Old Apple Cultivars as a Natural Source of Phenolics and Triterpenoids with Cytoprotective Activity on Caco-2 and HepG2 Cells.

Apples are among the most consumed fruits worldwide. They serve as an excellent source of compounds that have a positive impact on human health. While new varieties of apples are being developed, numerous varieties have been forgotten. In this article, we present the results of research on 30 old apple cultivars, focusing on both qualitative and quantitative determination of antioxidant properties, and content of total phenolics, phenolic acids, triterpenoids and polyphenols. Our analyses show significant differences in the total content of each group of compounds between apple cultivars, as well as the phytochemical profile. The richest source of antioxidants was revealed to be 'Reneta Blenheimska' and 'Ksiaze Albrecht Pruski' varieties, but the highest amount of phenolics had 'James Grieve' and 'Kantówka Gdanska' (KG). Among studied apples KG, 'Krótkonózka Królewska' and 'Grochówka' (G) were the richest source of phenolic acids and polyphenols, whereas G, 'James Grieve' and 'Krótkonózka Królewska' had the highest level of triterpenoids. Based on these findings, we selected two cultivars, G and KG, for further in vitro cell line-based studies. Based on biological activity analyses, we demonstrated not only antioxidant potential but also proapoptotic and cytoprotective properties within human-originated Caco-2 and HepG2 cell lines. In the era of a dynamically growing number of lifestyle diseases, it is particularly important to draw the attention of producers and consumers to the need to choose fruit varieties with the highest possible content of health-promoting compounds and, therefore, with the strongest health-promoting properties.

Clinical and microbiological outcomes of subgingival instrumentation supplemented with high-dose omega-3 polyunsaturated fatty acids in periodontal treatment - a randomized clinical trial.

PURPOSE: This study aimed to evaluate the impact of dietary supplementation with omega-3 polyunsaturated fatty acids (PUFAs) eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) combined with scaling and root planing (SRP) in untreated periodontitis stage III and IV. METHODS: Forty patients were randomly assigned to the test group receiving SRP plus omega-3 PUFAs (n = 20) or control group receiving SRP alone (n = 20). Clinical changes of pocket probing depths (PD), clinical attachment level (CAL), bleeding on probing (BOP) and rates of closed pockets (PPD ≤ 4 mm without BOP) were evaluated at baseline and after 3 and 6 months. Phorphyromonas gingivalis, Tanarella forsythia, Treponema denticola and Aggregatibacter actinomycetemcomitans counts were analysed at baseline and at 6 months. Serum was subjected to lipid gas chromatography/mass spectrometry analysis at baseline and at 6 months. RESULTS: Significant improvement of all clinical parameters at 3 and 6 months was observed in both groups. For the primary outcome "change of mean PD," no significant difference was detected between the groups. Patients treated with omega-3 PUFAs demonstrated significantly lower rates of BOP, higher gain of CAL and higher number of closed pockets at 3 months in comparison to the control group. After 6 months, no clinical differences between the groups were found, with the exception of lower BOP rates. Moreover, in the test group, the number of key periodontal bacteria was significantly lower than in the control group at 6 months. Increased proportions of serum n-3 PUFAs and decreased proportions of n-6 PUFAs were detected at 6 months in the patients from the test group. CONCLUSION: High-dose omega-3 PUFA intake during non-surgical treatment of periodontitis results in short-term clinical and microbiological benefits. The study protocol was approved by the ethical committee of Medical University of Lodz (reference number RNN/251/17/KE) and registered at clinicaltrials.gov (NCT04477395) on 20/07/2020.

Natural fish oil improves the differentiation and maturation of oligodendrocyte precursor cells to oligodendrocytes in vitro after interaction with the blood-brain barrier.

