Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications
Clove essential oil (<i>Eugenia caryophyllata</i> essential oil, ECEO) is known for its high eugenol content and notable antimicrobial properties. However, the volatility and instability of its active compounds hinder broader pharmaceutical applications. <b>Methods:</b> This...
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| author | Alina Ionela Stancu Magdalena Mititelu Anton Ficai Lia-Mara Ditu Mihaela Buleandră Irinel Adriana Badea Elena Pincu Marius Constantin Stoian Oana Brîncoveanu Adina Boldeiu Eliza Oprea |
| author_facet | Alina Ionela Stancu Magdalena Mititelu Anton Ficai Lia-Mara Ditu Mihaela Buleandră Irinel Adriana Badea Elena Pincu Marius Constantin Stoian Oana Brîncoveanu Adina Boldeiu Eliza Oprea |
| author_sort | Alina Ionela Stancu |
| collection | DOAJ |
| description | Clove essential oil (<i>Eugenia caryophyllata</i> essential oil, ECEO) is known for its high eugenol content and notable antimicrobial properties. However, the volatility and instability of its active compounds hinder broader pharmaceutical applications. <b>Methods:</b> This study characterised the chemical composition of ECEO and comparatively evaluated four <i>β</i>-cyclodextrin (<i>β</i>-CD) encapsulation methods: kneading, co-precipitation, lyophilisation, and co-precipitation–lyophilisation for eugenol, eucalyptol, and ECEO. Encapsulation efficiency, physicochemical properties, and antimicrobial potential were assessed. Analytical techniques included Gas Chromatography–Mass Spectrometry (GC-MS), Headspace GC-MS (HS-GC-MS), Differential Scanning Calorimetry (DSC), Job’s method, and Dynamic Light Scattering (DLS). <b>Results:</b> GC-MS identified eugenol (90.67%), eugenyl acetate (4.77%), and (E)–<i>β</i>-caryophyllene (3.98%) as major components of ECEO, while HS-GC-MS indicated a slightly reduced eugenol content (86.46%). The kneading method yielded the highest encapsulation efficiency for eugenol, whereas the co-precipitation–lyophilisation method was optimal for eucalyptol. DSC thermograms confirmed complex formation, and DLS analysis revealed nanostructures averaging 186.4 nm in diameter (PDI = 0.298). Antimicrobial assays showed MIC values ranging from 0.039 mg/mL to 10,000 mg/mL. Notably, ECEO and its <i>β</i>-CD complex displayed enhanced efficacy against <i>Escherichia coli</i> (0.039 mg/mL), surpassing the reference antibiotic gentamicin (0.049 mg/mL). <b>Conclusions:</b> <i>β</i>-Cyclodextrin encapsulation significantly enhances the stability and bioactivity of volatile antimicrobial compounds, thereby supporting their potential integration into advanced essential oil-based pharmaceutical formulations. |
| format | Article |
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| institution | Kabale University |
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| language | English |
| publishDate | 2025-06-01 |
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| spelling | doaj-art-e55bffa843594d4ea96bb38532ed4ff62025-08-20T03:56:47ZengMDPI AGPharmaceutics1999-49232025-06-0117785210.3390/pharmaceutics17070852Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical ApplicationsAlina Ionela Stancu0Magdalena Mititelu1Anton Ficai2Lia-Mara Ditu3Mihaela Buleandră4Irinel Adriana Badea5Elena Pincu6Marius Constantin Stoian7Oana Brîncoveanu8Adina Boldeiu9Eliza Oprea10Department Science and Engineering of Oxide Materials and Nanomaterials, Faculty of Chemical Engineering and Biotechnology, National University of Science and Technology Politehnica Bucharest, 1-7 Polizu Street, 011061 Bucharest, RomaniaDepartment of Clinical Laboratory and Food Safety, Faculty of Pharmacy, University of Medicine and Pharmacy Carol Davila, 6 Traian Vuia Street, 020956 Bucharest, RomaniaDepartment Science and Engineering of Oxide Materials and Nanomaterials, Faculty of Chemical Engineering and Biotechnology, National University of Science and Technology Politehnica Bucharest, 1-7 Polizu Street, 011061 Bucharest, RomaniaDepartment of Botany and Microbiology, Faculty of Biology, University of Bucharest, Portocalilor 1-3, 77206 Bucharest, RomaniaDepartment of Analytical Chemistry and Physical Chemistry, Faculty of Chemistry, University of Bucharest, 