Dataset Information

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins.

ABSTRACT: This review presents the main properties of hydroxycinnamic acid (HCA) derivatives and their potential application as agents for the prevention and treatment of neurodegenerative diseases. It is partially focused on the successful use of these compounds as inhibitors of amyloidogenic transformation of proteins. Firstly, the prerequisites for the emergence of interest in HCA derivatives, including natural compounds, are described. A separate section is devoted to synthesis and properties of HCA derivatives. Then, the results of molecular modeling of HCA derivatives with prion protein as well as with ?-synuclein fibrils are summarized, followed by detailed analysis of the experiments on the effect of natural and synthetic HCA derivatives, as well as structurally similar phenylacetic and benzoic acid derivatives, on the pathological transformation of prion protein and ?-synuclein. The ability of HCA derivatives to prevent amyloid transformation of some amyloidogenic proteins, and their presence not only in food products but also as natural metabolites in human blood and tissues, makes them promising for the prevention and treatment of neurodegenerative diseases of amyloid nature.

SUBMITTER: Muronetz VI

PROVIDER: S-EPMC7594092 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins.

Muronetz Vladimir I VI Barinova Kseniya K Kudryavtseva Sofia S Medvedeva Maria M Melnikova Aleksandra A Sevostyanova Irina I Semenyuk Pavel P Stroylova Yulia Y Sova Matej M

Molecules (Basel, Switzerland) 20201012 20

This review presents the main properties of hydroxycinnamic acid (HCA) derivatives and their potential application as agents for the prevention and treatment of neurodegenerative diseases. It is partially focused on the successful use of these compounds as inhibitors of amyloidogenic transformation of proteins. Firstly, the prerequisites for the emergence of interest in HCA derivatives, including natural compounds, are described. A separate section is devoted to synthesis and properties of HCA d ...[more]

PMID: 33053854

Similar Datasets

Project description:Hydroxycinnamic acid derivatives (HCA) are a type of phenolic acid that occurs naturally. HCA are widely known for their anti-inflammatory, anti-cancer, and especially antioxidant capabilities; however, a comprehensive study of the mechanism and kinetics of the antiradical activity of these compounds has not been performed. Here, we report a study on the mechanisms and kinetics of hydroperoxyl radical scavenging activity of HCA by density functional theory (DFT) calculations. The ability of HCA to scavenge hydroperoxyl radicals in physiological environments was studied. The results showed that HCA had moderate and weak HOO˙ antiradical activity in pentyl ethanoate solvent, with the overall rate constant k overall = 8.60 × 101 - 3.40 × 104 M-1 s-1. The formal hydrogen transfer mechanism of phenyl hydroxyl groups defined this action. However, in water at physiological pH, 2-coumaric acid (1), 4-coumaric acid (2), caffeic acid (3), ferulic acid (4), sinapic acid (5) and 4-hydroxyphenylpyruvic acid (7) exhibit a significant HOO˙ antiradical activity with k total = 105 - 108 M-1 s-1 by the electron transfer reaction of the phenolate anions. Following a rise in pH levels in most of the studied substances, the overall rate constant varied. The acid 5 exhibited the highest HOO˙ radical scavenging activity (log(k overall) = 4.6-5.1) at pH < 5; however, at pH = 5.4-8.8, the highest HOO˙ radical scavenging activity were observed for 3 with log(k overall) = 5.2-5.7. At pH > 6.2, acids 2, 3, 4, and 5 presented the largest radical scavenging activity. By contrast, acid 3-coumaric acid (8) had the lowest antiradical activity at most pH values. Thus, the hydroperoxyl radical scavenging activity in pentyl ethanoate follows the order 3 > 5 > 1 ∼ 2 ∼ 4 ∼ 6 (homovanillic acid) ∼ 7 > 8, whereas it follows the order 3 > 2 ∼ 4 ∼ 5 > 6 ∼ 7 > 1 > 8 in water at pH = 7.40. The activity of 1, 2, 3, 4, 5, 6, and 7 are faster than those of the reference Trolox, suggesting that these HCA could be useful natural antioxidants in the aqueous physiological environment.

Dataset Information

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins.

Publications

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets