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22. Modeling the liquid‐liquid chromatography separation of cannabinoids from hemp extracts.

Author

Luca, Simon Vlad, Gerigk, Melanie, Arshad, Ahmad Adeel, and Minceva, Mirjana

Subjects
*CANNABINOIDS, *COUNTERCURRENT chromatography, *HEMP, *CHROMATOGRAPHIC analysis, *CANNABIDIOL, *TETRAHYDROCANNABINOL, *CANNABINOID receptors
Abstract

The separation of cannabinoids from hemp materials is nowadays one of the most promising industrial applications of liquid‐liquid chromatography (LLC). Despite various experimental research efforts to purify cannabinoids, there are currently few works on process modeling. Thus, this study aimed to explore a straightforward approach to model the LLC separation of cannabinoids from two hemp extracts with different compositions. The feed materials were simplified to mixtures of preselected key components (i.e., cannabidiol, tetrahydrocannabinol, cannabigerol, and cannabinol). The elution profiles of cannabinoids were simulated using the equilibrium‐cell model with an empirical nonlinear correlation. The model parameters were derived from the elution profiles of single‐solute pulse injections. For the validation of the proposed approach, LLC separations with the two hemp extracts were performed in descending mode with the solvent system composed of hexane/methanol/water 10/8/2 (v/v/v). The injected sample concentrations were gradually increased from 5 to 100 mg/mL. The results showed that the approach could describe reasonably well the elution behavior of the cannabinoids, with deviations of only 1–2 min between simulated and experimental elution times. However, to improve the prediction accuracy, the model parameters can be refitted to the elution profiles of 3–4 systematically selected pulse injections with specific hemp extracts. [ABSTRACT FROM AUTHOR]

Published
2024
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26. Phenolic compounds of Iris adriatica and their antimycobacterial effects

Author

Ochensberger Sandra, Alperth Fabian, Mitić Božena, Kunert Olaf, Mayer Stefanie, Mourão Maria Ferreira, Turek Ivana, Luca Simon Vlad, Skalicka-Woźniak Krystyna, Maleš Željan, Hruševar Dario, Duka Ivan, and Bucar Franz

Subjects
iris adriatica, radix iridis, phenolic compounds, mycobacterium smegmatis, resistance modulation, ethidium bromide, mic, Pharmaceutical industry, HD9665-9675
Abstract

Little is known about the pharmacological activities of Iris adriatica (Iridaceae), a plant endemic to Dalmatia (Croatia). We therefore performed a bioassay-guided fractionation including high-performance counter current chromatography (HPCCC) and antibacterial tests using Mycobacterium smegmatis mc2 155. One obtained fraction was found to be antimycobacterially active with a MIC of 64 mg L−1. Furthermore, fractions were tested for resistance modulatory effects using ethidium bromide as substrate. We were able to identify the pure isoflavonic compounds irigenin and irilone and a fraction containing mainly benzophenone 2,4,6-trihydroxy-4-methoxy-benzophenone, responsible for the resistance-modulatory activity of this plant.

Published
2019
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32. Bioactivity-guided isolation of trypanocidal coumarins and dihydro-pyranochromones from selected Apiaceae plant species

Author

Krishnan, Sandhya R, Skiba, Adrianna, Luca, Simon Vlad, Marcourt, Laurence, Wolfender, Jean-Luc, Skalicka-Woźniak, Krystyna, and Gertsch, Jürg

