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Aromatic plants and essential oils have many applications in medicine, pharmaceuticals, cosmetics, and the food industry. The essential oil of the flowering aerial parts of Achillea grandifolia, obtained by hydrodistillation, was analyzed for its constituents and investigated for antimicrobial and radical scavenging activity. The essential oil was characterized by a high amount of oxygenated monoterpenes (72.7%) with 1,8-cineole (29.2%) and camphor (23.4%) being the most abundant. Sesquiterpenes were present in smaller quantities (4.8%). Antimicrobial activity was tested against eight ATCC bacterial strains and two ATCC strains of Candida albicans. The essential oil exhibited highly pronounced antimicrobial activity against Micrococcus luteus with a MIC value of 3.50 μg/mL, as well as significant antimicrobial activity (

Cinnamon bark is used worldwide due to its characteristic flavour and medicinal properties. Ceylon cinnamon or “true” cinnamon bark refers to the dried inner bark of the shoots of Cinnamomum verum J. Presl, originated from Sri Lanka. The bark of some other species of this genus, Cinnamomum cassia Blume (Chinese cinnamon), C. burmanni (Nees & T. Nees) Blume (Indonesian cinnamon), and C. loureiroi Nees (Saigon cinnamon) are also marketed and sold as cinnamon. They are characterised by a significantly higher amount of coumarin compared to Ceylon cinnamon bark. Since coumarin may be potentially hepatotoxic, the aim of this study was to determine coumarin level in commercial samples of cinnamon bark and in cinnamon-containing dietary supplements present on the Serbian market. HPLC analysis showed lowest coumarin content in Ceylon cinnamon bark samples (0.08-0.15 mg g-1), whereas other samples contained a significantly higher amounts of coumarin (1.38-5.80 mg g-1). Cinnamon based dietary supplements contained 0.007-1.19 mg coumarin/tablet. The obtained results indicate that the majority of commercial samples of cinnamon bark on the Serbian market do not originate from the Ceylon cinnamon but from other species of this genus, and that consumed amount of certain products should be taken into account since the tolerable daily intake of coumarin is limited.

In the present research, the chemical composition of aerial parts of cultivated citral chemotype of Thymus pannonicus All. (Lamiaceae), growing at different soil conditions was studied. Two plant lineages were unfertilized or treated using either nitrogen or phosphorus fertilizers at different concentration levels. Essential oil (EO) content, EO composition, and composition of hydromethanol extracts (MEs) were compared to the results obtained for wild growing plants in order to evaluate the potential of T. pannonicus for its industrial production. EO content (%, V/m) in cultivated samples varied between 0.32-0.75% and 0.62–1.05% within two examined lineages, whereas the herbs from the natural habitat contained 0.49–1.29% of EO. GC-FID/MS analysis showed that citral, i.e. mixture of isomers geranial and neral, was the most abundant constituent in all EOs (51.90–81.96%). HPLC analysis revealed that total caffeic acid derivatives, with rosmarinic acid (RA) as the most abundant compound in all extracts, as well as total apigenin glycosides contents were significantly higher in the extracts originating from the cultivated herbs (112.15–184.94 mg/g and 5.08–15.29 mg/g, respectively), in comparison to the extracts of the herbs from the natural habitats (67.61–98.75 mg/g and 1.17–1.32 mg/g). In general, the composition of cultivated herbs varied less than that of samples originating from natural habitats, indicating that controlled cultivation of citral chemotype of T. pannonicus can provide herbal drug with favourable characteristics. Only minor differences were observed between cultivated samples treated with different fertilizers.

