octyl-caffeate and caffeic-acid

The synthesis, cytotoxicity, anti-leishmanial and anti-trypanosomal activities of twelve triclosan-caffeic acid hybrids are described herein. The structure of the synthesized products was elucidated by a combination of spectrometric analyses. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis, which is the most prevalent Leishmania species in Colombia, and against Trypanosoma cruzi, which is the pathogenic species to humans. Cytotoxicity was evaluated against human U-937 macrophages. Eight compounds were active against L. (V) panamensis (18-23, 26 and 30) and eight of them against T. cruzi (19-22, 24 and 28-30) with EC

Topics: Antiprotozoal Agents; Caffeic Acids; Cell Line; Cell Survival; Dose-Response Relationship, Drug; Humans; Leishmania; Macrophages; Molecular Structure; Parasitic Sensitivity Tests; Structure-Activity Relationship; Triclosan; Trypanosoma cruzi

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 (C. We determined the distributions of a series of caffeic acid derivatives in intact soybean emulsions by employing a specifically designed chemical probe located in the interfacial region of the emulsion. We also determined the AO efficiencies in the very same emulsions. We demonstrate that the variation of the percentage of AO in the interfacial region of soybean oil-in-water emulsions with the AO HLB parallels that of their antioxidant efficiency.. The results provide physical evidence that the variations in the efficiency of homologous series of antioxidants in emulsions are the result of differences in their distribution. The results confirm that, with other things being equal, there is a direct relationship between the percentage of AO in the interfacial region of the emulsions and their efficiency, providing a natural explanation, based on molecular properties, of the cut-off effect. © 2016 Society of Chemical Industry.

Topics: Antioxidants; Caffeic Acids; Diazonium Compounds; Emulsions; Fat Emulsions, Intravenous; Hydrophobic and Hydrophilic Interactions; Indicators and Reagents; Kinetics; Models, Chemical; Molecular Structure; Molecular Weight; Soybean Oil; Surface-Active Agents

Ten ester derivatives from caffeic acid were synthesized, and their antinociceptive properties are evaluated in mice. The most active compound, dodecyl ester derivative, exhibited potent and dose-related activity against the writhing test, with a calculated ID(50) value of 15.1 (11.9-19.1)micromol/kg and MI of 78.8% being several times more active than reference drugs. It was also effective in other experimental models, such as formalin, capsaicin and glutamate-induced pain tests, but was inactive in the hot-plate test. Although the mechanism of action has still not been elucidated, these results appear to support its therapeutic potential against painful diseases.

Topics: Analgesics; Animals; Caffeic Acids; Mice; Molecular Structure; Pain; Structure-Activity Relationship

In the present study, we investigated the effects and mechanisms of a novel potent antioxidant, octyl caffeate, on the induction of iNOS expression by lipopolysaccharide (LPS) and interferon-gamma (IFN-gamma) in cultured primary rat aortic smooth muscle cells (RASMCs) in vitro and LPS-induced hypotension in vivo. Octyl caffeate (0.1-1.0 microM) exerted a concentration-dependent inhibition of iron-catalyzed lipid peroxidation in rat brain homogenates. Furthermore, octyl caffeate (20, 50, and 100 microM) concentration-dependently diminished the initial rate of superoxide-induced NBT reduction and the enzymatic activity of xanthine oxidase. It also concentration-dependently (1-50 microM) inhibited the NO production, iNOS protein and messenger RNA expressions upon stimulation by LPS (100 microg/mL)/IFN-gamma (100U/mL) in RASMCs. In addition, we found that octyl caffeate did not significantly affect IkappaBalpha degradation stimulated by LPS/IFN-gamma in RASMCs. On the other hand, octyl caffeate (10 and 50 microM) significantly suppressed activation of c-Jun-N-terminal kinase and extracellular signal-regulated kinase. Moreover, octyl caffeate (10mg/kg, i.v.) significantly inhibited the fall in mean arterial pressure stimulated by LPS (7.5mg/kg) in rats. In conclusion, we demonstrate that a novel potent antioxidant, octyl caffeate, significantly ameliorates circulatory failure of endotoxemia in vivo by a mechanism involving suppression of iNOS expression through inactivation of mitogen-activated protein kinases in RASMCs.

Topics: Animals; Antioxidants; Aorta; Caffeic Acids; Cell Culture Techniques; Cell Survival; Cells, Cultured; Gene Expression Regulation, Enzymologic; Interferon-gamma; Kinetics; Lipopolysaccharides; Male; Muscle, Smooth, Vascular; Nitric Oxide Synthase; Nitric Oxide Synthase Type II; Rats; Rats, Wistar; RNA, Messenger; Shock, Septic; Superoxides; Transcription, Genetic