Supplementary data for the article: Aćimović, M.; Pezo, L.; Tešević, V.; Čabarkapa, I.; Todosijević, M. QSRR Model for Predicting Retention Indices of Satureja Kitaibelii Wierzb. Ex Heuff. Essential Oil Composition. Industrial Crops and Products 2020, 154, 112752. https://doi.org/10.1016/j.indcrop.2020.112752

Supplementary material for: [https://doi.org/10.1016/j.indcrop.2020.112752]Related to published version: [https://cherry.chem.bg.ac.rs/handle/123456789/4209

A Validation Model for Prediction of Kovats Retention Indices of Compounds Isolated from Origanum spp. and Thymus spp. Essential Oils

This work aimed to obtain a validated model for the prediction of retention times of compounds isolated from Origanum heracleoticum, Origanum vulgare, Thymus vulgaris, and Thymus serpyllum essential oils. In total 68 experimentally obtained retention times of compounds, which were separated and detected by GC-MS were further used to build the prediction models. The quantitative structure–retention relationship was employed to foresee the Kovats retention indices of compounds acquired by GC-MS analysis, using eight molecular descriptors selected by a genetic algorithm. The chosen descriptors were used as inputs for the four artificial neural networks, to construct a Kovats retention indices predictive quantitative structure–retention relationship model. The coefficients of determination in the training cycle were 0.830; 0.852; 0.922 and 0.815 (for compounds found in O. heracleoticum, O. vulgare, T. vulgaris and T. serpyllum essential oils, respectively), demonstrating that these models could be used for prediction of Kovats retention indices, due to low prediction error and high r2.

Bioactivity of essential oils from cultivated winter savory, sage and hyssop

Species of the Lamiaceae family have enjoyed a rich tradition of use for flavoring, food preservation, and medicinal purposes, due to their curative and preventive properties. Cultivated winter savory (Satureja montana L.), sage (Salvia officinalis L.) and hyssop (Hyssopus officinalis L.) are produced for seed, herb, and essential oil. Dominant compounds in S. montana essential oil were carvacrol (43.2%) and thymol (28.4%), while CIS-thujone (27.1%) and camphor (19.3%), followed by trans-thujone and 1,8-cineole were the major compounds in S. officinalis essential oil. As for H. officinalis essential oil, CIS-and trans-pinocamphone (41.1% and 20.5%, respectively) were the most abundant compounds, followed by b-pinene. S. montana essential oil exhibit the highest antimicrobial properties, as well as antioxidant capacity, compared to other tested essential oils. Furthermore, H. officinalis essential oils showed higher antioxidant activity than that of S. officinalis. The aim of this investigation was to determine the composition and bioactivity of essential oils of mentioned varieties. Presented results show that S. montana essential oil could be proposed as a valuable source of natural preservatives

Chemical Composition and Antibacterial Activity of Angelica archangelica Root Essential Oil

Roots of wild growing Angelica archangelica L. from Mt. Ozren (Serbia) were subjected to hydrodistillation and GC-MS analysis. The roots contained 0.10% of essential oil with alpha-pinene (29.7%), delta-3-carene (14.2%), and a mixture of beta-phellandrene and limonene (13.2%) as main compounds. The modified resazurin microtiter-plate assay was used to evaluate the antibacterial activity of the essential oil against Staphylococcus aureus and Escherichia coli. The minimum inhibitory concentration (MIC) values were 14.2 mu L/mL for S. aureus and 28.4 mu L/mL for E. coli, while the minimum bactericidal concentrations (MBC) were 56.8 mu L/mL and 113.6 mu L/mL, respectively. According to the obtained results, the angelica root essential oil can be applied as a natural preservative in food and as a natural antibiotic for the treatment of several infectious diseases caused by these two bacteria

Chemical Characterization and Antibacterial Activity of Essential Oil of Medicinal Plants from Eastern Serbia

The objective of this study was to evaluate wild growing Satureja kitaibelii, Thymus serpyllum, Origanum vulgare, Achillea millefolium and Achillea clypeolata with respect to their essential oil (EO) content, composition and antimicrobial activity. The five species were collected at Mt. Rtanj and the village of Sesalac, Eastern Serbia. The main EO constituents of Lamiaceae plants were p-cymene (24.4%), geraniol (63.4%) and germacrene D (21.5%) in Satureja kitaibelii, Thymus serpyllum and Origanum vulgare ssp. vulgare, respectively. A. millefolium EO had multiple constituents with major ones being camphor (9.8%), caryophyllene oxide (6.5%), terpinen-4-ol (6.3%) and 1,8-cineole (5.6%), while the main EO constituents of A. clypeolata were 1,8-cineole (45.1%) and camphor (18.2%). Antimicrobial testing of the EO showed that Staphylococcus aureus (Gram-positive) was more sensitive to all of the tested EOs than Escherichia coli (Gram-negative). S. kitaibelii EO showed the highest antimicrobial activity against both tested bacterial strains. This is the first study to characterize the EO composition and antimicrobial activity of these five medicinal species from Eastern Serbia in comparison with comprehensive literature data. The results can be utilized by the perfumery, cosmetics, food and pharmaceutical industries, but also for healing purposes in self-medication

