Steroidal Aglycone Research Articles

Antioxidant and anti-glycation activities of Mandevilla velutina extract and effect on parasitemia levels in Trypanosoma cruzi experimental infection: In vivo, in vitro and in silico approaches

Ethnopharmacological relevanceMandevilla velutina (Mart. Ex Stadelm.) Woodson, known in Brazil as "infalível" and "jalapa", is a medicinal plant native from the Cerrado region (Brazilian Savannah). The underground organ (xylopodium) of this species is prepared as ethanolic extract or infusion and it is commonly used in traditional medicine to treat snake venom. Although, locals and indigenous populations from Cerrado have used M. velutina for the treatment of infection by Trypanosoma cruzi (Chagas’ disease). Aim of the studyThis study aimed to evaluate the in vitro antioxidant and anti-glycation activities of the crude hydroethanolic extract of M. velutina xylopodium. Besides, it aimed to evaluate its effect on parasitemia levels in vivo T. cruzi experimental infection. In addition, this study aimed to determine possible interactions between the main compound of the extract and molecular targets associated with survival and virulence of T. cruzi in silico approaches. Materials and methodsDetermination of total polyphenols, flavonoids and steroidal aglycones content were performed. In addition, high performance liquid chromatography (HPLC) was carried out to identify main compounds of the extract. Antioxidant activity was determined by DPPH radical scavenging, ferric ion reducing power (FRAP), Thiobarbituric acid reactive species (TBARS) and Oxygen Radical Absorbance Capacity (ORAC) methods. Anti-glycation activity was demonstrated through relative mobility in electrophoresis (RME), determination of free amino groups and inhibition of AGEs formation. Determination of the action of extract in parasitemia levels was performed by T. cruzi experimental infection of mice and nitrite levels were measured in the serum of animals evaluated in this study. Molecular docking analyses of the main compound (Velutinol A) with DNA and molecular targets associated with survival and virulence of T. cruzi. ResultsPhytoconstituents evaluation exhibited the presence polyphenols, flavonoids and steroidal aglycone, and HPLC identified the major presence of Velutinol A. Antioxidant and anti-glycation evaluations showed that the extract present significant activity in all methods evaluated. In addition, extract reduced the number of trypomastigotes and increased the survival of treated animals. The treatment using extract showed an interference in the synthesis of physiological nitric oxide as an immune response to infection. In silico assays demonstrated interaction between Velutinol A and DNA and molecular targets of T. cruzi. ConclusionsThe results showed that the hydroethanolic extract of M. velutina xylopodium contains bioactive compounds including polyphenols, flavonoids and steroidal aglycones (mainly Velutinol A) of which may be responsible for the antioxidant, anti-glycation and anti-parasitic activity against T. cruzi. Trypanocidal activity of M. velutina compounds may be linked to their influence on NO synthesis during infection and/or their capacity to bind and inhibit molecules associated to virulence and survival of T. cruzi.

Incorporation of nitrogen in antinutritional Solanum alkaloid biosynthesis.

Steroidal glycoalkaloids (SGAs) are specialized metabolites produced by hundreds of Solanum species including food crops, such as tomato, potato and eggplant. Unlike true alkaloids, nitrogen is introduced at a late stage of SGA biosynthesis through an unknown transamination reaction. Here, we reveal the mechanism by which GLYCOALKALOID METABOLISM12 (GAME12) directs the biosynthesis of nitrogen-containing steroidal alkaloid aglycone in Solanum. We report that GAME12, a neofunctionalized γ-aminobutyric acid (GABA) transaminase, undergoes changes in both active site specificity and subcellular localization to switch from its renown and generic activity in core metabolism to function in a specialized metabolic pathway. Moreover, overexpression of GAME12 alone in engineered S. nigrum leaves is sufficient for de novo production of nitrogen-containing SGAs. Our results highlight how hijacking a core metabolism GABA shunt enzyme is crucial in numerous Solanum species for incorporating a nitrogen to a steroidal-specialized metabolite backbone and form defensive alkaloids.

