Encapsulation In Cyclodextrins Research Articles

Antiproliferative Effects in Colorectal Cancer and Stabilisation in Cyclodextrins of the Phytoalexin Isorhapontigenin.

Isorhapontigenin has been proposed as a better alternative for oral administration than the famous resveratrol, as it shares many biological activities, but with a structure that could make its delivery easier. Although this hydrophobic structure could enhance bioavailability, it could also be a disadvantage in the development of products. In this research, we study the antiproliferative activity of this stilbene against colorectal cancer and overcome its limitations through molecular encapsulation in cyclodextrins. The cytotoxic activity against human colorectal cancer cells of isorhapontigenin was similar to that of resveratrol or piceatannol, supporting its use as a bioactive alternative. The study of the encapsulation through fluorescence spectroscopy and molecular docking revealed that the complexation satisfies a 1:1 stoichiometry and that HP-β-CD is the most suitable CD to encapsulate this stilbene. Through a spectrophotometric assay, it was observed that this CD could double the basal water solubility, exceeding the solubility of other hydroxylated stilbenes. The stability of these inclusion complexes was higher at a pH below 9 and refrigeration temperatures. Moreover, the use of CDs retained more than 78% of isorhapontigenin after storage for 12 weeks, compared to 15% in free form. Overall, these findings could help design novel formulations to better deliver isorhapontigenin.

Cyclodextrin Inclusion Complexes for Improved Drug Bioavailability and Activity: Synthetic and Analytical Aspects.

Many active pharmaceutical ingredients show low oral bioavailability due to factors such as poor solubility and physical and chemical instability. The formation of inclusion complexes with cyclodextrins, as well as cyclodextrin-based polymers, nanosponges, and nanofibers, is a valuable tool to improve the oral bioavailability of many drugs. The microencapsulation process modifies key properties of the included drugs including volatility, dissolution rate, bioavailability, and bioactivity. In this context, we present relevant examples of the stabilization of labile drugs through the encapsulation in cyclodextrins. The formation of inclusion complexes with drugs belonging to class IV in the biopharmaceutical classification system as an effective solution to increase their bioavailability is also discussed. The stabilization and improvement in nutraceuticals used as food supplements, which often have low intestinal absorption due to their poor solubility, is also considered. Cyclodextrin-based nanofibers, which are polymer-free and can be generated using environmentally friendly technologies, lead to dramatic bioavailability enhancements. The synthesis of chemically modified cyclodextrins, polymers, and nanosponges based on cyclodextrins is discussed. Analytical techniques that allow the characterization and verification of the formation of true inclusion complexes are also considered, taking into account the differences in the procedures for the formation of inclusion complexes in solution and in the solid state.

Molecular encapsulation and bioactivity of gnetol, a resveratrol analogue, for use in foods.

BACKGROUNDGnetol is a stilbene whose characterization and bioactivity have been poorly studied. It shares some bioactivities with its analogue resveratrol, such as anti‐inflammatory, anti‐thrombotic, cardioprotective and anti‐cancer activities. However, the low solubility of stilbenes may limit their potential applications in functional foods. Encapsulation in cyclodextrins could be a solution.RESULTSThe antioxidant activity of gnetol was evaluated by 2,2′‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid) radical cation and ferric reducing antioxidant power methods (Trolox equivalents 13.48 μmol L−1 and 37.08 μmol L−1 respectively at the highest concentration) and it was higher than that of resveratrol, and depending on the method, similar or higher to that of oxyresveratrol. Spectrophotometric and spectrofluorimetric characterization of gnetol is published for the first time. Moreover, its water solubility was determined and improved almost threefold after its molecular encapsulation in cyclodextrins, as well as its stability after storage for a week. A physicochemical and computational study revealed that cyclodextrins complex gnetol in a 1:1 stoichiometry, with better affinity for like 2‐hydroxypropyl‐β‐cyclodextrin (K F = 4542.90 ± 227.15 mol−1 L). Temperature and pH affected the encapsulation constants.CONCLUSIONThese results could increase interest of gnetol as an alternative to the most studied stilbene, resveratrol, as well as aid in the development of more stable inclusion complexes that improve its aqueous solubility and stability so that it can be incorporated into functional foods. © 2022 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

Encapsulation of Phenolic Compounds from a Grape Cane Pilot-Plant Extract in Hydroxypropyl Beta-Cyclodextrin and Maltodextrin by Spray Drying.