The blood-brain barrier (BBB) tightly controls the microenvironment of the central nervous system (CNS) to allow neurons to function properly. Additionally, emerging studies point to the beneficial effect of natural oils affecting a wide variety of physiological and pathological processes in the human body. In this study, using an in vitro model of the BBB, we tested the influence of natural fish oil mixture (FOM) vs. borage oil (BO), both rich in long-chain polyunsaturated fatty acids (LC-PUFAs) and monounsaturated fatty acids (MUFAs) such as oleic acid (C18:1n9c) or nervonic acid (NA), on human oligodendrocyte precursor cells (hOPCs) during their maturation to oligodendrocytes (OLs) regarding their ability to synthesize myelin peptides and NA. We demonstrated that FOM, opposite to BO, supplemented endothelial cells (ECs) and astrocytes forming the BBB, affecting the function of hOPCs during their maturation. This resulted in improved synthesis of myelin basic protein (MBP), myelin oligodendrocyte glycoprotein (MOG), proteolipid protein (PLP), and NA in mature OLs. This effect is probably the result of BBB cell and hOPC stimulation via free fatty acid receptors (FFARs), which increases insulin growth factor-1 (IGF-1), ciliary neurotrophic factor (CNTF), and brain-derived neurotrophic factor (BDNF) and inhibits fibroblast growth factor 2 (FGF-2) synthesis. The unique formula of fish oil, characterized by much more varied components compared to those of BOs, also improved the enhancement of the tight junction by increasing the expression of claudin-5 and VE-cadherin on ECs. The obtained data justify consideration of naturally derived fish oil intake in human diet as affecting during remyelination.

Chemical and Biological Characteristics of Oxytropis pseudoglandulosa Plant of Mongolian Origin.

Oxytropis pseudoglandulosa is used in Mongolian traditional medicine due to its numerous reported health-promoting effects. To date, there are very few scientific reports that describe this species. In this article, its volatile oil composition, lipid extract composition, total phenolic and flavonoid content, antibacterial and allergenic properties are elucidated for the first time. Hexadecanoic acid, fokienol and tricosane were determined as the most notable components of the volatile oil, at 13.13, 11.46 and 5.55%, respectively. Methyl benzoate was shown to be the most abundant component of lipid extract at 40.69, followed by (E)-prop-2-enoic acid, 3-phenyl- and benzenepropanoic acid, at 18.55 and 9.97%. With a TPC of 6.620 mg GAE g-1 and TFC of 10.316 mg QE g-1, the plant extract of O. pseudoglandulosa indicated good antioxidant activity measured by IC50 at 18.761 µg mL-1. Of the 12 tested microorganisms, B. subtilis and S. cerevisiae were the shown to be most susceptible to the plant extract, with MIC at 2.081 and 0.260% (v/v), respectively. Bet v 1-a major birch pollen allergen found in plant-based foods-was determined to be at 192.02 ng g-1 with ELISA. Such a wide spectrum of biological activity indicated by O. pseudoglandulosa lends credence for its application in food industry. Its exerted antioxidant and antimicrobial effects could improve preservation of low-processed food dedicated for consumers afflicted with allergies. Hexadecanoic acid supplemented in foods with dietary plant extracts could add to the potential anti-inflammatory impact. The analysis of lipid makeup suggests O. pseudoglandulosa extract could also be considered as natural pesticide in organic farming.

The Current State of Knowledge about Essential Oil Fumigation for Quality of Crops during Postharvest.

Prolonging crops' shelf-life while retaining their high quality is a major issue related to postharvest management. During storage, fruits and vegetables are exposed to microbial attacks, which may cause spoilage. Crop deterioration causes the loss of physical properties and drops in quality and nutritional value. Hence, new techniques to improve the resistance of food products are being explored. One promising technique is fumigation. Essential oils and their constituents, due to their antimicrobial properties, are likely to be used as fumigants, as they are highly volatile, effective in low concentrations, biodegradable, and safe. Papers indicate that some of them can improve their quality by increasing the content of antioxidants. This comprehensive review aims to present the current state of knowledge about the influence of essential oil fumigation on crop quality. It covers antioxidant capacity, the content of some bioactive compounds, physicochemical properties, decay properties, and sensory attributes of fruits and vegetables treated with essential oil vapors. The review indicates that this technique might be an interesting field for further exploration due to the promising results presented in the studies. Moreover, the review presents major objectives for current studies and indicates a lack of recent papers in this field.