Steroidal scaffold decorations in Solanum alkaloid biosynthesis

Steroidal glycoalkaloids (SGAs) are specialized metabolites produced by hundreds of Solanum species, including important vegetable crops such as tomato, potato, and eggplant. Although it has been known that SGAs play important roles in defense in plants and “anti-nutritional” effects (e.g., toxicity and bitterness) to humans, many of these molecules have documented anti-cancer, anti-microbial, anti-inflammatory, anti-viral, and anti-pyretic activities. Among these, α-solasonine and α-solamargine isolated from black nightshade (Solanum nigrum) are reported to have potent anti-tumor, anti-proliferative, and anti-inflammatory activities. Notably, α-solasonine and α-solamargine, along with the core steroidal aglycone solasodine, are the most widespread SGAs produced among the Solanum plants. However, it is still unknown how plants synthesize these bioactive steroidal molecules. Through comparative metabolomic-transcriptome-guided approach, biosynthetic logic, combinatorial expression in Nicotiana benthamiana, and functional recombinant enzyme assays, here we report the discovery of 12 enzymes from S. nigrum that converts the starting cholesterol precursor to solasodine aglycone, and the downstream α-solasonine, α-solamargine, and malonyl-solamargine SGA products. We further identified six enzymes from cultivated eggplant that catalyze the production of α-solasonine, α-solamargine, and malonyl-solamargine SGAs from solasodine aglycone via glycosylation and atypical malonylation decorations. Our work provides the gene tool box and platform for engineering the production of high-value, steroidal bioactive molecules in heterologous hosts using synthetic biology.

Merging total synthesis and NMR technology for deciphering the realistic structure of natural 2,6-dideoxyglycosides.

The structural identification and efficient synthesis of bioactive 2,6-dideoxyglycosides are daunting challenges. Here, we report the total synthesis and structural revision of a series of 2,6-dideoxyglycosides from folk medicinal plants Ecdysanthera rosea and Chonemorpha megacalyx, which feature pregnane steroidal aglycones bearing an 18,20-lactone and glycans consisting of 2,6-dideoxy-3-O-methyl-β-pyranose residues, including ecdysosides A, B, and F and ecdysantheroside A. All the eight possible 2,6-dideoxy-3-O-methyl-β-pyranoside stereoisomers (of the proposed ecdysantheroside A) have been synthesized that testify the effective gold(I)-catalyzed glycosylation methods for the synthesis of various 2-deoxy-β-pyranosidic linkages and lays a foundation via nuclear magnetic resonance data mapping to identify these sugar units which occur promiscuously in the present and other natural glycosides. Moreover, some synthetic natural compounds and their isomers have shown promising anticancer, immunosuppressive, anti-inflammatory, and anti-Zika virus activities.

Role of diosgenin extracted from Helicteres isora L in suppression of HIV-1 replication: An in vitro preclinical study

BackgroundDiosgenin, an essential sapogenin steroid with significant biological implications, is composed of a hydrophilic sugar moiety intricately linked to a hydrophobic steroid aglycone. While the antiviral properties of diosgenin against numerous RNA viruses have been extensively documented, its potential in combating Human Immunodeficiency Virus infections remains unexplored. Experimental procedureThis current investigation presents a comprehensive and systematic analysis of extracts derived from the leaves of Helicteres isora, which are notably enriched with diosgenin. Rigorous methodologies, including established chromatographic techniques and Fourier-transform infrared spectroscopy were employed for the characterization of the active diosgenin compound followed by molecular interaction analyses with the key HIV enzymes and mechanistic validation of HIV inhibition. Key resultsThe inhibitory effects of extracted diosgenin on the replication of HIV-1 were demonstrated using a permissive cellular system, encompassing two distinct subtypes of HIV-1 strains. Computational analyses involving molecular interactions highlighted the substantial occupancy of critical active site pocket residues within the key HIV-1 proteins by diosgenin. Additionally, the mechanistic underpinnings of diosgenin activity in conjunction with standard controls were elucidated through specialized colorimetric assays, evaluating its impact on HIV-1 Reverse Transcriptase and Integrase enzymes. ConclusionsTo our current state of knowledge, this study represents the inaugural demonstration of the anti-HIV efficacy inherent to diosgenin found in the leaves of Helicteres isora, and can be taken further for drug design and development for the management of HIV infection.