The extraction yield of Juglans nigra L. leaves was assessed at different ethanol concentrations (0–96% (v/v)) and solvent-to-solid ratios (5–20 kg kg−1). The response surface methodology (RSM) and artificial neural network with genetic algorithms (ANN-GA) were developed to optimize the extraction variables. The RSM and ANN-GA models determined 50% (v/v) ethanol concentration and 20 kg kg−1 solvent-to-solid ratio as optimal conditions, ensuring an extraction yield of 27.69 and 27.19 g 100 g−1 of dry leaves. The phenolic compounds in optimal extract were quantified: 3-O-caffeoylquinic acid (2.27 mg g−1of dry leaves), quercetin-3-O-galactoside (10.99 mg g−1 of dry leaves) and quercetin-3-O-rhamnoside (15.07 mg g−1of dry leaves) using high-performance liquid chromatography (HPLC). The minerals in optimal extract were quantified: macro-elements (the relative order by content was: K > Mg > Ca) using inductively coupled plasma optical emission spectrometry (ICP-OES) and micro-elements (the relative order by content was: Zn > Rb > Mn > I>Sr > Ni > Cu > Co > V > Ag > Se) using inductively coupled plasma mass spectrometry (ICP-MS). The extraction coefficients for minerals were determined and were highest for K (64.3%) and I (53.5%). Optimization of extraction process resulted in high extraction yield from J. nigra leaves and optimal extract containing different phytochemical compounds. This is the peer-reviewed version of the article: Rajković, K. M.; Vasić, M.; Drobac, M.; Mutić, J.; Jeremić, S.; Simić, V.; Stanković, J. Optimization of Extraction Yield and Chemical Characterization of Optimal Extract from Juglans Nigra L. Leaves. Chemical Engineering Research and Design 2020, 157, 25–33. [https://doi.org/10.1016/j.cherd.2020.03.002]

The composition of leaf and flower essential oils of eight Heracleum taxa (populations collected in Serbia, Montenegro, North Macedonia and Slovenia) was statistically analyzed to evaluate its chemosystematic significance. Investigated taxa included H. orphanidis and the representatives of H. sphondylium group: H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicum subsp. pollinianum, H. pyrenaicum subsp. orsinii and H. verticillatum. Hydrodistilled essential oils were analyzed by GC–FID and GC–MS. Chemosystematic significance was evaluated using multivariate statistics: principal component analysis (PCA), non-metric multidimensional scaling (NMDS) and unweighted pair-group arithmetic averages clustering (UPGMA). Statistical analyses included our previously published data on the composition of essential oils of eight leaf and three flower samples, as well as the data on the composition of the oils of additional eight leaf and five flower samples obtained in the current work. Leaf and flower essential oils of H. sphondylium group members were dominated by various sesquiterpenes, phenylpropanoids and/or monoterpenes. Heracleum orphanidis leaf and flower essential oils were rich in aliphatic esters, mostly octyl acetate. Statistical analysis of the composition of leaf essential oils, as well as of flower oils, demonstrated the grouping of investigated populations of these Heracleum taxa according to their systematics, i.e., separation of H. orphanidis from the representatives of H. sphondylium group, and grouping of H. pyrenaicum subspecies within this group. Morphologically related H. sibiricum and H. ternatum were closely located in PCA and NMDS and in UPGMA even shared the same cluster.

The plants of the genus Armoracia P. Gaertn., B. Mey. & Scherb. (Brassicaceae) contain glucosinolates, which volatile hydrolysis products are known for their antimicrobial activity. In this work, the composition and antimicrobial activity of the root volatiles of wild-growing Armoracia macrocarpa (Waldst. & Kit.) Kit. ex Baumg., obtained by hydrodistillation, were analysed for the first time. These results were compared with those of widely used horseradish, A. rusticana P. Gaertn., B. Mey. & Scherb. Additionally, the possibility of the propagation of A. macrocarpa from the roots, and impact of its cultivation on the composition and antimicrobial activity of the root volatiles were investigated. The GC-FID and GC–MS analysis revealed that all A. macrocarpa root volatile fractions were dominated by berteroin (55.0–59.0%) and lesquerellin (34.1–36.4%), and were significantly different from horseradish root volatile fraction. In microdilution method, A. macrocarpa volatile fractions exhibited weak/no antibacterial activity, while their effect against standard strain (MICs = 4.8–9.3 μg/mL) and clinical isolates (MICs = 25–119 μg/mL) of Candida albicans was significant. Horseradish volatiles exhibited better antibacterial and slightly weaker anticandidal activity. Armoracia macrocarpa represents a new source of raw materials with potential use in pharmaceutical and food industries, as well as in cookery. Preliminary results indicated the possibility of its cultivation, which is required for its preservation and sustainable usage.

