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Melanoma is an enormous global health burden, and should be effectively addressed with better therapeutic strategies. Therefore, new therapeutic agents are needed for the management of this disease. The aim of this study was the investigation of cytotoxic activity of some isoquinoline alkaloid standards and extracts obtained from Sanguinaria canadensis—collected before, during, and after flowering—against three different human melanoma cells (A375, G361, SK-MEL-3). The cytotoxicity of these extracts was not previously tested on these melanoma cell lines. Determination of alkaloid contents was performed by HPLC-DAD using Polar RP column and mobile phase containing acetonitrile, water, and 1-butyl-3-methylimidazolium tetrafluoroborate. The cytotoxicity of alkaloid standards was investigated by determination of cell viability and calculation of IC50 values. Significant differences were observed in the alkaloids content and cytotoxic activity of the extracts, depending on the season of collection of the plant material. In the Sanguinaria canadensis extracts high contents of sanguinarine (from 4.8543 to 9.5899 mg/g of dry plant material) and chelerythrine (from 42.7224 to 6.8722 mg/g of dry plant material) were found. For both of these alkaloids, very high cytotoxic activity against the tested cell lines were observed. The IC50 values were in the range of 0.11–0.54 µg/mL for sanguinarine and 0.14 to 0.46 µg/mL for chelerythrine. IC50 values obtained for Sanguinaria canadensis extracts against all tested cell lines were also very low (from 0.88 to 10.96 µg/mL). Cytotoxic activity of alkaloid standards and Sanguinaria canadensis extracts were compared with the cytotoxicity of anticancer drugs—etoposide, cisplatin, and hydroxyurea. In all cases except the one obtained for cisplatin against A375, which was similar to that obtained for Sanguinaria canadensis after flowering against the same cell line, IC50 values obtained for anticancer drugs were higher than the IC50 values obtained for sanguinarine, chelerythrine, and Sanguinaria canadensis extracts. Our results showed that Sanguinaria canadensis extracts and isoquinoline alkaloids, especially sanguinarine and chelerythrine, could be recommended for further in vivo experiments in order to confirm the possibility of their application in the treatment of human melanomas.
Tomasz Tuzimski; Anna Petruczynik; Tomasz Plech; Barbara Kaproń; Anna Makuch-Kocka; Małgorzata Szultka-Młyńska; Justyna Misiurek; Bogusław Buszewski. Determination of Cytotoxic Activity of Sanguinaria canadensis Extracts against Human Melanoma Cells and Comparison of Their Cytotoxicity with Cytotoxicity of Some Anticancer Drugs. Molecules 2021, 26, 1738 .
AMA StyleTomasz Tuzimski, Anna Petruczynik, Tomasz Plech, Barbara Kaproń, Anna Makuch-Kocka, Małgorzata Szultka-Młyńska, Justyna Misiurek, Bogusław Buszewski. Determination of Cytotoxic Activity of Sanguinaria canadensis Extracts against Human Melanoma Cells and Comparison of Their Cytotoxicity with Cytotoxicity of Some Anticancer Drugs. Molecules. 2021; 26 (6):1738.
Chicago/Turabian StyleTomasz Tuzimski; Anna Petruczynik; Tomasz Plech; Barbara Kaproń; Anna Makuch-Kocka; Małgorzata Szultka-Młyńska; Justyna Misiurek; Bogusław Buszewski. 2021. "Determination of Cytotoxic Activity of Sanguinaria canadensis Extracts against Human Melanoma Cells and Comparison of Their Cytotoxicity with Cytotoxicity of Some Anticancer Drugs." Molecules 26, no. 6: 1738.