Literature Review : The Effects of Antioxidant Saponins in Herbal Plants on Testicular Histology of Rats with Diabetes Mellitus and The Review of Islamic Perspective

Introduction: Diabetes mellitus is a metabolic disorder. Diabetes mellitus can cause a decrease in sperm count, sperm motility, testosterone hormone, erectile ability, libido and testicular weight. Antidiabetic drugs consumed long-term can cause side effects; therefore, alternative treatment is needed using herbal medicinal plants. Saponins in plants are a complex class of complex natural compounds with a large molecular mass, namely steroid or triterpenoid aglycones with one or more sugar/glycoside chains. Saponins function as antioxidants. This study aims to determine the effect of saponins as one of the antioxidants on the testicular organs of rats (Rattus norvegicus) Wistar strain-induced Streptozotocin. Methods: This study used the Literature Review method with a narrative literature review type. The data collection technique uses a search for several research databases through Google Scholar and Mendeley. This research has four journals that will review. Results: The results showed that herbal plants have bioactive compounds such as flavonoids, alkaloids, terpenoids, tannins, and saponins that have antidiabetic effects with different mechanisms in reducing blood glucose levels repairing damage to testicular tissue of diabetes mellitus rats. Conclusion: Antioxidant saponins in herbal plants influence improving and supporting the repair of testicular histology damage in diabetic cases. Allah SWT grows a wide variety of plants that have enormous benefits for humans, including food and medicine, because Allah SWT created various kinds of plants with multiple uses.

Chemical Constituents, Biological Activities, and Proposed Biosynthetic Pathways of Steroidal Saponins from Healthy Nutritious Vegetable-Allium.

Allium is a common functional vegetable with edible and medicinal value. Allium plants have a special spicy taste, so they are often used as food and seasoning in people's diets. As a functional food, Allium also has abundant biological activities, some of which are used as drugs to treat diseases. By consuming Allium on a daily basis, people can receive active compounds of natural origin, thereby improving their health status and reducing the likelihood of disease. Steroidal saponins are important secondary metabolites of Allium, which are formed by the steroidal aglycone group and sugar. Steroidal saponins have various physiological activities, such as hypoglycemic, antiplatelet aggregation, anti-inflammatory, antitumor, antimicrobial, and enzyme activity inhibition, which is one of the key reasons why Allium has such significant health benefits. The structural diversity and rich biological activities of steroidal saponins make Allium important plants for both food and medicine. In this paper, the chemical structures, biological activities, and structure-activity relationships of steroidal saponins isolated from Allium are reviewed, and the biosynthetic pathways of some key compounds are proposed as well, to provide a molecular reference basis based on secondary metabolites for the health value of Allium.

Total Synthesis of Starfish Cyclic Steroid Glycosides. Part 1, Synthesis of the Aglycone and Attempts at Installation of the Sugar Units

Comprehensive SummarySepositoside A (1) is the major and first cyclic steroid glycoside isolated from starfishes, which features a strained 16‐membered ring formed by tethering C3 and C6 of the steroid aglycone with a linear trisaccharide. We conceived a convergent synthetic plan in which sepositoside A was disconnected into a disaccharide and a steroid‐glucose hybrid ether. The desired 3β,6β‐dihydroxy‐Δ7,8‐23‐ one aglcyone was readily prepared from dehydroepiandrosterone in 12 steps. The etherification of the 6β‐hydroxy‐Δ7,8‐steroid with a variety of hexopyranoside‐C6‐electrophiles and CO2‐extrusion of a steroid‐pyranose hybrid carbonate were extensively studied; however, formation of the desired steroid‐pyranose etherate linkage has not been successful. Model studies on the β‐selective installation of the (1→2)‐linked disaccharide onto the steroidal C3β‐OH with the corresponding disaccharide α‐imidates were also examined, however, formation of the α‐glycosides prevailed. The present results force us to explore alternative approaches to construct the steroid‐pyranose etherate linkage and stepwise assembly of the glycans en route to the starfish cyclic steroid glycosides, which will be presented in two articles that follow.

