Evaluation of Some Essential Oils Obtained from Selected Romania Lamiaceae Species in Complex with Hydroxypropyl - gamma-cyclodextrin

“…Menezes et al indicated that (-)-linalool was successfully incorporated in β-cyclodextrin [14]. In a study conducted by Santos and coworkers it was shown that following inclusion of the sesquiterpene β-Caryophyllene in methyl-β-cyclodextrin, a significant improvement of biological properties were recorded [15].…”