Quantitative structure-retention relationship study of oxothiazolidines using multivariate analysis

Hromatografsko ponašanje 23 novosintetisana 2-alkiliden-4-oksotiazolidina ispitivano je u uslovima reverzno-fazne planarne hromatografije, uz upotrebu dve stacionarne faze (oktadecil-modifikovan (RP-18) i cijano-modifikovan (CN) silika-gel). Dvokomponentne smeše methanol/voda, acetonitril/voda i tetrahidrofuran/voda su korišćene kao mobilne faze. Linearna zavisnost RM vrednosti od zapreminskog udela organske komponente u mobilnoj fazi utvrđena je za sva ispitivana jedinjenja, sa visokom vrednošću korelacionog koeficijenta (r > 0,99). Ispitivani 4-oksotiazolidini predstavljaju kongenernu seriju jedinjenja, što potvrđuje značajan nivo korelacije dobijen pri poređenju RM 0 vrednosti i drugih hromatografskih parametara (m, C0 i PC1). Svi hromatografski parametri lipofilnosti (RM 0, m, C0 i PC1) poređeni su sa izračunatim log P vrednostima. Statistički parametri ovih zavisnosti pokazali su da RM 0 vrednosti mnogo pouzdanije opisuju lipofilnosti od preostalih hromatografskih parametara (m, C0 i PC1). Analiza glavnih komponenata je primenjena na retencione podatke u cilju utvrđivanja sličnosti i razlika između upotrebljenih hromatografskih sistema. Višestruka linearna regresija (MLR) i parcijalna regresija najmanjih kvadrata (PLS) su omogućile ispitivanje odnosa između molekulskih deskriptora ispitivanih N-supstituisanih 2-alkiliden-4-oksotiazolidina i retencionih podataka određenih primenom dva hromatografska sistema (tetrahidrofuran/voda na RP-18 i CN stacionarnoj fazi). Potpuna geometrijska optimizacija izvršena je pomoću AM1 semi-empirijske molekulsko-orbitalne metode, nakon čega je set fizičko-hemijskih molekulskih deskriptora izračunat iz optimizovanih struktura. Poređenjem statističkih parametara odabran je model gde je na najbolji način opisana veza između seta izračunatih deskriptora i RM 0 vrednosti. Dobra prediktivna moć MLR i PLS modela dobijenih za kalibracioni set podataka potvrđena je na podacima iz test seta. Molekulski deskriptori uključeni u odabrane MLR i PLS modele su slične prirode, a u sve dobijene modele uključen je parametar lipofilnosti (log P) što ukazuje na značaj lipifilnosti i njen uticaj na retenciju N-supstituisanih 2-alkiliden-4- oksotiazolidina.The chromatographic behavior of 23 new 2-alkylidene-4-oxothiazolidine derivates was investigated by means of the reversed-phase thin-layer chromatography (RP TLC) on RP-18 and CN stationary phases. Binary mixtures of methanol/water, acetonitrile/water and tetrahydrofuran/water were used as mobile phases. Linear relationships between the volume fraction of the organic mobile phase modifier and the RM values were established for each solute with the high correlation coefficient values (r > 0.99). The investigated 4-oxothiazolidines are a congeneric set of compounds, and significant correlations were obtained between the chromatographically determined RM 0 and other retention parameters (m, C0, and PC1). All lipophilicity parameters (RM 0, m, C0, and PC1) obtained from the reversed-phase experiments were compared with the calculated log P values. Statistical parameters of these correlations showed that RM 0 values were more suitable for lipophilicity estimation than other retention parameters (m, C0, and PC1). Principal Component Analysis was performed on retention data in an attempt to reflect the similarities and differences among different chromatographic systems. Multiple linear regression (MLR) and partial least squares regression (PLS) were performed to investigate relation between the structural descriptors of N-substituted 2-alkylidene-4-oxothiazolidines and chromatographic retention determined for the two chromatographic systems (tetrahydrofuran/water on RP-18 and CN stationary phases). Full geometry optimization based on Austin Model 1 (AM1) semiempirical molecular orbital method was carried out and a set of physicochemical molecular descriptors was calculated from the optimized structures. The best relationships in a set of calculated descriptors and RM 0 values were chosen on the basis of comparison of the statistical parameters. The statistical parameters of MLR and PLS models built for training set show a significant predictive ability. The descriptors included in the chosen MLR and PLS models were of similar nature. Lipophilicity parameter (log P) selected out of a large set of possible molecular descriptors in all models, indicated the importance of lipophilicity and its influence on the retention behavior of the N-substituted 2-alkylidene-4-oxothiazolidines

