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Monodesmosidic oleanene-type saponins from kidney vetch (Anthyllis vulneraria L.) with hemolytic activity
Abstract and Figures
Two undescribed monodesmosidic oleanene-type saponins, namely 3β-O-{[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-saikogenin G (1) and 3β-O-{[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl}-16-deoxysaikogenin F (2), named anthylloside A and B, have been isolated from an acetone-water extract from aerial parts of kidney vetch (A. vulneraria L.). Isolation of 1 and 2 was achieved by solvent partition with EtOAc and subsequent repeated chromatographic purification. The structures of the isolated compounds were elucidated by spectrometric (HR-MS) and spectroscopic methods (¹H- and ¹³C-NMR, UV, IR and CD), as well as GC–MS analysis of samples after 1 N HCl hydrolysis and subsequent derivatization. The configuration and conformation of both 1 and 2 were assigned by means of comprehensive 2D-NMR analyses including ¹H-¹H−COSY, ROESY, decoupled gHSQC, gHMBC and selective 1D-TOCSY experiments. Moreover, 1 and 2 possess significant hemolytic activity, which was assessed in a blood agar assay and compared to that of three reference saponins.
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... The membranolytic properties of NE, HE and TE are compared by determining their hemolytic activities (HA) as a standard method [29,35,47,[51][52][53][54]. HA is evaluated by determining the evolution of the hemoglobin release in solution when a suspension of red blood cells is exposed to increasing concentrations of the tested molecules. ...
Saponins are specific metabolites abundantly present in plants and several marine animals. Their high cytotoxicity is associated with their membranolytic properties, i.e., their propensity to disrupt cell membranes upon incorporation. As such, saponins are highly attractive for numerous applications, provided the relation between their molecular structures and their biological activities is understood at the molecular level. In the present investigation, we focused on the bidesmosidic saponins extracted from the quinoa husk, whose saccharidic chains are appended on the aglycone via two different linkages, a glycosidic bond, and an ester function. The later position is sensitive to chemical modifications, such as hydrolysis and methanolysis. We prepared and characterized three sets of saponins using mass spectrometry: (i) bidesmosidic saponins directly extracted from the ground husk, (ii) monodesmosidic saponins with a carboxylic acid group, and (iii) monodesmosidic saponins with a methyl ester function. The impact of the structural modifications on the membranolytic activity of the saponins was assayed based on the determination of their hemolytic activity. The natural bidesmosidic saponins do not present any hemolytic activity even at the highest tested concentration (500 µg·mL−1). Hydrolyzed saponins already degrade erythrocytes at 20 µg·mL−1, whereas 100 µg·mL−1 of transesterified saponins is needed to induce detectable activity. The observation that monodesmosidic saponins, hydrolyzed or transesterified, are much more active against erythrocytes than the bidesmosidic ones confirms that bidesmosidic saponins are likely to be the dormant form of saponins in plants. Additionally, the observation that negatively charged saponins, i.e., the hydrolyzed ones, are more hemolytic than the neutral ones could be related to the red blood cell membrane structure.
Leguminosae is one of the largest families of ethnopharmacological importance. Most of the legumes are biochemical factories for the production of a variety of secondary metabolites (SMs) that are effective in treating various diseases. These important SMs produced by legumes are directly or indirectly of great importance for bios. SMs consisting of terpenoids, phenols, and nitrogen-containing compounds exhibit various biological activities such as anti-inflammatory, antitumor, antiviral, and antibacterial. In the meantime, the biofortification of plant foods has recently garnered a great deal of consideration, as it attempts to improve the consumption of vitamins, minerals, and antioxidants, which are essential because of their importance to human health and disease prevention. Moreover, the definition of biofortification has been expanded to include not just the micronutrient enhancement but also the crop nutritional content enhancement by the addition of SMs. In this perspective, the investigation of a plant’s SMs is crucial to the improvement of a new breed of plants that partially compensate for Western diets’ inferior nutritional quality with improved quality food sources. This chapter articulates different aspects of medicinal legumes including plant breeding, biotechnology techniques, and new breakthroughs in genomic approaches as a useful implement for biofortification of SMs and the improvement of healthful food options.
A new species of Anthyllis endemic to central Apennine growing in dry pastures on limestone in the montane belt, within Abruzzo and Lazio administrative regions (central Italy), is here described and illustrated and the IUCN assessment is proposed. This new species belongs to the morphologically very variable Anthyllis vulneraria species complex and it is close to A. pulchella (south-eastern Europe and Caucasus), but it can be clearly distinguished by its smaller flowers, mainly light yellow-coloured, bracts longer than flowers, calyx pink-coloured (usually only at apex) and size of cauline leaves and leaflets. Furthermore, the name A. pulchella is here lectotypified, by a second-step typification, on a specimen preserved at PAD.
