{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T20:56:12Z","timestamp":1790283372335,"version":"4.1.0"},"reference-count":63,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2021,11,12]],"date-time":"2021-11-12T00:00:00Z","timestamp":1636675200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The essential oil component \u03b1-pinene has multiple biological activities. However, its application is limited owing to its volatility, low aqueous solubility, and chemical instability. For the aim of improving its physicochemical properties, \u03b1-pinene was encapsulated in conventional liposomes (CLs) and drug-in-cyclodextrin-in-liposomes (DCLs). Hydroxypropyl-\u03b2-cyclodextrin\/\u03b1-pinene (HP-\u03b2-CD\/\u03b1-pinene) inclusion complexes were prepared in aqueous solution, and the optimal solubilization of \u03b1-pinene occurred at HP-\u03b2-CD:\u03b1-pinene molar ratio of 7.5:1. The ethanol-injection method was applied to produce different formulations using saturated (Phospholipon 90H) or unsaturated (Lipoid S100) phospholipids in combination with cholesterol. The size, the phospholipid and cholesterol incorporation rates, the encapsulation efficiency (EE), and the loading rate (LR) of \u03b1-pinene were determined, and the storage stability of liposomes was assessed. The results showed that \u03b1-pinene was efficiently entrapped in CLs and DCLs with high EE values. Moreover, Lipoid S100 CLs displayed the highest LR (22.9 \u00b1 2.2%) of \u03b1-pinene compared to the other formulations. Both carrier systems HP-\u03b2-CD\/\u03b1-pinene inclusion complex and Lipoid S100 CLs presented a gradual release of \u03b1-pinene. Furthermore, the DPPH radical scavenging activity of \u03b1-pinene was maintained upon encapsulation in Lipoid S100 CLs. Finally, it was found that all formulations were stable after three months of storage at 4 \u00b0C.<\/jats:p>","DOI":"10.3390\/molecules26226840","type":"journal-article","created":{"date-parts":[[2021,11,12]],"date-time":"2021-11-12T08:10:22Z","timestamp":1636704622000},"page":"6840","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Encapsulation of \u03b1-Pinene in Delivery Systems Based on Liposomes and Cyclodextrins"],"prefix":"10.3390","volume":"26","author":[{"given":"Zahraa","family":"Hammoud","sequence":"first","affiliation":[{"name":"Bioactive Molecules Research Laboratory, Doctoral School of Sciences and Technologies, Faculty of Sciences, Lebanese University, Jdeidet El-Metn 90656, Lebanon"},{"name":"UMR-5280, CNRS-University Lyon-1, 5 rue de la Doua, 69100 Villeurbanne, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5636-5426","authenticated-orcid":false,"given":"Maya","family":"Kayouka","sequence":"additional","affiliation":[{"name":"Bioactive Molecules Research Laboratory, Doctoral School of Sciences and Technologies, Faculty of Sciences, Lebanese University, Jdeidet El-Metn 90656, Lebanon"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2504-2541","authenticated-orcid":false,"given":"Adriana","family":"Trifan","sequence":"additional","affiliation":[{"name":"Department of Pharmacognosy, Faculty of Pharmacy, Grigore T. Popa University of Medicine and Pharmacy of Iasi, 16, 700115 Iasi, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4773-0329","authenticated-orcid":false,"given":"Elwira","family":"Sieniawska","sequence":"additional","affiliation":[{"name":"Department of Natural Products Chemistry, Medical University of Lublin, 20-093 Lublin, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0916-9243","authenticated-orcid":false,"given":"Jouda Mediouni Ben","family":"Jem\u00e2a","sequence":"additional","affiliation":[{"name":"Laboratory of Biotechnology Applied to Agriculture, National Agricultural Research Institute of Tunisia (INRAT), University of Carthage, El Menzah 1004, Tunisia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2151-9894","authenticated-orcid":false,"given":"Abdelhamid","family":"Elaissari","sequence":"additional","affiliation":[{"name":"UMR-5280, CNRS-University Lyon-1, 5 rue de la Doua, 69100 Villeurbanne, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2134-9423","authenticated-orcid":false,"given":"H\u00e9l\u00e8ne","family":"Greige-Gerges","sequence":"additional","affiliation":[{"name":"Bioactive Molecules Research Laboratory, Doctoral School of Sciences and Technologies, Faculty of Sciences, Lebanese University, Jdeidet El-Metn 90656, Lebanon"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,11,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"R1231","DOI":"10.1111\/1750-3841.12492","article-title":"Essential Oils: Extraction, Bioactivities, and Their Uses for Food Preservation","volume":"79","author":"Tongnuanchan","year":"2014","journal-title":"J. Food Sci."