Melanoma is a serious form of skin cancer that begins in cells known as melanocytes. While it is less common than the other forms of skin cancer, melanoma is more dangerous because of its ability to spread to other organs more rapidly if it is not treated at an early stage. The number of people diagnosed with melanoma has increased over the last few decades. The most widely used treatments include surgery, chemotherapy, and radiation therapy. The search for new drugs to treat various cancers is one of the most important challenges of modern scientific research. Some isoquinoline alkaloids found in different plant species have strong cytotoxic effects on various cancer cells. We tested the effect of isoquinoline alkaloids and extracts obtained from various parts of Mahonia aquifolium collected in various vegetation seasons on human melanoma cancer cells and our data indicated that investigated extract induced significant reduction in cell viability of Human malignant melanoma cells (A375), human Caucasian malignant melanoma cell line (G361), and human malignant melanoma cell line (SKMEL3 cancer cell lines in a dose- and time-dependent manner. Differences in cytotoxic activity were observed for extracts obtained from various parts of Mahonia aquifolium. Significant differences were also obtained in the alkaloids content and cytotoxic activity of the extracts depending on the season of collection of plant material. Our investigations exhibit that these plant extracts can be recommended for further in vivo experiments in order to confirm the possibility of their use in the treatment of human melanomas.
Tomasz Tuzimski; Anna Petruczynik; Barbara Kaproń; Anna Makuch-Kocka; Małgorzata Szultka-Młyńska; Justyna Misiurek; Grażyna Szymczak; Bogusław Buszewski. Determination of Cytotoxic Activity of Selected Isoquinoline Alkaloids and Plant Extracts Obtained from Various Parts of Mahonia aquifolium Collected in Various Vegetation Seasons. Molecules 2021, 26, 816 .
AMA StyleTomasz Tuzimski, Anna Petruczynik, Barbara Kaproń, Anna Makuch-Kocka, Małgorzata Szultka-Młyńska, Justyna Misiurek, Grażyna Szymczak, Bogusław Buszewski. Determination of Cytotoxic Activity of Selected Isoquinoline Alkaloids and Plant Extracts Obtained from Various Parts of Mahonia aquifolium Collected in Various Vegetation Seasons. Molecules. 2021; 26 (4):816.
Chicago/Turabian StyleTomasz Tuzimski; Anna Petruczynik; Barbara Kaproń; Anna Makuch-Kocka; Małgorzata Szultka-Młyńska; Justyna Misiurek; Grażyna Szymczak; Bogusław Buszewski. 2021. "Determination of Cytotoxic Activity of Selected Isoquinoline Alkaloids and Plant Extracts Obtained from Various Parts of Mahonia aquifolium Collected in Various Vegetation Seasons." Molecules 26, no. 4: 816.
Quinolizidine alkaloids exhibit various forms of biological activity. A lot of them were found in the Leguminosae family, including Laburnum and Genista. The aim of the study was the optimization of a chromatographic system for the analysis of cytisine and N-methylcytisine in various plant extracts as well as an investigation of the cytotoxic activities of selected alkaloids and plant extracts obtained from Laburnum anagyroides, Laburnum anagyroides L. quercifolium, Laburnum alpinum, Laburnum watereri, Genista germanica, and Genista tinctoria against various cancer cell lines. The determination of investigated compounds was performed by High Performance Liquid Chromatography with Diode Array Detection (HPLC-DAD), while High Performance Liquid Chromatography coupled with Quadrupole Time-of-Flight–Mass Spectrometry (HPLC-QTOF-MS) was applied for the qualitative analysis of plant extracts. The retention, separation selectivity, peaks shape, and systems efficiency obtained for cytisine and N-methylcytisine in different chromatographic systems were compared. The application of columns with alkylbonded and phenyl stationary phases led to a very weak retention of cytisine and N-methylcytisine, even when the mobile phases containing only 5% of organic modifiers were used. The strongest retention was observed when hydrophilic interaction chromatography (HILIC) or especially when ion exchange chromatography (IEC) were applied. The most optimal system in terms of alkaloid retention, peak shape, and system efficiency containing an strong cation exchange (SCX) stationary phase and a mobile phase consisted of 25% acetonitrile and formic buffer at pH 4.0 was applied for investigating alkaloids analysis in plant extracts. Cytotoxic properties of the investigated plant extracts as well as cytisine and N-methylcytisine were examined using human tongue squamous carcinoma cells (SCC-25), human pharyngeal squamous carcinoma cells (FaDu), human triple-negative breast adenocarcinoma cell line (MDA-MB-231), and human breast adenocarcinoma cell line (MCF-7). The highest cytotoxic activity against FaDu, MCF-7, and MDA-MB cancer cell lines was observed after applying the Genista germanica leaves extract. In contrast, the highest cytotoxic activity against SCC-25 cell line was obtained after treating with the seed extract of Laburnum watereri. The investigated plant extracts exhibit significant cytotoxicity against the tested human cancer cell lines and seem to be promising for further research on its anticancer activity.