Supplementary data for the article: Smailagić, A.; Veljović, S.; Gašić, U. M.; Dabić-Zagorac, D.; Stanković, M.; Radotić, K.; Natić, M. Phenolic Profile, Chromatic Parameters and Fluorescence of Different Woods Used in Balkan Cooperage. Industrial Crops and Products 2019, 132, 156–167. https://doi.org/10.1016/j.indcrop.2019.02.017

Supplementary material for: [https://doi.org/10.1016/j.indcrop.2019.02.017]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2832]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/2835

Supplementary data for article: Pantelić, M. M.; Zagorac, D. Č. D.; Ćirić, I. Ž.; Pergal, M. V.; Relić, D. J.; Todić, S. R.; Natić, M. M. Phenolic Profiles, Antioxidant Activity and Minerals in Leaves of Different Grapevine Varieties Grown in Serbia. Journal of Food Composition and Analysis 2017, 62, 76–83. https://doi.org/10.1016/j.jfca.2017.05.002

Supplementary material for: [https://doi.org/10.1016/j.jfca.2017.05.002]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2505]Related to accepted version: [http://cherry.chem.bg.ac.rs/handle/123456789/3063

Analysis of Phenolic Compounds for the Determination of Grafts (in) Compatibility Using In Vitro Callus Cultures of Sato-Zakura Cherries

The aim of this study was to prove that under in vitro conditions, the adhesiveness of the callus between rootstock and scion, the development of callus cells at the points of fusion, and the presence of phenolic components are closely related to the level of (in) compatibility of the grafting combinations between Sato-zakura cherry cultivars (‘Amanogawa’, ‘Kanzan’, and ‘Kiku-shidare-zakura’) and commercial rootstocks. Prunus avium, Prunus ‘Colt’, Prunus mahaleb and Prunus serrulata were used as compatible and Prunus serotina and Pyrus communis ‘Pyrodwarf’ were used as two potentially incompatible rootstocks. The results indicated the significant manifestations of the early signs of the incompatibility on the callus junction. Phenols, as well as tissue senescence, were very precisely localized by toluidine blue and alcian blue as well as safranin staining, which can indicate the early signs of the callus incompatibility in some grafting unions. In the callus unions of Prunus avium with ‘Amanogawa’ and ‘Kiku-shidare-zakura’ the results of chemical analyses indicated that the existence of several flavonols, flavones and phenol acids could be involved in the incompatibility process in grafted combination. The detection of flavonol astragalin in the unions can be a biomarker of compatibility between scion and the rootstock, while some polyphenols, such as neochlorogenic acid, sinapic acid, ellagic acid, caffeic acid, baicalein, naringenin, apigenin and luteolin can be used as the indicators of graft incompatibility. p-coumaric acid and ferulic acid could be used for detection of delayed incompatibility

Characterization and Clonal Selection of Serbian Autochthonous Variety Prokupac (Vitis vinifera L.)

The first reported occurrence of Vitis vinifera in Balkan dates in the Neolithic period in the form of wild grape. Early traces of viticulture and winemaking in the territory of Serbia are vessels from the Iron Age (~ 400 BC) and the Bronze Age (~ 200 BC). Over the last few decades, interest in autochthonous varieties in Serbia is constantly increasing, especially for growing native varieties, such as Prokupac, Smederevka, Tamjanika and Bagrina. Prokupac is the most important Serbian autochthonous red wine variety (the first written records about growing Prokupac in Serbia date from 12th century), well adapted to the ecological conditions of its birthplace with corresponding phonological features. When compared with germplasm representing the classical ecogeographic grouping of grapevine cultivars, Prokupac is clustered within the Convar pontica subconvar balcanica taxon, supporting his indigenous origin. The main objective of this work is to present characterization of the Prokupac variety by means of ampelographic and molecular analysis, as well as grape and wine chemical characteristics. Long-term cultivation in diverse ecological conditions has caused the Prokupac to become a mixture of clones (genotypes). Therefore in order to preserve and improve autochthonous grapevine varieties in Serbia, work on variety clonal selection was initiated and till now, 12 clones of Prokupac were already identified and recognized. The most important features of these clones will be also presented.Chapter