Saponins: Research Progress and Their Potential Role in the Post-COVID-19 Pandemic Era.

In the post-COVID-19 pandemic era, the new global situation and the limited therapeutic management of the disease make it necessary to take urgent measures in more effective therapies and drug development in order to counteract the negative global impacts caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) and its new infectious variants. In this context, plant-derived saponins-glycoside-type compounds constituted from a triterpene or steroidal aglycone and one or more sugar residues-may offer fewer side effects and promising beneficial pharmacological activities. This can then be used for the development of potential therapeutic agents against COVID-19, either as a therapy or as a complement to conventional pharmacological strategies for the treatment of the disease and its prevention. The main objective of this review was to examine the primary and current evidence in regard to the therapeutic potential of plant-derived saponins against the COVID-19 disease. Further, the aim was to also focus on those studies that highlight the potential use of saponins as a treatment against SARS-CoV-2. Saponins are antiviral agents that inhibit different pharmacological targets of the virus, as well as exhibit anti-inflammatory and antithrombotic activity in relieving symptoms and clinical complications related to the disease. In addition, saponins also possess immunostimulatory effects, which improve the efficacy and safety of vaccines for prolonging immunogenicity against SARS-CoV-2 and its infectious variants.

A review of phytochemistry, medicinal uses and pharmacological actions of shigru

Shigru (Moringa oleifera Lam.) is a medicinally important plant and is used for the treatment of different diseases. In Ayurveda Samhita, Shigru is mentioned nearly by all Aachrayas for nutritional as well as medicinal purpose. Different parts of the plants like bark leaves, seeds, flowers, roots, and immature pods contains abundance of important phyto-constituents like terpenoids, alkaloids, tannins, steroidal aglycones and reducing sugars. Various preperations of Moringa oleifera are used for their anti-inflammatory, anti-hypertentisive , diuretic, anti-microbial, anti-oxidant, anti-diabetic, anti-hyperlipidemic, anti-neoplastic, antipyretics, anti-ulcer, cardio-protectant and Hepato-protectant activities. The present study aims to collect nearly all available information about Ayurvedic aspect Phyto-chemical constituents, medicinal uses as well as pharmacological properties.

Preliminary Antibacterial Screening of the Whole Stem of Rothmannia whitfieldii

Aim: To assess the antibacterial activity of the crude ethanolic and water extracts of the stem of Rothmannia whitfieldii on clinically isolated and typed pathogenic bacterial strains.
 Study Design: This experiment was performed in duplicates under aseptic condition.
 Place and Duration of Study: Department of Microbiology, University of Nigeria, Nsukka, Enugu State, Nigeria between April 2005 to August, 2005.
 Methodology: Whole dried stem specimen of Rothmannia whitfieldii was extracted by maceration and screened for antibacterial activity using agar well-diffusion technique. Five typed bacterial strains namely, Staphylococcus aureus (ATCC 12600), Pseudomonas aeruginosa (ATCC 10145), Escherichia coli (ATCC 11775), Salmonella kintambo (SSRL 113) and Bacillus subtilis (ATCC 6051), and six locally isolated clinical strains (Escherichia coli, Salmonella typhi, P. aeruginosa, S. aureus and two Proteus species designated as Proteus I and Proteus II), were tested for susceptibility to the plant extract.
 Results: Phytochemical analysis revealed the presence of flavonoids, saponnins, tannins, carbohydrates and steroidal aglycone. Alkaloid was present in trace amount only in the ethanolic extract. The ethanolic extract exhibited a wider spectrum of activity, being effective against 81.8% of the test organisms compared with the cold-water extract (54.5%) or hot water extracts (27.3%). The minimum inhibitory concentrations (MICs) varied not only with the test organisms but also with the various extracts of the plant.
 Conclusion: All the extracts had bacteriostatic activity on the susceptible organisms and none was bactericidal. The screening test results authenticate the folkloric claims that Rothmannia whitfieldii is medicinal against gastrointestinal diseases and aid in wound healing.

