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Exploring the interaction between functional carbohydrate polymers and small-molecule active compounds
Naturally occurring carbohydrates polymers and their functional derivatives play important roles in the research and technology development in the food, nutrition, and pharmaceutical areas. A major property of these polymeric materials is to associate, enable, enhance, and/or deliver small-molecule active compound such as phytochemicals, nutraceuticals, and active pharmaceutical ingredients (APIs). The goal of this project was to synthesize and characterize phytoglycogen-based materials and study their structure-function relationships in association with selected small-molecule active compounds, including resveratrol, a food-related poorly water-soluble phenolic compound, griseofulvin, an insoluble API, and CCVJ (9-(2-carboxy-2-cyanovinyl) julolidine) a molecular rotor used as a structural probe of polymeric materials.
In this study, phytoglycogen (PG) was derivatives to phytoglycogen octenyl succinate (PG-OS), hydroxypropyl phytoglycogen (HPP), and octenylsuccinate hydroxypropyl phytoglycogen (OHPP). PG, HPP, and OHPP were evaluated for their efficacy in improving the solubility and Caco-2 permeation of resveratrol and griseofulvin, and using CCVJ, PG-OS was evaluated on its performance at oil-water interface in comparison with OSA-starch, acacia gum, and sodium caseinate. The results showed that: 1) PG, HPP, and OHPP substantially improved the soluble amount and Caco-2 monolayer permeation of resveratrol and griseofulvin, and anti-fungal efficacy of griseofulvin in the aqueous system were significantly enhanced; suggesting that the active ingredients were effective solubilized and released to become bioavailable, 2) among all PG-based biopolymers, OHPP showed superior performance in solubilizing resveratrol and griseofulvin, and 3) in the oil-water two-layer model system, PG-OS, OSA-starch, acacia gum, and sodium caseinate all affected the transferring of CCVJ from oil to aqueous phase, and the effect was monitored and interpreted by the emission spectra of molecular rotor; in the emulsion system, the emission peak wavelength of CCVJ was correlated with the amount of biopolymer adsorbed at the interface of emulsion droplets, and the molecular rotor-based method can be used to characterize the interfacial adsorption of biopolymer at the interface in oil-in-water emulsion.
This study provides information on the interactions between phytoglycogen-based biopolymers and poorly water-soluble active ingredients, and may potentially supports the study of new functional ingredients interaction with phytoglycogen-based biopolymers in aqueous system. Furthermore, this work allowed us to advance the use of molecular rotor as new analytical tool to study the physicochemical properties of biopolymer.