Supplementary data for the article: Ristivojević, P.; Dimkić, I.; Trifković, J.; Berić, T.; Vovk, I.; Milojkovič-Opsenica, D.; Stanković, S. Antimicrobial Activity of Serbian Propolis Evaluated by Means of MIC, HPTLC, Bioautography and Chemometrics. PLoS ONE 2016, 11 (6). https://doi.org/10.1371/journal.pone.0157097

Supplementary material for: [https://doi.org/10.1371/journal.pone.0157097]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2261

Supplementary data for article: Mosić, M.; Trifković, J.; Vovk, I.; Gašić, U.; Tešić, Ž.; Šikoparija, B.; Milojković-Opsenica, D. Phenolic Composition Influences the Health-Promoting Potential of Bee-Pollen. Biomolecules 2019, 9 (12). https://doi.org/10.3390/biom9120783

Supplementary material for: [https://doi.org/10.3390/biom9120783]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/3774

Supplementary data for article: Mosić, M.; Trifković, J.; Vovk, I.; Gašić, U.; Tešić, Ž.; Šikoparija, B.; Milojković-Opsenica, D. Phenolic Composition Influences the Health-Promoting Potential of Bee-Pollen. Biomolecules 2019, 9 (12). https://doi.org/10.3390/biom9120783

Supplementary material for: [https://doi.org/10.3390/biom9120783]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/3774

Phenolic Composition Influences the Health-Promoting Potential of Bee-Pollen

Supplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3775

Evidence for a cyanine link between propargylamine drugs and monoamine oxidase clarifies the inactivation mechanism

The authors acknowledge the financial support from the Slovenian Research Agency (research core funding No. P1-0005 and P1-0012). We thank COST CA15135 for facilitating collaboration on multi-target compounds and providing support for publication. Part of this work was also supported by the bilateral cooperation between the Royal Society of Edinburgh and the Slovenian Academy of Sciences and Arts and by COST Action CM1103 which facilitated short research visits in Ljubljana and St Andrews, respectively.Successful propargylamine drugs such as deprenyl inactivate monoamine oxidase (MAO), a target in multi-faceted approaches to prevent neurodegeneration in the aging population, but the chemical structure and mechanism of the irreversible inhibition are still debated. We characterized the covalent cyanine structure linking the multi-target propargylamine inhibitor ASS234 and the flavin adenine dinucleotide in MAO-A using a combination of ultra-high performance liquid chromatography, spectroscopy, mass spectrometry, and computational methods. The partial double bond character of the cyanine chain gives rise to 4 interconverting geometric isomers of the adduct which were chromatographically separated at low temperatures. The configuration of the cyanine linker governs adduct stability with segments of much higher flexibility and rigidity than previously hypothesized. The findings indicate the importance of intramolecular electrostatic interactions in the MAO binding site and provide key information relevant to incorporation of the propargyl moiety into novel multi-target drugs. Based on the structure, we propose a mechanism of MAO inactivation applicable to all propargylamine inhibitors.Publisher PDFPeer reviewe

Određivanje alfa lipoinske kiseline u dijetetskim suplementima i doziranim oblicima

