propyl-caffeate and caffeic-acid

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

Propyl caffeate was synthesized to produce lipophilic antioxidant, which used caffeic acid and propanol as starting materials, acidic ionic liquid as catalyst. The highest yield of propyl caffeate (98.7±0.8%) have been achieved under the optimum as follows: 1-butylsulfonic-3-methylimidazolium tosylate showed the best catalytic performance, molar ratio of caffeic acid to propanol was 1:20, reaction temperature was 90°C and the amount of acidic ionic liquid was 40%. The relationship between temperature and the forward rate constant gave the activation energy of 33.6 kJ mol(-1), which indicated that acidic ionic liquid possesses high catalytic activity in the synthesis of PC. And the activity of acidic ionic liquid was not inhibited by the water produced during the esterification process. More importantly, this reaction system can even proceed smoothly when initial water content was 5%.

Topics: 1-Propanol; Alkanesulfonic Acids; Antioxidants; Caffeic Acids; Catalysis; Esterification; Hydrophobic and Hydrophilic Interactions; Imidazoles; Ionic Liquids; Water

The aim of this study was to evaluate the caffeic acid (1) and ester derivatives (2-10) against Candida albicans biofilm and to investigate whether these compounds are able to inhibit the biofilm formation or destroy pre-formed biofilm. Caffeic acid ester 7, cinnamic acid ester 8 and 3,4-dihydroxybenzoic acid ester 10 are more active than fluconazole, used as reference drug, both on biofilm in formation with MIC50 values of 32, 32 and 16μg/mL, respectively, and in the early stage of biofilm formation (4h) with MIC50 values of 64, 32 and 64μg/mL, respectively. These esters result also more active than fluconazole on mature biofilm (24h), especially 8 and 10 with MIC50 values of 64μg/mL.

Topics: Antifungal Agents; Biofilms; Caffeic Acids; Candida albicans; Cell Line, Tumor; Cell Survival; Humans; Microbial Sensitivity Tests

Caffeic acid and its naturally occurring derivative caffeic acid phenethyl ester (CAPE) have antiproliferative and cytotoxic properties in a variety of cancer cell lines without displaying significant toxicity toward healthy cells, and are considered to be potential anticancer agents. However, little is known about their effects on prostate cancer cells. We synthesized and evaluated the effects of caffeic acid, CAPE (2) and 18 synthetic derivatives on cell viability and androgen-dependent cell proliferation, subcellular localisation and expression of androgen receptor (AR) and secretion of prostate-specific antigen (PSA) in LNCaP human hormone-dependent prostate cancer cells. Several synthetic derivatives of CAPE were strong, concentration-dependent cytotoxic agents in LNCaP cells with IC50 values in the 6.8-26.6 μM range, potencies that were up to five-fold greater than that of CAPE (33.7±4.0 μM). A number of caffeic acid derivatives were inhibitors of androgen-stimulated LNCaP cell proliferation with concomitant inhibition of DHT-stimulated PSA secretion. Compound 24 was the most cytotoxic and antiproliferative caffeic acid derivative (IC50 values of 6.8±0.3 and 2.4±0.8 μM, respectively) inhibiting DHT-stimulated cell proliferation and PSA secretion statistically significantly at concentrations as low as 0.3 μM. Exposure to DHT increased cytoplasmic and nuclear AR levels and co-treatment with increasing concentrations of compound 24 or CAPE (2), notably, further increased these levels. In conclusion, a number of synthetic derivatives of caffeic acid are potent inhibitors of androgen-dependent prostate cancer cell proliferation and viability, acting, at least in part, via an antiandrogenic mechanism that involves increased nuclear accumulation of (presumably inactive) AR.

Topics: Antineoplastic Agents; Caffeic Acids; Cell Line, Tumor; Cell Proliferation; Cell Survival; Cinnamates; Humans; Male; Prostate-Specific Antigen; Prostatic Neoplasms; Receptors, Androgen; Structure-Activity Relationship

Propyl caffeate has the highest antioxidant activity among caffeic acid alkyl esters, but its industrial production via enzymatic transesterification in batch reactors is hindered by a long reaction time (24h). To develop a rapid process for the production of propyl caffeate in high yield, a continuous-flow microreactor composed of a two-piece PDMS in a sandwich-like microchannel structure was designed for the transesterification of methyl caffeate and 1-propanol catalyzed by Novozym 435 in [B mim][CF3SO3]. The maximum yield (99.5%) in the microreactor was achieved in a short period of time (2.5h) with a flow rate of 2 μL/min, which kinetic constant Km was 16 times lower than that of a batch reactor. The results indicated that the use of a continuous-flow packed bed enzyme microreactor is an efficient method of producing propyl caffeate with an overall yield of 84.0%.

Topics: Batch Cell Culture Techniques; Biocatalysis; Bioreactors; Biotechnology; Caffeic Acids; Enzymes, Immobilized; Fungal Proteins; Ionic Liquids; Kinetics; Lipase; Miniaturization; Recycling; Rheology; Temperature

The anticancer activities of alkyl esters and NO-donors of ferulic acid (FA) and caffeic acid (CA) were assessed by a high-throughout screening (HTS) method, and the structure-activity relationships were described. CA alkyl esters had better anticancer activities than FA alkyl esters with the same alkyl substituent. Mono-nitrates and phenylfuroxan nitrates were more potent than the dual nitrates. Phenylsulfonylfuroxan nitrates of FA, especially compounds 8b-8d, exhibited more potent activities in anticancer.

Topics: Antineoplastic Agents; Caffeic Acids; Cell Line, Tumor; Cell Proliferation; Coumaric Acids; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; HeLa Cells; High-Throughput Screening Assays; Humans; Molecular Structure; Stereoisomerism; Structure-Activity Relationship