Background
Bupleurum is one of the most important traditional Chinese medicines and an ingredient in many compound preparations. It is widely used together with other drugs in clinical practice, and thus there is great potential for drug–drug interactions. Saikosaponin D (SsD) is a major bioactive triterpenoid saponin extracted from Bupleurum with anti-inflammatory, anticancer, antioxidative, and antihepatic fibrosis effects. Effects of the main components of Bupleurum on cytochromes P450 (CYPs) need to be clarified in the clinical application of combination therapies of formulations containing SsD or Bupleurum.
Purpose
This study aimed to investigate the effects of SsD on the CYP1A2 and CYP2D6 mRNAs, protein expression, and relative enzyme activities in HepaRG cells.
Methods
HepaRG cells were cultured with SsD at concentrations of 0.5, 1, 5 and 10 μM for 72 hours. mRNA and protein expression of CYP1A2 and CYP2D6 were analyzed with real-time PCR and Western blot analysis. Relative enzyme activities were analyzed with HPLC based on consumption of the specific probe substrate.
Results
SsD significantly induced expression of mRNA and increased relative activity of CYP1A2 in HepaRG cells after the cells had been treated with SsD at concentrations of 1, 5 and 10 μM. SsD also induced protein expression of CYP1A2 at concentrations of 5 and 10 μM. SsD exhibited an inductive effect on CYP2D6 mRNA and protein expression, while increasing the relative activity of CYP2D6 at concentrations of 5 and 10 μM.
Conclusion
This study is the first to investigate the effect of SsD on CYP1A2 and CYP2D6 in HepaRG cells, and the results may provide some useful information on potential drug–drug interactions related to clinical preparations containing SsD or Bupleurum.
Medicinal plants are widely used in folk medicine but quite often their composition and biological effects are hardly known. Our study aimed to analyze the composition, cytotoxicity, antimicrobial, antioxidant activity and cellular migration effects of Anthyllis vulneraria, Fuchsia magellanica, Fuchsia triphylla and Lysimachia nummularia used in the Romanian ethnomedicine for wounds. Liquid chromatography with mass spectrometry (LC-MS/MS) was used to analyze 50% (v/v) ethanolic and aqueous extracts of the plants’ leaves. Antimicrobial activities were estimated with a standard microdilution method. The antioxidant properties were evaluated by validated chemical cell-free and biological cell-based assays. Cytotoxic effects were performed on mouse fibroblasts and human keratinocytes with a plate reader-based method assessing intracellular adenosine triphosphate (ATP), nucleic acid and protein contents and also by a flow cytometer-based assay detecting apoptotic–necrotic cell populations. Cell migration to cover cell-free areas was visualized by time-lapse phase-contrast microscopy using standard culture inserts. Fuchsia species showed the strongest cytotoxicity and the highest antioxidant and antimicrobial activity. However, their ethanolic extracts facilitated cell migration, most probably due to their various phenolic acid, flavonoid and anthocyanin derivatives. Our data might serve as a basis for further animal experiments to explore the complex action of Fuchsia species in wound healing assays.
Two new oleanane-type triterpenoids, 13,28-epoxy-23-hydroxy-11-oleanene-3-one (1) and 13,28- epoxy-21β ,23-dihydroxy-11-oleanene-3-one (2), along with seven known compounds, have been isolated from the aerial parts of Buddleja asiatica Lour. All structures were elucidated by spectroscopic techniques (NMR, MS, UV, and IR).
The main targets of this work were to determine the phenolic content of Anthyllis vulneraria (A. vulneraria) leaves and flowers and to evaluate their antioxidant activity. Total polyphenols and flavonoid content (TPC and TFC, respectively) were determined. Antioxidant capacity was evaluated by the Ferric Reducing Antioxidant Power (FRAP), the Oxygen Radical Absorbance Capacity (ORAC), the Trolox Equivalent Antioxidant Capacity (TEAC) and the diphenyl picrylhydrazyl (DPPH) assays, and by the analysis of primary and secondary oxidation products in oil-in-water emulsions and in raw beef patties during storage. The results revealed that the flowers of the A. vulneraria contained the highest content of total polyphenols and flavonoids and extracts from these tissues exhibited the strongest antioxidant activity, as they were more effective at retarding lipid oxidation in oil-in-water emulsions and raw beef patties than extracts from the leaves which had a potent antioxidant effect only at the beginning of the oxidation process. The results of this study allowed us to obtain a deep knowledge about the properties of A. vulneraria and confirmed the possibility of using its biologically active extracts in the food, cosmetic and pharmaceutical industries.
Over the past decades, a number of phytochemicals have been reported to possess potent pharmacological effects. Saikosaponins represent a group of oleanane derivatives, usually as glucosides, which are commonly found in medicinal plants Bupleurum spp., which have been used as traditional Chinese medicine for more than 1,000 years in China. Emerging evidence suggests that saikosaponins have many pharmacological effects, including sedation, anticonvulsant, antipyretic, antiviral, immunity, anti-inflammation, antitumor properties, protecting liver and kidney and so on. The present review provides a comprehensive summary and analysis of the pharmacological properties of saikosaponins, supporting the potential uses of saikosaponins as a medicinal agent.