Hemijska karakterizacija i antibakterijska aktivnost etarskog ulja semena divlje anđelike

The aim of the present study was to clarify the chemical composition of essential oil from seeds of Angelica (Angelica sylvestris) plants growing wild in Serbia. In the essential oil, a total of 27 compounds were detected, among which 22 compounds were identified (comprising 97.9% of all compounds), while five were unidentified (comprising 2.1%). The main components were limonene (66.6%) and alpha-pinene (19.0%), followed by camphene (1.9%), alpha-phellandrene (1.6%), bornyl acetate (1.6%), and trans-caryophyllene (1.0%), while all other compounds were present in amounts of less than 1.0%. The antibacterial effect of the essential oil of wild Angelica seeds was tested against two pathogenic bacteria that cause food poisoning, viz., Staphylococcus aureus and Escherichia coli. According to the obtained results, S. aureus was more sensitive to A. sylvestris seed oil than E. coli. The minimal inhibitory concentrations were 28.40 mu L/mL and 56.81 mu L/mL, respectively, confirming a good antibacterial activity potential of the essential oil against E. coli and S. aureus, and indicating possibilities for its application in the food and pharmaceutical industries.Cilj ovog istraživanja je bio da se utvrdi hemijski sastav etarskog ulja divlje anđelike (Angelica sylvestris) dobijenog hidrodestilacijom semena samoniklih biljaka iz Srbije. U etarskom ulju utvrđeno je 27 komponenti (koje čine 97.9%), među kojima je pet nedeterminisanih komponenti (koje čine 2.1%). Dominantne komponente su limonen (66.6%) i α-pinen (19.0%), a potom slede kamfen (1.9%), α-felandren (1.6%), bornil acetat (1.6%) i trans-kariofilen (1.0%), dok su ostale komponente bile prisutne sa manje od 1.0%. Takođe, cilj ispitivanja je bio i antibakterijski efekat ovog ulja na dve patogene bakterije koje su uzročnici trovanja hranom: Staphylococcus aureus i Escherichia coli. Na osnovu rezultata, utvrđeno je da je S. aureus značajno osetljiviji na uticaj etarskog ulja semena A. sylvestris u poređenju sa E. coli. Minimalna inhibitorna koncentracija je bili 28.40 µL/mL i 56.81 µL/mL, što potvrđuje dobru antibakterijsku aktivnost na obe bakterije, kao i na mogućnost njegove primene u prehrambenoj i farmaceutskoj industriji

Hemijski sastav etarskog ulja Achillea clypeolata Sibth. & Sm. i QSRR model za predviđanje retencionog vremena

The aim of this study was the prediction model of retention indices of compounds from the aboveground parts of Achillea clypeolata Sibth. & Sm. essential oil, obtained by hydrodistillation and analysed by GC–MS. The quantitative structure–retention relationship analysis was applied in order to anticipate the retention time of the obtained compounds. The selection of the seven molecular descriptors was done by a genetic algorithm. The chosen descriptors were uncorrelated and were used to construct an artificial neural network. A total of 40 experimentally obtained retention indices was used to build this prediction model. The coefficient of determination for the training, testing and validation cycles were: 0.950, 0.825 and 1.000, respectively, indicating that this model could be used for prediction of retention indices for A. clypeolata, essential oil compounds.Cilj ove studije bio je izrada modela za predviđanja retencionog vremena hemijskih jedinjenja iz esencijalnog ulja nadzemnih delova biljke Achillea clypeolata Sibth. & Sm., dobijenog hidrodistilacijom i analiziranog GC–MS tehnikom. Kvantitativna analiza hemijske strukture i predviđanja retencionog vremena (quantitative structure – retention relationship – QSRR) je primenjena da bi se predvidelo vreme zadržavanja hemijskih jedinjenja dobijenih korišćenjem GC–MS analize. Izbor sedam molekulskih deskriptora izvršen je korišćenjem faktorske analize i genetskog algoritma. Primećeno je da izabrani deskriptori nisu bili u međusobnoj korelaciji, pa su korišćeni kao ulazni podaci pri izgradnji veštačke neuronske mreže. U izgradnji modela predviđanja retencionih vremena korišćeno je ukupno 40 eksperimentalno dobijenih retencionih vremena. Koeficijent determinacije tokom ciklusa pripreme, testiranja i validacije dostigao je vrednosti 0,950; 0,825 i 1,000, redom, što ukazuje na to da se ovaj model može koristiti za predviđanje retencionih vremena hemijskih jedinjenja dobijenih iz esencijalnog ulja A. clypeolata

