Wieslaw Oleszek
Polish Academy of Sciences, Life Sciences, Faculty Member
- Major research interests· Isolation, purification, structural and quantitative determination of natural produ... moreMajor research interests· Isolation, purification, structural and quantitative determination of natural products (saponins, phenolics, glycoalkaloids, glucosinolates, resorcinols, cyanogenic glucosides)· Biological activity of natural products · Natural antioxidants and anticancerogens, nutraceuticals· Chemical ecology· Plant-plant and plant-microorganism interactions· Allelopathy· Post harvest quality of agricultural products· Biosynthesis of natural products(Major research interests· Isolation, purification, structural and quantitative determination of natural products (saponins, phenolics, glycoalkaloids, glucosinolates, resorcinols, cyanogenic glucosides)· Biological activity of natural products · Natural antioxidants and anticancerogens, nutraceuticals· Chemical ecology· Plant-plant and plant-microorganism interactions· Allelopathy· Post harvest quality of agricultural products· Biosynthesis of natural products)edit
Based on the literature data from 1973 to 2022, this work summarizes reports on spiro-flavonoids with a spiro-carbon at the center of their structure and how this affects their isolation methods, stereochemistry, and biological activity.... more
Based on the literature data from 1973 to 2022, this work summarizes reports on spiro-flavonoids with a spiro-carbon at the center of their structure and how this affects their isolation methods, stereochemistry, and biological activity. The review collects 65 unique structures, including spiro-biflavonoids, spiro-triflavonoids, spiro-tetraflavonoids, spiro-flavostilbenoids, and scillascillin-type homoisoflavonoids. Scillascillin-type homoisoflavonoids comprise spiro[bicyclo[4.2.0]octane-7,3′-chromane]-1(6),2,4-trien-4′-one, while the other spiro-flavonoids contain either 2H,2′H-3,3′-spirobi[benzofuran]-2-one or 2′H,3H-2,3′-spirobi[benzofuran]-3-one in the core of their structures. Spiro-flavonoids have been described in more than 40 species of eight families, including Asparagaceae, Cistaceae, Cupressaceae, Fabaceae, Pentaphylacaceae, Pinaceae, Thymelaeaceae, and Vitaceae. The possible biosynthetic pathways for each group of spiro-flavonoids are summarized in detail. Anti-inflammat...
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Abstract Humulus lupulus L. is known to have preservative, mild sedative, hypnotic, and estrogenic properties that are related to its chemical composition. Hops are widely used in brewing, also in pharmacy, and cosmetics. Moreover, the... more
Abstract Humulus lupulus L. is known to have preservative, mild sedative, hypnotic, and estrogenic properties that are related to its chemical composition. Hops are widely used in brewing, also in pharmacy, and cosmetics. Moreover, the continuous development of biological research creates new application possibilities. The present paper was to measure the previously demonstrated antiradical and antioxidant properties of hop bitter acids and prenylflavonoids using a human plasma test system. Firstly, lupulin-associated metabolites were collected into two A–B fractions which were phytochemically characterized using UPLC–PDA–MS/MS analyses. Fraction A was a mixture of α- and β-acids (623 mg/g of dry weight (DW)) and fraction B was enriched in α-acids (275 mg/g DW) and xanthohumol (102 mg/g DW). Hop bitter acid preparation (A) was a better scavenger of 2,2′-azinobis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals compared with extract B, however, both extracts presented rather a moderate antiradical activity (25–30 % of Trolox power). For comparison, a commercial mixture of bitter acids showed a similar effect to extract A, while xanthohumol had little activity. Both A–B preparations demonstrated antioxidant capacity in established plasma test system in vitro as the protective effect on plasma macromolecules against oxidative stress induced by H2O2/Fe was observed. A mixture of bitter acids (extract A) was found to be highly active, more than extract B, in lipid peroxidation and protein carbonylation tests – alleviated oxidative stress by 65–95 %. The obtained results broaden the current state of knowledge about the multifunctional activities of hops-associated metabolites and demonstrate that bitter acids make an important contribution, no less than prenylflavonoids, to the antioxidant capacity of hop cones extract.
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The influence of methyl jasmonate on anthocyanin accumulation in roots ofKalanchoe blossfedianaplants was studied. Methyl jasmonate (JA-Me), at a concentration of 5.0 to 40.0 mg.l−1, substantially increased anthocyanin accumulation in... more
The influence of methyl jasmonate on anthocyanin accumulation in roots ofKalanchoe blossfedianaplants was studied. Methyl jasmonate (JA-Me), at a concentration of 5.0 to 40.0 mg.l−1, substantially increased anthocyanin accumulation in roots of intact plants, when it was applied as a solution under natural light conditions. The production of anthocyanin depended on the concentration of methyl jasmonate and the age of the plant. The stimulatory effect was higher in older plants ofK. blossfeldianathan in younger ones. When leaves were removed methyl jasmonate slightly stimulated anthocyanin accumulation compared with intact plants. The obtained results indicate that leaves are necessary for the anthocyanin accumulation in the roots. In isolated roots methyl jasmonate did not affect the accumulation of anthocyanins in light conditions. Seven anthocyanins were documented in the roots of control plants and 8 anthocyanins in the roots of JA-Me treated ones. JA-Me increased the level of ant...
