Changes in the Physicochemical Properties of Piperine/<i>β</i>-Cyclodextrin due to the Formation of Inclusion Complexes

Ezawa, Toshinari; Inoue, Yutaka; Tunvichien, Sujimon; Suzuki, Rina; Kanamoto, Ikuo

doi:10.1155/2016/8723139

Cited by 27 publications

(45 citation statements)

References 29 publications

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“…these modifications affect its absorption rate and enhance its bioavailability. A recent study on non-covalent interactions between piperine and native β-cyclodextrin underlined the increased water solubility of piperine due to the formation of a piperine-β-cyclodextrin inclusion complex in solution [45].…”

Section: Chemistry Of Piperine and Its Importance For The Compound's mentioning

confidence: 99%

Piperine: Old Spice and New Nutraceutical?

Smilkov

Ackova

Cvetkovski

et al. 2019

CPD

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Background: Many of the activities associated with pepper fruits have been attributed to piperine, the most active compound present in these spices. Objective: This paper aims to provide an overview of the known properties of piperine, i.e. piperine’s chemistry, its physiological activity, documented interactions as a bioenhancer and reported data concerning its toxicity, antioxidant properties and anticancer activity. Discussion: It is known that piperine possesses several properties. In its interaction with other drugs, it can act as a bioavailability enhancer; this effect is also manifested in combination with other nutraceuticals, e.g. with curcumin, i.e. piperine can modify curcumin’s antioxidant, anti-inflammatory, antimicrobial and anticancer effects. Piperine displays significant immunomodulating, antioxidant, chemopreventive and anticancer activity; these effects have been shown to be dose-dependent and tissue-specific. However, the main limitation associated with piperine seems to be its low bioavailability, a disadvantage that innovative formulations are overcoming. Conclusion: It is predicted that an increasing number of studies will focus on piperine, especially those directed towards unraveling its properties at molecular level. The current knowledge about the action of piperine will form a foundation for ways to improve piperine’s bioavailability e.g. exploitation of different carrier systems. The therapeutical applications of this compound will be clarified, and piperine will be recognized as an important nutraceutical.

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Section: Chemistry Of Piperine and Its Importance For The Compound's mentioning

confidence: 99%

Piperine: Old Spice and New Nutraceutical?

Smilkov

Ackova

Cvetkovski

et al. 2019

CPD

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“…In the past, the Inoue and co‐workers have studied the physicochemical properties and solubility of piperine with α‐ and γ‐cyclodextrin (CD). With α‐CD, piperine forms a 1:2 complex, while with β‐ and γ‐CD it forms a 1:1 complex ,. Furthermore, the amount of dissolved piperine was increased by about 16 times in the presence of β‐CD .…”

Section: Introductionmentioning

confidence: 97%

“…With α‐CD, piperine forms a 1:2 complex, while with β‐ and γ‐CD it forms a 1:1 complex ,. Furthermore, the amount of dissolved piperine was increased by about 16 times in the presence of β‐CD . Srinivasan and co‐workers have studied the possible use of serum albumin as a carrier for piperine .…”

Section: Introductionmentioning

confidence: 99%

Piperine Encapsulation within Cucurbit[n]uril (n=6,7): A Combined Experimental and Density Functional Study

2018

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The formation of host-guest between piperine and cucurbit [n] uril (n = 6,7) molecules were studied using experimental and density functional theory (DFT) calculations. The host-guest complexation was monitored using UV-Visible and isothermal calorimetric (ITC) methods. The obtained Jobs plot indicate the formation of 1:1 complex. ITC analysis shows a moderate binding of the guest to the host molecules. The enthalpy of binding and the free energy of formation were negative indicating the facile formation of inclusion complex at room temperature. DFT studies confirm the formation of stable inclusion complexes. In stable inclusion complex of piperine with cucurbit[6]uril, the aromatic moiety was found to be inside the cucurbituril cavity, while in the cucurbit[7]uril inclusion complex, the piperidine moiety was inside the cavity, which was further confirmed by time dependent-DFT study. The global reactivity descriptors analysis, indicate the formation of piperine inclusion complex with cucurbit[7]uril, could prevent the isomerization reaction of piperine. Atoms-in-molecules analysis shows the presence of extra inter and intramolecular bond critical points in the piperine inclusion complex with cucurbit[7]uril, which accounts for its extra stability. The computed intermolecular bond parameters confirm the existence of a non-covalent with partial electrostatic interactions between the guest and host molecules. Energy decomposition analysis, suggest the Pauli repulsion to be higher for the cucurbit[6]uril inclusion complex, while the dispersion plays a major role in stabilizing the cucurbit[7]uril inclusion complex, which was further corroborated by noncovalent index analysis.

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“…Nevertheless, out of the countless reports or CD inclusion compounds, those having pungent compounds as the guest are, to the best of our knowledge, under a dozen. Among them, piperine, which is the pungent component of black pepper, has been complexed with native CDs (α-CD, β-CD, and γ-CD) [23,24], and capsaicin from chilies has been complexed by hydroxypropyl-β-CD [25]. Also reported are complexes of allyl isothiocyanate, the pungent compound from wasabi, with the native hosts α-CD and β-CD [26][27][28] and with randomly methylated β-CD (RAMEB) [29], as well as β-CD complexes with benzyl-and phenylethyl isothiocyanates [30].…”

Section: Introductionmentioning

confidence: 99%

Solid γ-Cyclodextrin Inclusion Compound with Gingerols, a Multi-Component Guest: Preparation, Properties and Application in Yogurt

et al. 2020

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Gingerols from the rhizome of fresh ginger (Zingiber officinale) were obtained by a simple extraction, followed by purification. The gingerols extract was composed of 6-gingerol (54%), 8-gingerol (20%), and 10-gingerol (26%). It was included into γ-cyclodextrin by classic co-dissolution procedures. Solid-state characterisation of γ-cyclodextrin·gingerols shows that this inclusion compound features 1:1 host-to-guest stoichiometry and that it is a microcrystalline powder with a crystalline cell that belongs to the tetragonal space group 4212, having the host molecules stacked in infinite channels where the gingerols are accommodated. In chimico studies with ABTS•+ scavenging, NO• scavenging, β-carotene peroxidation, and 5-LOX inhibition show that γ-cyclodextrin is a suitable carrier for gingerols, because it does not alter their reactivity towards these substances. Yogurt was tested as a matrix for the incorporation of gingerols and γ-cyclodextrin·gingerols into foodstuff. The colour of the fortified yogurt suffered little alterations. In the case of yogurt with the inclusion compound, γ-cyclodextrin·gingerols, as fortificant, these alterations were not perceptible to the naked eye. Moreover, yogurt with γ-cyclodextrin·gingerols showed a good antioxidant activity, thus being suitable for use in nutraceutical applications.

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Changes in the Physicochemical Properties of Piperine/β-Cyclodextrin due to the Formation of Inclusion Complexes

Cited by 27 publications

References 29 publications

Piperine: Old Spice and New Nutraceutical?

Piperine: Old Spice and New Nutraceutical?

Piperine Encapsulation within Cucurbit[n]uril (n=6,7): A Combined Experimental and Density Functional Study

Solid γ-Cyclodextrin Inclusion Compound with Gingerols, a Multi-Component Guest: Preparation, Properties and Application in Yogurt

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