Chemical and Biological Profile and Allergenicity of Thymus baicalensis Plant of Mongolian Origin.

Thymus baicalensis is a medicinal plant recognized as a traditional Mongolian therapeutic and health-promoting food supplement. The aim of the study was to check the suitability of the tested plant for supporting the treatment of certain diseases. The following study is the first one to showcase the versatile scope of characteristics of T. baicalensis, including its volatile oil composition, polyphenolic composition, lipid composition, phenolic and flavonoid contents, antioxidant activity, antimicrobial properties and ingestive allergenicity. Myrcene, at 26.15%, was shown to be the most abundant component of the volatile oil. Compounds known as inherent components of the Thymus genus: thymol and carvacrol made up only about 0.24% of the extracted oil. As much as 10.11 g kg-1 of polyphenol compounds were identified as derivatives of luteolin-7-O-glucuronide. The lipid extract was found to be rich in palmitic acid (31.05%), while unsaturated fatty acids were not reported. Spectrophotometric determination of the phenols and flavonoids indicated 7.541 mg of gallic acid g-1 and 4.345 mg of quercitin g-1, respectively. The free radical scavenging activity was determined by the 2,2-difenylo-1-pikrylohydrazyl method at IC50 = 206.97 µg mL-1. The extracts also had a strong inhibitory effect on M. flavus and P. fluorescenes bacteria, as well as S. cerevisiae yeasts. The Bet v 1 and profilin allergens in T. baicalensis were reported at 175.17 ng g-1 and 1.66 ng g-1, respectively.

Antibacterial Activity of Selected Essential Oil Compounds Alone and in Combination with ß-Lactam Antibiotics Against MRSA Strains.

This study aimed to determine the effect of selected essential oil compounds (EOCs) on the antibacterial activity of ß-lactam antibiotics (ßLAs) against methicillin-resistant Staphylococcus aureus (MRSA) strains. The following parameters were studied: antibiotic susceptibility testing, detection of mecA gene and evaluation of genotypic relativity of isolates using molecular techniques, analysis of chemical composition applying Fourier-transform infrared (FTIR) spectroscopy, and determination of antibacterial activity of EOCs alone and in combination with ßLAs against MRSA strains using microdilution and checkerboard methods. It was found that all isolates expressed MRSA and resistance phenotypes for macrolides, lincosamides, and streptogramins B. All isolates harbored the mecA gene and belonged to three distinct genotypes. Eight of the 10 EOCs showed efficient antimicrobial activity against the MRSA reference strain. The analysis of interaction between EOCs and ßLAs against the MRSA reference strain revealed a synergistic and additive effect of the following combinations: methicillin (Met)-linalyl acetate (LinAc), penicillin G (Pen)-1,8-cineole (Cin), and Pen-LinAc. Analysis of EOC-ßLA interactions showed a synergistic and additive effect in the following combinations: Met-LinAc (against low- and high-level ßLAs resistance strains), Pen-Cin, and Pen-LinAc (against low-level ßLAs resistance strains). It was also confirmed that changes in phosphodiester, -OH, -CH2 and -CH3 groups may change the interactions with ßLAs. Moreover, the presence of two CH3O- moieties in the Met molecule could also play a key role in the synergistic and additive mechanism of LinAc action with Met against MRSA strains. Direct therapy using a Met-LinAc combination may become an alternative treatment method for staphylococcal infections caused by MRSA. However, this unconventional therapy must be preceded by numerous cytotoxicity tests.

Anticandidal activity of Lactobacillus spp. in the presence of galactosyl polyols.