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The ethyl acetate fraction of the methanolic extract of Yucca schidigera Roezl ex Ortgies bark exhibited moderate acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity (IC50 47.44 and 47.40 µg mL−1,... more
The ethyl acetate fraction of the methanolic extract of Yucca schidigera Roezl ex Ortgies bark exhibited moderate acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity (IC50 47.44 and 47.40 µg mL−1, respectively). Gel filtration on Sephadex LH-20 and further RP-C18 preparative HPLC of EtOAc fraction afforded 15 known and 3 new compounds, stereoisomers of larixinol. The structures of the isolated spirobiflavonoids 15, 26, and 29 were elucidated using 1D and 2D NMR and MS spectroscopic techniques. The relative configuration of isolated compounds was assigned based on coupling constants and ROESY (rotating-frame Overhauser spectroscopy) correlations along with applying the DP4+ probability method in case of ambiguous chiral centers. Determination of absolute configuration was performed by comparing calculated electronic circular dichroism (ECD) spectra with experimental ones. Compounds 26 and 29, obtained in sufficient amounts, were evaluated for activities a...
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The work is aimed at phytochemical characterization and In Vitro evaluation of antioxidant actions, anti-inflammatory effects, and cytotoxicity of purified extracts from three rupturewort (Herniaria L.) species, i.e., Herniaria glabra... more
The work is aimed at phytochemical characterization and In Vitro evaluation of antioxidant actions, anti-inflammatory effects, and cytotoxicity of purified extracts from three rupturewort (Herniaria L.) species, i.e., Herniaria glabra (HG), H. polygama (HP), and H. incana herb (HIh). The total phenolic content established in the purified extracts (PEs) of HIh, HP, and HG was 29.6, 24.0, and 13.0%, respectively. Thirty-eight non-saponin metabolites were identified using LC-HR-QTOF-ESI-MS; however, only 9 were common for the studied Herniaria species. The most abundant phenolic compound in HG-PE was narcissin (7.4%), HP-PE shared 3 major constituents, namely cis-2-hydroxy-4-methoxycinnamic acid 2-O-β-glucoside (cis-GMCA, 5.8%), narcissin (5.4%), and rutin (5.3%). Almost half of HIh phenolic content (14.7%) belonged to oxytroflavoside A (7-O-methylkaempferol-3-O-[3-hydroxy-3-methylglutaryl-(1→6)]-[α-rhamnopyranosyl-(1→2)]-β-galactopyranoside). Antioxidant properties of the Herniaria PE...
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Recently, Diaporthe has been considered the most frequently isolated genera of endophytic fungi, having a broad spectrum of host plants and a worldwide distribution. The endophytic Diaporthe strain used in the present work came from the... more
Recently, Diaporthe has been considered the most frequently isolated genera of endophytic fungi, having a broad spectrum of host plants and a worldwide distribution. The endophytic Diaporthe strain used in the present work came from the Fungal Collection of Phytopathology and Mycology Subdepartment, University of Life Sciences in Lublin (Poland), and was isolated from healthy Prunus domestica shoots during previous studies. Due to the possibility of using the Diaporthe endophytes as a promising option for plant disease management, the main goal of the research was to study the antagonistic effect of endophytic Diaporthe strain against six phytopathogens: Verticillium dahliae, Botrytis cinerea, Fusarium avenaceum, F. sprotrichioides, Alternaria alternata, and Trichothecium roseum based on the dual culture assay and to determine the catabolic profile of the endophyte by using Biolog FF Plates. The dual-culture test assay revealed the ability of the endophytic Diaporthe to limit the gr...
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Two triterpene saponins, including a novel serjanic acid derivative, were isolated from Chenopodium hybridum L. (Amaranthaceae) aerial parts. Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR).... more
Two triterpene saponins, including a novel serjanic acid derivative, were isolated from Chenopodium hybridum L. (Amaranthaceae) aerial parts. Their structures were elucidated by a combination of spectroscopic methods (MS, 1D and 2D NMR). Both compounds were evaluated for cytotoxicity and selectivity on skin, prostate, gastrointestinal, thyroid and lung cancer cells. Their effect was dose and time-dependent with varied potency, the highest against prostate PC3 and melanoma WM793, where IC50 was lower than the reference drug doxorubicin. Structure–activity relationship is briefly discussed.