Grape canes, the main byproducts of the viticulture industry, contain high-value bioactive phenolic compounds, whose application is limited by their instability and poorly solubility in water. Encapsulation in cyclodextrins allows these drawbacks to be overcome. In this work, a grape cane pilot-plant extract (GCPPE) was encapsulated in hydroxypropyl beta-cyclodextrin (HP-β-CD) by a spray-drying technique and the formation of an inclusion complex was confirmed by microscopy and infrared spectroscopy. The phenolic profile of the complex was analyzed by LC-ESI-LTQ-Orbitrap-MS and the encapsulation efficiency of the phenolic compounds was determined. A total of 42 compounds were identified, including stilbenes, flavonoids, and phenolic acids, and a complex of (epi)catechin with β-CD was detected, confirming the interaction between polyphenols and cyclodextrin. The encapsulation efficiency for the total extract was 80.5 ± 1.1%, with restrytisol showing the highest value (97.0 ± 0.6%) and (E)-resveratrol (32.7 ± 2.8%) the lowest value. The antioxidant capacity of the inclusion complex, determined by ORAC-FL, was 5300 ± 472 µmol TE/g DW, which was similar to the value obtained for the unencapsulated extract. This formulation might be used to improve the stability, solubility, and bioavailability of phenolic compounds of the GCPPE for water-soluble food and pharmaceutical applications.

Tetrahydrocurcumin encapsulation in cyclodextrins for water solubility improvement: Synthesis, characterization and antifungal activity as a new biofungicide

The solubility of the scarcely water-soluble molecule tetrahydrocurcumin (THC), a promising curcumin derivative to be used as biopesticide, was enhanced through the formation of inclusion complexes with different cyclodextrins (CDs). Randomly methylated β-cyclodextrin (MeβCD) gave the best results among the different CDs whose size, substituent or structure was changing. Differential scanning calorimetry as well as 1H- and 2D-Nuclear Magnetic Resonance (NMR) proved the inclusion of THC in MeβCD. Rotating-frame Overhauser effect spectroscopy NMR especially illustrated specific interactions of aromatic protons of THC and protons located inside the CD cavity. The complex formation between THC and MeβCD was studied using the Higuchi and Connor method, giving an association constant of 591 M−1. THC-loaded MeβCD did not show any growth inhibition of the target fungus Fusarium graminearum. However, THC-loaded MeβCD polymers exhibited 25% inhibition of the fungal growth, thus making them promising material for solvent-free, aqueous and bio-based fungicide formulations.

In vivo antinociceptive and anti-inflammatory potential of hesperidin and its cyclodextrin inclusion compounds

Introduction. This study aims to evaluate the antinociceptive activity on inflammatory and non-inflammatory nociception models, as well as the anti-inflammatory action of hesperidin and its inclusion compounds with beta-cyclodextrin and hydroxypropyl-beta-cyclodextrin. Material and method. For these experiments, we employed nociception models using thermal, chemical and pressure stimuli and an inflammation model for the evaluation of inflammatory edema by plethysmometer test. Results and discussions. The obtained results demonstrate that the HES-βCD inclusion compounds exhibited antinociceptive action predominantly on experimental non-inflammatory nociception models, while HES-HP-βCD exhibited anti-inflammatory and antinociceptive activities predominantly in inflammatory nociception models. Conclusions. This research may be the starting point for future studies regarding the improvement of biopharmaceutical qualities of HES by encapsulation in cyclodextrins. Keywords: hesperidin, cyclodextrin inclusion compunds, antinociceptive, anti-inflammatory activity,

Study of the fluorescence and interaction between cyclodextrins and neochlorogenic acid, in comparison with chlorogenic acid

Neochlorogenic acid, a less-studied isomer of chlorogenic acid, has been seen to posses antioxidant, antifungal, anti-inflammatory and anticarcinogenic effects, which makes it an interesting candidate for incorporation in functional foods. However, its poor solubility in water and susceptibility to oxidation make such a task difficult. To overcome that, its encapsulation in cyclodextrins (CDs) is proposed. The fluorescence of neochlorogenic acid in different pH conditions was analyzed, and caffeic acid was proved to be the fluorescent moiety in the molecule. An encapsulation model whereby the ligand poses two potential complexation sites (caffeic and D-(-)-quinic moieties), showed that α-CD and HP-β-CD formed the best inclusion complexes with neochlorogenic acid, followed by M-β-CD, β-CD and γ-CD. Molecular docking with the two best CDs gave better scores for α-CD, despite HP-β-CD providing stabilization through H-bonds. The encapsulation of chlorogenic acid led to a similar CD order and scores, although constants were higher for α-CD, β-CD and M-β-CD, lower for HP-β-CD, and negligible for γ-CD. The protonation state affected these results leading to a different order of CD preference. The solubility and the susceptibility to oxidation of neochlorogenic acid improved after complexation with α-CD and HP-β-CD, while the antioxidant activity of both isomers was maintained.

