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Michał Gleńsk
Department of Pharmacognosy and Herbal Medicines, Wroclaw Medical University, Borowska 211a, 50-556 Wrocław, Poland

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Journal article
Published: 25 May 2021 in Industrial Crops and Products
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Senga Sengana is a common strawberry (Fragaria × ananassa Duch.) cultivar growing in southern Poland. From leaves of this popular horticultural plant six triterpenoids were obtained including one glycoside nigaichigoside F1. All compounds were isolated by repeated silica gel column chromatography and preparative HPLC on Reverse phase RP-18. Their structures were evaluated by modern HR-MS and NMR techniques. This is the first report concerning triterpenoids constituents in Senga Sengana cultivar leaves and the only one that describes isolation of these compounds from the strawberry leaves. From all compounds nigaichigoside F1 is the dominant constituent. Compound T1 (3β, 19α, 23α-trihydroxy-2-oxoolean-12-en-28-oic acid) is a new triterpenoid, not previously described in nature. As triterpenoids are responsible for many biological effects the strawberry leaf extracts enriched in triterpenoid constituents may also be involved in antifungal, antitumor, antidiabetic and antinociceptive activities. The latter two activities could be especially linked to the presence of euscaphic acid and nigaichigoside F1, respectively. Overall, this study suggests that strawberry leaves are a promising waste and a valuable source of bioactive compounds for the food and pharmaceutical industry.

ACS Style

Michał Gleńsk; Marta K. Dudek; Agata Rybacka; Maciej Włodarczyk; Izabela Fecka. Triterpenoids from strawberry Fragaria × ananassa Duch. cultivar Senga Sengana leaves. Industrial Crops and Products 2021, 169, 113668 .

AMA Style

Michał Gleńsk, Marta K. Dudek, Agata Rybacka, Maciej Włodarczyk, Izabela Fecka. Triterpenoids from strawberry Fragaria × ananassa Duch. cultivar Senga Sengana leaves. Industrial Crops and Products. 2021; 169 ():113668.

Chicago/Turabian Style

Michał Gleńsk; Marta K. Dudek; Agata Rybacka; Maciej Włodarczyk; Izabela Fecka. 2021. "Triterpenoids from strawberry Fragaria × ananassa Duch. cultivar Senga Sengana leaves." Industrial Crops and Products 169, no. : 113668.

Journal article
Published: 17 April 2021 in Pharmaceutics
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European goldenrod (Solidago virgaurea L.) has long been applied in traditional medicine and recommended in the prophylaxis of urinary tract infections (UTIs). However, research describing the antibacterial properties of goldenrod is very limited. Therefore, the aim of the study was to determine the effect of S. virgaurea extract on the survival and biofilm formation of uropathogenic Escherichia coli. The interactions between the goldenrod extract and antibiotics used in UTIs were established. The influence of the extract on the duration of the post-antibiotic effects (PAE) and post-antibiotic sub-MIC effects (PASME) of amikacin and ciprofloxacin were determined. Extract composition was analyzed using coupled UHPLC/MS and the spectrophotometric method. The survival of bacteria was established using the serial dilution assay. The crystal violet assay for biofilm quantification was also used. PAE and PASME were investigated using the viable count method. The obtained results indicate that S. virgaurea extract limits the survival of planktonic forms of bacteria and reduces 24-h biofilm. However, the combination of S. virgaurea extract with antibiotics weakens their antibacterial activity and shortens the duration of PAE and PASME. Therefore, when deciding to use a combination of S. virgaurea extract and amikacin/ciprofloxacin, it is necessary to take into account their antagonistic activity.

ACS Style

Dorota Wojnicz; Dorota Tichaczek-Goska; Michał Gleńsk; Andrzej Hendrich. Is it Worth Combining Solidago virgaurea Extract and Antibiotics against Uropathogenic Escherichia coli rods? An In Vitro Model Study. Pharmaceutics 2021, 13, 573 .

AMA Style

Dorota Wojnicz, Dorota Tichaczek-Goska, Michał Gleńsk, Andrzej Hendrich. Is it Worth Combining Solidago virgaurea Extract and Antibiotics against Uropathogenic Escherichia coli rods? An In Vitro Model Study. Pharmaceutics. 2021; 13 (4):573.

Chicago/Turabian Style

Dorota Wojnicz; Dorota Tichaczek-Goska; Michał Gleńsk; Andrzej Hendrich. 2021. "Is it Worth Combining Solidago virgaurea Extract and Antibiotics against Uropathogenic Escherichia coli rods? An In Vitro Model Study." Pharmaceutics 13, no. 4: 573.