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The study is based on phytochemical profiling and in vitro evaluation of biological effects of phenolic acid derivatives-rich Herniaria fractions, isolated from two rupturewort (Herniaria L.) species, i.e. Herniaria incana Lam. (syn. H.... more
The study is based on phytochemical profiling and in vitro evaluation of biological effects of phenolic acid derivatives-rich Herniaria fractions, isolated from two rupturewort (Herniaria L.) species, i.e. Herniaria incana Lam. (syn. H. besseri Fisch. ex Hornem) and H. polygama J. Gay (syn. H. odorata). For the first time, the composition of phenolic compounds of these species was extensively evaluated by both LC-HR-QTOF-ESI-MS and Nuclear Magnetic Resonance spectroscopy (NMR). LC-MS analyses of H. polygama revealed 72 tentatively identified compounds, while H. incana - 63. Only 8% of the metabolites reported in this work have been previously described for Herniaria spp. Most of the identified specialized metabolites were cinnamic and benzoic acid derivatives. Phenolic fraction of H. incana herb contained flavonoids as well. A multi-step chromatographic separation of phenolic fractions from H. polygama yielded three known cinnamic and one benzoic acid derivates, and from H. incana - 4 known flavonoids and one previously undescribed, i.e. rhamnocitrin-3-O-[3-hydroxy-3-methylglutaryl-(1 → 6'')]-[α-rhamnopyranosyl-(1 → 2'')]-β-glucopyranoside. Antioxidant properties of the examined fractions (1-50 μg/ml) were assessed in human blood plasma under the conditions of peroxynitrite-induced oxidative stress. Measurements of well-known biomarkers such as 3-nitrotyrosine, protein thiol groups, thiobarbituric acid-reactive substances and the ferric reducing ability of blood plasma revealed the protective effect of Herniaria fractions against oxidative damage to blood plasma components. Furthermore, the examined fractions effectively ameliorated the inflammatory response of the concanavalin A-stimulated human peripheral blood mononuclear cells (PBMCs). Additionally, cellular safety of the fractions was confirmed in PBMCs.
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ETHNOPHARMACOLOGICAL RELEVANCE The Cleomaceae family is known for its richness in secondary metabolites and different Cleome species are used in folk medicine. Cleome amblyocarpa and Cleome arabica are medicinal herbs used in Tunisia and... more
ETHNOPHARMACOLOGICAL RELEVANCE The Cleomaceae family is known for its richness in secondary metabolites and different Cleome species are used in folk medicine. Cleome amblyocarpa and Cleome arabica are medicinal herbs used in Tunisia and other North Africa countries to treat various diseases such as diabetes, rheumatism, colic, pain and digestive disorders. AIM OF THE STUDY To our knowledge, few data are available about the nutritional value, phytochemical components and biological effects of C. arabica and C. amblyocarpa cultivated in Tunisia. For this reason, the present survey aimed to determine the nutritional value, bioactive compounds and pharmacological properties of the leaves of these two species of Cleome. MATERIALS AND METHODS To characterize and determine the bioactive compounds in both extracts of leaves of Cleome species, ultra-performance liquid chromatography-mass spectrometry (UPLC-MS) was used. The various nutritional parameters were analyzed, in particular the amounts of protein, carbohydrates, ash, fiber, and total lipids. Vitamin E and fatty acid profiles were also evaluated by HPLC-DAD-FLD and GC-FID, respectively. The acute toxic effects of leaf extracts in mice at concentrations of 100, 500 and 800 mg/kg body weight have been investigated. The anti-inflammatory effect of leaves extracts was examined by means of the in vitro and in vivo models. The in vivo anti-inflammatory test was assessed by means of the carrageenan induced paw edema in rats. For the in vitro anti-inflammatory assay, the red blood cells membrane stabilization and protein denaturation methods were employed. The analgesic effect of hydroalcoholic extracts of leaves was also assessed by acetic acid induced writhing model in mice. RESULTS The phytochemical composition and the nutritional values of the leaves of C. amblyocarpa and C. arabica were determined. Our results revealed that the leaves of C. amblyocarpa are rich in flavonoids and glucosinolates. On the other hand, these latter metabolites are not present in the C. arabica extract and the leaves are characterized by the presence of flavones, methoxyflavones and their glycosides. Our findings revealed that the leaves of the two species contain a potential quantity of vitamins; proteins, carbohydrates and dietary fiber, and their hydroalcoholic extracts indicated substantial anti-inflammatory and antinociceptive activities in all the tests. Additionally, the data from the acute toxicity test proved that the leaf extracts did not cause any mortality or signs of toxicity in animals at doses up to 800 mg/kg. CONCLUSIONS The results obtained in this investigation demonstrated that the leaves of C. arabica and C. amblyocarpa are a valuable source of nutrients and active substances. Our observations support the traditional utilize of these two Cleome species for the treatment of painful diseases and as a source of natural anti-inflammatory agents.
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In the rumen, the dietary components, mainly carbohydrates, are transformed by the microorganisms to short chain fatty acids, which are used as a basic source of energy for the host (Agarwal et al., 2009). Moreover, the intermediates of... more
In the rumen, the dietary components, mainly carbohydrates, are transformed by the microorganisms to short chain fatty acids, which are used as a basic source of energy for the host (Agarwal et al., 2009). Moreover, the intermediates of this process, such as hydrogen, are rapidly converted to methane by the Archaea. Thus, methanogenesis causes 2 to 12% loss of dietary gross energy (Johnson & Johnson, 1997). The produced CH4 is one of the most important greenhouse gases (GHG), which global warming potential is 23 times higher than CO2 (IPCC, 2007). The livestock account for 37% of global antrophogenic methane emissions (IPCC, 2007). According to Lesschen et al. (2011) the highest GHG production in the European Union come from the dairy sector, with emission of 195 Tg CO2-eq/ year and beef sector with 192 Tg CO2-eq/year. Moreover, production of 1 kg of beef was associated with release of 22.6 kg CO2-eq what was the highest level among agricultural sectors (Lesschen et al., 2011). Ther...