In a search for novel food additives/functional food ingredients, chemical composition, and antioxidant and antimicrobial activities of Thymus dacicus Borbas (Lamiaceae) flowering aerial parts dry methanol extract and essential oil were tested for the first time. HPLC analysis of the extract revealed that among dominant polyphenols, rosmarinic acid was the most abundant (71.33 ± 1.11 mg/g). Monoterpenes geranial (34.4%) and neral (23.9%) prevailed in the oil, analyzed by GC and GC–MS. The extract showed pronounced antioxidant activity, with FRAP value of 5.16 ± 0.19 mmol Fe 2+ /g, OH radical SC 50 of 18.85 μg/mL (determined by 2-deoxyribose assay) and DPPH radical SC 50 of 28.04 μg/mL. Eight out of ten tested microbial strains were susceptible to the oil in microdilution test. Furthermore, for the combination of the oil and vancomycin/gentamicin, synergism was demonstrated against MRSA, Klebsiella pneumoniae and Escherichia coli in checkerboard test. Obtained results encourage further research of this herb as potentially beneficial ingredient in foodstuffs.

Geranium species are widely used in traditional medicine of Balkan. The aim of this work was to investigate and compare chemical composition of volatile fractions obtained by hydrodistillation from aerial parts of G. macrorrhizum, G. phaeum, G. sanguineum, G. robertianum, G. palustre, G. pyrenaicum, G. columbinum and G. lucidum as well as from underground parts of G. macrorrhizum and G. phaeum, originated from Vlasina plateau in South Eastern Serbia. The volatiles were analyzed using GC/MS and GC-FID. G. palustre volatiles have been studied for the first time with β-selinene (18.6 %) as a characteristic compound. The cluster analysis revealed separation of volatiles into two main groups. Volatile fractions of G. macrorrhizum were separated from all other samples due to high sesquiterpene content (92.3 % in aerial and 94.6 % in underground parts). The volatile fractions of other samples were mainly composed of sesquiterpenes (10.8–61.8 %), diterpenes (12.9–43.0 %) and fatty acids and their derivatives (6.6–21.6 %) with the exception of volatile fraction of G. phaeum underground parts which was dominated only by fatty acids and their derivatives (76.6 %). The results presented in this article contribute to the knowledge on the chemistry of this genus and advances the knowledge on flora of southeast Serbia.

The composition of essential oils obtained by hydrodistillation from dried stems and inflorescences of Cymbopogon nervatus (Hochst.) Chiov. (Poaceae) growing wild in Western and Eastern Sudan and collected at two different periods, was analyzed by GC and GC–MS. The most dominant constituents in the oils were p -menthadienols, trans - p -mentha-1(7),8-dien-2-ol (19.9–32.6%), cis-p -mentha-1(7),8-dien-2-ol (18.9–23.3%), trans-p -mentha-2,8-dien-1-ol (10.6–21.0%) and cis-p -mentha-2,8-dien-1-ol (8.1–10.4%). The essential oil of inflorescence from the Western Sudan was tested for spasmolytic activity using three different experimental models: against spontaneous contractions, and contractions induced with ACh and KCl. The oil exhibited strong, significant and concentration-dependent spasmolytic activity. Applied in concentration of 200 μg/ml, the oil showed 88.44 ± 16.78% of maximal spasmolytic effect of atropine (6.4 μM) against spontaneous contraction. Essential oil (90 μg/ml) inhibited ACh-induced contractions as well, and reduced the effect of the highest applied concentration of ACh to 37.29 ± 16.16%. Additionally, the oil exhibited strong activity against contractions induced with KCl (80 mM) and in concentration of 200 μg/ml, completely abolished the contractile effect of KCl. The essential oil of inflorescence from the Western Sudan was also tested for antioxidant activity by DPPH assay and showed moderate anti-DPPH activity (SC 50 23.8 μl/ml).