Communication
Published: 29 February 2020 in Biomolecules
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So far, only a few primrose species have been analyzed regarding their saponin composition and content. Moreover, the roots of only two of them are defined by the European Union (EU) Pharmacopoeia monograph and commercially utilized by the pharmaceutical industry. Thus, this study intended to find some new sources of main triterpene saponins from Primulae radix, namely primulasaponins I and II together with the closely related sakurasosaponin. Using isolated standards, UHPLC-ESI-HRMS served to assess over 155 Primulaceae members qualitatively and quantitatively. Nine examples of plants accumulating over 5% of primulasaponin I in their roots were found. Among them, in one case, it was found as the almost sole secondary metabolite with the concentration of 15–20% (Primula grandis L.). A reasonable content of primulasaponin II was found to be typical for Primula vulgaris Huds. and P. megaseifolia Boiss. & Bal. The sakurasosaponin level was found in seven species to exceed 5%. The finding of new, single and rich sources of the abovementioned biomolecules among species that were never analyzed phytochemically is important for future research and economic benefit. The chemotaxonomic significance of the occurrence of these three saponins in Primulaceae is discussed.

ACS Style

Maciej Włodarczyk; Paweł Pasikowski; Kinga Osiewała; Aleksandra Frankiewicz; Andrzej Dryś; Michał Gleńsk. In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family. Biomolecules 2020, 10, 376 .

AMA Style

Maciej Włodarczyk, Paweł Pasikowski, Kinga Osiewała, Aleksandra Frankiewicz, Andrzej Dryś, Michał Gleńsk. In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family. Biomolecules. 2020; 10 (3):376.

Chicago/Turabian Style

Maciej Włodarczyk; Paweł Pasikowski; Kinga Osiewała; Aleksandra Frankiewicz; Andrzej Dryś; Michał Gleńsk. 2020. "In Search of High-Yielding and Single-Compound-Yielding Plants: New Sources of Pharmaceutically Important Saponins from the Primulaceae Family." Biomolecules 10, no. 3: 376.

Brief report
Published: 13 December 2019 in Journal of Natural Products
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Prolonged storage of technical abamectin as well as avermectin B1a samples yielded a previously unknown derivative, designated here as compound 1. Detailed NMR analysis and X-ray crystallography allowed us to determine the structure of this compound and revealed the presence of a hydroperoxide group (−OOH) attached stereoselectively with configuration S to the C-8a carbon. This surprising result involves the formation of the peroxide bond in solid crystalline avermectin B1a upon exposure to air with no involvement of light or recognized catalytic factors and is consistent with a topotactic mechanism for the oxidation reaction. Compound 1 is stable in the absence of reducing agents and has potential as a starting point in structural modification of the tetrahydrofuran ring of avermectin B1a. It could also serve as a marker in assessing the quality of stored technical abamectin.

ACS Style

Jan A. Gliński; John Proudfoot; Izabela Madura; Huaping Zhang; Michał Gleńsk; Victor Day; Marta K. Dudek. Spontaneous Stereoselective Oxidation of Crystalline Avermectin B1a to Its C-8a-(S)-Hydroperoxide. Journal of Natural Products 2019, 82, 3477 -3481.

AMA Style

Jan A. Gliński, John Proudfoot, Izabela Madura, Huaping Zhang, Michał Gleńsk, Victor Day, Marta K. Dudek. Spontaneous Stereoselective Oxidation of Crystalline Avermectin B1a to Its C-8a-(S)-Hydroperoxide. Journal of Natural Products. 2019; 82 (12):3477-3481.

Chicago/Turabian Style

Jan A. Gliński; John Proudfoot; Izabela Madura; Huaping Zhang; Michał Gleńsk; Victor Day; Marta K. Dudek. 2019. "Spontaneous Stereoselective Oxidation of Crystalline Avermectin B1a to Its C-8a-(S)-Hydroperoxide." Journal of Natural Products 82, no. 12: 3477-3481.

