Preliminary Phytochemical and Biological Evaluation of Rudbeckia hirta Flowers.

Black-eyed Susan (Rudbeckia hirta L.), a flowering plant with various traditional medicinal uses, has recently garnered interest for its therapeutic properties. However, little is known about the potential therapeutic activities of the plant species. The current study focused on conducting a comprehensive investigation into the chemical composition and bioactivity of black-eyed Susan cultivated in Romania. Untargeted metabolite profiling and UHPLC-HR-MS phytochemical analysis of the studied extract revealed the presence of more than 250 compounds pertaining to different classes, including sesquiterpene lactones, polyphenolic acids, flavonoids, amino acids, and fatty acids. The tested extract exhibited inhibitory activity against Gram-positive bacteria and showed promising antifungal activity. It also demonstrated potent antioxidant properties through iron chelation and 15-LOX inhibition capacities, as well as inhibition of cell growth, particularly on the MCF-7 cell line, suggesting potential anticancer effects. Therefore, current research provides valuable information on the antioxidant, antimicrobial, and antitumor potential of Rudbeckia hirta flowers. Implicitly, the discovery of such a wide range of biosubstances, together with the biological activity observed for the studied extract in these preliminary in vitro studies, paves the way for future investigation of the potential application of the plant in the pharmaceutical and nutraceutical sectors.

Spiro-Flavonoids in Nature: A Critical Review of Structural Diversity and Bioactivity.

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-inflammatory and anticancer activities are the most important biological activities of spiro-flavonoids, both in vitro and in vivo. Our work identifies the most promising natural sources, the existing challenges in assigning the stereochemistry of these compounds, and future research perspectives.

Detailed metabolite profiling and in vitro studies of Urospermum picroides as a potential functional food.

Wild edible plants (WEP) are part of the Mediterranean culinary culture and can be used as famine foods in times of severe food shortages. Urospermum picroides is a WEP that grows under harsh conditions and represents an opportunity to expand and diversify the global food supply. However, little is known about its chemical profile. In this study, liquid chromatography coupled to HRESIMS allowed the identification of 77 metabolites in U. picroides extract, among which 12 sesquiterpene-amino acid conjugates are reported here for the first time. Due to the novelty of these conjugates, GNPS molecular networking was used to provide information on their fragmentation pathway. Further, the sesquiterpene enriched U. picroides extract showed a moderate anti-inflammatory effect in LPS-stimulated THP1-macrophages by increasing IL-10 secretion while decreasing pro-inflammatory IL-6 secretion at 50 µg/mL. Our study provides evidence for the potential use of U. picroides as an anti-inflammatory functional food and nutraceutical agent.

Liquid-liquid chromatography isolation of Petasites hybridus sesquiterpenes and their LC-HR-MS/MS and NMR characterization.

Petasites hybridus L. (butterbur, Asteraceae) is a well-known medicinal plant traditionally used as a remedy for neurological, respiratory, cardiovascular, and gastrointestinal disorders. Eremophilane-type sesquiterpenes (petasins) are considered to be the major bioactive constituents of butterbur. However, efficient methods to isolate high-purity petasins in sufficient amounts for further analytical and biological testing are lacking. In this study, various sesquiterpenes were separated from a methanol rootstock extract of P. hybridus with liquid-liquid chromatography (LLC). The appropriate biphasic solvent system was selected using the predictive thermodynamic model COSMO-RS and shake-flask experiments. After the selection of the feed (extract) concentration and operating flow rate, a batch LLC experiment was performed with n-hexane/ethyl acetate/methanol/water 5/1/5/1 (v/v/v/v). For those LLC fractions containing petasin derivatives with purities < 95%, a preparative high-performance liquid chromatography purification step followed. All isolated compounds were identified by state-of-the-art spectroscopic methods, i.e., liquid chromatography coupled with high-resolution tandem mass spectrometry and nuclear magnetic resonance techniques. As a result, six compounds were obtained, namely 8ß-hydroxyeremophil-7(11)-en-12,8-olide, 2-[(angeloyl)oxy]eremophil-7(11)-en-12,8-olide, 8α/ß-H-eremophil-7(11)-en-12,8-olide, neopetasin, petasin, and isopetasin. The isolated petasins can be further used as reference materials for standardization and pharmacological evaluation.

