Cyclodextrins as carriers for kavalactones in aqueous media: Spectroscopic characterization of (S)-7,8-dihydrokavain and β-cyclodextrin inclusion complex

Bilia, Anna Rita; Bergonzi, Maria Camilla; Vincieri, Franco Francesco; Bari, Lorenzo Di

doi:10.1016/j.jpba.2010.01.037

Cited by 14 publications

(6 citation statements)

References 17 publications

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“…Hisbiscus mucilage has been investigated as a hydrophilic excipient (Jani and Shah, ). Other similar excipients in this class have been shown to improve extraction efficacy of natural‐product‐derived compounds and to modulate absorption dynamics (Pescitelli et al ., ). Taken together it seems likely that the mucilage is acting as an excipient with properties of binding, emulsification and stabilization.…”

Section: Discussionmentioning

confidence: 97%

Pacific Island 'Awa (Kava) Extracts, but not Isolated Kavalactones, Promote Proinflammatory Responses in Model Mast Cells

Shimoda

Park

Stokes

et al. 2012

Phytotherapy Research

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Kava (‘Awa) is a traditional water-based beverage in Pacific island communities, prepared from the ground root and stems of Piper methysticum. Kava use is associated with an ichthyotic dermatitis and delayed type hypersensitivity reactions. In the current study we collated preparative methodologies from cultural practitioners and recreational kava users in various Pacific communities. We standardized culturally-informed aqueous extraction methods and prepared extracts that were subjected to basic physicochemical analysis. Mast cells exposed to these extracts displayed robust intracellular free calcium responses, and concomitant release of pro-inflammatory mediators. In contrast, mast cells were refractory to single or combinatorial stimulation with kavalactones including methysticin, dihydromethysticin and kavain. Moreover, we reproduced a traditional modification of the kava preparation methodology, pre-mixing with the mucilage of Hibiscus taliaceus, and observed its potentiating effect on the activity of aqueous extracts in mast cells. Taken together, these data indicate that water extractable active ingredients may play a role in the physiological and pathophysiological effects of kava, and suggests that mast cell activation may be a mechanistic component of kava-related skin inflammations.

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Section: Discussionmentioning

confidence: 97%

Pacific Island 'Awa (Kava) Extracts, but not Isolated Kavalactones, Promote Proinflammatory Responses in Model Mast Cells

Shimoda

Park

Stokes

et al. 2012

Phytotherapy Research

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“…In the presence of both cyclodextrins, the diffusion of the drug was significantly reduced with respect to that of the free drug, although it is not completely the same as that calculated on the basis of DOSY signals of the CDs (Table 4). This may be related to the fast equilibrium between the bonded and the free drug, as suggested by Pescitelli et al 34 Assuming that the bound and the free ZAL undergo a fast exchange on the diffusion timescale, the observed ZAL diffusion coefficient (D obs ) is an average of the bound (D complex ) and the free (D free ) drug: …”

mentioning

confidence: 89%

Stability and Structure of Inclusion Complexes of Zaleplon with Natural and Modified Cyclodextrins

Jablan¹,

Weitner²,

Gabričević³

et al. 2011

Croat. Chem. Acta

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Abstract. The interaction between zaleplon (ZAL) and different cyclodextrins in aqueous solutions was investigated by spectrofluorimetric and phase solubility studies. Stability constants determined by both methods showed that among natural cyclodextrins, β-cyclodextrin (βCD) formed the most stabile complex but its solubilizing efficiency was limited. Among βCD derivatives, the complex stability and solubilisation efficiency decreased in order: randomly methylated-βCD (RAMEB) > sulphobutylether-βCD (SBEβCD ) > hydroxypropyl-βCD (HPβCD). The inclusion complexes of ZAL with βCD and RAMEB were further characterised by 1 H-NMR spectroscopy and the inclusion complex formation was confirmed in both cases. ROESY spectra showed two binding modes between ZAL and βCD which exist simultaneously in the solution. The first binding mode occurs by the inclusion of the phenyl ring of ZAL into the βCD central cavity via the wider rim of the cyclodextrin cone and is dominant. The second one is formed by the inclusion of pyrazolo[1,5-a]pyrimidine ring of ZAL.(doi: 10.5562/cca1800)

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“…This usually enhances drug solubility in aqueous solutions and affects the chemical characteristics of the encapsulated drug [7][8][9][10]. This fascinating property enables them to be successfully utilized as drug carriers [11][12][13], separation reagents [14], enzyme mimics [15], and photochemical sensors [16], etc. Hydroxypropyl-␤-cyclodextrin (HP␤CD, Fig.…”

Section: Introductionmentioning

confidence: 99%

Alpinetin/hydroxypropyl-β-cyclodextrin host–guest system: Preparation, characterization, inclusion mode, solubilization and stability

Chen

Yang

et al. 2012

Journal of Pharmaceutical and Biomedical Analysis

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Cyclodextrins as carriers for kavalactones in aqueous media: Spectroscopic characterization of (S)-7,8-dihydrokavain and β-cyclodextrin inclusion complex

Cited by 14 publications

References 17 publications

Pacific Island 'Awa (Kava) Extracts, but not Isolated Kavalactones, Promote Proinflammatory Responses in Model Mast Cells

Pacific Island 'Awa (Kava) Extracts, but not Isolated Kavalactones, Promote Proinflammatory Responses in Model Mast Cells

Stability and Structure of Inclusion Complexes of Zaleplon with Natural and Modified Cyclodextrins

Alpinetin/hydroxypropyl-β-cyclodextrin host–guest system: Preparation, characterization, inclusion mode, solubilization and stability

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