Yeasts have a substantial impact on the contamination and loss of food. In this study, we applied bacteria of the genus Lactobacillus as natural biopreservatives. Anticandidal strains of bacteria were selected from among 60 strains of bacteria grown which were each with nine polyols or galactosyl polyols. Polyols and galactosyl polyols can act as prebiotics for lactic acid bacteria and can enhance the antifungal properties of bacteria by affecting their metabolism. The galactosyl polyols significantly improved the anticandidal activity of most of the bacteria we tested. Based on the screening, the most promising strains of bacteria were selected, and their metabolites (both primary and secondary) and enzymatic activity were characterized in the presence of polyols and galactosyl polyols. The qualitative and quantitative content of bacterial metabolites depended both on the bacterial strain and the type of culture medium. A wide variety of antifungals produced by bacteria, such as fatty acids, hydroxy fatty acids, and other acidic products with potential antagonistic activity (phenyllactic acid or hydroxyphenyllactic acid) were detected. The bacteria produced a high concentration of phenyllactic acid in the presence of galactosyl polyols (up to 84.3 mg/L). This finding could suggest that this metabolite may have a significant impact on the antifungal properties of lactobacilli against yeast. Galactosyl polyols influenced the enzymes involved in the synthesis of fatty acids and hydroxylated fatty acids (esterase lipase, acid phosphatase, and α-glucosidase). The mechanism of the antifungal effect of lactobacilli may be based on the synergistic effect of their primary and secondary metabolites, in particular phenyllactic acid.

Naturally Occurring Nervonic Acid Ester Improves Myelin Synthesis by Human Oligodendrocytes.

The dysfunction of oligodendrocytes (OLs) is regarded as one of the major causes of inefficient remyelination in multiple sclerosis, resulting gradually in disease progression. Oligodendrocytes are derived from oligodendrocyte progenitor cells (OPCs), which populate the adult central nervous system, but their physiological capability to myelin synthesis is limited. The low intake of essential lipids for sphingomyelin synthesis in the human diet may account for increased demyelination and the reduced efficiency of the remyelination process. In our study on lipid profiling in an experimental autoimmune encephalomyelitis brain, we revealed that during acute inflammation, nervonic acid synthesis is silenced, which is the effect of shifting the lipid metabolism pathway of common substrates into proinflammatory arachidonic acid production. In the experiments on the human model of maturating oligodendrocyte precursor cells (hOPCs) in vitro, we demonstrated that fish oil mixture (FOM) affected the function of hOPCs, resulting in the improved synthesis of myelin basic protein, myelin oligodendrocyte glycoprotein, and proteolipid protein, as well as sphingomyelin. Additionally, FOM reduces proinflammatory cytokines and chemokines, and enhances fibroblast growth factor 2 (FGF2) and vascular endothelial growth factor (VEGF) synthesis by hOPCs was also demonstrated. Based on these observations, we propose that the intake of FOM rich in the nervonic acid ester may improve OL function, affecting OPC maturation and limiting inflammation.

Effect of Co-Inoculation with Saccharomyces cerevisiae and Lactic Acid Bacteria on the Content of Propan-2-ol, Acetaldehyde and Weak Acids in Fermented Distillery Mashes.