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Zieli\u0144ska, A., Ferreira, N.R., Durazzo, A., Lucarini, M., Cicero, N., Mamouni, S.E., Silva, A.M., Nowak, I., Santini, A., and Souto, E.B. (2019). Development and Optimization of Alpha-Pinene-Loaded Solid Lipid Nanoparticles (SLN) Using Experimental Factorial Design and Dispersion Analysis. Molecules, 24.","DOI":"10.3390\/molecules24152683"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1055\/s-0035-1558095","article-title":"Lavandula Angustifolia and Lavandula Latifolia Essential Oils from Spain: Aromatic Profile and Bioactivities","volume":"82","author":"Carrasco","year":"2015","journal-title":"Planta Med."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2704","DOI":"10.3390\/molecules17032704","article-title":"Antibacterial Activity and Anticancer Activity of Rosmarinus Officinalis L. Essential Oil Compared to That of Its Main Components","volume":"17","author":"Wang","year":"2012","journal-title":"Molecules"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"294","DOI":"10.1186\/s13068-018-1285-7","article-title":"Synthesis and Techno-Economic Assessment of Microbial-Based Processes for Terpenes Production","volume":"11","author":"Wu","year":"2018","journal-title":"Biotechnol. Biofuels"},{"key":"ref_6","first-page":"459582","article-title":"Terpenes: Natural Products for Controlling Insects of Importance to Human Health\u2014A Structure-Activity Relationship Study","volume":"2016","author":"Dambolena","year":"2016","journal-title":"Psyche J. Entomol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"961","DOI":"10.1016\/j.biopha.2017.06.031","article-title":"Potential Protective Effects of Alpha-Pinene against Cytotoxicity Caused by Aspirin in the IEC-6 Cells","volume":"93","author":"Bouzenna","year":"2017","journal-title":"Biomed. Pharmacother."},{"key":"ref_8","first-page":"479","article-title":"Chemical Composition, Antioxidant and Antimicrobial Activities of Essential Oil from Wedelia Prostrata","volume":"12","author":"Dai","year":"2013","journal-title":"EXCLI J."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"152","DOI":"10.1016\/j.indcrop.2013.09.001","article-title":"Antimicrobial Efficacy of Mutellina Purpurea Essential Oil and \u03b1-Pinene against Staphylococcus Epidermidis Grown in Planktonic and Biofilm Cultures","volume":"51","author":"Sieniawska","year":"2013","journal-title":"Ind. Crop. Prod."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"731","DOI":"10.1142\/S0192415X15500457","article-title":"Alpha-Pinene Exhibits Anti-Inflammatory Activity through the Suppression of MAPKs and the NF-\u039aB Pathway in Mouse Peritoneal Macrophages","volume":"43","author":"Kim","year":"2015","journal-title":"Am. J. Chin. Med."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1016\/j.jphs.2015.01.008","article-title":"Anti-Tumor Effect of \u03b1-Pinene on Human Hepatoma Cell Lines through Inducing G2\/M Cell Cycle Arrest","volume":"127","author":"Chen","year":"2015","journal-title":"J. Pharmacol. Sci."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Hao, D.C., Gu, X.-J., and Xiao, P.G. (2015). Phytochemical and Biological Research of Cannabis Pharmaceutical Resources. Medicinal Plants, Elsevier.","DOI":"10.1016\/B978-0-08-100085-4.00011-6"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"214305","DOI":"10.1063\/1.5003726","article-title":"The Gas Phase Structure of \u03b1-Pinene, a Main Biogenic Volatile Organic Compound","volume":"147","author":"Neeman","year":"2017","journal-title":"J. Chem. Phys."},{"key":"ref_14","first-page":"23695","article-title":"Technical Note: Detection and Identification of Radical Species Formed from \u03b1-Pinene\/Ozone Reaction Using DMPO Spin Trap","volume":"9","author":"Pavlovic","year":"2009","journal-title":"Atmos. Chem. Phys. Discuss."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1007\/s10874-007-9071-0","article-title":"Evaluation of \u03b1- and \u03b2-Pinene Degradation in the Detailed Tropospheric Chemistry Mechanism, MCM v3.1, Using Environmental Chamber Data","volume":"57","author":"Pinho","year":"2007","journal-title":"J. Atmos. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1550","DOI":"10.1016\/j.biotechadv.2014.10.010","article-title":"Application of Nanotechnology for the Encapsulation of Botanical Insecticides for Sustainable Agriculture: Prospects and Promises","volume":"32","author":"Campos","year":"2014","journal-title":"Biotechnol. Adv."