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Phospholipids with conjugated linoleic acid (CLA), which are potential lipid prodrugs, were synthesised. CLA was obtained by the alkali-isomerisation of linoleic acid and was subsequently used in the synthesis of 1,2-di(conjugated)linoleoyl-sn-glycero-3-phosphocholine in good (82 %) yield. 1-Palmitoyl-2-(conjugated)linoleoyl-sn-glycero-3-phosphocholine was obtained by a two-step synthesis in 87 % yield. All the compounds were tested in an in vitro cytotoxicity assay against two human cancer cell lines, HL-60 and MCF-7, and a mouse fibroblast cell line, Balb/3T3. The free form of CLA exhibited the highest activity against all cancer cell lines. Results obtained for the Balb/3T3 line proved that phosphatidylcholine derivatives decreased the cytotoxic effect of CLA against healthy cell lines.

The global limitation of fossil fuels impels scientists to search for new energy sources. A good alternative is biodiesel produced from crop plants. However, its production requires huge quantities of farmland, fertilizers and fresh water, which is in conflict with the human demand for water for consumption and land for food production. Thus, production of single cell oil (SCO) by oleaginous microorganisms remains the best solution for the coming years. Whereas most microorganisms require fresh water for proper cell metabolism, in this study we demonstrate that the unconventional yeast Yarrowia lipolytica is able to produce huge quantities of fatty acid in seawater-based medium. Here we shown that Y. lipolytica is able to produce fatty acids in medium based on seawater and crude glycerol as the main carbon source, which allows for low-cost production of SCO, is beneficial for industrial application and is ecologically friendly.

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Three novel enantiomeric pairs of bromolactones possesing a 2,5-dimethylphenyl substituent at the β-position of the lactone ring have been synthesized from corresponding enantiomeric (E)-3-(2′,5′-dimethylphenyl)hex-4-enoic acids (4) by kinetically controlled bromolactonization with N-bromosuccinimide (NBS). γ-Bromo-δ-lactones (5) were isolated as the major products. Absolute configurations of stereogenic centers of γ-bromo-δ-lactones (5) were assigned based on X-ray analysis; configurations of cis δ-bromo-γ-lactones (6) and trans δ-bromo-γ-lactones (7) were determined based on mechanism of bromolactonization. Synthesized compounds exhibited significant antiproliferative activity towards the four canine cancer cell lines (D17, CLBL-1, CLB70, and GL-1) and one human cancer line (Jurkat). Classifying the compounds in terms of activity, the most active were enantiomers of trans δ-bromo-γ-lactones (7) followed by enantiomers of cis isomer (6) and enantiomeric γ-bromo-δ-lactones (5). Higher activity was observed for all stereoisomers with S configuration at C-4 in comparison with their enantiomers with 4R configuration. Synthesized compounds did not induce hemolysis of erythrocytes. The results of the interaction of bromolactones with red blood cell membranes suggest that these compounds incorporate into biological membranes, concentrating mainly in the hydrophilic part of the bilayer but have practically no influence on fluidity in the hydrophobic region. The differences in interactions with the membrane between particular enantiomers were observed only for γ-lactones: stronger interactions were found for enantiomer 4R,5R,6S of cis γ-lactone (6) and for enantiomer 4S,5R,6S of trans γ-lactone (7).

Spectroscopic methods combined with statistics have recently gathered substantial interest in pedological studies. Near-infrared (NIR) spectroscopy has been utilized, for example, for reconstructions of the history and transformations of Chernozems, although no similar research was conducted based on mid-infrared (MIR). In this paper, the relevance of MIR spectroscopy was tested in studies on the origin/affinity of organic matter from chernozemic soils. Samples collected from three vegetation classes (grasslands, forests and arable lands) were investigated using MIR spectroscopy in order to create a statistical model, which was applied on buried profiles of unknown origin. The results showed a clear disjunction of vegetation classes. Samples of buried soil were placed in the space between all classes, indicating the relation to variable vegetation. Therefore, arable lands should not be omitted in paleoecological reconstructions, because we cannot exclude the cultivation of fertile soils before their burial. It was concluded that MIR methods may have similar applicability to NIR spectroscopy. Additionally, MIR spectra may also be discriminated according to the recognized soil type, which allows for direct reconstructions of the transformation trends in buried profiles.

Dedicated to Prof. Paweł Kafarski in honor of his scientific achievements within his career AbstractAn efficient synthesis of [2,3-bis(acyloxy)propyl]phosphonocholines is described. The reaction pathway for the synthesis involves the Michaelis-Arbuzov reaction of allyl bromide with triethyl phosphite and epoxidation of the resulting diethyl (prop-2-en-1-yl)phosphonate (1) with m-CPBA to afford the phosphonated diol (3). The acylation of diol (3) with carboxylic acids gave a series of diacyloxypropylphosphonates (4). The introduction of choline to a pyridinium salt of [2,3-bis(acyloxy)propyl]phosphonic acid (5) was the most intensively studied reaction. The total yield of a six-step sequence synthesis of a series of phosphonolipids was in the range of 30-40%.