Metabolic profiling of Ochradenus baccatus Delile. utilizing UHPLC-HRESIMS in relation to the in vitro biological investigations.

Ochradenus baccatus Delile (Resedaceae) is a desert plant with edible fruits native to the Middle East. Few investigators have reported antibacterial, antiparasitic and anti-cancer activities of the plant. Herein we evaluated the cytotoxic activity of O. baccatus using four cell lines and a zebrafish embryo model. Additionally, liquid chromatography coupled with mass spectroscopy was performed to characterize the extract's main constituents. The highest cytotoxicity was observed against human cervical adenocarcinoma (HeLa), with CC50 of 39.1 µg/mL and a selectivity index (SI) of 7.23 (p < 0.01). Metabolic analysis of the extract resulted in the annotation of 57 metabolites, including fatty acids, flavonoids, glucosinolates, nitrile glycosides, in addition to organic acids. The extract showed an abundance of hydroxylated fatty acids (16 peaks). Further, 3 nitrile glycosides have been identified for the first time in Ochradenus sp., in addition to 2 glucosinolates. These identified phytochemicals may partially explain the cytotoxic activity of the extract. We propose O. baccatus as a possible safe food source for further utilization to partially contribute to the increasing food demand specially in Saharan countries.

Absolute configuration of spiro-flavostilbenoids from Yucca schidigera Roezl ex Ortgies: First indication of (2R)-naringenin as the key building block.

The absolute configurations of the known but unusual spiro-flavostilbenoids found in the bark of Yucca schidigera Roezl ex Ortgies, were determined by applying time-dependent density functional theory simulation of electronic circular dichroism spectra. The absolute configurations obtained were as follows: (2S,3R) for yuccaol A, yuccaol D and yuccalide A; (2S,3S) for yuccaol B, yuccaol C and yuccaol E; (2S,3S,2'S,3'S) for gloriosaol A; (2S,3R,2'S,3'R) for gloriosaol C; (2S,3S,2'S,3'R) for gloriosaol D; (2S,3R,2'S,3'S) for gloriosaol E. These findings indicate that the compounds are all biosynthetic derivatives either of (2R)-naringenin and trans-resveratrol or of trans-3,3',5,5'-tetrahydroxy-4'-methoxystilbene. In contrast, gloriosaols are direct derivatives of yuccaols (note that substituting by stilbenoid changes the absolute configuration of C-2 naringenin carbon to 2S). A putative mechanism for their biosynthesis is proposed taking into account key aspects of regio- and stereoselectivity. Yuccaol B and gloriosaol A showed in vitro moderate inhibitory effects against acetyl-/butyrylcholinesterases (AChE/BChE) with IC50 values of 43/81 and 45/65 µM respectively. The selectivity index values calculated from the IC50 values of BChE and AChE were 1.9 and 1.4. Molecular docking simulations showed their interaction with the peripheral anionic site of human AChE and the catalytic site of the human BChE.

Iphiona mucronata (Forssk.) Asch. & Schweinf. A Comprehensive Phytochemical Study via UPLC-Q-TOF-MS in the Context of the Embryo- and Cytotoxicity Profiles.

Iphiona mucronata (Family Asteraceae) is widely distributed in the Eastern desert of Egypt. It is a promising plant material for phytochemical analysis and pharmacologic studies, and so far, its specific metabolites and biological activity have not yet been thoroughly investigated. Herein, we report on the detailed phytochemical study using UPLC-Q-TOF-MS approach. This analysis allowed the putative annotation of 48 metabolites belonging to various phytochemical classes, including mostly sesquiterpenes, flavonoids, and phenolic acids. Further, zebrafish embryotoxicity has been carried out, where 100 µg/mL extract incubated for 72 h resulted in a slow touch response of the 10 examined larvae, which might be taken as a sign of a disturbed peripheral nervous system. Results of in vitro testing indicate moderate cytotoxicity towards VERO, FaDu, and HeLa cells with CC50 values between 91.6 and 101.7 µg/mL. However, selective antineoplastic activity in RKO cells with CC50 of 54.5 µg/mL was observed. To the best of our knowledge, this is the first comprehensive profile of I. mucronata secondary metabolites that provides chemical-based evidence for its biological effects. A further investigation should be carried out to precisely define the underlying mechanisms of toxicity.

