Aggregation property of glycyrrhizic acid and its interaction with cyclodextrins analyzed by dynamic light scattering, isothermal titration calorimetry, and NMR.
The structural properties of glycyrrhizic acid, a sweet-tasting constituent of Glycyrrhiza glabra, and its interaction with cyclodextrins were analyzed using dynamic light scattering, isothermal titration calorimetry, and NMR. The dynamic light scattering and NMR studies showed that glycyrrhizic acid forms a water-soluble aggregate that disperses upon the addition of γ-cyclodextrin. The high sweetness of glycyrrhizic acid can be closely correlated with this aggregation, because the multimers of glycyrrhizic acid can simultaneously bind to the sweet taste receptors on the human tongue. The isothermal titration calorimetry experiments demonstrated that γ-cyclodextrin binds to glycyrrhizic acid more strongly than β-cyclodextrin, however, both reactions are accompanied by a favorable change in binding entropy. Considering the large negative change in heat capacity that is observed during the binding of γ-cyclodextrin, the main driving force for the binding is hydrophobic interactions with dehydration, which is typical for inclusion complex. NMR experiments showed that γ-cyclodextrin interacts with the central part of the aglycone moiety, not the glucuronic acid moieties, resulting in high binding affinity. It should also be noted that the two distinct complexes of glycyrrhizic acid with γ-cyclodextrin would exist in aqueous solution.
Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, 1-5 Hangi-cho, Shimogamo, Sakyo-ku, Kyoto, Kyoto 606-8522, Japan.
Yusuke
Y
Izutani
Graduate School of Science and Technology, Kyoto Institute of Technology, Goshokaido-cho, Matsugasaki, Sakyo-ku, Kyoto, Kyoto 606-8585, Japan.
Kenji
K
Kanaori
Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, 1-5 Hangi-cho, Shimogamo, Sakyo-ku, Kyoto, Kyoto 606-8522, Japan. Electronic address: oda@kpu.ac.jp.
Masayuki
M
Oda
D002151:Calorimetry; D003505:Cyclodextrins / Q000737:chemistry / Q000378:metabolism*; D019695:Glycyrrhizic Acid / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D012542:Scattering, Radiation; D013816:Thermodynamics
D003505:Cyclodextrins; D019695:Glycyrrhizic Acid
Aggregation; Binding thermodynamics; Dispersion; Multimodal inclusion complex