Anna Petruczynik; Karol Wróblewski; Justyna Misiurek; Tomasz Plech; Karolina Szalast; Krzysztof Wojtanowski; Tomasz Mroczek; Grażyna Szymczak; Monika Waksmundzka-Hajnos; Piotr Tutka. Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity. Toxins 2020, 12, 557 .
AMA StyleAnna Petruczynik, Karol Wróblewski, Justyna Misiurek, Tomasz Plech, Karolina Szalast, Krzysztof Wojtanowski, Tomasz Mroczek, Grażyna Szymczak, Monika Waksmundzka-Hajnos, Piotr Tutka. Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity. Toxins. 2020; 12 (9):557.
Chicago/Turabian StyleAnna Petruczynik; Karol Wróblewski; Justyna Misiurek; Tomasz Plech; Karolina Szalast; Krzysztof Wojtanowski; Tomasz Mroczek; Grażyna Szymczak; Monika Waksmundzka-Hajnos; Piotr Tutka. 2020. "Determination of Cytisine and N-Methylcytisine from Selected Plant Extracts by High-Performance Liquid Chromatography and Comparison of Their Cytotoxic Activity." Toxins 12, no. 9: 557.
Alkaloids have protective functions for plants and can play an important role in living organisms. Alkaloids may have a wide range of pharmacological activities. Many of them have cytotoxic activity. Nowadays, cancer has become a serious public health problem. Searching for effective drugs with anticancer activity is one of the most significant challenges of modern scientific research. The aim of this study was the investigation of cytotoxic activity of extracts obtained from Corydalis lutea root and herb, Dicentra spectabilis root and herb, Fumaria officinalis, Macleaya cordata leaves and herb, Mahonia aquifolia leaves and cortex, Meconopsis cambrica root and herb on FaDu, SCC-25, MCF-7, and MDA-MB-231 cancer cell lines. The cytotoxic activity of these extracts has not been previously tested for these cell lines. The aim was also to quantify selected alkaloids in the investigated extracts by High Performance Liquid Chromatography (HPLC). The analyses of alkaloid content were performed using HPLC in reversed phase (RP) mode using Polar RP column and mobile phase containing acetonitrile, water and ionic liquid (IL). Cytotoxic effect of the tested plant extracts and respective alkaloid standards were examined using human pharyngeal squamous carcinoma cells (FaDu), human tongue squamous carcinoma cells (SCC-25), human breast adenocarcinoma cell line (MCF-7), human triple-negative breast adenocarcinoma cell line (MDA-MB-231). All investigated plant extracts possess cytotoxic activity against tested cancer cell lines: FaDu, SCC-25, MCF-7, and MDA-MB-231. The highest cytotoxic activity against FaDu, SCC-25, and MCF-7 cell lines was estimated for Macleaya cordata leaf extract, while the highest cytotoxic activity against MDA-MB-231 cell line was obtained for Macleaya cordata herb extract. Differences in cytotoxic activity were observed for extracts obtained from various parts of investigated plants. In almost all cases the cytotoxic activity of investigated plant extracts, especially at the highest concentration against tested cell lines was significantly higher than the activity of anticancer drug etoposide. Our investigations exhibit that these plant extracts can be recommended for further in vivo experiments to confirm their anticancer activity.