Isolation of Mirificin and Other Bioactive Isoflavone Glycosides from the Kudzu Root Lyophilisate Using Centrifugal Partition and Flash Chromatographic Techniques.

Pueraria lobata (Willd.) Ohwi is a legume taxon native to Southeast Asia and widely used in traditional medicine systems of that region. The therapeutic applications of the underground parts of this species (known as kudzu root) are related to its high content of isoflavones, mainly the characteristic C-glycoside derivatives. Within this group, the most explored compound both phytochemically and pharmacologically is puerarin. However, current scientific findings document important anti-biodegenerative effects for some of the minor isoflavones from kudzu roots. Therefore, the main objective of the study was to develop an original preparative method that allowed the efficient isolation of closely related hydrophilic daidzein C-glycosides, including mirificin, from vacuum-dried aqueous-ethanolic extracts of kudzu roots. For this purpose, the combined centrifugal partition (CPC) and flash chromatographic (FC) techniques were elaborated and used. The optimized biphasic solvent system in CPC, with ethyl acetate, ethanol, water, and 0.5% (V/V) acetic acid as a mobile phase modifier, enabled the purification and separation of the polar fraction containing bioactive isoflavones and ultimately the isolation of mirificin, 3'-hydroxy- and 3'-methoxypuerarin, puerarin, and daidzin using FC. The identity of isoflavones was confirmed using spectroscopic (UV absorption and nuclear magnetic resonance) and mass spectrometric methods. The determined purity of isolated mirificin was 63%.

Neuroprotective Effect of Yucca schidigera Roezl ex Ortgies Bark Phenolic Fractions, Yuccaol B and Gloriosaol A on Scopolamine-Induced Memory Deficits in Zebrafish.

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 (15-LOX) inhibition tests were performed in vitro. All pure compounds and fractions under study exerted anxiolytic and procognitive action. Moreover, strong anti-oxidant capacity was observed, whereas weak inhibition towards cholinesterases was found. Thus, we may conclude that the observed behavioral effects are complex and result rather from inhibition of oxidative stress processes and influence on cholinergic muscarinic receptors (both 15-LOX and scopolamine assays) than effects on cholinesterases. Y. schidigera is a source of substances with desirable properties in the prevention and treatment of neurodegenerative diseases.

Qualitative and Quantitative Analysis of Secondary Metabolites in Morphological Parts of Paulownia Clon In Vitro 112® and Their Anticoagulant Properties in Whole Human Blood.

It is not easy to find data in the scientific literature on the quantitative content of individual phytochemicals. It is possible to find groups of compounds and even individual compounds rather easily, but it is not known what their concentration is in cultivated or wild plants. Therefore, the subject of this study was to determine the content of individual compounds in the new Paulownia species, Oxytree, developed in a biotechnology laboratory in 2008 at La Mancha University in Spain. Six secondary metabolites were isolated, and their chemical structure was confirmed by spectral methods. An analytical method was developed, which was then used to determine the content of individual compounds in leaves, twigs, flowers and fruits of Paulownia Clon in Vitro 112®. No flavonoids were found in twigs and fruits of Oxytree, while the highest phenylethanoid glycosides were found in twigs. In this study, we also focused on biological properties (anticoagulant or procoagulant) of extract and four fractions (A-D) of different chemical composition from Paulownia Clon in Vitro 112 leaves using whole human blood. These properties were determined based on the thrombus-formation analysis system (T-TAS), which imitates in vivo conditions to assess whole blood thrombogenecity. We observed that three fractions (A, C and D) from leaves decrease AUC10 measured by T-TAS. In addition, fraction D rich in triterpenoids showed the strongest anticoagulant activity. However, in order to clarify the exact mechanism of action of the active substances present in this plant, studies closer to physiological conditions, i.e., in vivo studies, should be performed, which will also allow to determine the effects of their long-term effects.

Determination of phenolic profiles of Herniaria polygama and Herniaria incana fractions and their in vitro antioxidant and anti-inflammatory effects.

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 â†’ 6'')]-[α-rhamnopyranosyl-(1 â†’ 2'')]-ß-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.

Phytochemical Profile, Antioxidant Activity, and Cytotoxicity Assessment of Tagetes erecta L. Flowers.

