Inclusion Complexes of Copaiba (Copaifera multijuga Hayne) Oleoresin and Cyclodextrins: Physicochemical Characterization and Anti-Inflammatory Activity

Abstract

Complexation with cyclodextrins (CDs) is a technique that has been extensively used to increase the aqueous solubility of oils and improve their stability. In addition, this technique has been used to convert oils into solid materials. This work aims to develop inclusion complexes of Copaifera multijuga oleoresin (CMO), which presents anti-inflammatory activity, with β-cyclodextrin (β-CD) and hydroxypropyl-β-cyclodextrin (HP-β-CD) by kneading (KND) and slurry (SL) methods. Physicochemical characterization was performed to verify the occurrence of interactions between CMO and the cyclodextrins. Carrageenan-induced hind paw edema in mice was carried out to evaluate the anti-inflammatory activity of CMO alone as well as complexed with CDs. Physicochemical characterization confirmed the formation of inclusion complex of CMO with both β-CD and HP-β-CD by KND and SL methods. Carrageenan-induced paw edema test showed that the anti-inflammatory activity of CMO was maintained after complexation with β-CD and HP-β-CD, where they were able to decrease the levels of nitrite and myeloperoxidase. In conclusion, this study showed that it is possible to produce inclusion complexes of CMO with CDs by KND and SL methods without any change in CMO’s anti-inflammatory activity.

Development and Evaluation of Antimicrobial and Modulatory Activity of Inclusion Complex of Euterpe oleracea Mart Oil and β-Cyclodextrin or HP-β-Cyclodextrin

“…Figure 2 depicts the FT-IR spectra of EOO, β-CD, HP-β-CD and the EOO-β-CD and EOO-HP-β-CD inclusion complexes obtained by either kneading (KND) or slurry (SL). The EOO spectrum ( Figure 2A) showed relevant bands at wavenumbers of 2924-2849, 1745, 1458 and 1161 cm −1 that can be assigned to C-H stretching vibrations, C=O stretching vibrations, C=C asymmetric deformation and C-O stretching vibrations, respectively, while the β-CD spectrum ( Figure 2B) showed others at 3302, 1155 and 1024 cm −1 , corresponding to O-H stretching vibrations, C-O asymmetric deformation and C-O-C symmetric stretching vibrations, thereby confirming the results of Pinheiro et al [2]. As expected, the HP-β-CD spectrum (Figure 2E) exhibited the same characteristic bands detected for β-CD, besides the additional band at 2918 cm −1 corresponding to C-H stretching vibrations, confirming the observations by Medarević et al [35].…”

“…Similarly to what observed by Pinheiro et al [2], HP-β-CD showed an endothermic peak ( Figure 6B) with Tonset = 37.25 °C (ΔH = 6.47 J/g and Tpeak = 37.05 °C) related to water release from its β-CD exhibited an endothermic peak ( Figure 6A) involving ∆H = 231.02 J/g with Tonset = 30.94 • C and Tpeak = 73.71 • C, likely due to water release from its cavity, and a second event occurred at Tonset = 223.50 • C (∆H = 0.75 J/g and Tpeak = 226.68 • C), similarly to the observations of Nascimento et al [3]. It was not possible to identify eventual endothermic events related to β-CD mass loss at high temperatures [2,40] because a maximum temperature of 300 • C was set in this study. β-CD complexes obtained by KND and SL showed similar behavior ( Figure 6A) with Tonset = 27.07 • C (∆H = 48.46 J/g and Tpeak = 42.72 • C) and 24.07 • C (∆H = 142.10 J/g and Tpeak = 48.86 • C), respectively, both related to dehydration, but occurring at lower temperatures when compared to β-CD.…”

“…Similarly to what observed by Pinheiro et al [2], HP-β-CD showed an endothermic peak ( Figure 6B) with Tonset = 37.25 • C (∆H = 6.47 J/g and Tpeak = 37.05 • C) related to water release from its surface, and a second event with Tonset = 240.39 • C (∆H = 1.98 J/g and Tpeak = 264.92 • C) related to the onset of mass loss, starting at 241.89 • C on the TG curve ( Figure 5B). HP-β-CD complexes obtained by KND and SL behaved similarly ( Figure 6B) with Tonset = 28.49 • C (∆H = 60.40 J/g and Tpeak = 68.32 • C) and Tonset = 37.33 • C (∆H = 35.79 J/g and Tpeak = 101.53 • C), respectively, both related to dehydration.…”

“…According to Martins da Silva et al [1], the chemical constituents present in a variety of oils exhibit different biological activities. The resin oil of Copaifera multijuga, commonly used as an anti-inflammatory [2], the essential oil of Ocimum basilicum, applied as an antihyperalgesic [3], and the Allium sativum oil, displaying antioxidant and antimicrobial activities [4] similar to those of Euterpe oleracea oil [5,6], are a few examples.…”

In vitro evaluation of PVA gels loaded with Copaiba Oil and Duotrill®

“…However, sample PVA-O presented also bands related to copaiba oil. The copaiba oil bands were observed at: 2922 cm -1 , ν(-CH); 2854 cm -1 , ν(-CH 2 ); 1743 cm -1 , ν(-C=O); 1415 cm -1 , δ(-CH) [35] .…”