When considering the idea of sustainable development, as desirable future of our civilization, we tend to focus attention on biomass in general and particular plants and crops, as renewable resources of food and energy. Currently... more
When considering the idea of sustainable development, as desirable future of our civilization, we tend to focus attention on biomass in general and particular plants and crops, as renewable resources of food and energy. Currently celebrated International Year of Chemistry (IYC 2011) should, in our opinion, provide an inspiration for some wider perspective, in particular for rational exploitation of secondary metabolites (SM), which are often treated as waste materials of a prime commodity manufacturing process. Additionally, proper balance between three main methods of manufacturing: isolation from natural sources, biotechnology and chemical synthesis, should be considered for each and every chemical substance, needed to support our well being. Environmental considerations, employing green chemistry reasoning, should be given priority, before short term economic gains. Although there is no universally accepted theory explaining occurrence and function of SMs in microorganisms and pl...
Inhibition of cholinesterases remains one of a few available treatment strategies for neurodegenerative dementias such as Alzheimer’s disease and related conditions. The current study was inspired by previous data on anticholinesterase... more
Inhibition of cholinesterases remains one of a few available treatment strategies for neurodegenerative dementias such as Alzheimer’s disease and related conditions. The current study was inspired by previous data on anticholinesterase properties of diterpenoids from Perovskia atriplicifolia and other Lamiaceae species. The acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition by the three new natural compounds—(1R,15R)-1-acetoxycryptotanshinone (1), (1R)-1-acetoxytanshinone IIA (2), and (15R)-1-oxoaegyptinone A (3)—as well as, new for this genus, isograndifoliol (4) were assessed. Three of these compounds exhibited profound inhibition of butyrylcholinesterase (BChE) and much weaker inhibition of acetylcholinesterase (AChE). All compounds (1–4) selectively inhibited BChE (IC50 = 2.4, 7.9, 50.8, and 0.9 µM, respectively), whereas only compounds 3 and 4 moderately inhibited AChE (IC50 329.8 µM and 342.9 µM). Molecular docking and in silico toxicology prediction studi...
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Zinnia elegans (syn. Zinnia violacea) is a common ornamental plant of the Asteraceae family, widely cultivated for the impressive range of flower colors and persistent bloom. Given its uncomplicated cultivation and high adaptability to... more
Zinnia elegans (syn. Zinnia violacea) is a common ornamental plant of the Asteraceae family, widely cultivated for the impressive range of flower colors and persistent bloom. Given its uncomplicated cultivation and high adaptability to harsh landscape conditions, we investigated the potential use of Z. elegans as a source of valuable secondary metabolites. Preliminary classification of compounds found in a methanolic extract obtained from inflorescences of Z. elegans cv. Caroussel was accomplished using HR LC-MS techniques. The extract was then subjected to solid-phase extraction and separation using Sephadex LH-20 column chromatography, which resulted in several fractions further investigated for their antioxidant properties through lipoxygenase inhibition and metal chelating activity assays. Moreover, following additional purification procedures, structures of some active ingredients were established by NMR spectroscopy. The investigated fractions contained polyphenolic compounds ...
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Three previously undescribed cardenolides, acovenosigenin A 3-O-α-L-acofriopyranoside (1), 14-anhydroacovenosigenin A 3-O-[β-D-glucopyranosyl-(1″→4′)-O-α-L-acofriopyranoside] (2), and 14-anhydroacovenosigenin A... more
Three previously undescribed cardenolides, acovenosigenin A 3-O-α-L-acofriopyranoside (1), 14-anhydroacovenosigenin A 3-O-[β-D-glucopyranosyl-(1″→4′)-O-α-L-acofriopyranoside] (2), and 14-anhydroacovenosigenin A 3-O-[β-D-glucopyranosyl-(1″→4′)-O-α-L-acovenopyranoside] (3), together with the two already known ones, 14-anhydrodigitoxigenin 3-O-β-D-glucopyranoside (4) and acospectoside A (5), were isolated from the leaves of Acokanthera oblongifolia. The influence of cardenolides 1 – 3 and acovenoside A (found in the Acokanthera genus) on three cancer cell lines (HT29, HCT116, and AGS) was also investigated. The most promising results, in comparison with oxaliplatin, were obtained for compound 1, which was found to be highly cytotoxic for all tested cell lines, HT29 (IC50 = 63.49 nM), HCT116 (IC50 = 67.35 nM), and AGS (IC50 = 80.92 nM). Unfortunately, 1 also showed similar toxicity towards normal lymphocytes (IC50 = 98.03 nM).
