Development of cannabidiol full-spectrum oil/2,6-di-O-methyl-β-cyclodextrin inclusion complex with enhanced water solubility, bioactivity, and thermal stability

Li, Hang; Zhao, Qingsheng; Chang, Senlin; Chang, Tanran; Tan, Minghui; Zhao, Bing

doi:10.1016/j.molliq.2021.118318

Cited by 11 publications

(6 citation statements)

References 40 publications

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“…The DSC curve of FSE was a smooth straight line, indicating that there was no heat absorption or release of FSE, which indicated that FSE was in a disordered state. Β-CD had a wide absorption peak at 58–100 °C, which was due to dehydration [ 30 ], and the phase transition resulted in a high endothermic peak at approximately 310 °C. The DSC curve of FSE-CD showed that the wide absorption peak of β-CD disappeared, indicating that some of the water molecules bound to the CDs were replaced by natural product molecules, which indicated that the natural product was successfully contained in the CD’s cavity.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, cyclodextrin entrapped extraction, which increased the natural product content of Forsythia suspensa leaves in the products, thereby, increasing the antioxidant properties. Some studies have also found that the antioxidant activities of compounds become stronger after complexation, such as cannabidiol [ 30 ] and quercetin [ 34 ].…”

Section: Resultsmentioning

confidence: 99%

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Green Extraction of Forsythoside A, Phillyrin and Phillygenol from Forsythia suspensa Leaves Using a β-Cyclodextrin-Assisted Method

Qiao

Zha³

et al. 2022

Molecules

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In this study, a green process of β-cyclodextrin (β-CD)-assisted extraction of active ingredients from Forsythia suspensa leaves was developed. Firstly, the optimal process of extraction was as follows: the ratio between Forsythia suspensa leaves and β-CD was 3.61:5, the solid–liquid ratio was 1:36.3, the temperature was 75.25 °C and the pH was 3.94. The yields of forsythoside A, phillyrin and phillygenol were 11.80 ± 0.141%, 5.49 ± 0.078% and 0.319 ± 0.004%, respectively. Then, the structure characteristics of the β-CD-assisted extract of Forsythia suspensa leaves (FSE-β-CD) were analyzed using powder X-ray diffraction (PXRD), Fourier transform infrared spectroscopy (FT-IR), differential scanning calorimetry (DSC), scanning electron microscopy (SEM) and molecular docking to demonstrate that the natural active products from Forsythia suspensa leaves had significant interactions with the β-CD. Additionally, the loss of forsythoside A from aqueous FSE-CD at 80 °C was only 12%, compared with Forsythia suspensa leaf extract (FSE) which decreased by 13%. In addition, the aqueous solubility of FSE-CD was significantly increased to 70.2 g/L. The EC50 for scavenging DPPH and ABTS radicals decreased to 28.98 ug/mL and 25.54 ug/mL, respectively. The results showed that the β-CD-assisted extraction process would be a promising technology for bioactive compounds extracted from plants.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Green Extraction of Forsythoside A, Phillyrin and Phillygenol from Forsythia suspensa Leaves Using a β-Cyclodextrin-Assisted Method

Qiao

Zha³

et al. 2022

Molecules

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“…The 1741, 1634, 1582, and 1449 cm −1 bands were assigned to the benzene skeleton vibrations. The band at 1368 cm −1 is the bending vibration of CH 3 , and the 1224 cm −1 band was assigned to CO stretching vibration 47 . After CBD was embedded in chitosan films, the characteristic bands of cannabis oil at 3010, 2927, 2855, and 1745 cm −1 in all samples were observed.…”

Section: Resultsmentioning

confidence: 99%

Chitosan-based films with cannabis oil as a base material for wound dressing application