},{"key":"ref_17","first-page":"1285","article-title":"Morphology and Release Profile of Microcapsules Encapsulated Alpha-Pinene by Complex Coacervation","volume":"602\u2013604","author":"Wang","year":"2012","journal-title":"Adv. Mater. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"110","DOI":"10.1016\/j.foodres.2013.03.048","article-title":"Complexation Efficiency of Cyclodextrins for Volatile Flavor Compounds","volume":"53","author":"Ciobanu","year":"2013","journal-title":"Food Res. Int."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1007\/s10847-014-0385-7","article-title":"Investigation of Monoterpenes Complexation with Hydroxypropyl-\u03b2-Cyclodextrin","volume":"80","author":"Kfoury","year":"2014","journal-title":"J. Incl. Phenom. Macrocycl. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1002\/ffj.3395","article-title":"Captisol\u00ae: An Efficient Carrier and Solubilizing Agent for Essential Oils and Their Components","volume":"32","author":"Kfoury","year":"2017","journal-title":"Flavour Fragr. J."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1016\/j.carbpol.2015.04.048","article-title":"Liposomes Incorporating Cyclodextrin\u2013Drug Inclusion Complexes: Current State of Knowledge","volume":"129","author":"Gharib","year":"2015","journal-title":"Carbohydr. Polym."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/0378-5173(94)90361-1","article-title":"Drugs-in-Cyclodextrins-in Liposomes: A Novel Concept in Drug Delivery","volume":"112","author":"McCormack","year":"1994","journal-title":"Int. J. Pharm."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1016\/j.carbpol.2015.11.053","article-title":"Clove Essential Oil-in-Cyclodextrin-in-Liposomes in the Aqueous and Lyophilized States: From Laboratory to Large Scale Using a Membrane Contactor","volume":"138","author":"Sebaaly","year":"2016","journal-title":"Carbohydr. Polym."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1016\/j.foodchem.2016.09.110","article-title":"Drug-in-Cyclodextrin-in-Liposomes as a Carrier System for Volatile Essential Oil Components: Application to Anethole","volume":"218","author":"Gharib","year":"2017","journal-title":"Food Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"794","DOI":"10.1016\/j.jddst.2019.05.032","article-title":"First Study on the Release of a Natural Antimicrobial Agent, Estragole, from Freeze-Dried Delivery Systems Based on Cyclodextrins and Liposomes","volume":"52","author":"Gharib","year":"2019","journal-title":"J. Drug Deliv. Sci. Technol."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"119151","DOI":"10.1016\/j.ijpharm.2020.119151","article-title":"Drug-in-Hydroxypropyl-\u03b2-Cyclodextrin-in-Lipoid S100\/Cholesterol Liposomes: Effect of the Characteristics of Essential Oil Components on Their Encapsulation and Release","volume":"579","author":"Hammoud","year":"2020","journal-title":"Int. J. Pharm."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1016\/j.foodchem.2018.02.055","article-title":"First Evaluation of Drug-in-Cyclodextrin-in-Liposomes as an Encapsulating System for Nerolidol","volume":"255","author":"Azzi","year":"2018","journal-title":"Food Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"315","DOI":"10.3109\/08982100903544169","article-title":"Liposomal Formulations of Prilocaine: Effect of Complexation with Hydroxypropyl-\u00df-Cyclodextrin on Drug Anesthetic Efficacy","volume":"20","author":"Bragagni","year":"2010","journal-title":"J. Liposome Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1016\/j.ijpharm.2010.05.046","article-title":"New \u201cDrug-in Cyclodextrin-in Deformable Liposomes\u201d Formulations to Improve the Therapeutic Efficacy of Local Anaesthetics","volume":"395","author":"Maestrelli","year":"2010","journal-title":"Int. J. Pharm."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/j.ijpharm.2019.03.063","article-title":"Cyclodextrin-Membrane Interaction in Drug Delivery and Membrane Structure Maintenance","volume":"564","author":"Hammoud","year":"2019","journal-title":"Int. J. Pharm."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.ijpharm.2006.09.059","article-title":"Integrity of Liposomes in Presence of Cyclodextrins: Effect of Liposome Type and Lipid Composition","volume":"333","author":"Hatzi","year":"2007","journal-title":"Int. J. Pharm."