The compositions of hydrodistillated essential oils of Laser trilobum (L.) Borkh. rhizomes and fruits from Serbia, were investigated using GC and GC/MS. In the dark-blue rhizome oil forty-six compounds (93.1% of the total oil) were identified, with α-pinene (31.5%), γ-terpinene (9.0%), p-cymene (7.9%), β-pinene (6.1%) and 1,4-dimethylazulene (6.0%) as the major components. In the colorless fruits oil, twenty components (96.8% of the total oil) were identified, and the main constituents were limonene (51.6%) and perillaldehyde (26.8%). The antimicrobial activity of the oils was tested using the broth microdilution method against nine bacterial and two fungal strains. The oils revealed significant antimicrobial effect, mainly better than that of thymol, used as a reference compound. The strongest activity was recorded for the rhizome oil against Escherichia coli, Klebsiella pneumoniae and Candida albicans (MICs=25 μg/mL), and the fruit oil against C. albicans ATCC 10259 (MIC=12.5 μg/mL).

The composition of the essential oils and the furanocoumarin profiles of CH2 Cl2 extracts from underground parts and fruits of nine Heracleum taxa (Apiaceae) from Southeastern Europe were statistically analyzed to evaluate their chemosystematic significance. Eight investigated taxa (H. orphanidis and members of H. sphondylium group: H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicum subsp. pollinianum, H. pyrenaicum subsp. orsinii and H. verticillatum) belong to the type section of the genus. Additionally analyzed taxon, H. austriacum subsp. siifolium, belongs to H. sect. Wendia. Qualitative and quantitative analysis of the essential oils was performed by GC-FID and GC/MS, and of the furanocoumarins by LC/MS. Furanocoumarins were identified using standards and/or based on UV, MS, 1 H- and ROESY NMR spectra. Multivariate statistics (PCA, nMDS, UPGMA) of analyzed metabolites showed that the investigated taxa were grouped according to their taxonomic classification. PCA revealed the significance of some monoterpenes and (Z)-falcarinol of the underground parts oils, octyl esters of the fruit oils, and most of the total of 12 identified furanocoumarins.

Many Heracleum L. taxa (Apiaceae) are used as food and spices, and in traditional medicine. In this work, the chemical composition of Heracleum pyrenaicum subsp. orsinii (Guss.) F. Pedrotti and Pignatti root, leaf and fruit essential oils, their antimicrobial activity and cytotoxic effect on malignant and normal cells were investigated for the first time. The composition of the oils was analyzed by GC and GC–MS. Monoterpenes prevailed in the root oil, with β-pinene (38.6%) being dominant, while in the leaf oil, sesquiterpenes, mostly (E)-nerolidol (20.5%) and (E)-caryophyllene (17.0%), were the most abundant constituents. The fruit oil contained the majority of aliphatic esters, mainly octyl acetate (36.8%) and octyl hexanoate (22.1%). The antimicrobial activity was determined by microdilution method against eight bacteria and eight fungi (standard strains, clinical or food isolates). The best antibacterial activity, better than the activity of ampicillin, was shown by the root oil against Salmonella typhimurium, Escherichia coli and Pseudomonas aeruginosa. The strongest antifungal activity, stronger than the activity of ketoconazole, was exhibited by the leaf and root oils against Trichoderma viride, and by the root oil against Aspergillus ochraceus. The cytotoxic effect of the oils, determined by MTT test, was prominent against malignant HeLa, LS174 and A549 cells (IC50=6.49–14.56μg/mL). On the other hand, the oils did not show toxicity against normal MRC-5 cells at tested concentrations (IC50>200.00μg/mL). It can be concluded that investigated H. pyrenaicum subsp. orsinii oils represent potential new raw materials for food and pharmaceutical industry.

