Analysis of supercooling activity of tannin-related polyphenols☆
Introduction
Substances that affect freezing of water include heterogeneous ice nucleation substances, which raise freezing temperatures by enhancing ice nucleation [35], [36], anti-freeze substances such as anti-freeze proteins and glycoproteins, which inhibit ice crystal growth after ice nucleation [3], [10], [11], and anti-ice nucleation substances, which reduce freezing temperatures by promoting supercooling due to inhibition of ice nucleation [15], [16], [17], [23], [24], [38].
Among these various types of freeze-controlling substances, there have been few studies on anti-ice nucleation (supercooling-promoting) substances, and until recently only 16 kinds of single compounds such as proteins [5], [12], [19], [39] including antifreeze proteins [5], [12] and antifreeze glycoproteins [7], [12], [28], [39], polysaccharides [43], terpenoids [20], phenylpropanoids [18], polyvinyl alcohol (PVA) [12], [41], [42] and polyglycerol [41] in addition to crude extracts from a few kinds of plant seeds [2] had been identified as supercooling-promoting substances (for a list, see Kasuga et al. [15], [16]).
Recent studies on the mechanisms of winter adaptation of xylem parenchyma cells (XPCs) in trees by deep supercooling, however, have disclosed the presence of supercooling-promoting activity (SCA) in crude xylem extracts from several hardwood and softwood trees that contained deep supercooling XPCs [15], [26]. Furthermore, in studies on the mechanisms of deep supercooling of XPCs, four kinds of flavonol glycosides were identified as novel supercooling-promoting substances in deep supercooling XPCs of Katsura tree [16], [23]. Based on similarity in chemical structures with supercooling-promoting flavonol glycosides in XPCs, a further 26 flavonoid glycosides have been revealed to have SCA in many solutions containing different kinds of ice nucleators [17], [24].
A more recent study on the mechanisms of deep supercooling in XPCs of trees has further revealed four kinds of novel supercooling-promoting hydrolyzable gallotannins, including 2,2′,5-tri-O-galloyl-α,β-d-hamamelose (tri-GHam), 1,2,6-tri-O-galloyl-β-d-glucopyranose (tri-GGlc), 1,2,3,6-tetra-O-galloyl-β-d-glucopyranose (tet-GGlc) and 1,2,3,4,6-penta-O-galloyl-β-d-glucopyranose (pent-GGlc), in deep supercooling XPCs of Katsura tree [38].
Further discovery of supercooling-promoting substances that have high SCA toward diverse kinds of solutions may be useful for a wide variety of applications that require supercooling of water to lower temperatures, including supercooling preservation [33] as well as successful cryopreservation [14] in biological materials. In the present study, based on the discovery of novel supercooling-promoting hydrolyzable gallotannins from deep supercooling XPCs [38], supercooling activity of a wide variety of tannin-related polyphenols (TRPs) was examined in solutions containing different kinds of ice nucleators.
Section snippets
Tannin-related polyphenols (TRPs)
The TRPs used in this study are shown in Table 1, Table 2. The TRPs were grouped into tannin-related single compounds including hydrolyzable tannins, catechin derivatives, structural analogs of catechin and phenolcarboxylic acid derivatives (Table 1) as well as polyphenol mixtures and crude plant tannin extracts (Table 2). In these TRPs, although compounds belonging to structural analogs of catechin are not strictly included in TRPs, they were used for comparison of their effects on freezing
Results
The TRPs examined exhibited not only SCA (°C) but also INA (-°C) depending on solutions containing different kinds of ice nucleators. SCA and INA in tannin-related single compounds including hydrolyzable tannins, catechin derivatives, structural analogs of catechin and phenolcarboxylic acid derivatives are shown in Table 1, and SCA and INA in polyphenol mixtures and crude plant tannin extracts are shown in Table 2. Absolute FT50 values in control and experimental solutions of tannin-related
Discussion
All of the TRPs examined in this study, which were randomly selected from tannin-related single compounds and their mixtures, exhibited a variety of effects on freezing of solutions containing different kinds of ice nucleators by droplet freezing assays. In the mean difference of FT50 between control and experimental solutions (regardless of the presence or absence of significant differences), all of the TRP examined exhibited SCA in many solutions containing different kinds of ice nucleators (
Acknowledgments
We thank Dr. T. Inada and Dr. Y. Koyama in AIST, Japan for useful discussion, Taiyo Kagaku Co., Ltd., Amino Up Chemical Co., Ltd., and Katsuri Co., Ltd. for generous gifts of samples, and Ms. S. Yamamoto and Ms. Y. Kosuna for technical assistance.
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Statement of funding: This work was supported by Grants-in-Aid from Asahi Kasei Chemicals Corporation, COSMO OIL LUBRICANTS Co., Ltd., Nisshin Seifun Group Inc. and AMINO UP CHEMICAL Co., Ltd. to S.F. and K.A.