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The absorption spectra of twenty-one flavones including glycosides of apigenin, luteolin, chrysoeriol and tricin, nonacylated or acylated with coumaric, ferulic or sinapic acids, were examined to document the influence of acylation on... more
The absorption spectra of twenty-one flavones including glycosides of apigenin, luteolin, chrysoeriol and tricin, nonacylated or acylated with coumaric, ferulic or sinapic acids, were examined to document the influence of acylation on their spectral characteristics. Acylation did not shift the absorption maximum of band II, but the molar absorption coefficients of this band increased 1.3–2.0 fold. Acylation of apigenin and chrysoeriol glycosides did not shift the absorption maximum of band I and the absorption maxima of nonacylated and acylated compounds were at 319–334 nm, but this increased their molar absorption coefficients 1.7–3.0 fold. For luteolin and tricin glycosides, nonacylated compound maxima of absorption of band I were in the range of 342–349 nm. Acylation shifted band I absorption maxima to 329–340 nm and increased their molar absorption coefficient 1.6–1.8 fold. These data document that acylation of flavones leads to significant increase of their absorption in the 28...
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The purpose of this study was to establish the free amino acids profile of Viola tricolor collected from different habitats in Poland. Viola tricolor (heartsease) is a very popular plant found worldwide, classified both as weed and... more
The purpose of this study was to establish the free amino acids profile of Viola tricolor collected from different habitats in Poland. Viola tricolor (heartsease) is a very popular plant found worldwide, classified both as weed and medicinal plant. Based on a validated method, the following nineteen free amino acids were analyzed using liquid chromatography-electrospray ionization coupled to a triple quadrupole mass spectrometer (LC-ESI-MS/MS):alanine, glycine, leucine, valine, isoleucine, proline, phenylalanine, tryptophan, tyrosine, serine, threonine, methionine, asparagine, glutamine, lysine, arginine, histidine, aspartic acid, glutamic acid. The total free amino acids (TAA) ranged from 9938.0 to 11393.8 mg/kg of fresh weight. The variability of the investigated amino acids with respect to different habitat conditions was statistically assessed using the method of discriminant and cluster analysis. Alanine, valine, glutamine and aspartic acid were the most abundant free amino aci...
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Five new triterpenoid saponins, including 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid... more
Five new triterpenoid saponins, including 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-β-d-glucopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)-(4-O-acetyl)-β-d-quinovopyranosyl-(1→4)]-β-d-fucopyranoside (1), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-(6-O-acetyl)-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)-(4-O-acetyl)-β-d-quinovopyranosyl-(1→4)]-β-d-fucopyranoside (2), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)-(4-O-acetyl)-β-d-quinovopyranosyl-(1→4)]-β-d-fucopyranoside (3), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-β-d-glucopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-d-quinovopyranosyl-(1→4)]-β-d-fucopyranoside (4), 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-(6-O-acetyl)-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-[(4-O-acetyl)-β-d-quinovopyranosyl-(1→4)]-β-d-fucopyranoside (5) together with two known congeners, saponariosides A (6) and B (7) were isolated from the roots of Saponaria officinalis L. Their structures were elucidated by extensive spectroscopic methods, including 1D- (1H, 13C) and 2D-NMR (DQF-COSY, TOCSY, HSQC, and HMBC) experiments, HR-ESI-MS, and acid hydrolysis.
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Continuing our investigations on plants belonging to the Asclepiadaceae family, three new cardenolide glycosides,... more
Continuing our investigations on plants belonging to the Asclepiadaceae family, three new cardenolide glycosides, 3'-O-beta-D-glucopyranosylcalactin (1), 12-dehydroxyghalakinoside (2), and 6'-dehydroxyghalakinoside (3), along with the known ghalakinoside (4) and calactin (5), were isolated from the roots of Pergularia tomentosa. The structures of these compounds were elucidated by extensive spectroscopic methods including 1D- and 2D-NMR experiments as well as ESIMS analysis. The isolated cardenolides caused apoptotic cell death of Kaposi's sarcoma cells.
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Research Interests: Engineering, Chemistry, Biology, Secondary Ion Mass Spectrometry, Magnetic Resonance Spectroscopy, and 13 moreSaponins, STEROIDS, Medicine, Spectral analysis, Plant Roots, CHEMICAL SCIENCES, Agricultural and Food Chemistry, Liliaceae, Saponin, Diosgenin, Carbohydrate Sequence, Molecular Sequence Data, and Allium
Research Interests: Engineering, Botany, Chemistry, Traditional Medicine, Biology, and 15 moreMagnetic Resonance Spectroscopy, Flavonoids, Medicine, Fruit, High Performance Liquid Chromatography, Agricultural, Anthocyanins, High Pressure Liquid Chromatography, CHEMICAL SCIENCES, Liquid Chromatography / Electrospray Ionization Mass Spectrometry, Quercetin, Agricultural and Food Chemistry, Moraceae, Morus, and Kaempferol(Magnetic Resonance Spectroscopy, Flavonoids, Medicine, Fruit, High Performance Liquid Chromatography, Agricultural, Anthocyanins, High Pressure Liquid Chromatography, CHEMICAL SCIENCES, Liquid Chromatography / Electrospray Ionization Mass Spectrometry, Quercetin, Agricultural and Food Chemistry, Moraceae, Morus, and Kaempferol)
(Magnetic Resonance Spectroscopy, Flavonoids, Medicine, Fruit, High Performance Liquid Chromatography, Agricultural, Anthocyanins, High Pressure Liquid Chromatography, CHEMICAL SCIENCES, Liquid Chromatography / Electrospray Ionization Mass Spectrometry, Quercetin, Agricultural and Food Chemistry, Moraceae, Morus, and Kaempferol)
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A wide range of plant bioactive components (phytochemicals) have been identified as having potential to modulate the processes of fermentation in the rumen. The use of plants or plant extracts as natural feed additives has become a... more
A wide range of plant bioactive components (phytochemicals) have been identified as having potential to modulate the processes of fermentation in the rumen. The use of plants or plant extracts as natural feed additives has become a subject of interest not only among nutritionists but also other scientists. Although a large number of phytochemicals (e.g. saponins, tannins and essential oils) have recently been investigated for their methane reduction potential, there have not yet been major breakthroughs that could be applied in practice. A key tenet of this paper is the need for studies on the influence of plant components on methane production to be performed with standardized samples. Where there are consistent effects, the literature suggests that saponins mitigate methanogenesis mainly by reducing the number of protozoa, condensed tannins both by reducing the number of protozoa and by a direct toxic effect on methanogens, whereas essential oils act mostly by a direct toxic effec...