The roots of Bupleurum chinense have a long history in traditional medicine to treat infectious diseases and inflammatory disorders. Two major compounds, saikosaponins A and D, were reported to exert potent anti-inflammatory activity by inhibiting NF-κB. In the present study, we isolated new saikosaponin analogues from the roots of B. chinese interfering with NF-κB activity in vitro. The methanol-soluble fraction of the dichloromethane extract of Radix Bupleuri was subjected to activity-guided isolation yielding 18 compounds, including triterpenoids and polyacetylenes. Their structures were determined by spectroscopic methods as saikogenin D (1), prosaikogenin D (2), saikosaponins B2 (3), W (4), B1 (5), Y (6), D (7), A (8), E (9), B4 (10), B3 (11), and T (12), saikodiyne A (13), D (14), E (15) and F (16), falcarindiol (17), and 1-linoleoyl-sn-glycero-3-phosphorylcholine (18). Among them, 4, 15, and 16 are new compounds, whereas 6, previously described as a semi-synthetic compound, is isolated from a natural source for the first time, and 13–17 are the first reports of polyacetylenes from this plant. Nine saponins/triterpenoids were tested for inhibition of NF-κB signaling in a cell-based NF-κB-dependent luciferase reporter gene model in vitro. Five of them (1, 2, 4, 6, and 8) showed strong (> 50%, at 30 µM) NF-κB inhibition, but also varying degrees of cytotoxicity, with compounds 1 and 4 (showing no significant cytotoxicity) presenting IC50 values of 14.0 µM and 14.1 µM in the cell-based assay, respectively.
In the phytochemical investigation of Buddleja lindleyana, a new 3-acetyl substituted triterpene, 13, 28-epoxy-23-hydroxy-3β-acetoxy-olean-11-ene (1), together with four same skeleton type known compounds (2-5) were isolated. The structure of 1 was elucidated by means of extensive spectroscopic analysis. Their neuroprotective effect against 1-methyl-4-phenylpyridinium ion-induced (MPP+-induced) neurotoxicity in SH-SY5Y cells were evaluated. The structure activity relationship of compounds 1-5 has been discussed preliminarily.
Saponins are steroid or triterpenoid glycosides, common in a large number of plants and plant products that are important in human and animal nutrition. Several biological effects have been ascribed to saponins. Extensive research has been carried out in the membrane-permeabitising, immunostimulant, hypocholesterolaemic and anticarcinogenic properties of saponins and they have also been found to significantly affect reproduction in animals. These structurally diverse compounds have also been observed to kill protozoans and molluscs, to have an effect on cold blooded animals, also to have the analgesic, anti-nociceptive, antioxidant activity, to impair the digestion of protein, to cause hypoglycemia and to act as antifungal and antiviral agents.
Saponins, naturally occurring glycosides and triterpene glycosides in plants, are considered useful in the prophylaxis and treatment of several disorders, including malignancy. The effect of these substances is partly attributable to induction of both apoptosis and necrosis. Saponin has previously been shown to trigger hemolysis. Erythrocytes may avoid hemolysis by entering programmed cell death or eryptosis, characterized by cell shrinkage and cell membrane scrambling, leading to phosphatidylserine exposure at the erythrocyte surface. Eryptosis is triggered by increase of cytosolic Ca(2+) activity ([Ca(2+)] i ). The present study explored, whether exposure of human erythrocytes to saponin modifies [Ca(2+)] i , ceramide formation, hemolysis, and eryptosis. Cell volume was estimated from forward scatter, phosphatidylserine exposure from annexin V binding, hemolysis from hemoglobin release, [Ca(2+)] i from Fluo3-fluorescence, and ceramide utilizing specific antibodies. A 24 h exposure to saponin (15 µg/ml) resulted in a significant increase of annexin V binding and a significant stimulation of hemolysis. Saponin (15 µg/ml) further increased [Ca(2+)] i and ceramide formation. Annexin V binding was significantly blunted but not abrogated in the nominal absence of extracellular Ca(2+). Saponin thus triggers cell membrane scrambling, an effect partially due to entry of extracellular Ca(2+) and ceramide formation.
