Józef Kula

Essential Oils of Wild and Cultivated Carrots—the Chemical Composition and Antimicrobial Activity

Abstract The essential oil content and their chemical composition of herb, fowering and mature umbels of wild carrot growing in Poland (Daucus carota L. ssp. carota) as well as cultivated carrot seed oils were examined. The qualitative and quantitative analyses of the essential oils were performed using GC and GC/MS methods, and the results are given for the 1999 season. Generally, oils obtained from different parts of wild carrot plant consisted mainly of monoterpene hydrocarbons (72–84%), whereas the main compounds of the oil of cultivated carrot breeds (var. Koral and Perfekcja) were oxygenated sesquiterpenes (51% and 44%, respectively). A commercial sample of carrot seed oil available on the Polish market was also examined; monoterpenes were the main compounds (64% of the total oil). Antimicrobial properties of the oils obtained were compared using four species of bacteria and two species of fungi. The MICs were determined by the agar dilution method. The oils obtained from cultivated carrot seed were more effective against all tested organisms. The strongest overall activity was demonstrated by the commercial oil of cultivated carrot seeds.

Chemical Composition of the Essential Oil of Mentha pulegium L. from Bulgaria

Abstract The chemical composition of the essential oil of Mentha pulegium from Bulgaria has been determined by GC and GC/MS. The yields of oil obtained by water and steam distillation were 1.54% and 1.48%, respectively. The basic components, among the identified 21 were pulegone (42.9–45.4%), piperitenone (21.7–23.1%) and isomenthone (11.3–12.8%). There were no substantial qualitative differences between the oils obtained by water or steam distillation.

Composition of the Essential Oil from Wild Carrot Umbels (Daucus carota L. ssp. carota) Growing in Poland

Abstract The hydrodistilled oil obtained from plant umbels (Daucus carota L. ssp. carota) harvested in the wild was investigated by GC and GC/MS. One hundred components have been identified. The fraction of monoterpene hydrocarbons represented 83.8%, oxygenated monoterpenes represented 8.0% of the whole oil, whereas the sesquiterpene fraction represented 7.4% and other compounds 0.2% of the total composition. The most abundant constituents were α-pinene (41%), sabinene (18%), myrcene (7%), limonene (5%) and terpinen-4-ol (5%).

Transformation of Carotol into the Hydroindane‐Derived Musk Odorant

Ozonolysis of carotol (1) gives dihydroxy ketone 2 (63% yield), the absolute configuration of which was established by X-ray crystallography. An acidic dehydration of 2 delivers a mixture of isomeric ketones 3 and 4 (3:1) that, catalysed by Pd/C in cyclohexene, yields a 1:1 thermodynamic mixture of 3 and 6. Ketone 6 exhibits an intensive musk odour. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

Short synthetic route to the enantiomerically pure (R)-(+)-γ-decalactone

Abstract An efficient procedure for the preparation of homochiral (R)-(+)-γ-decalactone 4 based on castor oil ozonolysis is described. The key intermediate, (R)-(−)-1,3-nonandiol 1, was transformed into monotosylate 2 and then reacted with sodium cyanide to give (R)-(−)- 4 - hydroxydecanitrile 3. Treatment of the latter with a dilute hydrochloric acid provided the enantiomerically pure lactone 4.

12-nor-alloisolongifolan-11-one, a ketone with amber-like odour from longifolene

Acid-catalysed isomerization of longifolene 1 gives alloisolongifolene 2 which, after ozonolysis, creates ketone 3 with a rich, earthy and amber-like odour.

Chemical Composition of Origanum vulgare L. essential Oil from Bulgaria

Abstract The composition of the essential oil obtained by steam distillation of air-dried herb of Origanum vulgare L. ssp. vulgare harvested in the wild in Rhodopa Mountains, Bulgaria, has been studied by GC and GC-MS to identify 113 components. sesquiterpenes were the main components including spathulenol (20.7%), β-caryophyllene (9.9%) and caryophyllene oxide (5.7%). The oil recovered by hydrodistillation of waters represented 41% of oxygenated monoterpenes: 1,8-cineol (15%), α-terpineol (10.7%) and terpinen-4-ol (9.3%).

Synthesis of enantiomerically pure volatile compounds derived from (R)-3-hydroxynonanal

Abstract Practical preparations of enantiomerically pure R -configured 3-hydroxynonanal dimethyl acetal, 3-acetoxynonanal dimethyl acetal, methyl 3-acetoxynonanoate, δ-undecalactone, 1,3-nonanediol and its esters, 1,4-decanediol and its esters and 2-hexyltetrahydrofuran based on the ozonolysis product of commercial castor oil are described.

Further study on the one-pot synthesis of (E)-2-nonenal from castor oil

A one-step procedure is described for the synthesis of (E)-2-nonenal from commercial castor oil by ozonolysis in methanol, followed by reduction of the ozonide products with dimethyl sulfide and exposure of the resulting intermediate product to dilute sulfuric acid. The developed process allows the production of the aldehyde with a yield of 80% at a purity of 95%. The method has advantages over all those reported earlier, because of inexpensive raw material and reducing agent, recycling of the solvent and its unusual simplicity.

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 β-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.