Essential Oil Quality of Lavender Grown Outside Its Native Distribution Range: A Study from Serbia

The aim of this study was to test the quality (physicochemical and sensory odor properties) and bioactivity (antimicrobial and antioxidant activities) of the essential oils (EO) obtained from the most frequently cultivated lavender and lavandin varieties in Serbia, whose cultivation areas were previously reserved for warmer climates, outside the agroecological region of Serbia. Seven EO from true lavenders (L. angustifolia Mill. and cultivars: ‘Hidcote blue’, ‘Munstead’, ‘Primorska’), Croatian indigenous lavandin cultivar (L. intermedia ‘Budrovka’), lavandin ‘Grosso’ and one undetermined lavender sample (Lavandula sp.) showed compliance with standard requirements for lavender EO composition (contents of linalool 23.9–30.2% and 28.9–36.9%, and of linalyl acetate 22.2–32.2% and 6.9–20.7% in true lavender and lavandin samples, respectively). All EO were characterized as pleasant, with a floral aroma as a prominent odor. Samples exhibited high antimicrobial activities (3.5–14.2 µL mL-1 MIC and MBC values) against important Gram-positive (B. cereus and L. monocytogenes) and Gram-negative bacteria (E. coli) and yeasts (C. albicans), and high antioxidant capacity (IC50 values of 0.23–0.59 g AAE mL-1 EO). This preliminary research on the quality of lavender EOs reveals the potential of this species for the future of medicinal and aromatic plant species production and further diversification of agriculture in the area

Chemical composition of Origanum dictamnus and Origanum vulgare ssp. hirtum from Greece

Most of the Origanum species are locally distributed within the Mediterranean region where they grow in the mountainous areas on the islands. Due to this, the rate of endemism is high, as in case of dittany of Crete (O. dictamnus). O. vulgare possesses the largest distribution area and can be found throughout the Mediterranean region, however, the yield and quality of the essential oil is controlled genetically and strongly affected by the environmental influences. Origanum essential oils predominantly containing carvacrol, are generally of superior quality and highly valuable raw material for food as well as in pharmaceutical industry. Essential oil of O. dictimus contains 70.8% of carvacrol, while O. vulgare ssp. hirtum essential oil contains 78.5%. This study indicates the high quality of investigated Origanum species from Greece, and indicates it to be highly valuable raw material for food and in pharmaceutical industry

Chemical profile of Nepeta cataria L. var. citriodora (Becker) essential oil and in vitro evaluation of biological activities

Essential oil (EO) obtained by hydrodistillation in a Clevenger-type apparatus from aerial parts of Nepeta cataria L. var. citriodora (Becker), cultivated in Serbia was subjected to gas chromatography-mass spectroscopy (GC-MS) to determine the composition. Furthermore, N. cataria var. citriodora essential oil was tested to determine its antimicrobial, antioxidant, antihyperglycemic and anti-inflammatory activities in vitro. The antimicrobial activity was tested by broth microdilution method against 16 bacterial strains from American Type Culture Collection (ATCC). Four common tests for measuring in vitro antioxidant activity were used: 2, 2-diphenyl-1-picrylhydrazyl assay (DPPH), reducing power (RP), 2,2-azino-bis-3-ethylbenzothiazoline- 6-sulfonic acid (ABTS) and β-carotene bleaching assay (BCB). Antihyperglycemic activity was examined by using α-glucosidase inhibitory potential (AHgA), while anti-inflammatory activity (AIA) was determined by protein denaturation bioassay, using egg albumin. In total, 36 compounds were isolated and detected by GC-MS technique in N. cataria var. citriodora EO. The EO is mainly comprised of oxygenated monoterpenes (93.1%), and the main compounds were two monoterpenoid alcohols, nerol (38.5%) and geraniol (24.9%), followed by two aliphatic aldehyde, geranial (14.6%) and neral (11.0%). Antimicrobial activity of this EO shows growth inhibition of all tested bacteria strains, and exhibited good antioxidant, antihyperglycemic and anti-inflammatory activities. The EO obtained from N. cataria var. citriodora grown in Serbia shows valuable biological activity, indicating its potential for use as a supplement in everyday diet and as a natural preservative in food industry