The paper presents results of morphometric analysis of Anthyllis vulneraria L. in Poland based on 828 herbarium specimens. This study investigates five taxa which have been recognized in Poland: Anthyllis vulneraria L. ssp. vulneraria, Anthyllis vulneraria ssp. polyphylla (DC.) Nyman, A. vulneraria ssp. maritima (Schweigg.) Corb., A. vulneraria ssp. alpestris Asch. et Graebn. and A. vulneraria ssp. carpatica (Pant.) Nyman as well as three intermediate taxa of presumably hybrid origin. Multivariate statistical analyses of 12 quantitative and 10 qualitative characteristics revealed conspicuous variation within A. vulneraria. Analysis of variance (ANOVA), principal coordinate analysis (PCoA), correspondence analysis (CA) and discriminant analysis (DA) proved the taxonomic usefulness of quantitative characteristics such as number of rosette leaves, calyx length, inflorescence length, the ratio of leaf length/width, bract length as well as qualitative characteristics such as stem hairiness, calyx colour, calyx indumentum, distances between stem leaves and form of rosette leaves. The issues concerning intermediate morphotypes occurring in Poland and their status are discussed. Finally, a key for determination of taxa within A. vulneraria in Poland and distribution maps based on the material examined are provided.
Anthyllis vulneraria L. is a plant used in folk medicine for treatment of inflammation, disturbances of metabolism and acne and accelerates the healing of wounds. In this study, total phenolic, flavonoid and proanthocyannidin contents, and antioxidant activities of Anthyllis vulneraria polyphenols, flavonoids and tannins extracts were evaluated using in vitro assays. The quantitative estimation showed that leaves and flowers of Anthyllis vulneraria were rich in polyphenols (185.00 – 326.66 mg PE / g DW). Anthyllis vulneraria flowers extract contained the highest levels of total phenolic content (326.66 mg PE /g DW) and flavonoid content (0.14 mg CE /g DW). The leaves extract had the highest content of proanthocyannidins (1.07 %). Polyphenols, flavonoids and tannins were extracted from leaves and flowers of Anthyllis vulneraria. In DPPH (2, 2-Diphenyl-1-picrylhydrazyl) radical scavenging assay, all extracts had shown significant optimum inhibition (53.52 – 93.46 %). In addition the IC 50 values of the extracts in DPPH free radical scavenging assay, ranged from 1.06 to 15.00 mg/ml, compared to 0.12, 0.21 and 0.46 mg/ml for gallic acid, tannic acid and ascorbic acid respectively. A dose dependant curve was obtained for all extracts in the ferric reducing power assay (FRAP). However, the antioxidant potencies of ascorbic acid and sample extracts were comparable at low concentrations. The leaves and flowers of Anthyllis vulneraria provide a source of natural antioxidant, and may be beneficial to the health of consumers. They played an important role in protecting the human body against free radicals.
Anthyllis vulneraria L. (Fabaceae) s. lato includes many cryptic taxa, ranging from 25 to 60 subspecies according to different authors. The delimitation
of intraspecific taxa of A. vulneraria s. lato has always been complicated and inconsistent. Different data sets (multivariate
analyses of morphological variation, allozymes, chloroplast SSRs and ITS) have not resolved the existing problem with distinguishing
some subspecies. We used the amplified fragment length polymorphism (AFLP) analysis to describe the differentiation in this
species complex and to characterize variation on a geographic scale. Some correlation was found between genetic variability
and geographic distribution (western-eastern directional variation), but AFLP data analysis did not reveal clear intraspecific
structure of the seven analysed taxa. The analysed specimens did not comprise groups correlated with the subspecies.
Two new triterpene saponins ( 1- 2) together with three known saponins, deglucocyclamin I ( 3), cyclamin ( 4), and mirabilin ( 5), were isolated from the tubers of Cyclamen trocopteranthum. They were elucidated as 3 beta- O-{4- O-[3-hydroxyl-3-methylglutaryl]- beta-D-xylopyranosyl-(1 --> 2)- beta-D-glucopyranosyl-(1 --> 4)-[ beta-D-glucopyranosyl-(1 --> 2)]- alpha-L-arabinopyranosyl}-16 alpha-hydroxy-13 beta,28-epoxy-oleanan-30-al ( 1) and 3 beta- O-{4- O-[3-hydroxyl-3-methylglutaryl]- beta-D-xylopyranosyl-(1 --> 2)-[ beta-D-glucopyranosyl-(1 --> 6)]- beta-D-glucopyranosyl-(1 --> 4)-[ beta-D-glucopyranosyl-(1 --> 2)]- alpha-L-arabinopyranosyl}-16 alpha-hydroxy-20,30-lactone-olean-12-ene ( 2). Their structures were characterized mainly by a combination of 1D- and 2D-NMR techniques ( (1)H- (1)H COSY, TOCSY, NOESY, HSQC, and HMBC) and mass spectroscopy. Saponins 1, 3, and 4 showed a weak cytotoxic activity when tested against HT-29 and HCT 116 tumor colon cancer cells.
Triterpene pentacyclic sapogenin, 3beta,22beta,24-trihydroxy-olean-12-ene, soyasapogenol B, was isolated for the first time from the Anthyllis vulneraria L.. Identification and structure assignment was performed by 1H and 13C NMR spectroscopy.