Fatty acids (FAs), sterols, and triterpenes of dichloromethane extracts of the fruits of 8 Heracleum L. taxa (Apiaceae) from southeastern Europe were investigated by gas chromatography with flame ionization detector and gas chromatography with mass spectrometry. In order to analyze the FAs, their volatile methyl esters were obtained by saponification and subsequent esterification of oily supernatants of the fruit extracts. Dominant was petroselinic acid (42.8%-56.5%), followed by linoleic (20.3%-33.3%) and oleic acids (12.3%-13.7%). Sterols and triterpenes were analyzed as volatile derivatives obtained by the silanization of residual unsaponifiable fractions. Among them, the most abundant was β-sitosterol (44.9%-56.9%), followed by stigmasterol (15.7%-25.0%), Δ7-stigmastenol (6.6%-12.5%), and campesterol (5.2%-8.1%). The quantity of petroselinic acid was also determined by the external standard method (298.8-433.4 mg/g of oily supernatant). The obtained results show that the investigated plants are potential valuable sources of the compounds utilized in different industries.

Although some widespread, native cow parsnips (Heracleum L. spp., Apiaceae) had broad medicinal and culinary applications throughout history, the knowledge about their volatile constituents is insufficient. This work investigates the composition and bioactivities of H. sphondylium L. (HSPH), H. sibiricum L. (HSIB) and H. montanum Schleich. ex Gaudin (HMON) essential oils. The composition was tested by GC and GC-MS. (Z)-β-Ocimene was the most abundant in HSPH (28.9%) and HMON (20.4%) root oils, while in HSIB root oil, β-pinene (26.2%), methyl eugenol (22.3%) and elemicin (25.6%) prevailed. Leaf and flower oils were dominated by various sesquiterpenes (germacrene D, β-sesquiphellandrene, (E)-β-farnesene and/or (E)-caryophyllene) and/or phenylpropanoids (apiole, methyl eugenol, elemicin and/or (Z)-isoelemicin). Octyl acetate (57.5-67.1%) was the main constituent of all fruit oils. The antimicrobial activity was screened by a microdilution method against eight bacteria and eight fungi. The strongest antimicrobial effect, in several cases better than the activity of antibiotics, was shown by HSPH (MICs = 0.12-3.30 mg mL-1) and HMON (MICs = 0.10-1.30 mg mL-1) flower oils against bacteria, and HSIB fruit oil against fungi (MICs = 0.15-0.40 mg mL-1). The MTT test revealed that the oils were not or weakly cytotoxic against human malignant HeLa, LS174 and/or A549 cells (except HSPH root oil; IC50 = 5.72-24.31 μg mL-1) and that tested oils were not toxic against human normal MRC-5 cells (at 200.00 μg mL-1). Significant activity observed against microorganisms that are the common cause of foodborne diseases, food contamination and/or hospital-acquired infections justifies certain traditional uses of the investigated plants and represents a good basis for further research of these Heracleum oils.