Supplementary data for the article: Pavlović, A. V.; Papetti, A.; Zagorac, D. T. D.; Gašić, U. M.; Mišić, D. M.; Tešić, T. L.; Natić, M. M. Phenolics Composition of Leaf Extracts of Raspberry and Blackberry Cultivars Grown in Serbia. Industrial Crops and Products 2016, 87, 304–314. https://doi.org/10.1016/j.indcrop.2016.04.052

Supplementary material for: [https://doi.org/10.1016/j.indcrop.2016.04.052]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2257

Supplementary data for the article: Pavlović, A. V.; Papetti, A.; Zagorac, D. T. D.; Gašić, U. M.; Mišić, D. M.; Tešić, T. L.; Natić, M. M. Phenolics Composition of Leaf Extracts of Raspberry and Blackberry Cultivars Grown in Serbia. Industrial Crops and Products 2016, 87, 304–314. https://doi.org/10.1016/j.indcrop.2016.04.052

Supplementary material for: [https://doi.org/10.1016/j.indcrop.2016.04.052]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/2257

Characterization of Grapevine Varieties Indigenous to the Balkans Region

Central Balkan region is at the crossroads between Asia and Europe, on the line dividing various nations and civilizations of the East and the West. Due to its favorable climate and geological characteristics, it is an ancient wine growing region hosting a wide range of indigenous grapevine varieties, most of which are not internationally recognized.Also, numerous traditional local varieties, present in this area for centuries, are out of cultivation. Therefore, preservation and characterization of grapevine germplasm is important not only for the breeding process, but also for the improvement of modern varieties and their preservation for the future generations. Also, indigenous varieties as valuable resource of gen donors could be helpful when facing the challenges of climate changes. Unfortunately, during the last decade grapevine germplasm is undergoing a process of rapid genetic erosion, and as a consequence we are facing with the loss of varieties which are traditionally related to different winegrowing regions. The only way to prevent the loss of this heritage is to locate them, evaluate, preserve and precisely characterize them. In this Chapter the results of morphological and genetic characterization, as well as chemical characterization of some of the most important indigenous grapevine varieties in the central Balkan, such as Vranac, Krstač, Smederevka, Prokupac, Žilavka, Plavac Mali, and Istrian Malvasia will be summarized. These old varieties have passed through the process of natural selection and adapted to particular environmental conditions. As such, they represent irreplaceable genetic value for each country, and for the entire region.Chapter

Supplementary data for the article: Smailagić, A.; Stanković, D. M.; Vranješ Đurić, S.; Veljović, S.; Dabić Zagorac, D.; Manojlović, D.; Natić, M. Influence of Extraction Time, Solvent and Wood Specie on Experimentally Aged Spirits – A Simple Tool to Differentiate Wood Species Used in Cooperage. Food Chemistry 2021, 346, 128896. https://doi.org/10.1016/j.foodchem.2020.128896.

Supplementary material for: [https://doi.org/10.1016/j.foodchem.2020.128896]Related to published version: [https://cherry.chem.bg.ac.rs/handle/123456789/4455

Ispitivanje profila flavan-3-ola grožđa i vina autohtonih sorti vinove loze primenom tankoslojne hromatografije

Flavan-3-ols belong to the group of flavonoids and they are located primarily in the grape seeds, then in the skins and, in small amounts, in the pulp. In this work flavan-3-ol profiles of diverse autochthonous grape varieties and corresponding wines were investigated by thin-layer chromatography (TLC). Separation of flavanols was done on silica gel TLC plates with toluene/acetone/formic acid mixture as mobile phase. Plates were derivatised with p dimethylaminocinamaldehyde reagent (DMACA) as visualization solution. As a result, flavan-3-ol profiles (chemical fingerprints) of individual parts of berries and corresponding wines were obtained. The similar flavan-3-ol profiles were established in all examined seed samples. Also, (+) catechin was found in all investigated seed extracts. However, different intensity of the zones indicated differences in the content of individual flavanols among the varieties. A slightly larger content of flavan-3-ol was found in skin extracts of white varieties compared to red ones. In the case of wines, the profiles were richer in flavan-3-ols in comparison to skins, but the intensity of zones was lower than intensity obtained for seed extracts