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"542","DOI":"10.1006\/jcis.1996.0335","article-title":"Interaction of Natural and Modified \u03b2-Cyclodextrins with a Biological Membrane Model of Dipalmitoylphosphatidylcholine","volume":"180","author":"Puglisi","year":"1996","journal-title":"J. Colloid Interface Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/j.chemphyslip.2015.07.017","article-title":"Interaction of Fluorescent Phospholipids with Cyclodextrins","volume":"194","author":"Denz","year":"2016","journal-title":"Chem. Phys. Lipids"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1822","DOI":"10.1016\/j.bbamem.2013.04.002","article-title":"Organization of Fluorescent Cholesterol Analogs in Lipid Bilayers\u2014Lessons from Cyclodextrin Extraction","volume":"1828","author":"Milles","year":"2013","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/S0009-3084(00)00122-5","article-title":"Cyclodextrin-Catalyzed Extraction of Fluorescent Sterols from Monolayer Membranes and Small Unilamellar Vesicles","volume":"105","author":"Akerlund","year":"2000","journal-title":"Chem. Phys. Lipids"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1248\/cpb.48.48","article-title":"Interactions of Cyclodextrins with Dipalmitoyl, Distearoyl, and Dimyristoyl Phosphatidyl Choline Liposomes. A Study by Leakage of Carboxyfluorescein in Inner Aqueous Phase of Unilamellar Liposomes","volume":"48","author":"Nishijo","year":"2000","journal-title":"Chem. Pharm. Bull."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1016\/j.ijpharm.2007.01.015","article-title":"Study of the Relationship between Lipid Binding Properties of Cyclodextrins and Their Effect on the Integrity of Liposomes","volume":"338","author":"Piel","year":"2007","journal-title":"Int. J. Pharm."},{"key":"ref_38","unstructured":"Li, J., and Perdue, E.M. (1995, January 2\u20137). Physicochemical Properties of Selected Monoterpenes. Proceedings of the 209th ACS National Meeting, Anaheim, CA, USA."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"328","DOI":"10.1016\/j.foodhyd.2018.03.006","article-title":"Novel Findings for Quercetin Encapsulation and Preservation with Cyclodextrins, Liposomes, and Drug-in-Cyclodextrin-in-Liposomes","volume":"81","author":"Azzi","year":"2018","journal-title":"Food Hydrocoll."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1016\/j.ijpharm.2019.02.022","article-title":"New Findings on the Incorporation of Essential Oil Components into Liposomes Composed of Lipoid S100 and Cholesterol","volume":"561","author":"Hammoud","year":"2019","journal-title":"Int. J. Pharm."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1128\/mr.59.2.201-222.1995","article-title":"Mechanisms of Membrane Toxicity of Hydrocarbons","volume":"59","author":"Sikkema","year":"1995","journal-title":"Microbiol. Rev."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1016\/j.colsurfb.2017.11.002","article-title":"Interaction of Semiochemicals with Model Lipid Membranes: A Biophysical Approach","volume":"161","author":"Rodriguez","year":"2018","journal-title":"Colloids Surf. B Biointerfaces"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/j.jddst.2017.12.009","article-title":"Effect of Hydroxypropyl-\u03b2\u2013Cyclodextrin on Lipid Membrane Fluidity, Stability and Freeze-Drying of Liposomes","volume":"44","author":"Gharib","year":"2018","journal-title":"J. Drug Deliv. Sci. Technol."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"16026","DOI":"10.1074\/jbc.271.27.16026","article-title":"Cellular Cholesterol Efflux Mediated by Cyclodextrins. Demonstration of Kinetic Pools and Mechanism of Efflux","volume":"271","author":"Yancey","year":"1996","journal-title":"J. Biol. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2118","DOI":"10.1016\/S0006-3495(02)73972-6","article-title":"Probing Red Cell Membrane Cholesterol Movement with Cyclodextrin","volume":"83","author":"Steck","year":"2002","journal-title":"Biophys. J."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1039\/C8SM01937A","article-title":"Cholesterol in Phospholipid Bilayers: Positions and Orientations inside Membranes with Different Unsaturation Degrees","volume":"15","author":"Ermilova","year":"2019","journal-title":"Soft Matter"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1227","DOI":"10.1021\/bi0520840","article-title":"Cholesterol Hydroxyl Group Is Found to Reside in the Center of a Polyunsaturated Lipid Membrane","volume":"45","author":"Harroun","year":"2006","journal-title":"Biochemistry"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"9417","DOI":"10.1039\/C6SM01777K","article-title":"Lipid Bilayer Thickness Determines Cholesterol\u2019s Location in Model Membranes","volume":"12","author":"Marquardt","year":"2016","journal-title":"Soft Matter"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.jconrel.2005.01.010","article-title":"Liposome-Encapsulated Vincristine, Vinblastine and Vinorelbine: A Comparative Study of Drug Loading and Retention","volume":"104","author":"Zhigaltsev","year":"2005","journal-title":"J. Control. Release"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"313","DOI":"10.1002\/ffj.2019","article-title":"A Review on Cyclodextrin Encapsulation of Essential Oils and Volatiles","volume":"25","author":"Marques","year":"2010","journal-title":"Flavour Fragr. J."