Four new triterpenoid saponins, 3-O-([beta-D-glucopyranosyl-(1-->2)]-beta-D-galactopyranosyl)-11alpha-methoxy-23-hydroxylongispinogenin, 3-O-([beta-D-glucopyranosyl-(1-->2)]-beta-D-galactopyranosyl)-11alpha-methoxy-23,29-dihydroxylongispinogenin, 3-O-([beta-D-glucopyranosyl-(1-->2)]-beta-D-galactopyranosyl)-29-hydroxysaikogenin F and 3-O-([beta-D-glucopyranosyl-(1-->2)]-beta-D-galactopyranosyl)-saikogenin F, have been isolated from Atriplex semibaccata. The structures were determined primarily by NMR spectroscopy. The assignment of NMR signals was performed by means of 1H-1H COSY, ROESY, HMQC and HMBC experiments.
Saponins are a diverse group of compounds widely distributed in the plant kingdom, which are characterized by their structure containing a triterpene or steroid aglycone and one or more sugar chains. Consumer demand for natural products coupled with their physicochemical (surfactant) properties and mounting evidence on their biological activity (such as anticancer and anticholesterol activity) has led to the emergence of saponins as commercially significant compounds with expanding applications in food, cosmetics, and pharmaceutical sectors. The realization of their full commercial potential requires development of new processes/processing strategies to address the processing challenges posed by their complex nature. This review provides an update on the sources, properties, and applications of saponins with special focus on their extraction and purification. Also reviewed is the recent literature on the effect of processing on saponin structure/properties and the extraction and purification of sapogenins.
There is now a large body of theory concerning algebraic varieties over finite fields, and many conjectures exist in this area that are of great interest to researchers in number theory and algebraic geometry. This 1995 book is concerned with the arithmetic of diagonal hypersurfaces over finite fields, with special focus on the Tate conjecture and the Lichtenbaum-Milne formula for the central value of the L-function. It combines theoretical and numerical work, and includes tables of Picard numbers. Although this book is aimed at experts, the authors have included some background material to help non-specialists gain access to the results.
Extracts of kidney vetch ( Anthyllis vulneraria L.) are becoming increasingly interesting as ingredients for the health and cosmetics industry. However, comprehensive phytochemical investigations of this plant are scant in the literature. Thus, the aim of the present work was an in‐depth characterization of semi‐polar constituents from A. vulneraria . To capture a broad spectrum of compounds, aerial parts of A. vulneraria were extracted with EtOH/water and the resulting crude extracts fractionated by partition between AcOEt and BuOH. Secondary plant metabolites were analyzed by HPLC‐ESI‐MS n and GC‐MS. In a fraction obtained from the BuOH extract via Amberlite ® XAD‐7 purification glycosides of kaempferol, quercetin, isorhamnetin and rhamnocitrin were detected by LC‐MS n , besides flavonoids acylated with meglutol (3‐hydroxy‐3‐methylglutaric acid), acetic and ferulic acids. Moreover, aglycons were analyzed in extracts after 1N HCl hydrolysis and derivatization with BSTFA. GC‐MS analysis of the hydrolysates revealed the incidence of compounds like meglutol, OH/OMe‐substituted benzoic acids, ferulic and fatty acids, flavonoids, sugars and the triterpenoid medicagenic acid. Furthermore, a hemolytic activity was detected in the AcOEt extract using a blood‐agar assay, and this was ascribed to the occurrence of saponins. In a saponin fraction, obtained from the AcOEt extract by chromatographic purification, two main saponins were characterized by LC‐MS n and HR‐ESI‐MS n . A pure sapogenin could be isolated via VLC and CC purification upon acid hydrolysis of the saponins and assigned to saikogenin D by NMR analysis.
Abstract Saponins are a class of natural compounds present in pulses having surface active properties. These compounds show variation in type, structure and composition of their aglycone moiety and oligosaccharide chains. Saponins have plasma cholesterol lowering effect in humans and are important in reducing the risk of many chronic diseases. Moreover, they have shown strong cytotoxic effects against cancer cell lines. However, more epidemiological and clinical studies are required for the proper validation of these health promoting activities. Processing and cooking promotes the loss of saponins from foods. The effect of soaking, sprouting and cooking on the stability and bioavailability of saponins in pulses is an important area which should be thoroughly worked out for achieving desirable health benefits. In the present review, the structures, contents and health benefits of saponins present in pulses are discussed. Moreover, the effect of processing (of pulses) on the saponins is also highlighted.
Verbascum species (Scrophulariaceae), which are widespread plants in Anatolia, are used as expectorant and mucolytic in folk medicine. In this paper, the chemical constituents of saponins, iridoid and phenylethanoid glycosides, monoterpene glucoside, neolignan glucosides, flavonoids, steroids, spermine alkaloids and other compounds of these species are reviewed.