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 different antioxidant assays (metal chelating activity and lipoxygenase inhibition) and to in vitro cytotoxicity assessment. Generally, the biological assays showed promising results for the investigated fraction compared to the initial extract. Given the encouraging outcome of the in vitro assays, further purification and structural analysis of compounds from T. erecta extracts, as well as further in vivo investigations are justified.

Pulmonaria obscura and Pulmonaria officinalis Extracts as Mitigators of Peroxynitrite-Induced Oxidative Stress and Cyclooxygenase-2 Inhibitors-In Vitro and In Silico Studies.

The Pulmonaria species (lungwort) are edible plants and traditional remedies for different disorders of the respiratory system. Our work covers a comparative study on biological actions in human blood plasma and cyclooxygenase-2 (COX-2) -inhibitory properties of plant extracts (i.e., phenolic-rich fractions) originated from aerial parts of P. obscura Dumort. and P. officinalis L. Phytochemical profiling demonstrated the abundance of phenolic acids and their derivatives (over 80% of the isolated fractions). Danshensu conjugates with caffeic acid, i.e., rosmarinic, lithospermic, salvianolic, monardic, shimobashiric and yunnaneic acids were identified as predominant components. The examined extracts (1-100 µg/mL) partly prevented harmful effects of the peroxynitrite-induced oxidative stress in blood plasma (decreased oxidative damage to blood plasma components and improved its non-enzymatic antioxidant capacity). The cellular safety of the extracts was confirmed in experimental models of blood platelets and peripheral blood mononuclear cells. COX-2 inhibitor screening evidently suggested a stronger activity of P. officinalis (IC50 of 13.28 and 7.24 µg/mL, in reaction with synthetic chromogen and physiological substrate (arachidonic acid), respectively). In silico studies on interactions of main components of the Pulmonaria extracts with the COX-2 demonstrated the abilities of ten compounds to bind with the enzyme, including rosmarinic acid, menisdaurin, globoidnan A and salvianolic acid H.

Leaves of Cleome amblyocarpa Barr. And Murb. And Cleome arabica L.: Assessment of nutritional composition and chemical profile (LC-ESI-MS/MS), anti-inflammatory and analgesic effects of their extracts.

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.

Water Soldier Stratiotes aloides L.-Forgotten Famine Plant With Unique Composition and Antioxidant Properties.

Stratiotes aloides L. is common water plant in central Poland. Due to its expansive character, S. aloides L. can strongly affect the functioning of aquatic ecosystems. S. aloides L. was an important famine plant in central Poland. This plant was commonly collected and cooked until the turn of the 20th century. It has also been used to heal wounds, especially when these are made by an iron implement. The objective of the present work was to study the phenolic profile in the leaves and roots of S. aloides as well as their antioxidant potential and ability to inhibit lipoxygenase (LOX) in the light of their potential bioaccessibility. The dominant compound in its leaves was luteolin-7-O-hexoside-glucuronide (5.84 mg/g DW), whereas the dominant root component was chrysoeriol-7-O-hexoside-glucuronide (0.83 mg/g DW). Infusions from leaves, roots, and their 1:1 (v/v) mixture contained potentially bioaccessible antiradical compounds. S. aloides is a good source of water-extractable reductive compounds. Especially valuable are the leaves of this plant. The roots of S. aloides contained very active hydrophilic compounds able to chelate metal ions. However, their potential bioaccessibility was relatively low. The hydrophilic compounds from the leaves were the most effective XO inhibitors (EC50 = 9.91 mg DW/mL). The water-extractable compounds derived from the leaves and roots acted as uncompetitive LOX inhibitors.

Anticancer Potential and Capsianosides Identification in Lipophilic Fraction of Sweet Pepper (Capsicum annuum L.).

This study aimed to determine the health-promoting properties of sweet pepper by comparing the activity of fractions with variable lipophilicity. Fractions from red pericarp: aqueous (F1), 40% MeOH (F2), and 70% MeOH (F3) were analyzed for antiradical activity (with DPPH• and ABTS+•), and the contents of total phenolic compounds (TP), flavonoids (TF), and dihydroxycinnamic acids (TDHCA). The anticancer potential of the fractions was evaluated in vitro using different cancer cell lines: human colorectal carcinoma (HCT116) and PC-3 (prostate cancer cell). Fibroblast-like cells of L929 obtained from subcutaneous adipose tissue of mouse were used as normal cells. The highest content of TP, TF, and TDHCA along with the strongest antiradical activity was observed for fraction F2, while the strongest anticancer properties against PC-3 were observed in fraction F3. Fraction F3 primarily contained capsianoside derivatives, which had been isolated through chromatographic methods and identified by spectral methods. These analyses helped in identifying 8 compounds, including 3 new compounds.