Modified cyclodextrin type and dehydration methods exert a significant effect on the antimicrobial activity of encapsulated carvacrol and thymol.

The antimicrobial activity of essential oils and their constituents has led to increasing interest in using them as natural preservative agents. However, their high sensitivity to light and oxygen, their volatility and their low aqueous solubility are all obstacles to their application in the food, cosmetic or pharmaceutical industries. Encapsulation in cyclodextrins (CDs) is a solution for the application of such essential oils. The complexation of carvacrol and thymol with hydroxypropyl (HP)-α-, HP-β- and HP-γ-CD, the behavior of the solid complexes prepared by freeze-drying and spray-drying methods and the antibacterial activity of solid complexes were studied. Kc values of HP-α- and HP-γ-CD complexes with carvacrol (118.4 and 365.7L mol-1 ) and thymol (112.5 and 239.7L mol -1 ) were far lower than those observed for HP-β-CD complexes with carvacrol (2268.2L mol -1 ) and thymol (881.6L mol -1 ). The lower stability of HP-α- and HP-γ-CD complexes increased the release of compounds, thereby affecting the antimicrobial activity of carvacrol and thymol to a lesser extent than complexation with HP-β-CD, normally used in the encapsulation of carvacrol and thymol. HP-β-CD encapsulation of carvacrol and thymol markedly reduced their antimicrobial activity. The freeze-drying method barely affected the antimicrobial activity of carvacrol and thymol after encapsulation, while spray drying could be considered for the production of solid complexes in combination with the appropriate CD. It was thus demonstrated that HP-α- and HP-γ-CD are very suitable alternatives for the encapsulation of carvacrol and thymol with the purpose of preserving their bacteriostatic and bactericidal activities. © 2020 Society of Chemical Industry.

Preparation, Characterization, and Properties of Inclusion Complexes of Balofloxacin with Cyclodextrins.

The study mainly aimed to improve the aqueous solubility of Balofloxacin (BLFX) by preparing the inclusion complexes (ICs) of BLFX with cyclodextrins (CDs). In this study, ICs in solid state were obtained by using beta-CD (β-CD), 2-hydroxypropyl-β-CD (HP-β-CD), 2, 6-dimethyl-β-CD (DM-β-CD) through a freeze-drying technique. The formation of ICs was confirmed through Fourier-transform infrared spectroscopy, differential scanning calorimetry, powder X-ray diffraction, nuclear magnetic resonance, and scanning electron microscopy. Results demonstrated that the water solubility and dissolution rates of three ICs were distinctly improved than that of parent BLFX. Bacteriostatic experiment manifested that the antibacterial effect of BLFX was not inhibited after encapsulation in CDs. The damage of BLFX to kidney and liver cells was reduced. Consequently, successful preparation of the ICs of BLFX with CDs provided possibility for devising new dosage form of BLFX, which held great promise for further applications in clinical fields.

Encapsulation in cyclodextrins to widen the applications of essential oils

There is a growing interest for aromatic and biological properties of essential oils as alternatives to synthetic chemicals and drugs. However, essential oils and their components are poorly soluble in aqueous systems and are highly sensitive to degradation and evaporation. These drawbacks can be overcome by encapsulation into cyclodextrins, which are non-toxic cyclic oligosaccharides obtained from the enzymatic degradation of starch. Cyclodextrins inclusion complexes offer solutions to many limitations of the use of essential oils in the food, pharmaceutical and cosmetic industries. This article reviews essential oils encapsulation in cyclodextrins. The strength of binding between cyclodextrins and essential oils components covers a wide range of formation constants with values ranging from 13 to 166,338 M−1. The encapsulation in cyclodextrins can increase the aqueous solubility of essential oils up to 16-fold and reduce their photodegradation rates up to 44-fold, while ensuring a gradual release. We also discuss the effect of encapsulation on biological activities, such as antimicrobial and antioxidant properties of essential oils. Finally, we present novel cyclodextrin-based approaches in the sectors of textiles and nanofibres.