Research article
Published: 21 August 2019 in Natural Product Research
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Polypodium vulgare L. (Polypodiaceae) is a fern used in traditional Polish medicine as an expectorant to treat cough and pertussis. Additionally, it was used as a diuretic in renal diseases, especially in chronic nephritis and pyelonephritis. In our study, a water extract was prepared from the rhizome of common polypody and subsequently fractionated on a resin column. As a result, the mixture of flavan-3-ol derivatives was obtained after the column elution with 60% methanol. Further purification by various chromatographic techniques led us to the isolation of (+)-afzelechin (1), a new previously not reported (+)-afzelechin-7-O-α-l-arabinofuranoside (2), and three other monomer flavan-3-ol glycosides: (+)-afzelechin-7-O-β-d-apiofuranoside (3), (+)-catechin-7-O-α-l-arabinofuranoside (4) and (+)-catechin-7-O-β-d-apiofuranoside (5). Structures of the compounds were established by HR-ESI-MS, 1D and 2D NMR spectroscopy. The HSQC and HMBC NMR techniques were used in the structure elucidation of the position of sugar attachment.

ACS Style

Michał Gleńsk; Marta K. Dudek; Maciej Ciach; Maciej Włodarczyk. Isolation and structural determination of flavan-3-ol derivatives from the Polypodium vulgare L. rhizomes water extract. Natural Product Research 2019, 35, 1474 -1483.

AMA Style

Michał Gleńsk, Marta K. Dudek, Maciej Ciach, Maciej Włodarczyk. Isolation and structural determination of flavan-3-ol derivatives from the Polypodium vulgare L. rhizomes water extract. Natural Product Research. 2019; 35 (9):1474-1483.

Chicago/Turabian Style

Michał Gleńsk; Marta K. Dudek; Maciej Ciach; Maciej Włodarczyk. 2019. "Isolation and structural determination of flavan-3-ol derivatives from the Polypodium vulgare L. rhizomes water extract." Natural Product Research 35, no. 9: 1474-1483.

Journal article
Published: 12 July 2019 in Toxins
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Chelidonium majus (Papaveraceae) extracts exhibit antimicrobial activity due to the complex alkaloid composition. The aim of the research was to evaluate the antimicrobial potential of extracts from wild plants and in vitro cultures, as well as seven major individual alkaloids. Plant material derived from different natural habitats and in vitro cultures was used for the phytochemical analysis and antimicrobial tests. The composition of alkaloids was analyzed using chromatographic techniques (HPLC with DAD detection). The results have shown that roots contained higher number and amounts of alkaloids in comparison to aerial parts. All tested plant extracts manifested antimicrobial activity, related to different chemical structures of the alkaloids. Root extract used at 31.25–62.5 mg/L strongly reduced bacterial biomass. From the seven individually tested alkaloids, chelerythrine was the most effective against P. aeruginosa (MIC at 1.9 mg/L), while sanguinarine against S. aureus (MIC at 1.9 mg/L). Strong antifungal activity was observed against C. albicans when chelerythrine, chelidonine, and aerial parts extract were used. The experiments with plant extracts, individually tested alkaloids, and variable combinations of the latter allowed for a deeper insight into the potential mechanisms affecting the activity of this group of compounds.

ACS Style

Sylwia Zielińska; Magdalena Wójciak-Kosior; Magdalena Dziągwa-Becker; Michał Gleńsk; Ireneusz Sowa; Karol Fijałkowski; Danuta Rurańska-Smutnicka; Adam Matkowski; Adam Junka. The Activity of Isoquinoline Alkaloids and Extracts from Chelidonium majus against Pathogenic Bacteria and Candida sp. Toxins 2019, 11, 406 .

AMA Style

Sylwia Zielińska, Magdalena Wójciak-Kosior, Magdalena Dziągwa-Becker, Michał Gleńsk, Ireneusz Sowa, Karol Fijałkowski, Danuta Rurańska-Smutnicka, Adam Matkowski, Adam Junka. The Activity of Isoquinoline Alkaloids and Extracts from Chelidonium majus against Pathogenic Bacteria and Candida sp. Toxins. 2019; 11 (7):406.

Chicago/Turabian Style

Sylwia Zielińska; Magdalena Wójciak-Kosior; Magdalena Dziągwa-Becker; Michał Gleńsk; Ireneusz Sowa; Karol Fijałkowski; Danuta Rurańska-Smutnicka; Adam Matkowski; Adam Junka. 2019. "The Activity of Isoquinoline Alkaloids and Extracts from Chelidonium majus against Pathogenic Bacteria and Candida sp." Toxins 11, no. 7: 406.

