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β-环糊精与丁香酚、桉叶油素和丁香精油包合物的比较评价:药物应用的表征与抗菌活性评估

Comparative Evaluation of -Cyclodextrin Inclusion Complexes with Eugenol, Eucalyptol, and Clove Essential Oil: Characterisation and Antimicrobial Activity Assessment for Pharmaceutical Applications.

作者信息

Stancu Alina Ionela, Mititelu Magdalena, Ficai Anton, Ditu Lia-Mara, Buleandră Mihaela, Badea Irinel Adriana, Pincu Elena, Stoian Marius Constantin, Brîncoveanu Oana, Boldeiu Adina, Oprea Eliza

机构信息

Department 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, Romania.

Department of Clinical Laboratory and Food Safety, Faculty of Pharmacy, University of Medicine and Pharmacy Carol Davila, 6 Traian Vuia Street, 020956 Bucharest, Romania.

出版信息

Pharmaceutics. 2025 Jun 29;17(7):852. doi: 10.3390/pharmaceutics17070852.

Abstract

Clove essential oil ( 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. This study characterised the chemical composition of ECEO and comparatively evaluated four -cyclodextrin (-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). GC-MS identified eugenol (90.67%), eugenyl acetate (4.77%), and (E)--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 -CD complex displayed enhanced efficacy against (0.039 mg/mL), surpassing the reference antibiotic gentamicin (0.049 mg/mL). -Cyclodextrin encapsulation significantly enhances the stability and bioactivity of volatile antimicrobial compounds, thereby supporting their potential integration into advanced essential oil-based pharmaceutical formulations.

摘要

丁香精油(ECEO)以其高丁香酚含量和显著的抗菌特性而闻名。然而,其活性成分的挥发性和不稳定性阻碍了其更广泛的药物应用。本研究对ECEO的化学成分进行了表征,并比较评估了四种β-环糊精(β-CD)包封方法:捏合法、共沉淀法、冻干法以及共沉淀-冻干法对丁香酚、桉叶油素和ECEO的包封效果。评估了包封效率、理化性质和抗菌潜力。分析技术包括气相色谱-质谱联用(GC-MS)、顶空气相色谱-质谱联用(HS-GC-MS)、差示扫描量热法(DSC)、乔布氏法和动态光散射(DLS)。GC-MS鉴定出丁香酚(90.67%)、乙酸丁香酚酯(4.77%)和(E)-β-石竹烯(3.98%)是ECEO的主要成分,而HS-GC-MS显示丁香酚含量略有降低(86.46%)。捏合法对丁香酚的包封效率最高,而共沉淀-冻干法对桉叶油素最为适宜。DSC热谱图证实了复合物的形成,DLS分析显示纳米结构的平均直径为186.纳米(多分散指数PDI = 0.298)。抗菌试验表明最低抑菌浓度(MIC)值范围为0.039毫克/毫升至10000毫克/毫升。值得注意的是,ECEO及其β-CD复合物对金黄色葡萄球菌显示出增强的疗效(0.039毫克/毫升),超过了参考抗生素庆大霉素(0.049毫克/毫升)。β-环糊精包封显著提高了挥发性抗菌化合物的稳定性和生物活性,从而支持它们有可能整合到先进的基于精油的药物制剂中。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6292/12300126/ca32870e3492/pharmaceutics-17-00852-g001.jpg

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