Novel findings for quercetin encapsulation and preservation with cyclodextrins, liposomes, and drug-in-cyclodextrin-in-liposomes

The low solubility, poor bioavailability, and low chemical stability of quercetin (Quer) are the main drawbacks that limit its use as a food nutraceutical. In this study, the encapsulation in cyclodextrins (CDs), conventional liposomes (CLs), and drug-in-cyclodextrin-in-liposomes (DCLs) was conducted in order to improve the physicochemical properties of Quer. Phase solubility studies revealed an enhancement of Quer solubility upon complexation with various CDs. CLs composed of three different types of phospholipids (unsaturated egg Lipoid E80, unsaturated soybean Lipoid S100, and saturated soybean Phospholipon 90H) as well as DCLs were prepared by ethanol injection method and characterized. Liposomes constituted of Lipoid E80 showed small diameter, narrow size distribution, and higher encapsulation efficiency of Quer compared to the two other CLs. The photostability of Quer-loaded liposomes was also evaluated. Results show that Lipoid E80-liposomes allow a better protection of Quer against UV irradiation than those prepared using other lipids. This effect could be explained by their different membrane rigidity as determined by Atomic Force Microscopy (AFM). Moreover, the photostability of Quer was additionally improved when encapsulated in DCLs (SBE-β-CD/Quer inclusion complex in Lipoid E80 liposomes), in comparison to CLs. The same trend was obtained regarding the Quer stability in simulated gastrointestinal fluids. Finally, all liposome formulations were physically stable after 1 year of storage at 4 °C.

Novel trends in cyclodextrins encapsulation. Applications in food science

Cyclodextrins (CDs) are cyclic oligosaccharides composed of linked glucopyranose subunits. The main property of CDs is that their hydrophobic inner cavity forms inclusion complexes with a wide range of guest molecules, while the hydrophilic exterior enhances CD solubility in water. Because of their molecular inclusion capability, the properties of the materials with which they complex can be significantly modified. Particularly, solubility and stability of bioactive compounds to be used as nutraceuticals, could be improved by encapsulation in CDs. The available thermodynamic data are consistent with an exothermic and spontaneous inclusion processes. Phase solubility studies in liquid systems along with studies of physical properties of solids complex, help to elucidate complex stoichiometry and guest–CD interactions. The use of CD-complexes for improving molecules solubility and stability, for control release and as adjuvant in extraction processes, represents a promising innovative strategy in the food industry for the development of new ingredients and products.

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil.

Nerolidol (Ner), a major component of many plant essential oils, is known for its various biological properties. However, the low solubility of Ner in water and its susceptibility to degradation limit its application. The aim of our study was to improve the solubility and photostability of Ner through its encapsulation in different cyclodextrins (CDs). The formation constants of cis-, trans-Ner and their commercial mixture with various CDs (α-CD, β-CD, γ-CD, HP-β-CD, RAMEB, CRYSMEB and SBE-β-CD) were determined by phase solubility studies and confirmed by the spectral displacement UV-visible method. The solubility of cabreuva essential oil (EO) rich in trans-Ner was also evaluated by total organic carbon (TOC) analysis. The encapsulation efficiency (EE %) of Ner in HP-β-CD solid complexes was assessed by HPLC. The structural characterization of CD/trans-Ner inclusion complex was then conducted by NMR spectroscopy followed by molecular modelling studies. The effect of encapsulation on the Ner photostability was also carried out over time under UVB irradiation. AL-type phase-solubility diagrams were obtained, suggesting the formation of 1:1 CD/Ner inclusion complexes. The solubility of Ner was enhanced by approximately 70-fold in the presence of 10 mM HP-β-CD. Moreover, high EE % values were obtained for 5:1 and 10:1 HP-β-CD:Ner molar ratios. NMR and molecular modelling studies revealed the most stable structure for trans-Ner inside the CD cavity with the OH group oriented towards the wider rim of the CD. Finally, CD encapsulation of Ner as pure compound or as main component of the cabreuva EO, protected it from degradation. This effect was more pronounced as the concentration of CD increased. These findings suggested that CDs are promising encapsulating carriers for Ner by enhancing its solubility and stability and thereby its application in food industry.

