Physicochemical investigation and molecular modeling of cyclodextrin complexation mechanism with eugenol

Nuchuchua, Onanong; Saesoo, Somsak; Sramala, Issara; Puttipipatkhachorn, Satit; Soottitantawat, Apinan; Ruktanonchai, Uracha

doi:10.1016/j.foodres.2009.06.006

Cited by 62 publications

(31 citation statements)

References 29 publications

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“…2a, 3a, 4a, 5a, and 6a and was found to be in agreement with the reported thermogram of eugenol (Chaar et al 2004;Monteiro et al 2011;Nuchuchua et al 2009;Santos et al 2009). The DSC curve for the eugenol displayed one endothermic peak, at 258.81°C which attributed to the volatilization of eugenol (Monteiro et al 2011).…”

Section: Differential Scanning Calorimetrysupporting

confidence: 91%

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Unveiling the compatibility of eugenol with formulation excipients by systematic drug-excipient compatibility studies

et al. 2015

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Background: The drug-excipient compatibility studies were carried out with the possible excipients viz. Tween 80, Carbopol 940, chitosan, sodium alginate, and polycaprolactone (PCL) for their possible use in the formulation of eugenol loaded nanoemulsion gels and nanoparticles. Methods: The eugenol-excipient compatibility studies were carried out by visual observations, differential scanning calorimetry (DSC), infrared spectroscopy (FTIR), and high-performance thin-layer chromatography (HPTLC). Results: No notable change was observed in the samples on visual observation. From the results of the DSC studies, to a much extent, it was assumed that eugenol was not subjected to any interaction with the selected excipients for the proposed nanoemulsion gel and nanoparticles. But in some cases viz. polycaprolactone and Carbopol, though not to a significant level, slight deviation of the nature and position of the endothermic peaks of eugenol were observed. The results of the IR spectroscopy confirmed the compatibility of eugenol with Tween 80, Carbopol 940, chitosan, sodium alginate, and polycaprolactone. The retention factor of the HPTLC densitogram peaks for all the physical mixtures was well within the retention factor (R f ) value range observed for pure eugenol. Conclusions: The study results confirmed that eugenol is compatible with the selected excipients for the development of nanoemulsion gels and nanoparticles.

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Section: Differential Scanning Calorimetrysupporting

confidence: 91%

“…In addition, sharp peaks at 1637.56, 1610.56, and 1514.12 cm -1 were also found from eugenol, which could be due to C=C stretching of the aromatic moiety. The obtained spectrum was found to be well in agreement with the reported spectrum of eugenol (Nuchuchua et al 2009;Yang and Song, 2005).…”

Section: Infrared Spectroscopysupporting

confidence: 88%

Unveiling the compatibility of eugenol with formulation excipients by systematic drug-excipient compatibility studies

et al. 2015

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“…Nuchuchua et al correlated the computational and spectroscopic studies of inclusion complex of eugenol with a-CD, b-CD and HP-b-CD (2-hydroxypropyl-b-cyclodextrin) to find the relation between size of EOs constituent and size of internal cavity of encapsulate. 145 It was observed that eugenol released rapidly from a-CD complex due to its small size of internal cavity whereas the release was slow in case of b-CD and HP-b-CD complex due to the proper fitting and bonding of eugenol with the sites present in their internal cavities. 145 Similarly, Marques et al suggested that the encapsulation and release of volatile may depend on the size and the interaction sites present in the cavity of the different CDs.…”

Section: Release Characteristics Of Eos Encapsulatesmentioning

confidence: 99%

“…145 It was observed that eugenol released rapidly from a-CD complex due to its small size of internal cavity whereas the release was slow in case of b-CD and HP-b-CD complex due to the proper fitting and bonding of eugenol with the sites present in their internal cavities. 145 Similarly, Marques et al suggested that the encapsulation and release of volatile may depend on the size and the interaction sites present in the cavity of the different CDs. 38 The various processes involved in release of EOs are discussed in further sections and a general mechanism of release is shown in Fig.…”

Section: Release Characteristics Of Eos Encapsulatesmentioning

confidence: 99%

Polymeric Encapsulates of Essential Oils and Their Constituents: A Review of Preparation Techniques, Characterization, and Sustainable Release Mechanisms

et al. 2016

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Natural polymer based encapsulation of essential oil (EO) is one of the emerging and challenging area of research in perfumery, cosmetics, flavoring agents, preservatives, therapeutics, etc. The knowledge of formulation techniques and physico-chemical properties of the polymers are the basic requirements for the successful encapsulations of essential oils (EOs). This current review article is focused on a comparative account of various formulation techniques based on their applicability. For the first time, it also reviews various physico-chemical techniques used in the analysis of EO encapsulates to determine their stability, structure, surface morphology, and encapsulation efficiency. Further, the mechanisms involved in the release of EOs from encapsulates, along with various factors affecting their release, have also been discussed.

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“…Compound encapsulation in βCD is therefore an interesting technique to enhance the stability of these compounds [7][8][9] . Experimental data report that linalool and eugenol can form an inclusion complex host:guest ratio of 1:1 with βCD [10][11][12][13][14][15][16][17] . Unfortunately, no experimental data has revealed the host-guest ori- entation within the complex and inclusion complex interactions, which are important to elucidate the encapsulation mechanism.…”

Section: Introductionmentioning

confidence: 99%

Molecular calculations on β-cyclodextrin inclusion complexes with five essential oil compounds from Ocimum basilicum (sweet basil)

Lawtrakul¹,

Inthajak²,

Toochinda³

2014

ScienceAsia

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Molecular docking and quantum chemistry calculations were used to establish the molecular model of β-cyclodextrin inclusion complex with five major compounds found in Thai sweet basil (Ocimum basilicum) essential oils, which includes linalool, eugenol, methyl eugenol, estragole, and eucalyptol. The electronic structures and the binding energies of 1:1 inclusion complexes of host:guest ratio for all five compounds were modelled by B3LYP/6-31G (d) calculations both in the gas phase and in the aqueous phase using polarizable continuum methods. The results agree with the experimental data, which show the ability of the compounds in Thai sweet basil essential oils to form an inclusion complex with β-cyclodextrin.

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Physicochemical investigation and molecular modeling of cyclodextrin complexation mechanism with eugenol

Cited by 62 publications

References 29 publications

Unveiling the compatibility of eugenol with formulation excipients by systematic drug-excipient compatibility studies

Unveiling the compatibility of eugenol with formulation excipients by systematic drug-excipient compatibility studies

Polymeric Encapsulates of Essential Oils and Their Constituents: A Review of Preparation Techniques, Characterization, and Sustainable Release Mechanisms

Molecular calculations on β-cyclodextrin inclusion complexes with five essential oil compounds from Ocimum basilicum (sweet basil)

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