Structure–activity relationships in the hydrophobic interactions of polyphenols with cellulose and collagen

Abstract

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.

Protein Binding and Astringent Taste of a Polymeric Procyanidin, 1,2,3,4,6-Penta-O-galloyl-β-d-glucopyranose, Castalagin, and Grandinin

“…Grandinin is slightly more polar than castalagin (37) as expected since grandinin is the Cglycoside of castalagin. The estimated octanol water partition coefficient for castalagin, based on its chromatographic retention factor, is intermediate between pentagalloyl glucose and procyanidin (38). Clearly hydrophobicity is not the only characteristic that determines the tendency of a polyphenol to precipitate protein.…”

Gallic Acid: A Promising Lead Molecule for Drug Development

“…It occurs in plants in the form of free acids, esters, catechin derivatives and hydrolysable tannins. It also occur as methylated gallic acids e.g., syringic acid or galloyl conjugates of catechin derivatives, i.e., flanvan-3-ols, or polygalloyl esters of glucose, quinic acid or glycerol [3,4]. Gallic acid has been reported to elicit various biological activities such as antibacterial, anti-fungal, antiviral, anti-inflammatory, antioxidant, anticancer, anti-diabetic etc.…”

Isolation of polyphenols from the extracts of olive leaves (Olea europaea L.) by adsorption on silk fibroin

“…In the last century, the use of natural medicine has expanded and many researches have been performed on active components of herbs. These components are known as plant secondary metabolites [1] and possess higher antioxidative, antimicrobial, antiviral and anti-inflammatory properties [2][3][4]. Free radical scavenging properties of these metabolites can be explained by their high antioxidant activities.…”

“…Synthetic adsorbents have been applied for adsorbing valuable polyphenols from plant extracts [23][24][25][26][27][28][29]. Many biopolymers, such as collagen and cellulose have also been used as adsorbents for the recovery of polyphenols and the interaction between the biopolymers and antioxidative polyphenols have been widely investigated [1].…”