As a part of our ongoing studies on cytotoxic triterpenoid saponins from herbal medicines, phytochemical investigation of the roots of Bupleurum chinense DC. afforded four new saikosaponins (1-4), along with 16 known ones (5-20). Their structures were established by direct interpretation of their spectral data, mainly HR-ESI-MS, 1D NMR and 2D NMR, and by comparison with literature data. Among them, compound 20 was isolated from the natural product for the first time. The cytotoxicities of all compounds against five selected human cancer cell lines (A549, HepG2, Hep3B, Bcap-37 and MCF-7) were assayed. In general, a number of the isolated compounds exhibited potent cytotoxic activities against the five selected human cancer cell lines. In particular, compounds 3, 8-9, 11-13, 16 and 20 showed more potent cytotoxic activities against the HepG2 and A549 cell lines than the positive control 5-fluorouracil. Based on the primary screening results, the preliminary structure-activity relationship (SAR) studies were also discussed. The SAR results suggest that the 13,28-epoxy bridge, the orientation of the hydroxyl group and the type of the sugar units are important requirements for cytotoxicity and selectivity.
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Pairs of enantiomers of nine aldoses were separated by gas-liquid chromatography on an OV-17 capillary column as the trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R) carboxylates, which were obtained by the reaction of aldoses with L-cysteine methyl ester. This method was applied to the determination of the absolute configurations of the component monosaccharides of a Thladiantha saponin. © 1987, The Pharmaceutical Society of Japan. All rights reserved.
Anthyllis vulneraria (Leguminosae, subfamily Lotoideae) has been investigated for flavonoids by means of polyamide column chromatography and TLC. The following flavonols have been characterized: quercetin, kaempferol and isorhamnetin, previously reported in this genus, and rhamnocitrin (I), rhamnetin (II), 3,7,4′-trihydroxy-flavone (III), fisetin (IV) and geraldol (V). This last compound has only been isolated once before as a natural product.
Saponine 1 (6′-O-acetyl-3β-pregna-5,20-dienyl-α-l- galactopyranoside), containing l-galactose, has been isolated from the marine octocoral Muricea c.f. purpurea. Saponine 1 (6′-O-acetyl-3β-pregna-5, 20-dienyl-α-l-galactopyranoside), that contains a l-galactose moiety linked to the aglycone through an infrequent α-glycosidic bond, has been isolated from the marine octocoral Muricea c.f. purpurea. This constitutes the first report on the occurrence of l-Gal as a nonpolymeric natural product. A CD procedure for the absolute stereochemical assignment of saponins, based on the CD analysis of its perbenzoylated derivative, is proposed.
The application of 1D selective, 2D and 3D NMR techniques to the structure elucidation of verbascosaponin (1) is demonstrated. Combinations of ROESY and TOCSY are powerful tools. Each of these multidimensional ROESY-TOCSY and TOCSY-ROESY experiments provides detailed information about the sequence of oligosaccharide structures and the positions of glycosidation. The structure of a further saponin 2 from the officinal drug Flores Verbasci is determined as 3β-O-{α-L-rhamnopyranosyl-(1→4)-β-D-glucopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→2)-]-β-D-fucopyranosyl}-13β,28-epoxyolea-11-ene-16α,23α-diol.
Two new triterpenoid glycosides, mimengosides H (1) and I (2), were isolated from the fruits of Buddleja lindleyana Fort. Their structures were determined by extensive spectroscopic methods. Neuroprotective effects of these isolates against 1-methyl-4-phenylpyridinium ion-induced neurotoxicity in PC12 cells were evaluated. Pretreatment with compound 1 had potential protective effect in a concentration range from 0.1 to 1 μmol l⁻¹.
Saponins are bioactive compounds generally considered to be produced by plants to counteract pathogens and herbivores. Besides their role in plant defense, saponins are of growing interest for drug research as they are active constituents of several folk medicines and provide valuable pharmacological properties. Accordingly, much effort has been put into unraveling the modes of action of saponins, as well as in exploration of their potential for industrial processes and pharmacology. However, the exploitation of saponins for bioengineering crop plants with improved resistances against pests as well as circumvention of laborious and uneconomical extraction procedures for industrial production from plants is hampered by the lack of knowledge and availability of genes in saponin biosynthesis. Although the ability to produce saponins is rather widespread among plants, a complete synthetic pathway has not been elucidated in any single species. Current conceptions consider saponins to be derived from intermediates of the phytosterol pathway, and predominantly enzymes belonging to the multigene families of oxidosqualene cyclases (OSCs), cytochromes P450 (P450s) and family 1 UDP-glycosyltransferases (UGTs) are thought to be involved in their biosynthesis. Formation of unique structural features involves additional biosynthetical enzymes of diverse phylogenetic background. As an example of this, a serine carboxypeptidase-like acyltransferase (SCPL) was recently found to be involved in synthesis of triterpenoid saponins in oats. However, the total number of identified genes in saponin biosynthesis remains low as the complexity and diversity of these multigene families impede gene discovery based on sequence analysis and phylogeny. This review summarizes current knowledge of triterpenoid saponin biosynthesis in plants, molecular activities, evolutionary aspects and perspectives for further gene discovery.