The qualitative and quantitative composition of volatile compounds in fermented distillery mash determines the quality of the obtained distillate of agricultural origin (i.e., raw spirit) and the effectiveness of further purification steps. Propan-2-ol (syn. isopropyl alcohol), due to its low boiling point, is difficult to remove by rectification. Therefore, its synthesis needs to be limited during fermentation by Saccharomyces cerevisiae yeast, while at the same time controlling the levels of acetaldehyde and acetic acid, which are likewise known to determine the quality of raw spirit. Lactic acid bacteria (LAB) are a common but undesirable contaminant in distillery mashes. They are responsible for the production of undesirable compounds, which can affect synthesis of propan-2-ol. Some bacteria strains are able to synthesize isopropyl alcohol. This study therefore set out to investigate whether LAB with S. cerevisiae yeast are responsible for conversion of acetone to propan-2-ol, as well as the effects of the amount of LAB inoculum and fermentation parameters (pH and temperature) on the content of isopropyl alcohol, acetaldehyde, lactic acid and acetic acid in fermented mashes. The results of NMR and comprehensive two-dimensional gas chromatography coupled with time of flight mass spectrometry (GC × GC-TOF MS) analysis confirmed the ability of the yeast and LAB strains to metabolize acetone via its reduction to isopropyl alcohol. Efficient fermentation of distillery mashes was observed in all tested mashes with an initial LAB count of 3.34-6.34 log cfu/mL, which had no significant effect on the ethanol content. However, changes were observed in the contents of by-products. Lowering the initial pH of the mashes to 4.5, without and with LAB (3.34-4.34 log cfu/mL), resulted in a decrease in propan-2-ol and a concomitant increase in acetaldehyde content, while a higher pH (5.0 and 5.5) increased the content of propan-2-ol and decreased acetaldehyde content. Higher temperature (35 °C) promoted propan-2-ol synthesis and also resulted in increased acetic acid content in the fermented mashes compared to the controls. Moreover, the acetic acid content rose with increases in the initial pH and the initial LAB count.

The Increase of Triterpene Saponin Production Induced by Trans-Anethole in Hairy Root Cultures of Panax quinquefolium.

In vitro cultivation is an effective way to increase pharmaceutical production. To increase ginsenoside production in hairy root cultures of American ginseng, the present study uses trans-anethole as an elicitor. The content of nine triterpene saponins was determined: Rb1, Rb2, Rb3, Rc, Rd, Rg1, Rg2, Re and Rf. Trans-anethole was found to stimulate saponin synthesis regardless of exposure time (24 and 72 h). Twenty-four hour exposure to 1 µmol trans-anethole in the culture medium resulted in the highest increase of total saponin content (twice that of untreated roots), and optimum accumulation of Rb-group saponins, with ginsenoside Rc dominating (8.45 mg g-1 d.w.). In contrast, the highest mean content of protopanaxatriol derivatives was obtained for 10 µmol trans-anethole. The Re metabolite predominated, reaching a concentration of 5.72 mg g-1 d.w.: a 3.9-fold increase over untreated roots. Elicitation with use of trans-anethole can therefore be an effective method of increasing ginsenoside production in shake flasks.

Aspartic acid racemization of root dentin used for dental age estimation in a Polish population sample.

Precise age determination of unidentified bodies and human remains is one of the essential tasks of forensic science. The aim of this study was to assess the applicability of using the enantiomeric composition of aspartic acid racemization in root and crown dentin for dental age estimation using a Polish population sample. Coronal and root dentin from four teeth groups from the mandible were studied using gas chromatography with mass spectrometry. The results demonstrated a very high correlation between the chronological age and enantiomeric composition in both of the dentin samples. Individual linear equations of root dentin with correlation coefficients between 0.96 and 0.98 and a standard estimation error of ±2.95-4.84 years validated the application of aspartic acid racemization as a significant practical contribution to everyday forensic medical practice. Discrepancies in methodological aspects and modifications that simplify the protocol are presented.

Pichia cactophila and Kluyveromyces lactis are Highly Efficient Microbial Cell Factories of Natural Amino Acid-Derived Aroma Compounds.

The pivotal role of non-conventional yeast (NCY) species in formation of valuable aroma compounds in various food commodities is widely acknowledged. This fact inspires endeavors aiming at exploitation of food-derived NCYs as biocatalysts in natural aromas production. In this study, we isolated, characterized and evaluated aroma-producing capacity of two NCY representatives-Pichia cactophila 7.20 and Klyuveromyces lactis 6.10 strains. The strains were isolated from food-related habitats-goat-milk regional cheese and Swiss-type ripening cheese, respectively. Aroma profiles generated by the two strains cultured in a general rich medium were analyzed through solvent extraction and GC-MS analysis of the compounds retained in the culture media. Finally, the strains were tested in bioconversion cultures with branched chain- or aromatic amino acids as the sole nitrogen source, to assess capability of the strains towards formation of amino acid-derived aromas. The results showed extraordinary capacity of both strains for production of 2-phenylethanol (at more than 3 g/L) and isoamyl alcohol (approx. 1.5 g/L). A distinctive trait of 2-phenylethyl acetate synthesis at high concentrations (0.64 g/L) was revealed for P. cactophila 7.20 strain. Highly valued disulfide dimethyl as well as methionol acetate were identified amongst the aroma compounds synthesized by the strains.

