Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins

Kfoury, Miriana; Sahraoui, Anissa Lounès-Hadj; Bourdon, Natacha; Laruelle, Frédéric; Fontaine, Joël; Auezova, Lizette; Greige‐Gerges, Hélène; Fourmentin, Sophie

doi:10.1016/j.foodchem.2015.09.078

Cited by 86 publications

(67 citation statements)

References 38 publications

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“…5). The existing literature also showed the protective effect of CD towards other guests [13,30–33]. When comparing the photostability of trans -Ner in its pure form and in the EO, it can be noted that the degradation of trans -Ner alone ( K = 0.0145 min −1 ) was slightly different than trans -Ner in EO ( K = 0.0127 min −1 ).…”

Section: Resultsmentioning

confidence: 85%

“…Various encapsulation materials are used for food applications such as liposomes, phytosomes, cyclodextrins, dendrimers and many others [7–9]. The use of cyclodextrins (CDs) in food industry is currently flourishing due to their high potential to solubilize, stabilize and protect flavors and food ingredients [10–13]. CDs are non-toxic water-soluble cyclic oligosaccharides composed of six, seven or eight α-(1→4) glucopyranose units giving rise, respectively, to α-, β- and γ-CDs [14].…”

Section: Introductionmentioning

confidence: 99%

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

Azzi¹,

Danjou

Landy

et al. 2017

Beilstein J. Org. Chem.

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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.

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Section: Resultsmentioning

confidence: 85%

Section: Introductionmentioning

confidence: 99%

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

Azzi¹,

Danjou

Landy

et al. 2017

Beilstein J. Org. Chem.

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“…Focusing on EOs, and as previously discussed, they may present undesired features, such as volatility, poor aqueous solubility, and stability. Therefore, host-guest supramolecular complexes are often obtained by using solid-state-based methods [14] such as freeze-drying [76,77], coprecipitation [78], and the saturated approach [27], improving the solubility of the EO and thus allowing the use of NMR techniques for the quantitative and qualitative assessment of the complexation process [74]. For example, the complexation of eugenol with β-CD was obtained by using the saturation method, and the obtained complex, in the solid state, was characterized by either 1 H, 13 C, or 2D NMR techniques, confirming the thread of CD's cavity by the aromatic ring of the eugenol [27].…”

Section: On the Methods To Follow The Interactions Between Cyclodextrmentioning

confidence: 99%

“…Also from group II, surface tension has also been used to follow the effect of CDs on the aggregation and interfacial properties of surfactants in CD-surfactant-containing solutions [74] Phase solubility studies Cabreuva essential oil + HP-β-CD [74] Phase solubility studies β-caryophyllene + HP-β-CD [76] UV-vis Black pepper essential oil + HP-β-CD [76] Phase solubility studies CDs 1 + PPs 2 [77] Phase solubility studies, NMR, TGA, DSC β-CD + estragole [78] NMR β-CD + eugenol [27] NMR β-CD + rosmarinic acid [75] NMR Cyclohexylacetic acid + β-CD Phase solubility studies, NMR, HPLC Polymethoxyflavones + HP-β-CD [93] GC, total organic carbon, phase-solubility studies SBE-β-CD, SBE-γ-CD and HP-β-CD + EOS 6 [94,95] 1 CDs: alpha-cyclodextrin (α-CD), beta-cyclodextrin (β-CD), gamma-cyclodextrin (γ-CD), 2-hydroxypropyl-β-cyclodextrin (HP-β-CD), randomly methylated-beta-cyclodextrins (RAMEB), low methylated beta-cyclodextrin (CRYSMEB), and sulfobutylether β-cyclodextrin (SBE-β-CD) 2 PPs: trans-anethole, estragole, eugenol, isoeugenol (phenylpropenes), caffeic acid, p-coumaric acid, and ferulic acid (hydroxycinnamic acids) 3 UAS: ultrasonic attenuation spectroscopy APGs: glucopyranosides (octyl G8, decyl G10, dodecyl G12, tetradecyl G14) and two maltosides (decyl M10, dodecyl M12) 5 EOs: essential oils of cedarwood, clove, eucalyptus, and peppermint 6 EOS: essential oils of Artemisia dracunculus, Citrus reticulata Blanco, Citrus aurantifolia, Melaleuca alternifolia, Melaleuca quinquenervia, and Rosmarinus officinalis cineoliferum Table 2. Compilation of the most relevant techniques used to study the interactions between CDs and bio-based compounds.…”

mentioning

confidence: 99%

Interactions between Bio-Based Compounds and Cyclodextrins

Medronho¹,

Gonçalves²,

RaquelRodríguez-Solana³

et al. 2018

Cyclodextrin - A Versatile Ingredient

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Bio-based compounds, such as "green" surfactants and phytochemicals, are regarded as future sustainable resources for a vast range of applications in a modern society increasingly demanding economical, social, and environmental awareness. Natural compounds from plants (phytochemicals) are very sought by the pharmaceutical, cosmetic, and food industries. On the other hand, the growing interest in "green" surfactants (e.g., carbohydrate-based) is due to, inter alia, their preparation from renewable raw materials, ready biodegradability, and biocompatibility, among other reasons of fundamental, practical, economical, and environmental orders. Despite the wide range of potential applications of these bio-based compounds, their practical use is still limited due to many reasons such as poor aqueous solubility, volatility, reactivity, etc. Generally, when complexed with cyclodextrins, these biobased compounds enhance considerably their performance and potential applications. Thus, this chapter aims at recalling some general fundamental aspects of phytochemicals and "green" surfactants, such as structure, function, and applications. In addition, their interactions with cyclodextrins are discussed from a physicochemical point of view with special focus on the techniques, mathematic modeling, and thermodynamic parameters (e.g., interactions, stoichiometries, association constants, etc.).

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“…Examples of this group include trans-anethole, methyl chavicol, eugenol, isoeugenol, vanillin, safrole, myristicin and cinnamaldehyde [19,47] (Figure 8). …”

Section: Phenylpropenes (Benzene Derivatives)mentioning

confidence: 99%

Chemical Structure, Quality Indices and Bioactivity of Essential Oil Constituents

Morsy¹

2017

Active Ingredients From Aromatic and Medicinal Plants

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Essential oil (EO) is a mixture of low molecular weight constituents that are responsible for its characteristic aroma. These constituents include terpenoid and non-terpenoid hydrocarbons and their oxygenated derivatives. This chapter focuses on the heterogeneous composition of the essential oils. It discusses the usage of essential oil constituents as a key marker of the oil quality, freshness and unique characteristics. It describes the biological activity and synergistic effect of the essential oil constituents as antioxidant, antibacterial, antifungal and anticancer agents.

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Solubility, photostability and antifungal activity of phenylpropanoids encapsulated in cyclodextrins

Cited by 86 publications

References 38 publications

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

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

Interactions between Bio-Based Compounds and Cyclodextrins

Chemical Structure, Quality Indices and Bioactivity of Essential Oil Constituents

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