Toxicity of phenolipids: Protocatechuic acid alkyl esters trigger disruption of mitochondrial membrane potential and caspase activation in macrophages.

Phenolipids are a class of phenolic compounds with a lipidic moiety that have been receiving increasing attention due to their promising biological activities; however data regarding their toxicity and mechanism of action are scarce. A series of 11 phenolipids consisting of alkyl esters derivatives of the natural molecule protocatechuic acid was synthesized and evaluated against a panel of cancer and non-cancer cell lines [...]

Using pseudophase models to determine antioxidant distributions in emulsions: why dynamic equilibrium matters

Distributions of a homologous series of protocatechuic acid (PCA) derivatives of increasing lipophilicity were determined in stripped soybean oil-in-water emulsions and compared with their antioxidant (AO) efficiencies. The distribution was determined by employing a recently developed a kinetic method, based on the reaction between the hydrophobic 4-hexadecylbenzenediazonium ions (16-ArN2+) and the antioxidants [...]

Partitioning and antioxidative effect of protocatechuates in soybean oil emulsions: relevance of emulsifier concentration

Distributions of a homologous series of protocatechuic acid (PCA) derivatives of increasing lipophilicity were determined in stripped soybean oil-in-water emulsions and compared with their antioxidant (AO) efficiencies. The distribution was determined by employing a recently developed a kinetic method, based on the reaction between the hydrophobic 4-hexadecylbenzenediazonium ions (16-ArN2+) [...]

Free radicals and polyphenols: The redox chemistry of neurodegenerative diseases

The oxidation of bioorganic materials by air and, particularly, the oxidative stress involved in the cell loss and other pathologies associated with neurodegenerative diseases (NDs) are of enormous social and economic importance. NDs generally involve free radical reactions, beginning with the formation of an initiating radical by some redox, thermal or photochemical process [...]

Kinetic evidence for the formation of diazo ethers in the course of reactions between arenediazonium ions and antioxidants

The reactions between arenediazonium ions, ArN2+, and phenolic antioxidants, AOs, are of interest because ArN2+ are involved in carcinogenic and mutagenic processes in contrast to phenolic AOs, that have biological activity and potential beneficial effects on health, and because an ArN2+ is currently being employed as a chemical probe to assess the distribution of AOs in lipid-based food emulsions [...]

Physical evidence that the variations in the efficiency of homologous series of antioxidants in emulsions are due to differences in their partitioning

The relationships between the hydrophilic-lipophilic balance (HLB) of antioxidants (AOs) and their distributions and efficiencies in emulsions are not fully understood. Recent reports indicate that, for series of homologous antioxidants of different hydrophobicity, the variation of their efficiency with the HLB of the AO increases with the alkyl chain length up to a maximum (C3 -C8ester) followed by a decrease [...]