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

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

doi:10.1155/2016/8723139

Toshinari Ezawa, Ikuo Kanamoto + Show 3 more

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https://doi.org/10.1155/2016/8723139

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Abstract

Piperine (PP) is a pungent component in black pepper that possesses useful biological activities; however it is practically insoluble in water. The aim of the current study was to prepare a coground mixture (GM) of PP and β-cyclodextrin (βCD) (molar ratio of PP/βCD = 1/1) and subsequently evaluate the solubility of PP and physicochemical properties of the GM. DSC thermal behavior of the GM showed the absence of melting peak of piperine. PXRD profile of the GM exhibited halo pattern and no characteristic peaks due to PP and βCD were observed. Based on Job's plot, the PP/βCD complex in solution had a stoichiometric ratio of 1/1. Raman spectrum of the GM revealed scattering peaks assigned for the benzene ring (C=C), the methylene groups (CH2), and ether groups (C-O-C) of PP that were broaden and shifted to lower frequencies. SEM micrographs showed that particles in the GM were agglomerated and had rough surface, unlike pure PP and pure βCD particles. At 15 min of dissolution testing, the amount dissolved of PP in the GM was dramatically increased (about 16 times) compared to that of pure PP. Moreover the interaction between PP and βCD cavity was detected by 1H-1H NMR nuclear Overhauser effect spectroscopy NMR spectroscopy.

Highlights

Piperine [(2E,4E)-1-[5-(1,3-benzodioxol-5yl)-1-oxo-2,4-pentadienyl]piperidine, denoted here as PP] (Figure 1) is a component found in black pepper
The thermograms of intact PP, PP ground for 60 min, the physical mixture (PM) (PP/βCD = 1/1), and the Ground mixtures (GMs) (PP/βCD = 2/1) showed an endothermic peak due to the melting of PP at around 130∘C (Figure 2(a, b, d, e)), whereas it was not observed in the thermograms of GM (PP/βCD = 1/1) and GM (PP/βCD = 1/2) (Figure 2(f, g))
Differential Scanning Calorimetry (DSC) results suggested that PP/βCD complexes might be produced at a molar ratio of 1/1 or 1/2 PP/βCD

Summary

Introduction

Piperine [(2E,4E)-1-[5-(1,3-benzodioxol-5yl)-1-oxo-2,4-pentadienyl]piperidine, denoted here as PP] (Figure 1) is a component found in black pepper. PP has been reported for its slight insecticidal activity against third instar larvae of Culex pipiens pallens, Aedes aegypti, and A. togoi [2]. PP at a concentration of 100–500 μg/mL has been reported to exhibit antibacterial action against Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, and Escherichia coli [3]. PP has been reported to reduce thiobarbituric acid reactive substances and the degree of lipid peroxidation [4]. PP is relatively stable in black pepper; it is readily isomerized when exposed to ultraviolet light [8]. PP in pepper oleoresin must be shielded from light. Because of its low aqueous solubility, PP is unable to exhibit its beneficial actions properly

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