Nature of hydroxycinnamate-protein interactions

Rawel, Harshadrai M.; Rohn, Sascha

doi:10.1007/s11101-009-9154-4

Cited by 80 publications

(112 citation statements)

References 130 publications

(250 reference statements)

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“…Nonetheless, the formation covalent bonds in our mixtures cannot be completely excluded. The simultaneous presence of different types of interactions leading to the association of a phenolic acid with a protein molecule has been repeatedly demonstrated by numerous authors -as essentially reviewed by RAWEL and ROHN (2010).…”

Section: Resultsmentioning

confidence: 96%

The effect of the addition of selected phenolic acids on the rheological properties of heated solutions of whey proteins

Szwajgier¹,

Gustaw²

2015

Acta Alimentaria

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This study measured the fl ow behaviour of whey protein isolate mixtures with cinnamic or ferulic acids. Samples were heated in a vacuum (80 C, -0.9 atm, 280 r.p.m., 0.5 h). The fl ow curves of all samples showed a nonNewtonian shear thinning fl ow and the viscoelastic properties were typical for weak gel systems. At pH 6.0, 6.7, and 8.0, the highest shear stress values were obtained with 20, 40, and 40 mg of cinnamic acid g -1 protein, respectively. At pH 6.0, the use of ferulic acid (20 mg g -1 protein) resulted in the elevation of shear stress values, but at pH 8.0, ferulic acid caused a decrease in shear stress values in comparison to cinnamic acid. The thixotropic area (A T ) was increased in mixtures containing 20-40 mg cinnamic acid g -1 protein (at pH 6.7) and 20 mg of cinnamic acid g -1 protein (at pH 6.0). Similarly, the addition of ferulic acid (40 and 20 mg g -1 protein at pH 6.7 and 6.0, respectively) caused a signifi cant increase in A T . At pH 8.0, no signifi cant differences in A T values were observed between samples. Such systems can be applied with reference to health promoting foods such as WPI-based desserts.

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Section: Resultsmentioning

confidence: 96%

The effect of the addition of selected phenolic acids on the rheological properties of heated solutions of whey proteins

Szwajgier¹,

Gustaw²

2015

Acta Alimentaria

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“…The toxicity is an attribute of all meta and para dihydroxylated cinnamic acid derivatives (7, 10, 12) and has been reported in the literature for similar compounds [14,18,19]. The catechol moiety is prone to oxidation resulting in an o-quinone which can easily react with amino groups of proteins [20]. Hence, omitting the hydroxyl groups lead to 15 with antileishmanial activity in the same concentration range as 1 but with a fivefold lower cytotoxicity.…”

Section: The Catechol Moietymentioning

confidence: 94%

“…Substituting borneol with a less sterically demanding alcohol e.g., cyclohexanol (23) or eugenol (24) gives IC 50 values higher than 100 µM (L. major). Using thymol (10,11,19), menthol (12,13,20) or other bulky substituents like naphthol (22) or adamantol (21) preserves the activity. A similar pattern is found with L. donovani promastigotes.…”

Section: Influence Of the Bornyl Moietymentioning

confidence: 99%

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

et al. 2014

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Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC 50 = 48.8 µM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.

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“…Physiologically and technologically relevant data from the literature suggest that the majority of protein -polyphenol interactions may occur by non-covalent binding (102) , although both covalent and non-covalent binding are likely to occur simultaneously, as shown for the binding of chlorogenic acid to proteins (103) . Three types of non-covalent interactions have been suggested: hydrogen, hydrophobic and ionic bonding (104) . Plasma proteins are the most studied binding targets, especially albumin.…”

Section: Interaction Of Plant Phenols With Proteinsmentioning

confidence: 99%

Interaction of plant phenols with food macronutrients: characterisation and nutritional–physiological consequences

Zhang

Sun

et al. 2013

Nutr. Res. Rev.

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Polyphenols are dietary constituents of plants associated with health-promoting effects. In the human diet, polyphenols are generally consumed in foods along with macronutrients. Because the health benefits of polyphenols are critically determined by their bioavailability, the effect of interactions between plant phenols and food macronutrients is a very important topic. In the present review, we summarise current knowledge, with a special focus on the in vitro and in vivo effects of food macronutrients on the bioavailability and bioactivity of polyphenols. The mechanisms of interactions between polyphenols and food macronutrients are also discussed. The evidence collected in the present review suggests that when plant phenols are consumed along with food macronutrients, the bioavailability and bioactivity of polyphenols can be significantly affected. The protein -polyphenol complexes can significantly change the plasma kinetics profile but do not affect the absorption of polyphenols. Carbohydrates can enhance the absorption and extend the time needed to reach a maximal plasma concentration of polyphenols, and fats can enhance the absorption and change the absorption kinetics of polyphenols. Moreover, as highlighted in the present review, not only a nutrient alone but also certain synergisms between food macronutrients have a significant effect on the bioavailability and biological activity of polyphenols. The review emphasises the need for formulations that optimise the bioavailability and in vivo activities of polyphenols.

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Nature of hydroxycinnamate-protein interactions

Cited by 80 publications

References 130 publications

The effect of the addition of selected phenolic acids on the rheological properties of heated solutions of whey proteins

The effect of the addition of selected phenolic acids on the rheological properties of heated solutions of whey proteins

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

Interaction of plant phenols with food macronutrients: characterisation and nutritional–physiological consequences

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