Antifungal Activity of Lactobacillus pentosus LOCK 0979 in the Presence of Polyols and Galactosyl-Polyols.

The antifungal activity of Lactobacillus pentosus LOCK 0979 depends both on the culture medium and on the fungal species. In the control medium, the strain exhibited limited antagonistic activity against indicator food-borne molds and yeasts. However, the supplementation of the bacterial culture medium with polyols (erythritol, lactitol, maltitol, mannitol, sorbitol, xylitol) or their galactosyl derivatives (gal-erythritol, gal-sorbitol, gal-xylitol) enhanced the antifungal properties of Lactobacillus pentosus LOCK 0979. Its metabolites were identified and quantified by enzymatic methods, HPLC, UHPLC-MS coupled with QuEChERS, and GC-MS. The presence of polyols and gal-polyols significantly affected the acid metabolite profile of the bacterial culture supernatant. In addition, lactitol and mannitol were used by bacteria as alternative carbon sources. A number of compounds with potential antifungal properties were identified, such as phenyllactic acid, hydroxyphenyllactic acid, and benzoic acid. Lactobacillus bacteria cultivated with mannitol synthesized hydroxy-fatty acids, including 2-hydroxy-4-methylpentanoic acid, a well-described antifungal agent. Scanning electron microscopy (SEM) and light microscopy confirmed a strong antifungal effect of L. pentosus LOCK 0979.

Synthesis and Biotransformation of Bicyclic Unsaturated Lactones with Three or Four Methyl Groups.

The aim of this study was to obtain new unsaturated lactones by chemical synthesis and their microbial transformations using fungal strains. Some of these strains were able to transform unsaturated lactones into different hydroxy or epoxy derivatives. Strains of Syncephalastrum racemosum and Absidia cylindrospora gave products with a hydroxy group introduced into a tertiary carbon, while the Penicillium vermiculatum strain hydroxylated primary carbons. The Syncephalastrum racemosum strain hydroxylated both substrates in an allylic position. Using the Absidia cylindrospora and Penicillium vermiculatum strains led to the obtained epoxylactones. The structures of all lactones were established on the basis of spectroscopic data.

A comparative study on composition and antioxidant activities of supercritical carbon dioxide, hexane and ethanol extracts from blackberry (Rubus fruticosus) growing in Poland.

BACKGROUND: Large quantities of blackberry seeds are produced as a pomace during the processing of juice and jam production; this by-product is a very interesting raw material both for oil manufacturing and as a source of bioactive compounds. In this work the composition, yield and antioxidant activity of three types of Rubus fructicosus pomace extracts isolated by liquid extraction using solvents of different polarity, as well with supercritical CO2 fluid extraction have been compared. RESULTS: The highest extract yield was reported for Soxhlet extraction using ethanol as a solvent (14.2%). Supercritical carbon dioxide and hexane extracts were characterised by the highest content of phytosterols (1445 and 1583 mg 100 g-1 of extract, respectively) among which ß-sitosterol was the main one, while the concentration of tocopherols, with predominant γ-isomer, was the highest for both hexane and ethanol extracts, being 2364 and 2334 mg 100 g-1 , respectively. Using a GC-MS method 95 volatiles, in which non-saturated aldehydes were predominant, were identified in the essential oil of seed pomace and in the volatile oil isolated from supercritical extract. The ethanolic extract which is characterised by the highest phenolic content (9443 mg GAE 100 g-1 ) exhibited the highest antioxidant activity (according to the ABTS•+ and DPPH• assays). CONCLUSION: All pomace extracts examined were of high quality, rich in essential omega fatty acids and with a very high content of bioactive compounds, such as phytosterols and tocopherols. The high nutritional value of extracts from berry seed pomace could justify the commercialisation of specific extracts not only as food additives but also as cosmetic components. © 2017 Society of Chemical Industry.