Subjects
570 Life sciences, biology, 610 Medicine & health
Abstract

Bioactivity-guided isolation of natural products from plant matrices is widely used in drug discovery. Here, this strategy was applied to identify trypanocidal coumarins effective against the parasite Trypanosoma cruzi, the etiologic agent of Chagas disease (American trypanosomiasis). Previously, phylogenetic relationships of trypanocidal activity revealed a coumarin-associated antichagasic hotspot in the Apiaceae. In continuation, a total of 35 ethyl acetate extracts of different Apiaceae species were profiled for selective cytotoxicity against T. cruzi epimastigotes over host CHO-K1 and RAW264.7 cells at 10 μg/mL. A flow cytometry-based T. cruzi trypomastigote cellular infection assay was employed to measure toxicity against the intracellular amastigote stage. Among the tested extracts, Seseli andronakii aerial parts, Portenschlagiella ramosissima and Angelica archangelica subsp. litoralis roots exhibited selective trypanocidal activity and were subjected to bioactivity-guided fractionation and isolation by countercurrent chromatography. The khellactone ester isosamidin isolated from the aerial parts of S. andronakii emerged as a selective trypanocidal molecule (selectivity index ∼9) and inhibited amastigote replication in CHO-K1 cells, though it was significantly less potent than benznidazole. The khellactone ester praeruptorin B and the linear dihydropyranochromones 3'-O-acetylhamaudol and ledebouriellol isolated from the roots of P. ramosissima were more potent and efficiently inhibited the intracellular amastigote replication at < 10 μM. The furanocoumarins imperatorin, isoimperatorin and phellopterin from A. archangelica inhibited T. cruzi replication in host cells only in combination, indicative of superadditive effects, while alloimperatorin was more active in fractions. Our study reports preliminary structure-activity relationships of trypanocidal coumarins and shows that pyranocoumarins and dihydropyranochromones are potential chemical scaffolds for antichagasic drug discovery.

Published
2023

37. Evaluation of the Antiseizure Activity of Endemic Plant Halfordia kendack Guillaumin and Its Main Constituent, Halfordin, on a Zebrafish Pentylenetetrazole (PTZ)-Induced Seizure Model

Author

Skiba, Adrianna, primary, Kozioł, Ewelina, additional, Luca, Simon Vlad, additional, Budzyńska, Barbara, additional, Podlasz, Piotr, additional, Van Der Ent, Wietske, additional, Shojaeinia, Elham, additional, Esguerra, Camila V., additional, Nour, Mohammed, additional, Marcourt, Laurence, additional, Wolfender, Jean-Luc, additional, and Skalicka-Woźniak, Krystyna, additional

Published
2023
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41. Evaluation of Anti‐Alzheimer Activity of Synthetic Coumarins by Combination of in Vitro and in Silico Approaches

Author

Erdogan Orhan, Ilkay, primary, Deniz, F. Sezer Senol, additional, Salmas, Ramin Ekhteiari, additional, Irmak, Sule, additional, Acar, Ozden Ozgun, additional, Turgut, Gurbet Celik, additional, Sen, Alaattin, additional, Zbancioc, Ana‐Maria, additional, Luca, Simon Vlad, additional, Skiba, Adrianna, additional, Skalicka‐Woźniak, Krystyna, additional, and Tataringa, Gabriela, additional

Published
2022
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44. Influence of the post-harvest storage time on the multi-biological potential, phenolic and pyrrolizidine alkaloid content of comfrey (Symphytum officinale L.) roots collected from different European regions

Author

Trifan, Adriana, Zengin, Gokhan, Sinan, Kouadio Ibrahime, Esslinger, Nils, Grubelnik, Andreas, Wolfram, Evelyn, Skalicka-Woźniak, Krystyna, Minceva, Mirjana, Luca, Simon Vlad, Trifan, Adriana, Zengin, Gokhan, Sinan, Kouadio Ibrahime, Esslinger, Nils, Grubelnik, Andreas, Wolfram, Evelyn, Skalicka-Woźniak, Krystyna, Minceva, Mirjana, and Luca, Simon Vlad

Abstract

Comfrey (Symphytum officinale L.) roots are well-known bioactive ingredients included in various cosmeceutical and pharmaceutical preparations. In this study, the influence of the post-harvest storage on the chemico-biological potential of roots collected from different European regions and stored for up to six months was investigated. Total phenolic content (TPC) and total phenolic acid content (TPAC) were spectrophotometrically estimated, whereas the levels of individual phenolic and pyrrolizidine alkaloidal markers were determined by HPLC-DAD and HPLC-MS/MS, respectively. The changes in the biological potential was tracked via antioxidant (DPPH, ABTS, CUPRAC, and FRAP) and anti-enzymatic (cholinesterase, tyrosinase, glucosidase, and amylase) assays. TPC and TPAC varied from 6.48-16.57 mg GAE/g d.w. root and from 2.67-9.03 mg CAE/g, respectively. The concentration of the four phenolics (rosmarinic acid, globoidnan A, globoidnan B, rabdosiin) and six pyrrolizidine alkaloids generally showed maximum values at 1-3 months, after which their levels significantly decreased. With respect to the bioassays, the samples showed a wide range of antioxidant and anti-enzymatic effects; however, a direct storage time-bioactivity relationship was not observed. Similar conclusions were also revealed by the multivariate and correlation analyses. Our study could improve the current knowledge of the shelf-life properties of comfrey-based products and enhance their industrial exploitation.