Communication
Published: 04 July 2019 in Molecules
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HPLC profiling of phenolics in grape seed extracts revealed a prominent peak of an unknown substance with concentrations up to 5.3%. Spectroscopic data allowed the identification of the compound 1 as 1-(3',4'-dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol. 1 is known to be produced from catechin and epicatechin through anaerobic bacteria from human, as well as the rat, intestines. It was hypothesized that the marc remaining after expression of juice from grapes became infested during storage, resulting in the production of 1. Because compound 1 is infrequently found in nature and has never been found in grape seeds, its presence may be considered a marker of an unwanted anaerobic bacterial process occurring during production. The antioxidant potential of 1 was determined by DPPH, ABTS, and FRAP (ferric reducing antioxidant power) assays and compared to the potential of the following compounds: phloroglucine, pyrogallol, gallic acid, catechin, and epicatechin. Furthermore, it was established that 1 significantly reduced guinea pig ileum contraction induced by histamine.

ACS Style

Michał Gleńsk; William J. Hurst; Vitold B. Glinski; Marek Bednarski; Jan A. Gliński. Isolation of 1-(3',4'-Dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol from Grape Seed Extract and Evaluation of its Antioxidant and Antispasmodic Potential. Molecules 2019, 24, 2466 .

AMA Style

Michał Gleńsk, William J. Hurst, Vitold B. Glinski, Marek Bednarski, Jan A. Gliński. Isolation of 1-(3',4'-Dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol from Grape Seed Extract and Evaluation of its Antioxidant and Antispasmodic Potential. Molecules. 2019; 24 (13):2466.

Chicago/Turabian Style

Michał Gleńsk; William J. Hurst; Vitold B. Glinski; Marek Bednarski; Jan A. Gliński. 2019. "Isolation of 1-(3',4'-Dihydroxyphenyl)-3-(2″,4″,6″-trihydroxyphenyl)-propan-2-ol from Grape Seed Extract and Evaluation of its Antioxidant and Antispasmodic Potential." Molecules 24, no. 13: 2466.

Articles
Published: 03 July 2019 in Plant Biosystems - An International Journal Dealing with all Aspects of Plant Biology
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The phytotoxic potential of Veronica peregrina L. was assessed by determining its influence on the germination and growth of the test plant Sinapis alba L. and identification of the allelochemicals present in its tissues. The impact of water extracts of V. peregrina (the gradient of concentrations: 0.5%, 1%, 2% and 4%) on S. alba seed germination and growth (radicle and hypocotyl elongation) was studied in bioassay conducted on Petri dishes with 3-ply layer of filter paper. UHPLC/UV/MS (Ultra-high performance liquid chromatography with diode array detection coupled to electrospray time-of-flight mass spectrometry) was used to separate and identify the allelochemicals present in V. peregrina tissues. The material for the study (whole plants of V. peregrina) was sampled from two fishponds located in Lower Silesia in May of 2018. The results showed that V. peregrina inhibited the germination of seeds. The effect on shoots and roots growth was positive or negative depending on the concentration of extract—low concentrations stimulated while the high ones inhibited growth of seedlings. Three compounds probably responsible for allelopathic activity (protocatechuic acid, luteolin-7-O-glucuronide, verproside) were identified. Presented phytotoxic potential of the species may account for its competitiveness, thus explaining its invasive behavior.

ACS Style

Ludmiła Polechońska; Michał Gleńsk; Agnieszka Klink; Małgorzata Dambiec; Zygmunt Dajdok. Allelopathic potential of invasive wetland plant Veronica peregrina. Plant Biosystems - An International Journal Dealing with all Aspects of Plant Biology 2019, 154, 481 -487.

AMA Style

Ludmiła Polechońska, Michał Gleńsk, Agnieszka Klink, Małgorzata Dambiec, Zygmunt Dajdok. Allelopathic potential of invasive wetland plant Veronica peregrina. Plant Biosystems - An International Journal Dealing with all Aspects of Plant Biology. 2019; 154 (4):481-487.

Chicago/Turabian Style

Ludmiła Polechońska; Michał Gleńsk; Agnieszka Klink; Małgorzata Dambiec; Zygmunt Dajdok. 2019. "Allelopathic potential of invasive wetland plant Veronica peregrina." Plant Biosystems - An International Journal Dealing with all Aspects of Plant Biology 154, no. 4: 481-487.