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.fbio.2016.04.005","article-title":"Effect of Composition, Hydrogenation of Phospholipids and Lyophilization on the Characteristics of Eugenol-Loaded Liposomes Prepared by Ethanol Injection Method","volume":"15","author":"Sebaaly","year":"2016","journal-title":"Food Biosci."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1016\/j.ijpharm.2005.12.044","article-title":"Betamethasone-in-Cyclodextrin-in-Liposome: The Effect of Cyclodextrins on Encapsulation Efficiency and Release Kinetics","volume":"312","author":"Piel","year":"2006","journal-title":"Int. J. Pharm."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"505","DOI":"10.1007\/s10847-015-0533-8","article-title":"Barbigerone-in-Hydroxypropyl-\u03b2-Cyclodextrin-Liposomal Nanoparticle: Preparation, Characterization and Anti-Cancer Activities","volume":"82","author":"Qiu","year":"2015","journal-title":"J. Incl. Phenom. Macrocycl. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1016\/j.ijpharm.2016.09.043","article-title":"A Comparison between Conventional Liposome and Drug-Cyclodextrin Complex in Liposome System","volume":"513","author":"Wang","year":"2016","journal-title":"Int. J. Pharm."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1019","DOI":"10.1016\/j.foodchem.2007.11.046","article-title":"Antioxidative Activity of Rosmarinus Officinalis L. Essential Oil Compared to Its Main Components","volume":"108","author":"Wang","year":"2008","journal-title":"Food Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1080\/10942912.2019.1582541","article-title":"Antioxidant and Antibacterial Activity of Seven Predominant Terpenoids","volume":"22","author":"Wang","year":"2019","journal-title":"Int. J. Food Prop."},{"key":"ref_57","doi-asserted-by":"crossref","unstructured":"Yuan, J.-J., Qin, F., Tu, J.-L., and Li, B. (2017). Preparation, Characterization, and Antioxidant Activity Evaluation of Liposomes Containing Water-Soluble Hydroxytyrosol from Olive. Molecules, 22.","DOI":"10.3390\/molecules22060870"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1016\/j.foodchem.2015.01.067","article-title":"Preparation and Characterization of Clove Essential Oil-Loaded Liposomes","volume":"178","author":"Sebaaly","year":"2015","journal-title":"Food Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"8311","DOI":"10.1039\/C5CC02236C","article-title":"Solubilisation of a 2,2-Diphenyl-1-Picrylhydrazyl Radical in Water by \u03b2-Cyclodextrin to Evaluate the Radical-Scavenging Activity of Antioxidants in Aqueous Media","volume":"51","author":"Nakanishi","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"113156","DOI":"10.1016\/j.molliq.2020.113156","article-title":"Effect of Dimethylsulfoxide, Ethanol, \u03b1- and \u03b2-Cyclodextrins and Their Association on the Solubility of Natural Bioactive Compounds","volume":"310","author":"Nakhle","year":"2020","journal-title":"J. Mol. Liq."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"253","DOI":"10.1016\/S0927-7757(99)00281-2","article-title":"Zeta Potential, Effective Diameter and Multimodal Size Distribution in Oil\/Water Emulsion","volume":"159","author":"Chibowski","year":"1999","journal-title":"Colloids Surf. Physicochem. Eng. Asp."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.foodchem.2017.10.144","article-title":"Hydroxypropyl-\u00df-Cyclodextrin as a Membrane Protectant during Freeze-Drying of Hydrogenated and Non-Hydrogenated Liposomes and Molecule-in-Cyclodextrin-in- Liposomes: Application to Trans-Anethole","volume":"267","author":"Gharib","year":"2018","journal-title":"Food Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1016\/S0023-6438(95)80008-5","article-title":"Use of a Free Radical Method to Evaluate Antioxidant Activity","volume":"28","author":"Cuvelier","year":"1995","journal-title":"LWT Food Sci. Technol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/22\/6840\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:29:13Z","timestamp":1760167753000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/22\/6840"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,12]]},"references-count":63,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2021,11]]}},"alternative-id":["molecules26226840"],"URL":"https:\/\/doi.org\/10.3390\/molecules26226840","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,12]]}}}