Structure-activity relationships in the hydrophobic interactions of polyphenols with cellulose and collagen.
Polyphenol interactions with both cellulose and collagen in the solid state have been studied by using chromatography on cellulose and by evaluating the hydrothermal stability of the polyphenol treated sheepskin collagen. Twenty-four polyphenolic compounds were studied, including seven glucose-based gallotannins, five polyalcohol-based gallotannins, and twelve ellagitannins. In the cellulose-polyphenols systems, the polyphenol's affinity to cellulose is positively correlated with their molecular masses, the number of galloyl groups, and their hydrophobicity (logP). The polyphenol treatment increased the hydrothermal stability of collagen samples, and such effects are also positively correlated with the molecular masses, total number of galloyl groups and the hydrophobicity of polyphenols. Ellagitannins showed much weaker interactions with both biopolymers than gallotannins having similar molecular mass, the same number of galloyl groups, and the same number of phenolic hydroxyl groups. It is concluded that, for the polyphenol interactions with both cellulose and collagen, (1) the galloyl group of polyphenols is the functional group; (2) the strength of interactions are positively correlated with molecular size, the number of galloyl groups and the hydrophobicity of polyphenols; (3) the hydrophobic interactions are of great significance; and (4) the interactions are strongly dependent on the flexibility of galloyl groups.
Tang
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HR
Department of Chemistry, Royal Holloway, University of London, Egham Hill, Egham, Surrey TW20 0EX, UK. Huiru.Tang@imperial.ac.uk
Covington
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AD
Hancock
R A
RA
D000818:Animals; D002152:Calorimetry, Differential Scanning; D002482:Cellulose / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D003094:Collagen / Q000737:chemistry*; D004355:Drug Stability; D005419:Flavonoids / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D010636:Phenols / Q000737:chemistry*; D059808:Polyphenols; D012756:Sheep; D012867:Skin / Q000737:chemistry; D013329:Structure-Activity Relationship
D005419:Flavonoids; D010636:Phenols; D059808:Polyphenols; D002482:Cellulose; D003094:Collagen