Steroid glycosides from the roots of Marsdenia tenacissima

Eleven undescribed glycosylated C21 steroids and nine known homologous glycosides with diverse acyl substituents, as well as their common steroid aglycone, have been obtained from the roots of Marsdenia tenacissima. Their structures were elucidated mainly by comprehensive spectroscopic analyses and comparison with previously reported analogues, with the absolute configuration assignment being supported by chemical degradation, X-ray crystallography and ECD exciton chirality method. Among them, two pairs of regioisomers were found to exist as inseparable equilibrium mixtures due to an interesting intramolecular transesterification, and nicotinoyl substitution was first reported for metabolites from the title plant. Screening of these compounds in a panel of bioassays revealed that two glycosides displayed mild inhibition against butyrylcholinesterase.

An ester derivative of tenacigenin B from Marsdenia tenacissima (Roxb.) Wight et Arn reversed paclitaxel-induced MDR in vitro and in vivo by inhibiting both P-gp and MRP2

Ethnopharmacological relevanceMarsdenia tenacissima is a medicinal plant, used as a raw material for cancer treatment in China. In our previous studies, 11α-O-2-methylbutanoyl-12β-O-tigloyl-tenacigenin B (MT2), the main steroid aglycone isolated from M. tenacissima, was found to significantly enhance the antitumor activity of paclitaxel (PTX) in vivo. However, it is unclear whether MT2 reverses multidrug resistance (MDR) in tumors. Aim of the studyTo determine the role and mechanism of MT2 in reversing tumor MDR. Materials and methodsMDR cell line HeLa/Tax was established from the human cervical carcinoma cell line HeLa by long-term exposure to subtoxic concentrations of PTX and was used to evaluate the ability of MT2 to restore chemosensitivity of cells both in vitro and in a nude mouse model. The expression of P-glycoprotein (P-gp) and multidrug resistance-associated protein 2 (MRP2) was determined using western blotting and immunohistochemistry. The substrate transport function was assessed using an MDR function assay kit. The binding modes of MT2 and P-gp were determined using the conformation-sensitive anti-P-gp antibodies. The permeability and transport properties of MT2 were analyzed in Caco-2 cell monolayers. ResultsCompared to parental cells, HeLa/Tax cells overexpress P-gp and MRP2 and are approximately 100–360 fold more resistant to the anticancer drugs PTX, docetaxel, and vinblastine. MT2 at 5 or 10 μmol/L significantly increased the sensitivity of HeLa/Tax to these three anticancer drugs (18–56-fold decrease in IC50 value) and suppressed the expression of P-gp and MRP2. Knockdown of P-gp with small interfering RNA partially reversed MT2-induced sensitivity to PTX in HeLa/Tax cells. Moreover, MT2 directly inhibited P-gp-mediated substrate transport while interacting with membrane P-gp in non-substrate ways. MT2 was highly permeable and could not be transported in the Caco-2 cell monolayers. In nude mice bearing HeLa/Tax xenografts, the combination treatment with MT2 and PTX exerted a synergistic inhibitory effect on the growth of tumors and the expression of P-gp and MRP2 without increasing toxicity. ConclusionMT2 is a potential agent for reversing MDR. It impedes membrane drug efflux pumps by suppressing P-gp and MRP2 expression, and directly inhibiting the transport function of P-gp.

Pharmacokinetics, plasma protein binding, and metabolism of a potential natural chemosensitizer from Marsdenia tenacissima in rats