Anna Petruczynik; Tomasz Plech; Tomasz Tuzimski; Justyna Misiurek; Barbara Kaproń; Dorota Misiurek; Małgorzata Szultka-Młyńska; Bogusław Buszewski; Monika Waksmundzka-Hajnos. Determination of Selected Isoquinoline Alkaloids from Mahonia aquifolia; Meconopsis cambrica; Corydalis lutea; Dicentra spectabilis; Fumaria officinalis; Macleaya cordata Extracts by HPLC-DAD and Comparison of Their Cytotoxic Activity. Toxins 2019, 11, 575 .
AMA StyleAnna Petruczynik, Tomasz Plech, Tomasz Tuzimski, Justyna Misiurek, Barbara Kaproń, Dorota Misiurek, Małgorzata Szultka-Młyńska, Bogusław Buszewski, Monika Waksmundzka-Hajnos. Determination of Selected Isoquinoline Alkaloids from Mahonia aquifolia; Meconopsis cambrica; Corydalis lutea; Dicentra spectabilis; Fumaria officinalis; Macleaya cordata Extracts by HPLC-DAD and Comparison of Their Cytotoxic Activity. Toxins. 2019; 11 (10):575.
Chicago/Turabian StyleAnna Petruczynik; Tomasz Plech; Tomasz Tuzimski; Justyna Misiurek; Barbara Kaproń; Dorota Misiurek; Małgorzata Szultka-Młyńska; Bogusław Buszewski; Monika Waksmundzka-Hajnos. 2019. "Determination of Selected Isoquinoline Alkaloids from Mahonia aquifolia; Meconopsis cambrica; Corydalis lutea; Dicentra spectabilis; Fumaria officinalis; Macleaya cordata Extracts by HPLC-DAD and Comparison of Their Cytotoxic Activity." Toxins 11, no. 10: 575.
Background: Plants are an important origin of natural substances that the raw material for various pharmaceutical and therapeutic applications due to the presence of phytochemicals, such as alkaloids. Alkaloids, which are found in different plant species, possess numerous biological activities. Some alkaloids have strong cytotoxic effects on various cancer cells. The search for new drugs to treat various cancers is one of the most important challenges of modern scientific research. Objective: This study aimed to investigate of cytotoxic activity of extracts that were obtained from Chelidonium Majus; Berberis sp.; Thalictrum foetidum containing various alkaloids on selected cancer cell lines. The aim was also the quantification of selected alkaloids in the investigated extracts by HPLC. Methods: The analysis of alkaloids contents were performed while using HPLC in reversed phase (RP) mode using Polar RP column and mobile phase containing acetonitrile, water, and ionic liquid. The cytotoxic effect of the tested plant extracts and respective alkaloids’ standards were examined while using human pharyngeal squamous carcinoma cells (FaDu), human tongue squamous carcinoma cells (SCC-25), human breast adenocarcinoma cell line (MCF-7), and human triple-negative breast adenocarcinoma cell line (MDA-MB-231). Conclusion: All of the investigated plant extracts possess cytotoxic activity against cancer cell lines: FaDu, SCC-25, MCF-7, and MDA-MB-231. The highest cytotoxic activity against FaDu and MDA-MB-231 cells was observed for Chelidonium majus root extract, while the highest cytotoxic activity against SCC-25 and MCF-7 cells was estimated for the Thalictrum foetidum root extract. There obtained significant differences in the cytotoxic activity of extracts that were obtained from the roots and herbs of Chelidonium majus and Thalictrum foetidum. Based on these results, investigated plant extracts can be recommended for further investigations of anticancer activity.
Anna Petruczynik; Tomasz Tuzimski; Tomasz Plech; Justyna Misiurek; Karolina Szalast; Grażyna Szymczak. Comparison of Anticancer Activity and HPLC-DAD Determination of Selected Isoquinoline Alkaloids from Thalictrum foetidum, Berberis sp. and Chelidonium majus Extracts. Molecules 2019, 24, 3417 .
AMA StyleAnna Petruczynik, Tomasz Tuzimski, Tomasz Plech, Justyna Misiurek, Karolina Szalast, Grażyna Szymczak. Comparison of Anticancer Activity and HPLC-DAD Determination of Selected Isoquinoline Alkaloids from Thalictrum foetidum, Berberis sp. and Chelidonium majus Extracts. Molecules. 2019; 24 (19):3417.