The components of the saikosaponins a and b derived from the root of Bupleurum falcatum L. have been re-investigated. Saikosaponin b has been shown to consist of 16α, 23, 28-trihydroxyoleana-11,13(18)-dien-3β-yl D-glucopyranosyl-(1 → 3)-β-D-fucopyranoside (II)(saikosaponin b2) and 16α, 23,28-trihydroxy-11α-methoxy-olean-12-en-3β-yl D-glucopyranosyl-(1 → 3)-β-D-fucopyranoside (V)(saikosaponin b4), and saikosaponin a contains 16β, 23,28-trihydroxy-11α-methoxyolean-12-en-3β-yl D-glucopyranosyl-(1 → 3)-β-D-fucopyrano-side (XXI)(saikosaponin b3) and a small amount of 16β, 23,28-trihydroxyoleana-11,13(18)-dien-3β-yl D-glucopyranosyl-(1 → 3)-β-D-fucopyranoside (XXII)(saikosaponin b1).
The hemolytic properties and the adsorbability on red blood cells of saikosaponin a, saikosaponin d and 13 metabolites formed in the alimentary tract were investigated. Among these compounds, saikosaponin d and its intestinal product, prosaikogenin G, which possess an alpha-hydroxyl function at C16, showed the strongest hemolytic activity at the dose range of 1.0 to 5.0 micrograms/ml. Saikosaponin a and its intestinal product, prosaikogenin F, which possess a beta-hydroxyl function at C16, showed activity above 10 micrograms/ml. In this case, the monoglycoside, prosaikogenin F, showed the stronger activity than the diglycoside, saikosaponin a. Among the gastric products whose ether ring was cleaved to produce a carbinol, the monoglycosides, prosaikogenin A and prosaikogenin H, showed a slight activity above 25 micrograms/ml, and the saikogenins except saikogenin A were inactive. Saikogenin A, however, had hemolytic activity at a dose of 15 micrograms/ml. The adsorbabilities of these compounds on red blood cell membranes closely paralleled their degrees of hemolytic activity.
Within a valorization program of natural regional resources, 50 ethanolic extracts of 41 indigenous plants have been subjected to chemical tests and antiviral screening. Four plants: Bryonia dioìca, Anthyllis vulneraria, Matricaria chamomilla, and M. inodora inhibit the growth of poliovirus. Furthermore, three (A. vulneraria, M. Chamomilla, and M. inodora) have an antiherpetic effect.
From the aerial parts of Verbascum (V.) sinaiticum, V. thapsiforme, V. fruticulosum and Celsia roripifolia, seven new saikosaponin homologues, called mulleinsaponins I-VII, having 13,28-epoxy-olean-11-ene skelton were isolated together with eight known saikosaponin homologues, 3-O-beta-D-fucopyranosyl saikogenin F, saikosaponin a, desrhamnosylverbascosaponin, songarosaponins C, D, mimengoside A and buddlejasaponins I, IV. The structures of mulleinsaponins I-VII were characterized as 3-O-beta-D-glucopyronosyl-(1-->3)-beta-D-fucopyranosyl-6-deoxy- saikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-beta-D - fucopyranosyl-16-deoxysaikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-beta-D - fucopyranosyl-saikogenin F, 3-O-alpha-L-rhamnopyranosyl- (1-->4)-beta-D-glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-be ta -D-fucopyranosyl-21 beta-hydroxysaikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)-[beta- D- glucopyranosyl-(1-->2)]-beta-D-fucopyranosyl-21 beta-acetoxysaikogenin F, 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranosyl-(1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D- fucopyranosyl-16 beta-acetoxysaikogenin F and 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl- (1-->3)-[beta-D-glucopyranosyl-(1-->2)]-beta-D-fucopyranosylsaikogeni n F 16-O-beta-D-glucopyranoside, respectively, from chemical and spectroscopic evidence.
Saponins are steroid or triterpenoid glycosides, common in a large number of plants and plant products that are important in human and animal nutrition. Several biological effects have been ascribed to saponins. Extensive research has been carried out into the membrane-permeabilising, immunostimulant, hypocholesterolaemic and anticarcinogenic properties of saponins and they have also been found to significantly affect growth, feed intake and reproduction in animals. These structurally diverse compounds have also been observed to kill protozoans and molluscs, to be antioxidants, to impair the digestion of protein and the uptake of vitamins and minerals in the gut, to cause hypoglycaemia, and to act as antifungal and antiviral agents. These compounds can thus affect animals in a host of different ways both positive and negative.