Hungarian thyme (Thymus pannonicus All., Lamiaceae) is an aromatic herb used as traditional remedy, a refreshing beverage and a food aromatizer. Herbal teas, i.e., infusions, of Hungarian thyme from eight localities in Serbia were analyzed regarding their polyphenolic and volatile composition, and tested for their antioxidant and antimicrobial activity. The total polyphenolics content, determined by the Folin-Ciocalteu method, ranged from 1122.25 to 1979.93 mg gallic acid/L. HPLC analysis revealed rosmarinic acid (367.42–1199.47 mg/L) and luteolin glucuronides as the main polyphenolics. The volatile fractions of the infusions, analyzed by static headspace extraction coupled with GC and GC–MS analyses, contained citral, 3-octanone, 1-octen-3-ol, linalool and 1,8-cineole as the dominant constituents. The antioxidant activity of the infusions was examined through the ferric reducing antioxidant power (FRAP) (68.09–124.58 mmol Fe2+/L) and the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical tests (SC50 1.32–2.96 μL/mL). The antimicrobial activity was tested by the broth microdilution method against standard strains of Gram(+) Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis and Enterococcus faecalis and Gram(−) bacteria Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa, and one strain of yeast Candida albicans. The infusions inhibited microbial growth in the tested concentration range (31.25–500.00 μL/mL) and the strongest activity was exhibited against the strain of C. albicans (MIC 31.25–62.50 μL/mL). The antioxidant and antimicrobial properties of the infusions were, to some extent, in correlation with the composition and content of the polyphenolic compounds, whereas the volatiles noticeably influenced the exhibited antimicrobial activity.

In this work, the chemical composition, antimicrobial and cytotoxic activity of Heracleum verticillatum Pančić and H. ternatum Velen. root, leaf, and fruit essential oils were investigated. The composition was analyzed by GC and GC/MS. Heracleum verticillatum and H. ternatum root oils were dominated by monoterpenes, mostly β-pinene (23.5% and 47.3%, respectively). Heracleum verticillatum leaf oil was characterized by monoterpenes, mainly limonene (20.3%), and sesquiterpenes, mostly (E)-caryophyllene (19.1%), while H. ternatum leaf oil by the high percentage of phenylpropanoids, with (Z)-isoelemicin (35.1%) being dominant constituent. Both fruit oils contained the majority of aliphatic esters, mostly octyl acetate (42.3% in H. verticillatum oil and 49.0% in H. ternatum oil). The antimicrobial activity of the oils was determined by microdilution method against eight bacterial and eight fungal strains. The strongest effect was exhibited by H. verticillatum root oil, particularly against Staphylococcus aureus, Salmonella typhimurium (MICs = 0.14 mg/ml, MBCs = 0.28 mg/ml), and Trichoderma viride (MIC = 0.05 mg/ml, MFC = 0.11 mg/ml). Cytotoxic effect was determined by MTT test against malignant HeLa, LS174, and A549 cells (IC50 = 5.9 - 146.0 μg/ml), and against normal MRC-5 cells (IC50 > 120.1 μg/ml). The best effect was exhibited by H. verticillatum root oil on A549 cells (IC50 = 5.9 μg/ml), and H. ternatum root oil against LS174 cells (IC50 = 6.7 μg/ml).

The chemical composition and antimicrobial activity of essential oils of Laserpitium latifolium and L. ochridanum were investigated. The essential oils were isolated by steam distillation and characterized by GC-FID and GC/MS analyses. All essential oils were distinguished by high contents of monoterpenes, and α-pinene was the most abundant compound in the essential oils of L. latifolium underground parts and fruits (contents of 44.4 and 44.0%, resp.). The fruit essential oil was also rich in sabinene (26.8%). Regarding the L. ochridanum essential oils, the main constituents were limonene in the fruit oil (57.7%) and sabinene in the herb oil (25.9%). The antimicrobial activity of these essential oils as well as that of L. ochridanum underground parts, whose composition was reported previously, was tested by the broth-microdilution method against four Gram-positive and three Gram-negative bacteria and two Candida albicans strains. Except the L. latifolium underground-parts essential oil, the other investigated oils showed a high antimicrobial potential against Staphylococcus aureus, S. epidermidis, Micrococcus luteus, or Candida albicans (minimal inhibitory concentrations of 13.0-73.0 μg/ml), comparable to or even higher than that of thymol, which was used as reference compound.