Chicago/Turabian StyleAnna Petruczynik; Tomasz Tuzimski; Tomasz Plech; Justyna Misiurek; Karolina Szalast; Grażyna Szymczak. 2019. "Comparison of Anticancer Activity and HPLC-DAD Determination of Selected Isoquinoline Alkaloids from Thalictrum foetidum, Berberis sp. and Chelidonium majus Extracts." Molecules 24, no. 19: 3417.
An HPLC procedure on a polar reversed-phase column with mobile phases containing ionic liquid (IL) was developed for the analysis of selected alkaloids from different chemical groups. We aimed to obtain optimal conditions for the separation of alkaloids because widely used silica-based stationary phases exhibit a silanol effect, rendering analysis of basic analytes extremely difficult. Retention, separation selectivity, peak symmetry, and system efficiency were examined in various eluent systems containing different concentrations of IL and acetonitrile. The obtained results revealed substantial influence from the concentrations of IL, the organic modifier, and temperature on the retention behavior of the investigated alkaloids. The most selective and efficient chromatographic systems were applied for the analysis of several alkaloids in a plant extract.
Anna Petruczynik; Justyna Misiurek; Tomasz Tuzimski; Monika Waksmundzka-Hajnos. Application of Mobile Phases Containing Ionic Liquid for HPLC Analysis of Selected Isoquinoline Alkaloids. Journal of AOAC INTERNATIONAL 2017, 100, 1652 -1659.
AMA StyleAnna Petruczynik, Justyna Misiurek, Tomasz Tuzimski, Monika Waksmundzka-Hajnos. Application of Mobile Phases Containing Ionic Liquid for HPLC Analysis of Selected Isoquinoline Alkaloids. Journal of AOAC INTERNATIONAL. 2017; 100 (6):1652-1659.
Chicago/Turabian StyleAnna Petruczynik; Justyna Misiurek; Tomasz Tuzimski; Monika Waksmundzka-Hajnos. 2017. "Application of Mobile Phases Containing Ionic Liquid for HPLC Analysis of Selected Isoquinoline Alkaloids." Journal of AOAC INTERNATIONAL 100, no. 6: 1652-1659.
Selected alkaloids were chromatographed on cyanopropyl-silica thin layers using nonaqueous and aqueous eluents containing various free silanol blocker agents. Because of the strong retention of these basic compounds, nonaqueous eluents containing medium polar diluents, strongly polar modifiers, or aqueous eluents containing organic modifier, water, and silanol blockers (ammonia, diethylamine, and ionic liquid) were required for analysis. Mobile phases containing addition of acids were also tested for separation of investigated alkaloids. The most selective and efficient systems were used in two-dimensional separations of isoquinoline alkaloids’ mixture and plant extracts.
A. Petruczynik; J. Misiurek; S. Serafin; M. Waksmundzka-Hajnos. The effect of chromatographic conditions on the separation of selected alkaloids on CN-silica layers. Journal of Liquid Chromatography & Related Technologies 2017, 40, 1 -7.
AMA StyleA. Petruczynik, J. Misiurek, S. Serafin, M. Waksmundzka-Hajnos. The effect of chromatographic conditions on the separation of selected alkaloids on CN-silica layers. Journal of Liquid Chromatography & Related Technologies. 2017; 40 (5-6):1-7.
Chicago/Turabian StyleA. Petruczynik; J. Misiurek; S. Serafin; M. Waksmundzka-Hajnos. 2017. "The effect of chromatographic conditions on the separation of selected alkaloids on CN-silica layers." Journal of Liquid Chromatography & Related Technologies 40, no. 5-6: 1-7.