For the genus Anthyllis (Fam. Fabaceae, tribe Loteae), with few exceptions, little information is available on the genetic variation among and within species. This genus contains 20 species distributed throughout Europe, Africa, and the Mediterranean basin. The most widespread species is A. vulneraria, and over 30 intraspecies taxa have been identified based on plant morphology. To study the molecular phylogeny of the genus, the sequences of the internal transcribed spacers ITS1 and ITS2 of the nuclear ribosomal DNA of 10 Anthyllis species, including 11 subspecies of A. vulneraria and three subspecies of A. montana, were obtained and analysed together with sequences of five other species of the genus obtained from GenBank. Our results suggest that the genus Anthyllis is not monophyletic and is divided in two main clades: the Anthyllis sensu strictu and the "tetraphylla clade". The former includes most of the Anthyllis species, and the latter includes three annual species more closely related to Lotus. All the taxa were also analysed according to seven chloroplast microsatellites, and these data closely confirm the results obtained with the ITS phylogeny.
Plant saponins are widely distributed amongst plants and have a wide range of biological properties. The more recent investigations and findings into their biological activities were summarized. Isolation studies of saponins were examined to determine which are the more commonly studied plant families and in which families saponins have been identified.
Saikosaponins represent a group of oleanane derivatives, usually as glucosides, that are found in a number of plant families. Saikosaponins isolated from medicinal plants such as Bupleurum spp., Heteromorpha spp. and Scrophularia scorodonia have been reported to possess various biological activities, specifically antihepatitis, antinephritis, antihepatoma, anti‐inflammation, immunomodulation and antibacterial effects.
The aim of the present study was to examine the anticoronaviral activity of saikosaponins (A, B 2 , C and D) and their mode of action. Using the 2,3‐bis[2‐methoxy‐4‐nitro‐5‐sulfophenyl]‐5‐[(phenylamino) carbonyl‐2H‐tetrazolium hydroxide] (XTT) assay, results showed that all saikosaponins tested demonstrated antiviral activity at concentrations of 0.25–25 µmol/L, with the strongest activity being noted for saikosaponin B 2 (IC 50 = 1.7 ± 0.1 µmol/L). Interestingly, both saikosaponins A (50% cellular cytotoxicity (CC 50 ) concentration = 228.1 ± 3.8 µmol/L; selectivity index (SI) = 26.6) and B 2 (CC 50 = 383.3 ± 0.2 µmol/L; SI = 221.9) exhibited no cytotoxic effects on target cells at concentrations that achieved antiviral activity. In the time‐of‐addition studies, saikosaponin B 2 , at 6 µmol/L, significantly inhibited human coronavirus 229E infection following its addition at various time pre‐infection (−4 to −1 h), coinfection (0 h) and post‐infection (1–4 h). Furthermore, saikosaponin B 2 also showed an inhibitory effect on viral attachment and penetration.
The present results indicate that saikosaponin B 2 has potent anticoronaviral activity and that its mode of action possibly involves interference in the early stage of viral replication, such as absorption and penetration of the virus.
This paper contains first systematical revision of the results on traditional use of wild medicinal and aromatic herbs on the territory of Bosnia and Herzegovina (B&H)--west of Balkan Peninsula; Southeast of Europe. There have been detected 227 plants belonging to 71 different plant families, which are being used with ethno therapeutic purpose. Results were obtained by method of open ethno botanical interview which comprised 150 persons, whose average age was 63. Medicinal plants in ethno therapy are being used either in fresh, raw or dried condition. Different herbal parts, depending on period of vegetation season, sometimes even in winter, are basis for preparation of infusions (59%), decoct (19%), tinctures (4%). Especially original are balms known as Bosnian "mehlems", which are fresh cuted herbal parts mixed with lukewarm resin, raw cow butter or honey. In ethno therapy are mostly being used aerial plant organs. Majority of herbs is being used for treatment of illnesses of respiratory (22%), gastrointestinal (19%) and urinary and genital system (9%), for treatment of skin conditions (11%), as well as for nervous system and heart diseases (16%). The most original plants on the field of ethno pharmacology, comparing with ethno therapy practice of other regions, are as follows: Ballota nigra, Aesculus hippocastanum, Calluna vulgaris, Centaurea cyanus, Euphrasia rostkoviana, Geranium robertianum, Gentiana asclepiadea, Helichrysum italicum, Lycopodium clavatum, Marrubium vulgare, Nepeta cataria, Populus tremula, Ruta graveolens, Tamus communis, Teucrium montanum, T. chamaedrys, and endemic plants Gentiana lutea subsp. symphyandra, Teucrium arduini, Micromeria thymifolia, Satureja montana, S. subspicata, Rhamnus fallax and Viola elegantula. There haven't been noticed significant differences in the frequencies of medicinal plants use among different ethnical groups. But, it has been perceived that longer ethno therapeutic tradition possess inhabitants of sub- and Mediterranean areas, as well as inhabitants of the mountain areas of B&H, regardless their ethnicity.
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