Ethnopharmacological relevanceMarsdenia tenacissima (Roxb.) Wight et Arn is a medicinal plant mainly distributed in southwest China. It is used in folk medicine for the treatment of tumors and is synergistic with chemotherapies. In our previous study, 11α-O-2-methybutyryl-12β-O-tigloyl-tenacigenin B (MT2), a main steroid aglycone isolated from the total aglycones of M. tenacissima, significantly enhanced the in vivo antitumor effect of paclitaxel in mice bearing human tumor xenografts, showing its potential as a chemosensitizer. However, the pharmacokinetic characteristics, plasma protein binding rate, and metabolic profile of MT2 remain unclear. Aim of the studyTo elucidate the pharmacokinetic characteristics, plasma protein binding rate, and metabolic profile of MT2 in rats. Materials and methodsMT2 in rat plasma and phosphate-buffered saline was quantified using ultra performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method, while the MT2 metabolites in rat liver microsomes were analyzed using UPLC-triple time-of-flight MS/MS. ResultsFor intravenously administered MT2, the maximum plasma concentration and the area under the plasma concentration-time curve indicated dose dependency, while the elimination half-life time, the mean residence time, apparent volume of distribution and total apparent clearance values remained relatively unchanged in both the 5 mg/kg and 10 mg/kg groups. For orally administered MT2, the bioavailability was 1.08–1.11%. In rat plasma, MT2 exhibited a protein binding rate of 93.84–94.96%. In rat liver microsomes, MT2 was metabolized by oxidation alone or in combination with demethylation, and five MT2 metabolites were identified. ConclusionMT2 has low oral bioavailability and a high plasma protein binding rate in rats. After administration, MT2 is transformed into oxidative metabolites in the liver. To achieve a high blood concentration of MT2, it should be administered intravenously. These findings would serve as a reference for further MT2-based pharmacological study and drug development.

Taxonomic Characteristics and Phytochemical Constituents of Asystasiagangetica (L.) T. Anderson, a Member of Acanthaceae

This study examined the taxonomic characteristics of Asystasiagangetica; a perennial herb characterized by its trailing to erect habit and as a result, roots from the nodes. It is glabrous and grows up to 80±20 cm. There are simple leaves with petioles which are ovate in shape with opposite phyllotaxy and margins are even to slightly serrated, measuring up to 7±2 cm in length and 3±1 cm in width. The inflorescence is one-sided raceme with purplish-blue tubular flowers which is pentamerous. The fruits are dry dehiscent capsule up to 2±0.5 cm in length. The epidermal studies revealed presence of simple elongated to conical shaped multicellular trichomes and cyclocytic stomata which are amphistomatic in nature, though very scanty in adaxial foliar region. Anatomical study showcased a single layer in the epidermis. The hypodermis consists of 2 to 3 layers of collenchyma, the general cortex and pith is made of parenchyma and cuts across mid-ribs, petioles, stems, nodes and roots, occurring in similar locations except that the number of layers of cells are not the same and vascular bundle is open type. The phytochemical study revealed that the following secondary metabolites are present: alkaloids, saponins and cardiac glycosides while steroidal aglycones, not observed. This information here would assist for further delimitation of the species.

Previously undescribed pyridyl-steroidal glycoalkaloids and 23S,26R-hydroxylated spirostanoid saponin from the fruits of Solanum violaceum ortega and their bioactivities

Three previously undescribed pyridyl-steroidal glycoalkaloids, solanindiosides A‒C, one rare 23S,26R-hydroxylated spirostanoid saponin, and two steroidal alkaloid aglycones, solanindins A and B, derived from the acid hydrolysis of solanindiosides A‒C, were isolated from the fruits of Solanum violaceum, together with five known analogues, including two rare steroidal glycosides, two lignans and a diterpene. Structurally, they comprise a 16β-methoxy-23-deoxy-22,26-epimino-cholest-type skeleton moiety, and a 16β-methoxy-3,23-dideoxy-22,26-epimino-cholest-3,5-dien derivative. The hitherto undescribed structures were established on the basis of extensive spectroscopic analyses. Configurations of sugar moieties were resolved by chemical derivations. Solanindiosides A‒C, (22R,23S,25R,26R)-spirost-5-ene-3β,23,26-triol3-O-β-d-xylopyranosyl-(1→3)-β-d-glucopyranoside, solanindins A and B, and (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol were evaluated for their cytotoxic and antibacterial activities. (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol showed the most potent cytotoxic activity against MCF-7 cells (IC50 = 4.386 ± 0.098 μM), while solanindin B displayed some inhibitory effects against Staphylococcus aureus Rosenbach with MIC50 value of 37.32 ± 0.793 μM. In addition, (1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-[(2S,3R,4R)-tetrahydro-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-(hydroxymethyl)-2-furanyl]phenoxy]-1,3-propanediol induced dose dependent apoptosis effect in MCF-7 cells.