90-92 Panduri Street, 050663 Bucharest, RomaniaDepartment of Analytical Chemistry and Physical Chemistry, Faculty of Chemistry, University of Bucharest, 90-92 Panduri Street, 050663 Bucharest, RomaniaDepartment of Analytical Chemistry and Physical Chemistry, Faculty of Chemistry, University of Bucharest, 90-92 Panduri Street, 050663 Bucharest, RomaniaNational Institute for Research and Development in Microtechnologies, 126A Erou Iancu Nicolae Street, Voluntari City, Ilfov County, 077190 Bucharest, RomaniaNational Institute for Research and Development in Microtechnologies, 126A Erou Iancu Nicolae Street, Voluntari City, Ilfov County, 077190 Bucharest, RomaniaNational Institute for Research and Development in Microtechnologies, 126A Erou Iancu Nicolae Street, Voluntari City, Ilfov County, 077190 Bucharest, RomaniaDepartment of Botany and Microbiology, Faculty of Biology, University of Bucharest, Portocalilor 1-3, 77206 Bucharest, RomaniaClove essential oil (<i>Eugenia caryophyllata</i> essential oil, ECEO) is known for its high eugenol content and notable antimicrobial properties. However, the volatility and instability of its active compounds hinder broader pharmaceutical applications. <b>Methods:</b> This study characterised the chemical composition of ECEO and comparatively evaluated four <i>β</i>-cyclodextrin (<i>β</i>-CD) encapsulation methods: kneading, co-precipitation, lyophilisation, and co-precipitation–lyophilisation for eugenol, eucalyptol, and ECEO. Encapsulation efficiency, physicochemical properties, and antimicrobial potential were assessed. Analytical techniques included Gas Chromatography–Mass Spectrometry (GC-MS), Headspace GC-MS (HS-GC-MS), Differential Scanning Calorimetry (DSC), Job’s method, and Dynamic Light Scattering (DLS). <b>Results:</b> GC-MS identified eugenol (90.67%), eugenyl acetate (4.77%), and (E)–<i>β</i>-caryophyllene (3.98%) as major components of ECEO, while HS-GC-MS indicated a slightly reduced eugenol content (86.46%). The kneading method yielded the highest encapsulation efficiency for eugenol, whereas the co-precipitation–lyophilisation method was optimal for eucalyptol. DSC thermograms confirmed complex formation, and DLS analysis revealed nanostructures averaging 186.4 nm in diameter (PDI = 0.298). Antimicrobial assays showed MIC values ranging from 0.039 mg/mL to 10,000 mg/mL. Notably, ECEO and its <i>β</i>-CD complex displayed enhanced efficacy against <i>Escherichia coli</i> (0.039 mg/mL), surpassing the reference antibiotic gentamicin (0.049 mg/mL). <b>Conclusions:</b> <i>β</i>-Cyclodextrin encapsulation significantly enhances the stability and bioactivity of volatile antimicrobial compounds, thereby supporting their potential integration into advanced essential oil-based pharmaceutical formulations.https://www.mdpi.com/1999-4923/17/7/852<i>β</i>-cyclodextrin<i>Eugenia caryophyllata</i> essential oileugenolcyclodextrin inclusion complexesantimicrobial activity |
| spellingShingle | Alina Ionela Stancu Magdalena Mititelu Anton Ficai Lia-Mara Ditu Mihaela Buleandră Irinel Adriana Badea Elena Pincu Marius Constantin Stoian Oana Brîncoveanu Adina Boldeiu Eliza Oprea Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications Pharmaceutics <i>β</i>-cyclodextrin <i>Eugenia caryophyllata</i> essential oil eugenol cyclodextrin inclusion complexes antimicrobial activity |
| title | Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications |
| title_full | Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications |
| title_fullStr | Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications |
| title_full_unstemmed | Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications |
| title_short | Comparative Evaluation of <i>β</i>-Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications |
| title_sort | comparative evaluation of i β i cyclodextrin inclusion complexes with eugenol eucalyptol and clove essential oil characterisation and antimicrobial activity assessment for pharmaceutical applications |
| topic | <i>β</i>-cyclodextrin <i>Eugenia caryophyllata</i> essential oil eugenol cyclodextrin inclusion complexes antimicrobial activity |
| url | https://www.mdpi.com/1999-4923/17/7/852 |
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