Merkl R., Hrádková I., Filip V., Šmidrkal J. (2010): Antimicrobial and antioxidant properties of phenolic acids alkyl esters. Czech J. Food Sci., 28: 275-279.Some phenolic acids alkyl esters (methyl, ethyl, propyl, butyl and hexyl) and determine their antioxidant and antimicrobial activities were prepared. The antimicrobial activity against the tested microorganisms escherichia coli DMF 7503, Bacillus cereus DMF 2001, listeria monocytogenes DMF 5776, Fusarium culmorum DMF 0103, and Saccharomyces cerevisiae DMF 1017 was investigated and expressed by minimum inhibitory concentration (MIC) in the range of 1.2-20mM. The inhibitory activity of phenolic acids butyl esters was found to be higher than that of methyl esters (MIC below 1.25mM). The antioxidant activity of the selected phenolic acids alkyl esters was investigated by Rancimat method. The esters of 3,4-dihydroxyphenolic acids (protocatechuic and caffeic acids) exhibited higher antioxidant activities in comparison with the respective phenolic acids. The highest antioxidant activity was found in the case of caffeic alkyl esters.

During a 15-month period, samples of commercially pasteurised liquid whole egg (LWE) were tested for the presence of spoilage microflora. The total bacterial counts were 2.2 ± 0.6 log CFU/g and total lactic acid bacteria (LAB) counts were 1.9 ± 0.6 log CFU/g. Enterobacteriaceae were detected in 2 samples. Out of the tested samples, 45 LAB were isolated and identified, with 30 strains identified as Enterococcus faecium, 12 as Enterococcus faecalis, and 3 as Lactobacillus paracasei subsp. paracasei. All strains, except 6 strains of E. faecium, possessed lipolytic activity. All the E. faecalis strains and one strain of E. faecium showed a high proteolytic activity, while moderate proteolytic activity was shown by 3 lactobacilli strains. Minimum inhibitory concentration (MIC) of nisin and Micocin X was measured against groups of isolated strains, and ranged from 10.4 µg/ml to 41.7 µg/ml for nisin and from 0.2 mg/ml to 1.6 mg/ml for Micocin X. The LWEs supplemented with 6.25 mg/l of nisin or with 500 mg/ml of Micocin X were pasteurised at 65°C for 2.5 minutes. The shelf life of LWE with the addition of nisin or Micocin X stored under refrigerator conditions was extended by a minimum of 5 weeks.

Resveratrol and closely related stilbenoids belong to the most intensively studied biologically active compounds. This interest evoked several attempts to prepare such compounds in a convenient synthetic way. Our approach allowed obtaining largely methoxystilbenes, formed as E-isomers only (using Wittig–Horner synthesis as the key step), which were further demethylated by boron tribromide. The hydroxymethoxystilbenes (e.g. pterostilbene) were prepared using isopropyl protection, later selectively deprotected by boron trichloride. The method is suitable for preparing such compounds in a large amount. Effects of the obtained stilbene derivatives on immunobiological responses triggered by lipopolysacharide and interferon-γ were tested under in vitro conditions. Namely production of nitric oxide (NO) was investigated, and relation between the molecular structure and immunobiological activity was assessed.

Antioxidant properties of mono- and dihydroxyphenolic acids and their alkyl esters were examined, with emphasis on the relationship between their molecular structure and antioxidant activity. Test media with different tocopherol level were used for determining the oxidative stability: original refined sunflower oil (total tocopherols 149.0 mg/kg), partially tocopherol-stripped sunflower oil (total tocopherols 8.7 mg/kg) and distilled fatty acid methyl esters (FAME) as a tocopherol-free medium. The chemical reaction of tocopherols with diazomethane tested for the purpose to eliminate their antioxidant activity failed due to the negligible degree of methylation of hydroxyl group in the tocopherol molecule. Caffeic acid and protocatechuic acid (3,4-dihydroxyphenolic acids) and their alkyl esters were found to be more active antioxidants than monohydroxyphenolic acid (p-hydroxybenzoic acid), 2,5-dihydroxyphenolic acid (gentisic acid), 3-methoxy-4-hydroxyphenolic acids (vanillic and ferulic acids) and their corresponding alkyl esters. Naturally present tocopherols in refined sunflower oil proved to have a synergistic effect on gentisic acid but not on its alkyl esters. In contrast, tocopherols showed an antagonistic effect on alkyl esters of caffeic acid, because their protection factors decreased with increasing level of tocopherols in the test medium. Moreover, the antioxidant activity of these alkyl esters decreased with increasing length of their alkyl chain in conformity with the polar paradox hypothesis.Practical applications:Tocopherols as naturally present antioxidants influence considerably the antioxidant activity of other antioxidants added to plant oils used as a test medium. Distilled fatty acid methyl esters prepared from refined sunflower oil may serve as an optimal tocopherol-free test medium. Some alkyl esters of phenolic acids were evaluated to be applicable as natural more lipophilic antioxidants in comparison with phenolic acids.

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