Nootkatone encapsulation by cyclodextrins: Effect on water solubility and photostability

Nootkatone (NO) is a sesquiterpenoid volatile flavor, used in foods, cosmetics and pharmaceuticals, possessing also insect repellent activity. Its application is limited because of its low aqueous solubility and stability; this could be resolved by encapsulation in cyclodextrins (CDs). This study evaluated the encapsulation of NO by CDs using phase solubility studies, Isothermal Titration Calorimetry, Nuclear Magnetic Resonance spectroscopy and molecular modeling. Solid CD/NO inclusion complex was prepared and characterized for encapsulation efficiency and loading capacity using UV–Visible. Thermal properties were investigated by thermogravimetric-differential thermal analysis and release studies were performed using multiple headspace extraction. Formation constants (Kf) proved the formation of stable inclusion complexes. NO aqueous solubility, photo- and thermal stability were enhanced and the release could be insured from solid complex in aqueous solution. This suggests that CDs are promising carrier to improve NO properties and, consequently, to enlarge its use in foods, cosmetics, pharmaceuticals and agrochemicals preparations.

Essential oil components decrease pulmonary and hepatic cells inflammation induced by air pollution particulate matter

Outdoor air pollution and fine particulate matter (PM) were recently classified as carcinogenic to humans by the International Agency for Research on Cancer. The exposure to airborne particulate matter also contributes to cardiovascular and respiratory diseases, which are major public health concerns. Up to now, no work has evaluated the ability of essential oils as an alternative medicine to relieve the adverse health effects caused by airborne particulate matter. Here, we investigated for the first time the effects of four essential oil components, trans-anethole, estragole, eugenol and isoeugenol, on the reduction in inflammation induced by particulate matter with an aerodynamic diameter below 2.5 μm (PM2.5), in human bronchial epithelial (BEAS-2B) and human liver carcinoma (HepG2) cell lines. Anethole is a flavor component of anise and fennel, estragole is occurring in basil, eugenol occurs in clove bud oil and isoeugenol occurs in ylang-ylang. Essential oil components were tested either as free or hydroxypropyl-β-cyclodextrin-encapsulated forms. Control experiments showed that particulate matter (PM2.5) induced inflammation by secretion of pro-inflammatory cytokines IL-6 and IL-8. Our results show that the addition of either free or encapsulated essential oil components to particulate matter exposed cells decreased up to 96 % the cytokine IL-6 level, and by up to 87 % the cytokine IL-8 level. Overall our findings evidence for the first time that natural essential oil components counteract the inflammatory effects of particulate matter and that encapsulation in cyclodextrins preserved their properties.

Enhancement of antioxidant activity of green tea epicatechins in β-cyclodextrin cavity: Single-crystal X-ray analysis, DFT calculation and DPPH assay

Green tea catechins are potent antioxidant for prevention of various free radical-related diseases. Their antioxidant properties can be improved by encapsulation in cyclodextrins (CDs). Four inclusion complexes of β-CD with (–)-epicatechin (EC), (–)-epigallocatechin (EGC), (–)-epicatechin gallate (ECG) and (–)-epigallocatechin gallate (EGCG) have been investigated using single-crystal X-ray diffraction analysis combined with full geometry optimization by DFT/B3LYP calculation and the DPPH assay, aiming to deepen the understanding on their structure–antioxidant activity relationship. Scrutinizing the inclusion structures and conformational changes of the four encapsulated epicatechins reveals the common host–guest stabilization scheme and the epicatechin conformational flexibility facilitating the enhancement of activity. Thermodynamic stability order derived from DFT calculation in vacuum fairly agrees with the order of improved antioxidant capacity deduced from the DPPH assay, β-CD–EGCG>β-CD–ECG>β-CD–EGC≈β-CD–EC.

Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol.

Carvacrol and thymol have been widely studied for their ability to control food spoilage and to extend shelf-life of food products due to their antimicrobial and antioxidant activities. However, they suffer from poor aqueous solubility and pronounced flavoring ability that limit their application in food systems. These drawbacks could be surpassed by encapsulation in cyclodextrins (CDs). Applications of their inclusion complexes with CDs were reported without investigating the inclusion phenomenon in deep. In this study, inclusion complexes were characterized in terms of formation constants (Kf), complexation efficiency (CE), CD:guest molar ratio and increase in bulk formulation by using an UV–visible competitive method, phase solubility studies as well as 1H and DOSY 1H NMR titration experiments. For the first time, a new algorithmic treatment that combines the chemical shifts and diffusion coefficients variations for all guest protons was applied to calculate Kf. The position of the hydroxy group in carvacrol and thymol did not affect the stoichiometry of the inclusion complexes but led to a different binding stability with CDs. 2D ROESY NMR experiments were also performed to prove the encapsulation and illustrate the stable 3D conformation of the inclusion complexes. The structural investigation was accomplished with molecular modeling studies. Finally, the radical scavenging activity of carvacrol and thymol was evaluated by the ABTS radical scavenging assay. An improvement of this activity was observed upon encapsulation. Taken together, these results evidence that the encapsulation in CDs could be valuable for applications of carvacrol and thymol in food.

Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins

Effects of the encapsulation in cyclodextrins (CDs) on the solubility, photostability and antifungal activities of some phenylpropanoids (PPs) were investigated. Solubility experiments were carried out to evaluate the effect of CDs on PPs aqueous solubility. Loading capacities and encapsulation efficiencies of freeze-dried inclusion complexes were determined. Moreover, photostability assays for both inclusion complexes in solution and solid state were performed. Finally, two of the most widespread phytopathogenic fungi, Fusarium oxysporum and Botrytis cinerea, were chosen to examine the antifungal activity of free and encapsulated PPs. Results showed that encapsulation in CDs significantly increased the solubility and photostability of studied PPs (by 2 to 17-fold and 2 to 44-fold, respectively). Free PPs revealed remarkable antifungal properties with isoeugenol showing the lowest half-maximal inhibitory concentration (IC50) values of mycelium growth and spore germination inhibition. Encapsulated PPs, despite their reduced antifungal activity, could be helpful to solve drawbacks such as solubility and stability.

Promising applications of cyclodextrins in food: Improvement of essential oils retention, controlled release and antiradical activity

Essential oils (EOs) are gaining great interest as alternatives for harmful synthetic food preservatives. Due to their volatile nature, they could be applied in food packaging to improve food quality and extend shelf-life. To provide long-term effects of EOs by increasing their retention and ensuring controlled release of their components, they could be encapsulated in cyclodextrins (CDs). Herein, the ability of six CDs to retain nine EOs and to bind their individual components was investigated. Retention capacities and binding abilities of CDs were assessed by static headspace-gas chromatography (SH-GC) using a new validated “rapid method”. The ability of CDs to generate controlled release systems was examined by multiple headspace extraction (MHE). Finally, radical scavenging activity of free and encapsulated EOs was evaluated. The highest retention capacity toward the studied EOs was obtained for β-CD and its derivatives (69–78%). Also, β-CD and its derivatives showed, with one exception, the highest Kf values for all the studied guests. In addition, encapsulation in CDs reduced the releasing rate of EO components (from 1.43 to 2.43-fold for β-CD/Satureja montana EO used as a model). Furthermore, the inclusion complexes showed higher ABTS+ scavenging capacity than the free EOs. Results confirmed the usefulness of CDs as encapsulant for EOs and should encourage their application in food and as part of active packaging systems.

Barbigerone-in-hydroxypropyl-β-cyclodextrin-liposomal nanoparticle: preparation, characterization and anti-cancer activities

Lipophilic drugs have limited solubility in phospholipid systems, hence maximum entrapment levels in liposomes are known to be low. Barbigerone (Bar), an anti-cancer isoflavone, is water insoluble and an effective delivery route is through encapsulation in cyclodextrins (CDs) followed by a second encapsulation in liposomes. In this study, Bar or its inclusion complex [Bar/2-hydroxypropyl-β-CD (HP-β-CD)] were incorporated into liposomes prepared by the ethanol injection method. A 4.6-fold increase of encapsulation efficiency was achieved for the liposome–Bar/HP-β-CD complex (Bar/HP-β-CD/liposome) in comparison with the conventional Bar/liposome. The size of the Bar/HP-β-CD/liposome was 87.76 ± 1.45 nm and the zeta potential was −35.02 ± 0.50 mV. In addition, the liposomes remained stable in liquid form at 4 °C for at least 3 months. The Bar/HP-β-CD/liposome was evaluated for anti-cancer activity in hepatocarcinoma HepG2 and colon cancer C26 cells and showed comparable toxicity to that of plain Bar. In vivo studies in hepatic cancer xenografted nude mice model showed that Bar/HP-β-CD/liposome significantly inhibited tumor growth with a substantial increase in animal survival. In conclusion, the encapsulation of the Bar/HP-β-CD complex into liposomes could provide an alternative means for its potential use in cancer therapy.