Alfa lipoinska (tioktinska) kiselina se koristi u lečenju dijabetesne polineuropatije. Zbog svojih antioksidativnih svojstava, prisutna je u brojnim dijetetskim suplementima sama, kao i u kombinaciji sa aminokiselinama, L-karnitinom i drugim jedinjenjima. Dostupni podaci za kvantitativno određivanje alfa lipoinske kiseline su malobrojni. Usled toga, cilja našeg rada bio je da se razvije i validira TLC metoda za određivanje alfa lipoinske kiseline posle derivatizacije sa paladijum (II) hloridom. Za razdvajanje alfa lipoinske kiseline i njenog redukovanog oblika korišćene su RPTLC ploče veličine 20×10 cm, uz mobilnu fazu propanol-2 : methanol : aceton : voda : sirćetna kiselina u odnosu 6:4:2:8:0,2 v/v/v/v/v. Nakon razvijanja, hromatografske ploče su potapane u rastvor paladijum (II) hlorida, a žute zone formiranog kompleksa su merene na 375 nm. Retenciona vremena alfa lipoinske kiseline i njene redukovane forme su 45 i 32 nm. Zavisnost površine signala i količine nanete supstance ispitana je korišćenjem linearne regresione jednačine za opseg koncentracija 1 – 3 μg i polinomalne regresione jednačine drugog stepena za koncentracioni opseg 0,5 – 5 μg. Za datu metodu dobijene vrednosti koeficijenta korelacije (r=0,999), limit kvantifikacije (0,3 μg), rikaveri (98,5 – 105,2%) i preciznost (0,9 – 2,9%) su zadovoljavajući. Validirana hromatografska metoda je primenjena za određivanje alfa lipoinske kiseline u doziranim oblicima i dijetetskim suplementima. Nađeni sadržaj lipoinske kiseline (98,5 – 102,0%) u doziranim oblicima je u propisanim granicama, dok je u dijetetskim suplementima varirao u rasponu od 50 – 185%.Alpha lipoic (thioctic) acid is a drug used for the treatment of diabetic polyneuropathy. Due to its antioxidant properties alpha lipoic acid nowadays widely used in dietary supplement preparation alone and in combination with amino acids, L-carnitine and other compounds. There are not so many data available on the quantitative determination of alpha lipoic acid in dietary supplements. Therefore, the aim of these investigations was to develop and validated TLC method for determination of alpha lipoic acid after derivatization by Palladium (II) chloride reagent. The separation of alpha lipoic acid was performed on RPTLC plates (20 × 10 cm) using propanol-2 : methanol : acetone : water : acetic acid (6:4:2:8:0.2 v/v/v/v/v) as mobile phase. The plates were immersed in solutions of Palladium (II) chloride reagents and yellow spots were scanned at 375 nm. The retention times of alpha lipoic acid and its reduced form were 45 and 32 mm, respectively. Relationship of the peak areas and the amount of the substance applied was evaluated using the linear (1 -3 μg/spot) and second degree polynomial regression function (0.5 – 5 μg/spot). For the proposed procedure coefficient of correlation (r=0.999), limit of quantification (0.3 μg/spot), recovery (98.5 – 105.2 %) and precision (0.9 – 2.9%) were found to be satisfactory. The developed method was applied for determination of alpha lipoic acid in drugs dosage formulations and in dietary supplement preparation. The content of lipoic acid were found to be 98.5 – 102.0% in drug dosage formulations and 50 – 185.0% in some of dietary supplement preparations.Drugi kongres o dijetetskim suplementima sa međunarodnim učešćem, 10-12. decembar 2009., Beograd, Srbij

Supplementary data for the article: Ristivojević, P.; Dimkić, I.; Trifković, J.; Berić, T.; Vovk, I.; Milojkovič-Opsenica, D.; Stanković, S. Antimicrobial Activity of Serbian Propolis Evaluated by Means of MIC, HPTLC, Bioautography and Chemometrics. PLoS ONE 2016, 11 (6). https://doi.org/10.1371/journal.pone.0157097

Supplementary material for: [https://doi.org/10.1371/journal.pone.0157097]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2261

High-performance thin-layer chromatography - antibacterial assay first reveals bioactive clerodane diterpenes in giant goldenrod (Solidago gigantea Ait.)

The present work introduces a high-performance thin-layer chromatography (HPTLC)–direct bioautography method using the Gram-positive plant pathogenic bacterium, Rhodococcus fascians. The screening and isolation procedure comprised of a non-targeted high-performance thin-layer chromatography-effect-directed analysis (HPTLC–EDA) against Bacillus subtilis, B. subtilis subsp. spizizenii, R. fascians, and Aliivibrio fischeri, a targeted HPTLC–mass spectrometry (MS), and bioassay-guided column chromatographic (preparative flash and semi-preparative HPLC) fractionation and purification. The developed new separation methods enabled the discovery of four bioactive cis-clerodane diterpenes, solidagoic acid H (1), solidagoic acid E (2), solidagoic acid I (3), and solidagoic acid F (4), in the n-hexane extract of giant goldenrod (Solidago gigantea Ait.) leaf for the first time. These compounds were identified by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy. The initially used HPTLC method (chloroform – ethyl acetate – methanol 15:3:2, V/V/V) was changed (to n-hexane – isopropyl acetate – methanol – acetic acid 29:20:1:1, V/V/V/V) to achieve the separation of the closely related isomer pairs (1–2 and 3–4). Compounds 1 and 3 exhibited moderate antibacterial activity against the Gram-positive B. subtilis subsp. spizizenii and R. fascians bacterial strains in microdilution assays with half-maximal inhibitory concentration (IC50 ) values in the range of 32.3–64.4 μg/mL. The mass spectrometric fragmentation of the isolated compounds was interpreted and their previously published NMR assignments lacking certain resonances were completed