Comparative study of saponin for surfactant properties and potential application in personal care products

Surfactants are typically organic compounds containing hydrophobic and hydrophilic groups bearing polar and non-polar classes. Saponin is one of the surfactant classes present in the plant species with steroidal aglycone or triterpenoid and one or more chains of sugar characterized by its structure. Now days, consumers are becoming more aware of natural products associated with their physicochemical properties. Saponin's potential use as surfactant is caused by the combination of a non-polar sapogenin side chain and a water-soluble one, which is close to the structure of most lipophilic and hydrophilic molecular sections of synthetic surfactants. The foaming power of the 0.6% crude saponins solution, 0.6% SLS solution and 0.6% Tween 80 solution were found to be 80%, 93.87% and 97.56% respectively. It showed that 0.6% crude saponins possessed moderate foaming ability. The surface active properties of saponin were also compared with the synthetic surfactants such as sodium lauryl sulfate (SLS) and Tween 80. Surface tension of 0.6% solution of saponin, SLS and Tween 80 was determined as 37.39 mN/m, 26.15 mN/m and 37.18 mN /m respectively. Critical micelle concentration (CMC) values of saponin and Tween 80 was comparable.

Solanum steroidal glycoalkaloids: structural diversity, biological activities, and biosynthesis.

Covering: up to 1 October 2020Solanum steroidal glycoalkaloids (SGA), characterized by nitrogenous steroidal aglycone and glycoside residues, mainly occur in the Solanum species, including economically important edible plants such as potato, tomato, and eggplant. To date, 107 SGA assigned to six total skeletons have been identified from Solanum plants. SGA have unique structures and display significant pharmacological activities such as cytotoxic, antimicrobial, anticholesterol, and some are well-known poisons. The biosynthesis pathway, transcriptional regulation, and the evolution of SGA are also examined in detail. This report updates the chemical knowledge of the naturally occurring SGA from Solanum species, thereby providing an in-depth analysis of their diversity, biological activities, and biosynthesis.

Synthesis, Modification and Biological Activity of Diosgenyl β-d-Glycosaminosides: An Overview.

Saponins are a structurally diverse class of natural glycosides that possess a broad spectrum of biological activities. They are composed of hydrophilic carbohydrate moiety and hydrophobic triterpenoid or steroid aglycon. Naturally occurring diosgenyl glycosides are the most abundant steroid saponins, and many of them exhibit various pharmacological properties. Herein, we present an overview of semisynthetic saponins syntheses–diosgenyl β-d-glycosaminosides (d-gluco and d-galacto). These glycosides possess a 2-amino group, which creates great possibilities for further modifications. A wide group of glycosyl donors, different N-protecting groups and various reaction conditions used for their synthesis are presented. In addition, this paper demonstrates the possibilities of chemical modifications of diosgenyl β-d-glycosaminosides, associated with functionalisation of the amino group. These provide N-acyl, N-alkyl, N,N-dialkyl, N-cinnamoyl, 2-ureido and 2-thiosemicarbazonyl derivatives of diosgenyl β-d-glycosaminosides, for which the results of biological activity tests (antifungal, antibacterial, anti-cancer and hemolytic) are presented.

Saponins as Modulators of the Blood Coagulation System and Perspectives Regarding Their Use in the Prevention of Venous Thromboembolic Incidents.

Saponins comprise a heterogenous group of chemical compounds containing a triterpene or steroid aglycone group and at least one sugar chain. They exist as secondary metabolites, occurring frequently in dicotyledonous plants and lower marine animals. Plant saponin extracts or single saponins have indicated antiplatelet and anticoagulant activity. Venous thromboembolism (VTE), including deep venous thrombosis and pulmonary embolism, is a multifactorial disease influenced by various patient characteristics such as age, immobility, previous thromboembolism and inherited thrombophilia. This mini-review (1) evaluates the current literature on saponins as modulators of the coagulation system, (2) discusses the impact of chemical structure on the modulation of the coagulation system, which may further provide a basis for drug or supplement design, (3) examines perspectives of their use in the prevention of VTE. It also describes the molecular mechanisms of action of the saponins involved in the prevention of VTE.