Research Interests: Biology, Medicine, Biological Sciences, Population, Livestock, and 10 moreAnimal, Animal Feed, Animals, Methanogenesis, Bacteria, Plants, Methane, Fermentation, Plant extracts, and Rumen(Animal, Animal Feed, Animals, Methanogenesis, Bacteria, Plants, Methane, Fermentation, Plant extracts, and Rumen)
(Animal, Animal Feed, Animals, Methanogenesis, Bacteria, Plants, Methane, Fermentation, Plant extracts, and Rumen)
Crystalline saponins were isolated from red clover (Trifolium pratense L.) roots. They were a mixture of two glycosides showing no haemolytic or fungistatic activity. Acid hydrolysis of these saponins yielded soyasapogenols B. C. D. E and... more
Crystalline saponins were isolated from red clover (Trifolium pratense L.) roots. They were a mixture of two glycosides showing no haemolytic or fungistatic activity. Acid hydrolysis of these saponins yielded soyasapogenols B. C. D. E and F and rhamnose. xylose, arabinose glucose and glucuronic acid as sugar components. They were poorly or not soluble in water and well soluble in ethanol. Water suspensions of these saponins did not affect winter wheat seedling growth.
Research Interests: Chemistry, Plant Biology, Biology, Sugar, Medicago, and 5 moreXylose, Saponin, Hydrolysis, Rhamnose, and Red Clover
The separation of saponins derived from <em>Medicago lupulina</em> L. flowers yielded two saponin fractions. The first one, made up of crystalline saponins, readily precipitable from water solution, was a mixture of three... more
The separation of saponins derived from <em>Medicago lupulina</em> L. flowers yielded two saponin fractions. The first one, made up of crystalline saponins, readily precipitable from water solution, was a mixture of three glycosides of soyasapogenol B. Acid hydrolysis of these saponins yielded soyasapogenol B and its three artifacts: soyasapogenols C. D and F. Xylose, rhamnose, galactose, glucose and glucuronic acid were found as sugar constituents. The second fraction obtained by cholesterol precipitation consisted of seven haemolytically active medicagenic acid glycosides. Their hydrolysis furnished medicagenic acid and glucose, xylose, rhamnose and traces of glucuronic acid.
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The triterpene saponin fraction was isolated from <em>Trigonella monspeliaca</em> tops. It consisted of ten saponosides, three of which were determined to be medicagenic acid glycosides, the other seven - soyasapogenol... more
The triterpene saponin fraction was isolated from <em>Trigonella monspeliaca</em> tops. It consisted of ten saponosides, three of which were determined to be medicagenic acid glycosides, the other seven - soyasapogenol glucosides. Acid hydrolysis of the saponin fraction yielded medicagenic acid, soyasapogenol B and its artifacts soyasapogenol C, D and F. These data consitute the first report on the occurence of medicagenic acid and soyasapogenol glycosides in the genus <em>Trigonella</em>.
Research Interests: Chemistry, Plant Biology, Biology, Saponin, Hydrolysis, and 2 moreTrigonella and Acid hydrolysis(Trigonella and Acid hydrolysis)
(Trigonella and Acid hydrolysis)
Medicagenic acid, its 3-0-glucopyranoside and 3,28-di-(0-glucopyranoside), their methyl esters and acetyl derivatives were tested for their potential to retard the growth of the fungus <em>T. viride</em>. The varying... more
Medicagenic acid, its 3-0-glucopyranoside and 3,28-di-(0-glucopyranoside), their methyl esters and acetyl derivatives were tested for their potential to retard the growth of the fungus <em>T. viride</em>. The varying antifungal activities are discussed in relation to published data and to the applicability of <em>T.…
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For a long time the functional meaning of secondary metabolites synthesized by plants was neglected. It was just last decades when due to the rapid development of sophisticated analytical tools their function has been better understood.... more
For a long time the functional meaning of secondary metabolites synthesized by plants was neglected. It was just last decades when due to the rapid development of sophisticated analytical tools their function has been better understood. More and more research supported the idea that these compounds developed as a part of the plant’s own defense mechanisms against insult. Using modern analytical methods, numerous physiologically active plant constituents have been identified and their changes in plants in the reaction to environmental stresses were established. The same time this knowledge was used to identify natural products that provide benefits to man. These include the application of natural product in agrochemistry to replace harmful synthetic pesticides, in parmaceutical chemistry to heal number of chronic disease, in food industry to introduce health benefits (nutraceuticals, functional food) or in feed industry to replace growth promoting antibiotics. All these aspects will ...
