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. 2019 Jul 22;9(39):22586-22596.
doi: 10.1039/c9ra02336d. eCollection 2019 Jul 17.

Preparation of terpolymer capsules containing Rosmarinus officinalis essential oil and evaluation of its antifungal activity

Juliete Silva Neves  1 , Zita Lopes-da-Silva  2 , Maria de Sousa Brito Neta  3 , Sacha Braun Chaves  3 , Yanna Karla de Medeiros Nóbrega  2 , Angelo Henrique de Lira Machado  1 , Fabricio Machado  1
Affiliations

Preparation of terpolymer capsules containing Rosmarinus officinalis essential oil and evaluation of its antifungal activity

Juliete Silva Neves et al. RSC Adv. .

Abstract

The essential oil from Rosmarinus officinalis presents antifungal activity and is used in industry as a natural preserving agent. However, essential oils are unstable compounds. So, the encapsulation of essential oils is a technique used to protect it, minimizing degradation and reducing undesired interaction with the other formulation components. Thus, this work focuses on the synthesis of terpolymeric capsules containing essential oil from Rosmarinus officinalis, aiming to use it as an antifungal component in cosmetics. The capsules were obtained via terpolymerization of methyl methacrylate, styrene and methacrylic acid in a dispersed phase polymerization process. The properties of the polymers and the fungicide activity were evaluated. The studied essential oil presented a Minimum Inhibitory Concentration (MIC) ranging from 2.25 to 4.5 mg mL-1 and a Minimum Fungicidal Concentration (MFC) from 4.5 to 9.0 mg mL-1 for strains of Candida albicans, Candida glabrata and Candida parapsilosis, and after the encapsulation process, the antifungal activity of the oil was maintained. Additionally, cytotoxicity assays against fibroblast cell lines and human keratinocytes showed that the polymeric nanocapsules containing Rosmarinus officinalis essential oil can be regarded as a very promising material intended for cosmetics and drug delivery applications.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Chromatogram obtained by gas chromatography-mass spectrometry analysis of Rosmarinus officinalis essential oil, where the numbers from 1 to 11 correspond to the majority components, whose names are shown in the Table 4.
Fig. 2
Fig. 2. Nuclear magnetic resonance spectra of Rosmarinus officinalis essential oil.
Fig. 3
Fig. 3. Polymerization conversion profiles of copolymers methacrylic acid/methyl methacrylate (MAA/MMA) and the capsules of Rosmarinus officinalis essential oil with methacrylic acid/methyl methacrylate (MAA/MMA_R.O.).
Fig. 4
Fig. 4. Polymerization conversion profiles of capsules of Rosmarinus officinalis essential oil with methyl methacrylate/styrene (MMA/STY_R.O.).
Fig. 5
Fig. 5. Polymerization conversion profiles of terpolymers methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY) and the capsules of essential oil with methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY_R.O.).
Fig. 6
Fig. 6. Scanning electron microscopy (SEM) the copolymers capsules with (a) methacrylic acid/methyl methacrylate (MAA/MMA_R.O.), (b) methacrylic acid/methyl methacrylate (MAA/MMA), (c) methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY_R.O.) and (d) methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY).
Fig. 7
Fig. 7. Particle size distribution the copolymers capsules with (a) methacrylic acid/methyl methacrylate (MAA/MMA_R.O.), (b) methacrylic acid/methyl methacrylate (MAA/MMA), (c) methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY_R.O.) and (d) methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY).
Fig. 8
Fig. 8. Chemical structure of methyl methacrylate, methacrylic acid and styrene.
Fig. 9
Fig. 9. Molar mass distribution of soluble fraction of the copolymer and capsules with methacrylic acid/methyl methacrylate and the terpolymers and capsules with methacrylic acid/methyl methacrylate/styrene.
Fig. 10
Fig. 10. Thermogravimetric analysis of methacrylic acid/methyl methacrylate copolymers (MAA/MMA), the capsules with methacrylic acid/methyl methacrylate (MAA/MMA_R.O.) and methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY) and the methacrylic acid/methyl methacrylate/styrene terpolymers (MAA/MMA/STY_R.O.).
Fig. 11
Fig. 11. Chromatogram from gas chromatography-mass spectrometry analyses to evaluate the efficiency of the encapsulation in (a) 1,8-cineol and (b) camphor.
Fig. 12
Fig. 12. Candida albicans fungus culture plates treated with (a) 0.25% essential oil of Rosmarinus officinalis, (b) 0.25% of methacrylic acid/methyl methacrylate/styrene terpolymer (MAA/MMA/STY) (c) 0.25% of methacrylic acid/methyl methacrylate/styrene terpolymer with the encapsulated essential oil (MAA/MMA/STY_R.O.).
Fig. 13
Fig. 13. Peroxide index profile for methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY) terpolymer.
Fig. 14
Fig. 14. Evaluation of the cytotoxic activity of methacrylic acid/methyl methacrylate copolymers (MAA/MMA), the capsules with methacrylic acid/methyl methacrylate (MAA/MMA_R.O.) and methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY) and the methacrylic acid/methyl methacrylate/styrene terpolymers (MAA/MMA/STY_R.O.) against fibroblast cell line (FIBRO) after 24 h exposure at concentrations of 0.01 mg mL−1, 0.05 mg mL−1, 0.1 mg mL−1, 0.25 mg mL−1 and 0.5 mg mL−1. The confidence level for these analyzes was 95% (p < 0.05).
Fig. 15
Fig. 15. Evaluation of the cytotoxic activity of methacrylic acid/methyl methacrylate copolymers (MAA/MMA), the capsules with methacrylic acid/methyl methacrylate (MAA/MMA_R.O.) and methacrylic acid/methyl methacrylate/styrene (MAA/MMA/STY) and the methacrylic acid/methyl methacrylate/styrene terpolymers (MAA/MMA/STY_R.O.) against keratinocyte cell (HaCaT) after 24 h exposure at concentrations of 0.01 mg mL−1, 0.05 mg mL−1, 0.1 mg mL−1, 0.25 mg mL−1 and 0.5 mg mL−1. The confidence level for these analyzes was 95% (p < 0.05).
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