O peroksidnim antimalaricima

Several dicyclohexylidene tetraoxanes were prepared in order to gain a further insight into structure-activity relationship of this kind of antimalarials. The tetraoxanes 2-5, obtained as a cis/trans mixture, showed pronounced antimalarial activity against Plasmodium falciparum chloroquine susceptible D6, chloroquine resistant W2 and multidrug-resistant TM91C235 (Thailand) strains. They have better than or similar activity to the corresponding desmethyl dicyclohexylidene derivatives. Two chimeric endoperoxides with superior antimalarial activity to the natural product ascaridole were also synthesized.U ovom radu prikazana je sinteza nekoliko dicikiloheksilidenskih tetraoksana u cilju sagledavanja odnosa struktura-aktivnost ove vrste antimalarika. Jedinjenja 2-5 dobijena kao (cis,trans)-smese pokazala su izraženu antimalarijsku aktivnost prema D6, W2 i TM91C235 (Thailand) sojevima P. falciparum. Ona imaju bolju ili sličnu aktivnost od odgovarajućih desmetil cikloheksilidenskih derivata. Sintetisana su i dva endoperoksida himerne strukture znatno izraženije aktivnosti od prirodnog proizvoda askaridola.

Sesquiterpene Lactones of Amphoricarpos autariatus ssp autariatus from Montenegro - Antifungal Leaf - Surface Constituents

The composition of leaf cuticular neutral lipids of Amphoricarpos autariatus ssp. autariatus collected at canyon of river Tara (North Montenegro) was investigated by GC/MS (nonpolar fraction), LC-ESI TOF MS and H-1 NMR spectroscopy (more polar fraction). The nonpolar fraction (ca. 15% of the whole surface extract) contained C-27 (-) (33) n-alkanes, those with odd-number of carbons predominating. The LC-ESI MS and H-1 NMR of the more polar fraction revealed 13 sesquiterpene lactones, constituting ca. 97.5% of the lactone mixture, identified as the known guaianolides, so-called amphoricarpolides, found previously in the aerial parts of the genus. The lactone fraction exhibited considerable in vitro effect against eight fungi, i.e. Aspergillus ochraceus, A. niger, A. versicolor, Penicillium funiculosum, P. ochrochloron, Trichoderma viride, Fusarium verticillioides and Fulvia fulvum

Supplementary material for the article: Cvetković, M.; Anđelković, B.; Stevanović, V.; Jadranin, M.; Đorđević, I.; Tešević, V.; Milosavljević, S.; Gođevac, D. NMR-Based Metabolomics Study of Amphoricarpos Species from Montenegro. Phytochemistry Letters 2018, 25, 1–5. https://doi.org/10.1016/j.phytol.2018.03.013

Supplementary material for: [https://doi.org/10.1016/j.phytol.2018.03.013]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2148

Uticaj varijeteta višnje na hemijske i senzorne karakteristike rakije višnjevače

The chemical and sensorial characteristics of cherry brandy produced from five cherry varieties (Oblacinska, Celery's 16, Rexle, Heiman's Ruby and Heiman's Conserve) grown in Serbia were studied. Gas chromatography and gas chromatography-mass spectrometry analysis of these distillates led to the identification of 32 components, including 20 esters, benzaldehyde, 6 terpenes and 5 acids. The ethyl esters of C(8)-C(18) acids were the most abundant in all samples. The benzaldehyde content was quantified by high performance liquid chromatography with UV detection. The average benzaldehyde concentration in the samples ranged between 2.1 and 24.1 mg L(-1). The total sensory scores of the cherry brandies ranged between 17.30 to 18.05, with the cherry brandy produced from the Celery's 16 variety receiving the highest score (18.05).Ispitivane su hemijske i senzorske karakteristike rakije višnjevače proizvedene iz pet varijeteta višnje (Oblačinska, Celery's 16, Rexle, Heiman's Ruby i Heiman's Conserve) gajenih u Srbiji. Metodama gasne hromatografije i kombinacijom gasne hromatografije i masene spektrometrije u ekstrakatima identifikovana su 32 jedinjenja, 20 estara, benzaldehid, 6 terpena i 5 kiselina. Etil-estri C8-C18 kiselina su najobilniji u svim uzorcima. Sadržaj benzaldehida je određivan metodom tečne hromatografije uz UV detekciju. Prosečna količina benzaldehida u ispitivanim uzorcima bila je između 2,1 i 24,1 mg L-1. Ocene senzorskog ispitivanja rakija višnjevača su u rasponu od 17,30 do 18,05, dok je najbolje ocenjena (18,05) rakija proizvedena od varijeteta Celery's 16

Supplementary material for the article: Cvetković, M.; Anđelković, B.; Stevanović, V.; Jadranin, M.; Đorđević, I.; Tešević, V.; Milosavljević, S.; Gođevac, D. NMR-Based Metabolomics Study of Amphoricarpos Species from Montenegro. Phytochemistry Letters 2018, 25, 1–5. https://doi.org/10.1016/j.phytol.2018.03.013