Published
2022

45. Silver Nanoparticles Synthesized from Abies alba and Pinus sylvestris Bark Extracts: Characterization, Antioxidant, Cytotoxic, and Antibacterial Effects.

Author

Macovei, Irina, Luca, Simon Vlad, Skalicka-Woźniak, Krystyna, Horhogea, Cristina Elena, Rimbu, Cristina Mihaela, Sacarescu, Liviu, Vochita, Gabriela, Gherghel, Daniela, Ivanescu, Bianca Laura, Panainte, Alina Diana, Nechita, Constantin, Corciova, Andreia, and Miron, Anca

Subjects
SILVER fir, SCOTS pine, SILVER nanoparticles, ZETA potential, MELANOMA
Abstract

In recent years, phytofunctionalized AgNPs have attracted great interest due to their remarkable biological activities. In the present study, AgNPs were synthesized using Abies alba and Pinus sylvestris bark extracts. The chemical profile of these bark extracts was analyzed by LC-HRMS/MS. As a first step, the synthesis parameters (pH, AgNO3 concentration, ratio of bark extract and AgNO3, temperature, and reaction time) were optimized. The synthesized AgNPs were characterized by ATR-FTIR spectroscopy, DLS, SEM, EDX, and TEM. Their antioxidant, cytotoxic, and antibacterial properties were evaluated by the DPPH, ABTS, MTT, and broth microdilution assays, respectively. Abies alba and Pinus sylvestris bark extract-derived AgNPs were well-dispersed, spherical, small (average particle size of 9.92 and 24.49 nm, respectively), stable (zeta potential values of −10.9 and −10.8 mV, respectively), and cytotoxic to A-375 human malignant melanoma cells (IC50 = 2.40 ± 0.21 and 6.02 ± 0.61 μg/mL, respectively). The phytosynthesized AgNPs also showed antioxidant and antibacterial effects. [ABSTRACT FROM AUTHOR]

Published
2023
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47. Phytochemical and multi-biological characterization of two Cynara scolymus L. varieties: A glance into their potential large scale cultivation and valorization as bio-functional ingredients

Author

Luca, Simon Vlad, primary, Kulinowski, Łukasz, additional, Ciobanu, Cristina, additional, Zengin, Gokhan, additional, Czerwińska, Monika E., additional, Granica, Sebastian, additional, Xiao, Jianbo, additional, Skalicka-Woźniak, Krystyna, additional, and Trifan, Adriana, additional

Published
2022
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48. Additional file 1 of Symphytum ibericum Steven: LC–HRMS/MS-based phytochemical profile, in vitro antioxidant and enzyme inhibitory potential

Author

Trifan, Adriana, Zengin, Gokhan, Sinan, Kouadio Ibrahime, Skalicka-Woźniak, Krystyna, Minceva, Mirjana, and Luca, Simon Vlad

Abstract

Additional file 1: Figure S1. LC–HRMS/MS chromatograms (base peak chromatograms) of Symphytum ibericum LEAF extracts. Figure S2. LC–HRMS/MS chromatograms (base peak chromatograms) of Symphytum ibericum ROOT extracts. Figure S3. Fragmentation pathways proposed for rare phenolic acids Figure S4. Fragmentation pathways proposed for rare pyrrolizidine alkaloids

Published
2022
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50. Phyto-Functionalized Silver Nanoparticles Derived from Conifer Bark Extracts and Evaluation of Their Antimicrobial and Cytogenotoxic Effects

Author

Macovei, Irina, primary, Luca, Simon Vlad, additional, Skalicka-Woźniak, Krystyna, additional, Sacarescu, Liviu, additional, Pascariu, Petronela, additional, Ghilan, Alina, additional, Doroftei, Florica, additional, Ursu, Elena-Laura, additional, Rimbu, Cristina Mihaela, additional, Horhogea, Cristina Elena, additional, Lungu, Cristina, additional, Vochita, Gabriela, additional, Panainte, Alina Diana, additional, Nechita, Constantin, additional, Corciova, Maria Andreia, additional, and Miron, Anca, additional

Published
2021
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