Norditerpenoids with Selective Anti-Cholinesterase Activity from the Roots of Perovskia atriplicifolia Benth.

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 studies were also performed on the active compounds. Natural oxygenated norditerpenoids from the traditional Central Asian medicinal plant P. atriplicifolia are selective BChE inhibitors. Their high potential makes them useful candidate molecules for further investigation as lead compounds in the development of a natural drug against dementia caused by neurodegenerative diseases.

Reinvestigation of Herniaria glabra L. saponins and their biological activity.

Twelve undescribed triterpenoid pentacyclic glycosides, medicagenic acid (3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-ß-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-[ß-D-apiofuranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 3-O-ß-D-glucuronopyranosyl-28-O-{[α-L-rhamnopyranosyl-(1 → 2)]-3,4-O-diacetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[2-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[3-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[4-O-acetyl-α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid, 28-O-{[ß-D-glucopyranosyl-(1 → 2)]-[ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-12-ene-23,28-dioic acid), zanhic acid (3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}2ß,3ß,16α-trihydroxyolean-12-ene-23,28-dioic acid, 3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-ß-D-fucopyranosyl-(1→)}-2ß,3ß,16α-trihydroxyolean-12-ene-23,28-dioic acid), 29-hydroxy-medicagenic acid (3-O-ß-D-glucuronopyranosyl-28-O-{[ß-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 3)]-4-O-acetyl-ß-D-fucopyranosyl-(1→)}-2ß,3ß,29ß-trihydroxyolean-12-ene-23,28-dioic acid) and herniaric acid (28-O-{[6-O-acetyl-ß-D-glucopyranosyl-(1 → 2)]-[α-L-rhamnopyranosyl-(1 → 4)-ß-D-glucopyranosyl-(1 → 6)]-ß-D-glucopyranosyl-(1→)}-2ß,3ß-dihydroxyolean-18-ene-23,28-dioic acid) were isolated from the whole plant extract of Herniaria glabra L. (Caryophyllaceae), wild growing in the Ukraine. In addition, five known triterpenoid saponins; i.e. herniariasaponins 1, 4, 5, 6, and 7 were also isolated. Their structures were elucidated by HRESIMS, 1D and 2D NMR spectroscopy, as well as by comparison with the literature data. Twelve herniariasaponins, the purified crude extract, and the saponin fraction were evaluated in vitro for their xanthine oxidase, collagenase, elastase, and tyrosinase inhibitory activity. Moreover, herniariasaponins 4, 5, and 7 were screened for their cholinesterase inhibitory potential. As a result, no or low inhibition towards the mentioned enzymes was observed.

Yuccalechins A-C from the Yucca schidigera Roezl ex Ortgies Bark: Elucidation of the Relative and Absolute Configurations of Three New Spirobiflavonoids and Their Cholinesterase Inhibitory Activities.

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 against AChE and BChE, and they showed a weak inhibition only towards AChE (IC50 294.18 µM for 26, and 655.18 µM for 29). Furthermore, molecular docking simulations were performed to investigate the possible binding modes of 26 and 29 with AChE.

Chemical Profile and Antioxidant Activity of Zinnia elegans Jacq. Fractions.

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 such as chlorogenic acids and apigenin, kaempferol, and quercetin glycosides. Antioxidant assays showed that certain fractions exhibit moderate 15-LOX inhibition (Fr 2, IC50 = 18.98 µg/mL) and metal chelation (e.g., Fr 1-2, EC50 = 0.714-1.037 mg/mL) activities as compared to positive controls (20.25 µg/mL for kaempferol and 0.068 mg/mL for EDTA, respectively). For Fr 2, the 15-LOX inhibition activity seems to be related to the abundance of kaempferol glycosides. The NMR analyses revealed the presence of a kaempferol 3-O-glycoside, and a guanidine alkaloid previously not described in this species.