Supplementary material for: [https://doi.org/10.1016/j.phytol.2018.03.013]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2148

Further guaianolides from Amphoricarpos neumayeri ssp murbeckii from Montenegro

The aerial parts of Amphoricarpos neumayeri ssp. murbeckii afforded eleven guaianolides with the same relative (1 alpha H,4 beta H,5 alpha H, 7 alpha H) configuration of the basic skeleton. All of them contained a CH2OX (X = H, acetyl or isovaleroyl) group in 4 alpha-position, typical for amphoricarpolides. Four compounds (1-4) were isolated before from the same species, originating from different localities. Guaianolides 5-11 are new compounds. Compounds 7 and 8 were epoxidized at the 10 alpha(14)-position. Instead of the Delta(11(13))-double bond, observed in all previously isolated guaianolides from the same species, the four lactones contained 11 alpha,13-diol (8-10) or 11 alpha-OH, 13-chloro (11) moieties respectively

Određivanje dinamike kvantitativnog sadržaja juglona i antioksidativne aktivnosti u ekstraktu ploda mladog oraha (Juglans regia)

Fruits from three walnut cultivars were picked in three terms with the aim to determine the optimal harvesting time of green walnut fruits for the improvement fruit brandies. Quantity of juglone and its antioxidant activity was determined in the picked fruits. Juglone quantity was the highest in fruits weighing between 4.5 g and 6.5 g (harvesting time around June 1), and varied from 209.60 mg up to 735.00 mg in the cultivar Sheinovo, from 388.50 mg up to 418.60 mg in the cultivar Geisenheim 139 and from 325.50 mg up to 499.40 mg in the cultivar Geisenheim 251, in a sample of 100 fruits. In this phase, walnut fruits had the highest antioxidant activity, too. .Tehnikom visokoefikasne tečne hromatografije određivan je sadržaj juglona (5-hidroxi-1,4-naftohinona) u uzorcima mladog oraha različitih sorti i različite zrelosti berbi 2005. i 2006. godine. Pored toga određena je anatioksidativna aktivnost metanolnih ekstrakata uzoraka plodova. Koncentracije juglona se nalaze u opsegu 0,03-0,24 % za berbu 2005. i 0,03-0,08 % za berbu 2006. Svi uzorci su pokazali značajnu antioksidativnu aktivnost.

In vitro antitumor actions of extracts from endemic plant Helichrysum zivojinii

Background: The aim of this research was to determine the intensity and mechanisms of the cytotoxic actions of five extracts isolated from the endemic plant species Helichrysum zivojinii Cernjavski & Soska (family Asteraceae) against specific cancer cell lines. In order to evaluate the sensitivity of normal immunocompetent cells implicated in the antitumor immune response, the cytotoxicity of extracts was also tested against healthy peripheral blood mononuclear cells (PBMC). Methods: The aerial parts of the plants were air-dried, powdered, and successively extracted with solvents of increasing polarity to obtain hexane, dichloromethane, ethyl-acetate, n-butanol and methanol extracts. The cytotoxic activities of the extracts against human cervix adenocarcinoma HeLa, human melanoma Fem-x, human myelogenous leukemia K562, human breast adenocarcinoma MDA-MB-361 cells and PBMC were evaluated by the MTT test. The mode of HeLa cell death was investigated by morphological analysis. Changes in the cell cycle of HeLa cells treated with the extracts were analyzed by flow cytometry. The apoptotic mechanisms induced by the tested extracts were determined using specific caspase inhibitors. Results: The investigated Helichrysum zivojinii extracts exerted selective dose-dependent cytotoxic actions against selected cancer cell lines and healthy immunocompetent PBMC stimulated to proliferate, while the cytotoxic actions exerted on unstimulated PBMC were less pronounced. The tested extracts exhibited considerably stronger cytotoxic activities towards HeLa, Fem-x and K562 cells in comparison to resting and stimulated PBMC. It is worth noting that the cytotoxicity of the extracts was weaker against unstimulated PBMC in comparison to stimulated PBMC. Furthermore, each of the five extracts induced apoptosis in HeLa cells, through the activation of both intrinsic and extrinsic signaling pathways. Conclusion: Extracts obtained from the endemic plant Helichrysum zivojinii may represent an important source of novel potential antitumor agents due to their pronounced and selective cytotoxic actions towards malignant cells

Secondary metabolites of three endemic Centaurea L. species

The aerial parts of three endemic Centaurea L. species, namely C. tomorosii Micevski, C. soskae Hayek and C. galicicae Micevski, afforded the sesquiterpene lactone cnicin (1) and seven flavonoids: apigenin (2), isokaempferide (3), hispidulin (4), eupatorin (5), cirsimaritin (6), santoflavone (7) and salvigenin (8). The structures of the isolated compounds were determined by UV, H-1-NMR and C-13-NMR spectroscopy and HR-ESI-MS spectrometry. H-1-NMR spectroscopy was used as a method for the quantitative analysis of cnicin