Y. schidigera contains a number of unusual polyphenols, derivatives of resveratrol and naringenin, called spiro-flavostilbenoids, which have potent in vitro anti-inflammatory, antioxidant, and moderate cholinesterase inhibitory... more
Y. schidigera contains a number of unusual polyphenols, derivatives of resveratrol and naringenin, called spiro-flavostilbenoids, which have potent in vitro anti-inflammatory, antioxidant, and moderate cholinesterase inhibitory activities. To date, these compounds have not been tested in vivo for the treatment of neurodegenerative diseases. The aim of the present study was to evaluate the effects of both single spiro-flavostilbenoids (yuccaol B and gloriosaol A) and phenolic fractions derived from Y. schidigera bark on scopolamine-induced anxiety and memory process deterioration using a Danio rerio model. Detailed phytochemical analysis of the studied fractions was carried out using different chromatographic techniques and Nuclear Magnetic Resonance (NMR). The novel tank diving test was used as a method to measure zebrafish anxiety, whereas spatial working memory function was assessed in Y-maze. In addition, acetylcholinesterase/butyrylcholinesterase (AChE/BChE) and 15-lipooxygenase...
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Resveratrol is the natural phytoalexin found in considerable amounts in the skin of grapes, 7,8 mulberries, and peanuts 9 and in some medicinal plants. 10-12 In the last 10 years this compound received a lot of attention because of its... more
Resveratrol is the natural phytoalexin found in considerable amounts in the skin of grapes, 7,8 mulberries, and peanuts 9 and in some medicinal plants. 10-12 In the last 10 years this compound received a lot of attention because of its biological activities, as antimutagenic, 13 ...
Research Interests: Chemistry, Natural Products, Medicinal Plants, Medicine, Structural Analysis, and 15 moreBiological Sciences, California, Antioxidants, CHEMICAL SCIENCES, Bark, Antioxidant Activity, Isolation, Phenols, Beta Carotene, Ether, Natural, Biological activity, Linoleic Acid, Molecular Structure, and Medical and Health Sciences
Horse chestnut extracts are widely used in pharmacy and cosmetic industries. The main active constituents are saponins of oleane type, but seeds of horse chestnut also contain flavonoids, being glycosides of quercetin and kaempferol.... more
Horse chestnut extracts are widely used in pharmacy and cosmetic industries. The main active constituents are saponins of oleane type, but seeds of horse chestnut also contain flavonoids, being glycosides of quercetin and kaempferol. Their contribution to the overall ...
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The oxidative/nitrative stress induced by different factors plays an important role in the pathogenesis of various disorders, including cardiovascular diseases and cancer. Proanthocyanidins have antioxidative properties and may protect... more
The oxidative/nitrative stress induced by different factors plays an important role in the pathogenesis of various disorders, including cardiovascular diseases and cancer. Proanthocyanidins have antioxidative properties and may protect biomolecules (lipids, DNA, and proteins) exposed to reactive oxygen and nitrogen species, including peroxynitrite (ONOO(-)). The effects of proanthocyanidin fraction from Medemia argun nuts on oxidative/nitrative protein damages (determined by such parameters as level of thiol groups, carbonyl groups, and nitrotyrosine residues) and on the amount of glutathione (as an important component of redox status; using HPLC) in human blood platelets and plasma after treatment with peroxynitrite were studied in vitro. The preincubation of blood platelets and plasma with proanthocyanidin fraction from M. argun nuts (0.5-50 µg/ml) reduced the formation of 3-nitrotyrosine, diminished oxidation of thiol groups, and decreased the level of carbonyl groups in proteins caused by 100 µM peroxynitrite. An action of tested plant fraction and ONOO(-) evoked a significant increase of GSH in platelets and plasma in comparison with platelets and plasma treated with ONOO(-) only. The proanthocyanidin fraction from M. argun nuts can be useful as a protecting factor against oxidative/nitrative stress associated with different diseases (cancer, cardiovascular, and neurodegenerative diseases) and proanthocyanidins of M. argun nuts may be promising antioxidants.