Chełminiak-Dudkiewicz

Smolarkiewicz-Wyczachowski

Mylkie

et al. 2022

Sci Rep

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This study focuses on obtaining and characterizing novel chitosan-based biomaterials containing cannabis oil to potentially promote wound healing. The primary active substance in cannabis oil is the non-psychoactive cannabidiol, which has many beneficial properties. In this study, three chitosan-based films containing different concentrations of cannabis oil were prepared. As the amount of oil increased, the obtained biomaterials became rougher as tested by atomic force microscopy. Such rough surfaces promote protein adsorption, confirmed by experiments assessing the interaction between human albumin with the obtained materials. Increased oil concentration also improved the films' mechanical parameters, swelling capacity, and hydrophilic properties, which were checked by the wetting angle measurement. On the other hand, higher oil content resulted in decreased water vapour permeability, which is essential in wound dressing. Furthermore, the prepared films were subjected to an acute toxicity test using a Microtox. Significantly, the film's increased cannabis oil content enhanced the antimicrobial effect against A. fischeri for films in direct contact with bacteria. More importantly, cell culture studies revealed that the obtained materials are biocompatible and, therefore, they might be potential candidates for application in wound dressing materials.

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“…In recent years, there have been several studies indicating that the water solubility and stability of these cannabinoids can be increased through the inclusion complex with β-cyclodextrins (β-CD), about 2.1 mg/mL [ 22 , 23 , 24 , 25 , 26 ]. These inclusion complexes also exhibit greater in vitro effects against human cancer lines Hep G2 and A549 [ 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

“…Lv et al [ 22 ] reported that β-CD complexes with CBD in both of 1:1 and 2:1 host-guest stoichiometry. Li et al [ 24 ] revealed that CBD formed inclusion complex with β-CD in 1:1 stoichiometric ratio. Mannila et.al.…”

Section: Introductionmentioning

confidence: 99%

Structural Investigation of Beta-Cyclodextrin Complexes with Cannabidiol and Delta-9-Tetrahydrocannabinol in 1:1 and 2:1 Host-Guest Stoichiometry: Molecular Docking and Density Functional Calculations

Triamchaisri

Toochinda

Lawtrakul

2023

IJMS

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The complexation of β-cyclodextrin (β-CD) with cannabidiol (CBD) and Δ9-tetrahydrocannabinol (THC) was investigated using molecular docking and M062X/6-31G(d,p) calculations. The calculations suggested two possible complex formations of 1:1 and 2:1 host-guest molecular ratio of β-CD with CBD and THC. The preferred orientation of all complexes in this study exhibited the hydrogen bonding between hydroxy-substituted benzene ring of CBD and THC with the β-CD’s secondary hydroxy groups at the wide rim. The calculated complexation energies indicate that formation of the 2:1 complexes (−83.53 to −135.36 kcal/mol) was more energetically favorable and chemically stable than the 1:1 complexes (−30.00 to −34.92 kcal/mol). However, the deformation energies of the host and the guest components in the 2:1 complexes (37.47–96.91 kcal/mol) are much higher than those in the 1:1 complexes (3.49–8.69 kcal/mol), which means the formation processes of the 2:1 complexes are more difficult due to the rigidity of the dimeric β-CDs. Therefore, the inclusion complexes of β-CD with CBD and THC are more likely to be in 1:1 host-guest ratio than in 2:1 molecular ratio. The results of this study supported the experimental results that the complexation constant of 1:1 β-CD/CBD (Ks = 300 M−1) is greater than that of 2:1 β-CDs/CBD (Kss = 0.833 M−1). Altogether, this study introduced the fitting parameters that could indicate the stability of the molecular fits in complex formation of each stoichiometry host-guest ratio, which are important for the assessment of the inclusion mechanisms as well as the relationships of reactants and products in chemical reactions.

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Development of cannabidiol full-spectrum oil/2,6-di-O-methyl-β-cyclodextrin inclusion complex with enhanced water solubility, bioactivity, and thermal stability

Cited by 11 publications

References 40 publications

Green Extraction of Forsythoside A, Phillyrin and Phillygenol from Forsythia suspensa Leaves Using a β-Cyclodextrin-Assisted Method

Green Extraction of Forsythoside A, Phillyrin and Phillygenol from Forsythia suspensa Leaves Using a β-Cyclodextrin-Assisted Method

Chitosan-based films with cannabis oil as a base material for wound dressing application

Structural Investigation of Beta-Cyclodextrin Complexes with Cannabidiol and Delta-9-Tetrahydrocannabinol in 1:1 and 2:1 Host-Guest Stoichiometry: Molecular Docking and Density Functional Calculations

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