Volatiles as Chemosystematic Markers for Distinguishing Closely Related Species within the Pinus mugo Complex.

Headspace solid-phase microextraction (HS-SPME) coupled to GC/MS analysis was used to identify the constituents of pine-needle volatiles differentiating three closely-related pine species within the Pinus mugo complex, i.e., P. uncinata Ramond ex DC., P. uliginosa G.E.Neumann ex Wimm., and P. mugo Turra. Moreover, chemosystematic markers were proposed for the three analyzed pine species. The major constituents of the pine-needle volatiles were α-pinene (28.4%) and bornyl acetate (10.8%) for P. uncinata, δ-car-3-ene (21.5%) and α-pinene (16.1%) for P. uliginosa, and α-pinene (20%) and δ-car-3-ene (18.1%) for P. mugo. This study is the first report on the application of the composition of pine-needle volatiles for the reliable identification of closely-related pine species within the Pinus mugo complex.

Selected Compounds Structurally Related to Acyclic Sesquiterpenoids and Their Antibacterial and Cytotoxic Activity.

By implementing a common and industrially used method, 30 compounds which are structurally related to geranyl acetone, nerolidol, farnesal, farnesol and farnesyl acetate were obtained. Their antimicrobial activity against Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium, Escherichia coli, Klebsiella pneumoniae and Acinetobacter baumannii bacteria was investigated. Pharmacophore models were proposed based on the obtained results and 3D QSAR modelling. Cytotoxic effects against mainly human immortalised and normal cell lines of different origin (malignant melanoma MeWo, colorectal adenocarcinoma HT29, promyelocytic leukemia HL60, gingival fibroblasts HFIG, skin keratinocytes HaCaT and rat small intestine epithelium IEC6) were examined. The odour descriptions of newly synthesised compounds are given.

Composition of essential oils isolated from the needles of Pinus uncinata and P. uliginosa grown in Poland.

The compositions of mountain pine (Pinus uncinata) and peat-bog pine (P. uliginosa) needle essential oils were investigated. Enantiomeric compositions of selected monoterpene hydrocarbons were also examined. Respectively, fifty-three and seventy-six components of the essential oils were identified using GC-MS and retention indexes. The main group of essential oil components of mountain pine needles were monoterpenes, and bornyl acetate constituted approximately 30% (46.3 g/100 g) of the oil. In peat-bog pine essential oil, monoterpenes and sesquiterpenes exhibited a similar content (ca. 40%). Bornyl acetate and α-pinene were the main constituents of both essential oils. In the essential oil of P. uncinata needles, limonene, camphene, myrcene and (E)-ß-caryophyllene were also noticeable, while in the essential oil of P. uliginosa needles, Δ-car-3-ene, (E)-ß-caryophyllene, germacrene D, δ-cadinene, germacrene D 4-ol and α-cadinol were present in notable quantities. In both essential oils, borneol propionate, isobutyrate, 2-methylbutyrate and isovalerate were detected. Their presence was confirmed by synthesis and analysis of the standards; retention indexes on a non-polar column are published herein.

Synthesis of (S)-ricinoleic acid and its methyl ester with the participation of ionic liquid.

(R)-ricinoleic acid methyl ester obtained from commercial castor oil was transformed in a three-step procedure into its S-enantiomer in overall 36% yield using ionic liquid (1-butyl-3-methylimidazolium acetate) in the key step process. The developed procedure provides easy access to (S)-ricinoleic acid and its methyl ester of over 95% enantiomeric excess. Optical rotations of the newly obtained compounds as well as their chromatographic and spectral characteristics are provided and discussed in the context of enantiopurity both of the substrate material and the final products.