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Tagetes erecta L. is a popular ornamental plant of the Asteraceae family, which is widely cultivated not only for its decorative use, but also for the extraction of lutein. Besides carotenoid representatives, which have been extensively... more
Tagetes erecta L. is a popular ornamental plant of the Asteraceae family, which is widely cultivated not only for its decorative use, but also for the extraction of lutein. Besides carotenoid representatives, which have been extensively studied, other important classes of secondary metabolites present in the plant, such as polyphenols, could exhibit important biological activities. The phytochemical analysis of a methanolic extract obtained from T. erecta inflorescences was achieved using liquid chromatography–mass spectrometry (LC-MS) techniques. The extract was further subjected to a multistep purification process, which allowed the separation of different fractions. The total extract and its fractions contain several polyphenolic compounds, such as hydroxybenzoic and hydroxycinnamic acid derivatives, flavonols (especially quercetagetin glycosides), and several aglycons (e.g., quercetin, patuletin). One of the fractions, containing mostly quercetagitrin, was subjected to two diffe...
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ABSTRACT TLC-DPPH� test coupled with different image processing procedures have become an interesting technique to screen complex samples for the presence of free radical scavengers. Several procedures have already been published showing... more
ABSTRACT TLC-DPPH� test coupled with different image processing procedures have become an interesting technique to screen complex samples for the presence of free radical scavengers. Several procedures have already been published showing the possibility of obtaining quantitative data from TLC plates derivatized with methanolic solution of relatively stable free radical DPPH� (2,2-diphenyl-1-picrylhydrazyl). In this study two different image processing programs, ImageJ and Sorbfil TLC Videodensitometer, have been applied to study direct antioxidant properties of compounds separated from extracts obtained from selected varieties of Medicago sativa. M. sativa var. Radius possessed the greatest amount of compounds with direct antioxidant properties. The activity of the individual compounds has been compared to the activity of rutin, a flavonoid with well recognized antioxidant properties. Neither of the separated compounds was as active as the standard.
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Many natural products, particularly phenolic compounds, have been reported to have a strong inhibition against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), the key enzymes in the pathology of Alzheimer's disease (AD).... more
Many natural products, particularly phenolic compounds, have been reported to have a strong inhibition against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), the key enzymes in the pathology of Alzheimer's disease (AD). Therefore, we hypothesized that some xanthahumol, naringenin, and acyl phloroglucinol derivatives (1-14) isolated from Humulus lupulus L. (hops) may have an inhibitory potential against AChE and BChE. Inhibitory potential of compounds 1-14 were tested against AChE and BChE using ELISA microtiter assay. Different molecular docking simulations, including IFD and GOLD protocols, were implemented to verify the interactions between the ligands and the active site amino acids and also their binding energies inside the catalytic crevices of AChE and BChE. ADME/Tox analysis were used to determine pharmacological activities of the compounds. Among them, 3‑hydroxy‑xanthohumol (IC = 51.25 ± 0.88 µM) and xanthohumol (IC = 71.34 ± 2.09 µM), displayed a moderate...
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The phytochemical investigation of the whole plant extracts of Herniaria glabra L. (Caryophyllaceae) led to the identification and isolation of four known flavonoids, one known and three undescribed maltol derivatives, and benzyl... more
The phytochemical investigation of the whole plant extracts of Herniaria glabra L. (Caryophyllaceae) led to the identification and isolation of four known flavonoids, one known and three undescribed maltol derivatives, and benzyl β-gentiobioside. The structures were established by extensive 1D and 2D NMR spectroscopic analyses, as well as HRESIMS data. For the first time in Herniaria genus, as well as in Caryophylaceae family the presence of apiorutin {quercetin 3-O-[(D-apio-β-d-furanosyl-(1 → 2)-O-[-α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside]} and licoagroside B {maltol 3-O-[6-O-(3-hydroxy-3-methylglutaroyl)]-β-d-glucopyranoside} were revealed. Additionally, antioxidant actions of apiorutin, rutin, narcissin (isorhamentin 3-O-β-d-rutinoside) and licoagroside B were assessed in human blood plasma, exposed to the peroxynitrite-induced oxidative stress in vitro. The isolates partly reduced oxidative (oxidation of thiol groups) and nitrative (tyrosine nitration) damage to blood p...
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The study covers an evaluation of the influence of extracts (1-50 μg/ml), isolated from aerial parts of nine Trifolium L. species (i.e. T. alexandrinum, T. fragiferum, T. hybridum, T. incarnatum, T. pallidum, T. pratense, T. resupinatum... more
The study covers an evaluation of the influence of extracts (1-50 μg/ml), isolated from aerial parts of nine Trifolium L. species (i.e. T. alexandrinum, T. fragiferum, T. hybridum, T. incarnatum, T. pallidum, T. pratense, T. resupinatum var. majus, T. resupinatum var. resupinatum and T. scabrum) on haemostatic properties of blood plasma. The clot formation and fibrinolysis assay (CFF), blood clotting times, the extrinsic and intrinsic coagulation pathway-dependent polymerization of plasma fibrin were measured. The effects of plant extracts on amidolytic activity of thrombin were also evaluated and compared with argatroban, an antithrombotic drug. Cytotoxicity was assessed in a model of blood platelets and as the viability of peripheral blood mononuclear cells. While no changes in blood clotting times or fibrinolytic properties of blood plasma were found, some fractions impaired the blood plasma coagulation induced by the intrinsic coagulation pathway. Reduction in the maximal veloci...