In this study, authors propose a simple and cost-effective two-dimensional thin-layer chromatography (2D-TLC) method for the simultaneous determination of eleven standards alkaloids: allocryptopine (A), berberine (Be), boldine (Bo), chelidonine (Ch), glaucine (G), papaverine (Pa), emetine (E), columbamine (Col), magnoflorine (M), palmatine (Pal), and coptisine (Cop). Separation of the alkaloid mixture was achieved by 2D-TLC using an aqueous mobile phase (RP) in the first dimension (80% methanol + water + 0.05 mL−1 diethylamine) and a normal phase (NP) in the second dimension (18% methanol, 18% acetone in 63% diisopropyl ether containing 1% ammonia, v/v) on bilayer Multi-K CS5 plates. The composition of the mobile phases was optimized in terms of retention, separation selectivity, spots symmetry, and system efficiency. The procedure was evaluated in terms of natural samples analysis. Magnoflorine and berberine were identified in Thalictrum foetidum root extract. Additionally, the alkaloids in the extract sample were confirmed by high-performance liquid chromatography—diode-array detection method.
Tomasz Tuzimski; Anna Petruczynik; Justyna Misiurek. Separation of a mixture of eleven alkaloids by 2D-TLC on Multi-K CS5 plates and identification of analytes in Thalictrum foetidum root extract by TLC and HPLC—DAD. JPC – Journal of Planar Chromatography – Modern TLC 2017, 30, 142 -147.
AMA StyleTomasz Tuzimski, Anna Petruczynik, Justyna Misiurek. Separation of a mixture of eleven alkaloids by 2D-TLC on Multi-K CS5 plates and identification of analytes in Thalictrum foetidum root extract by TLC and HPLC—DAD. JPC – Journal of Planar Chromatography – Modern TLC. 2017; 30 (2):142-147.
Chicago/Turabian StyleTomasz Tuzimski; Anna Petruczynik; Justyna Misiurek. 2017. "Separation of a mixture of eleven alkaloids by 2D-TLC on Multi-K CS5 plates and identification of analytes in Thalictrum foetidum root extract by TLC and HPLC—DAD." JPC – Journal of Planar Chromatography – Modern TLC 30, no. 2: 142-147.
Retention parameters of galantamine and lycorine standards were determined on different columns, i.e., octadecyl silica, SM C18, and strong cation-exchange (SCX) columns with different aqueous mobile phases. Retention of alkaloids was investigated on C18, SM C18 columns with mobile phase containing 5% MeCN, 20% acetate buffer at pH 3.5, and 0.025 ML−1 diethylamine (DEA), and on SCX column with mobile phase containing 8% MeCN and phosphate buffer at pH 2.5. Better results were also obtained in ion-exchange chromatographic system. On the basis of results obtained in different chromatographic systems, simple, rapid, and sensitive high-performance liquid chromatography methods were developed for determining lycorine and galantamine in plant extracts from various species belonging to Amaryllidaceae family. Extracts were prepared from various parts of plants collected at different times of the growing season.
A. Petruczynik; Justyna Misiurek; Tomasz Tuzimski; R. Uszyński; Grażyna Szymczak; M. Chernetskyy; M. Waksmundzka-Hajnos. Comparison of different HPLC systems for analysis of galantamine and lycorine in various species of Amaryllidaceae family. Journal of Liquid Chromatography & Related Technologies 2016, 39, 574 -579.
AMA StyleA. Petruczynik, Justyna Misiurek, Tomasz Tuzimski, R. Uszyński, Grażyna Szymczak, M. Chernetskyy, M. Waksmundzka-Hajnos. Comparison of different HPLC systems for analysis of galantamine and lycorine in various species of Amaryllidaceae family. Journal of Liquid Chromatography & Related Technologies. 2016; 39 (12):574-579.
Chicago/Turabian StyleA. Petruczynik; Justyna Misiurek; Tomasz Tuzimski; R. Uszyński; Grażyna Szymczak; M. Chernetskyy; M. Waksmundzka-Hajnos. 2016. "Comparison of different HPLC systems for analysis of galantamine and lycorine in various species of Amaryllidaceae family." Journal of Liquid Chromatography & Related Technologies 39, no. 12: 574-579.