Communication
Published: 23 April 2019 in Molecules
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The phytochemistry of the genera Androsace, Cortusa, Soldanella, and Vitaliana, belonging to the Primulaceae family is not well studied so far. Hence, in this paper, we present the results of UHPLC-MS/MS analysis of several primrose family members as well as isolation and structure determination of two new saponins from Vitaliana primuliflora subsp. praetutiana. These two nor-triterpenoid saponins were characterized as (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-β-d-glucopyranosyl-(1→2)-O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one and (23S)-17α,23-epoxy-29-hydroxy-3β-[(O-α-l-rhamnopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-α-l-arabinopyranosyl-(1→6)-β-d-glucopyranosyl)oxy]-27-nor-lanost-8-en-25-one, respectively. Their structures were determined by high resolution mass spectrometry (HRMS), tandem mass spectrometry (MS/MS), one- and two-dimensional nuclear magnetic resonance spectroscopy (1D-, and 2D-NMR) analyses. So far, the 27-nor-lanostane monodesmosides were rarely found in dicotyledon plants. Therefore their presence in Vitaliana and also in Androsace species belonging to the Aretia section is unique and reported here for the first time. Additionally, eleven other saponins were determined by HRMS and MS/MS spectra. The isolated lanostane saponins can be considered as chemotaxonomic markers of the family Primulaceae.

ACS Style

Maciej Włodarczyk; Antoni Szumny; Michał Gleńsk. Lanostane-Type Saponins from Vitaliana primuliflora. Molecules 2019, 24, 1606 .

AMA Style

Maciej Włodarczyk, Antoni Szumny, Michał Gleńsk. Lanostane-Type Saponins from Vitaliana primuliflora. Molecules. 2019; 24 (8):1606.

Chicago/Turabian Style

Maciej Włodarczyk; Antoni Szumny; Michał Gleńsk. 2019. "Lanostane-Type Saponins from Vitaliana primuliflora." Molecules 24, no. 8: 1606.

Short communication
Published: 13 July 2015 in Natural Product Research
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The aim of this study was to evaluate the in vitro antioxidant and antimicrobial properties of the natural cyclic hydroxamic acid: 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA). Antioxidant activity of the isolated DIMBOA was examined using DPPH, FRAP and ABTS tests. It was found that DIMBOA exhibits a potent free-radical scavenging activity and a weaker iron (III) ions reducing activity. Antimicrobial activity against selected G(+), G(–) bacterial strains and against yeasts-like reference strains of fungi was investigated using disk-diffusion method. It has been shown that DIMBOA possess growth inhibitory properties against many strains of studied bacteria and fungi, such as Staphylococcus aureus, Escherichia coli as well as against Saccharomyces cerevisiae.

ACS Style

Michał Gleńsk; Beata Gajda; Roman Franiczek; Barbara Krzyżanowska; Izabela Biskup; Maciej Włodarczyk. In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]. Natural Product Research 2015, 30, 1305 -1308.

AMA Style

Michał Gleńsk, Beata Gajda, Roman Franiczek, Barbara Krzyżanowska, Izabela Biskup, Maciej Włodarczyk. In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]. Natural Product Research. 2015; 30 (11):1305-1308.

Chicago/Turabian Style

Michał Gleńsk; Beata Gajda; Roman Franiczek; Barbara Krzyżanowska; Izabela Biskup; Maciej Włodarczyk. 2015. "In vitro evaluation of the antioxidant and antimicrobial activity of DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one]." Natural Product Research 30, no. 11: 1305-1308.

Journal article
Published: 10 December 2014 in Chemistry & Biodiversity
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Elderberries are used in the preparation of pie, jelly, punch, wine, or liqueur, as well as in many herbal remedies and food supplements. Elderberry products may provide diaphoretic, diuretic, antioxidant, and immunostimulant activities that offer protection against cold and flu. Herein, we report for the first time the qualitative and quantitative evaluation of two isomeric triterpenoids isolated from Sambuci fructus. The analysis revealed that ursolic acid and oleanolic acid are present in Sambuci fructus. The average concentration of ursolic acid was ca. three times higher than the concentration of oleanolic acid. The triterpenoids were detected and quantified using chromatographic methods such as TLC and HPLC. Spectroscopic techniques, including HR-MS and 2D-NMR, allowed unequivocal structure determination.

ACS Style

Michał Gleńsk; Jan A. Gliński; Maciej Włodarczyk; Piotr Stefanowicz. Determination of Ursolic and Oleanolic Acid inSambuciFructus. Chemistry & Biodiversity 2014, 11, 1939 -1944.

AMA Style

Michał Gleńsk, Jan A. Gliński, Maciej Włodarczyk, Piotr Stefanowicz. Determination of Ursolic and Oleanolic Acid inSambuciFructus. Chemistry & Biodiversity. 2014; 11 (12):1939-1944.

Chicago/Turabian Style

Michał Gleńsk; Jan A. Gliński; Maciej Włodarczyk; Piotr Stefanowicz. 2014. "Determination of Ursolic and Oleanolic Acid inSambuciFructus." Chemistry & Biodiversity 11, no. 12: 1939-1944.