Steroidal Glycosides Research Articles

Biological Activities and Chemistry of Triterpene Saponins from Medicago Species: An Update Review.

Plants are known to be a great source of phytochemicals for centuries. Medicago, belonging to the Family Fabaceae, is a large and well spread genus comprising about 83 cosmopolitan species, of which one-third are annuals and span diverse ecological niches. Medicago species are rich in saponins mainly classified into three classes, namely, steroid alkaloid glycosides, triterpene glycosides, and steroid glycosides. These saponins are important compounds having diverse pharmacological and biological activities. As a whole, 95 of saponins are reported to date occurring in Medicago species using various latest extraction/isolation techniques. Considering the multiple biological and pharmacological potential of Medicago species due to saponins along with structural diversity, we compiled this review article to sum up the recent reports for the pharmacological potential of the Medicago's derived saponins in modern as well as traditional medication systems. The current manuscript produces data of chemical structures and molecular masses of all Medicago species saponins simultaneously. The toxicity of certain pure saponins (aglycones) has been reported in vitro; hederagenin appeared highly toxic in comparison to medicagenic acid and bayogenin against X. index, while soyasaponin I, containing soyasapogenol B as a glycone, appeared as the least toxic saponin. The diversity in the structural forms shows a close relationship for its biological and pharmacological actions. Moreover, saponins showed antioxidant properties and the mechanism behind antimicrobial potential also elaborated in this review article is mainly because of the side sugar groups on these compounds. The collected data presented herein include chemical structures and molecular masses of all saponins so far. Their biological activity and therapeutic potential are also discussed. This information can be the starting point for future research on this important genus.

Chemical constituents with inhibition against TNF-α from Merrillanthus hainanensis

Two new steroidal glycosides oxystauntoside A (1) and oxystauntoside B (2), together with sixteen known compounds (3–18) were isolated from the 95% ethanol extract of Merrillanthus hainanensis. Their structures were characterized by extensive spectroscopic analysis including NMR and mass spectra and single crystal X-ray crystallography. The absolute configuration of 1 and 2 were further determined by ECD calculations. All of these compounds were isolated from M. hainanensis for the first time. All the fractions and compounds were tested for the anti-inflammatory activity against the TNF-α factor. The ethyl acetate fraction showed the most potent inhibition (71.3%) at 10 μg/mL and compounds 5 (78.9%) and 9 (73.4%) in this fraction with both carboxyl and phenolic hydroxyl groups showed significant inhibition at 10 μM. Our study provided the first scientific report for the medicinal value of M. hainanensis.

Metabolomic profiling of wheat genotypes resistant and susceptible to root-lesion nematode Pratylenchus thornei.

Metabolic profiling of Pratylenchus thornei resistant and susceptible wheat genotypes indicates that fatty acid, glycerolipid and flavonoid classes of metabolites constitutively expressed in resistant wheat roots could reduce nematode reproduction. The root-lesion nematode Pratylenchus thornei reduces wheat production in many parts of the world. In this study the metabolic profiles of two wheat genotypes ‘QT16258’ (moderately resistant) and ‘Janz’ (susceptible) were compared at 8 weeks post inoculation with or without P. thornei. We performed untargeted liquid chromatography mass spectrometry analysis (LC–MS) of the wheat root samples. A total of 11,704 MS features were identified, out of which 765 MS features were annotated using in-house chemical standards. Principal components analysis (PCA) and partial least square discriminant analysis (PLS-DA) indicated dissimilarity of the metabolome between P. thornei resistant and susceptible genotypes. Two-way analysis of variance indicated that metabolic differences were mainly constitutive rather than induced by inoculation with P. thornei. Eighty-four annotated metabolites were significantly (p ≤ 0.01) higher in relative concentration in ‘QT16258’ than ‘Janz’ and belonged to the following classes of metabolites: flavonoids, fatty acids, glycerolipids, alkaloids, tannins, nucleotides, steroid glycosides and terpenoids. Eighty-five annotated metabolites were significantly (p ≤ 0.01) higher in relative concentration in ‘Janz’ than ‘QT16258’ and belonged to the following classes of metabolites: amino acids, sugars, flavonoids and alkaloids. Several metabolites at higher concentration in ‘QT16258’, including quercetin-3,4'-O-di-beta-glucoside (flavonoid), linoleic acid (fatty acid), lysophosphatidylethanolamine (glycerolipid), hirsutine (alkaloid), 1-methylsulfinylbutenyl-isothiocyanate (glucosinolate), could potentially strengthen the root cell walls to inhibit nematode penetration and/or reduce nematode motility. Some metabolites at higher concentrations in susceptible ‘Janz’, including phenolics, coniferyl alcohol and indole acetic acid conjugates, could be nematode attractants as well as part of a hypersensitive browning reaction to nematode invasion.

A Review on Saponin Biosynthesis and its Transcriptomic Resources in Medicinal Plants

Saponins are naturally occurring glycosides which are produced by various plant species with diverse biological properties. The surface-active properties of saponins differentiates them from other glycosides. They are classified mainly into steroid and triterpenoid glycosides based on the structure of hydrophobic aglycone unit. The synthesis of saponins and the genes involved in its biosynthesis can be identified by transcriptome profiling. Using high-throughput sequencing technologies, the steroid or triterpenoid saponin biosynthesis related genes have been discovered which can help boosting the molecular research in this biosynthetic pathway. This review mainly illustrates the importance of saponins and the transcriptome resources of important medicinal plants for identifying genes related to its biosynthesis. Furthermore, the significance of unexplored plants which are rich sources of saponins in future studies are also discussed in the current review.

Bamboo a Supplement to Human Health: A Comprehensive Review on its Ethnopharmacology, Phytochemistry, and Pharmacological Activity

:Bamboo species belonging to the Poaceae family, Poaceae has overall about 1,500 species, and 87 genera worldwide, randomly distributed between humid tropical, sub-tropical and mildmoderate regions across the globe. The plant has superior value in traditional indigenous systems of China, Ayurveda, Siddha, and Unani for its enormous medicinal and nutritional purposes since 2500 years. It was the apparent beginning of bamboo used as a medication, which was trailed by a series of modern research and consequently formed a core scientific ingredient in a research laboratory.:The current review is a critical study for the evaluation of state-of-the-art concerning phytochemistry, pharmacology and traditional uses of bamboo species of different genera, which put forward systemic research stratagems and to streamline the therapeutic exploration for the management of human ailments.:The present review documents systemic overview of the scientific reports relating to the different bamboo species from older text, ancient literature available in the last five to six decades, e-books and various online databases (PubMed, MEDLINE, Scopus, Google Scholar, Springer, Francis &Taylor, SciFinder, etc.). Additional information was acquired from conference proceedings, botanical books, and dissertations for this work.:Bamboo species belonging to six different genera were explored for its medicinal and ethnomedicinal uses for treatment of inflammatory disorders, ulcers, diabetes, solid tumour, blood purifier, menstrual disorders, and infertility to name a few. The therapeutic potentials, along with their mechanism of action, are concisely deliberated and recapitulated in this review. Bamboo is rich in its nutritive value and has been explored as food and fodder. Studies related to the biological activity of bamboo species revealed that they possess twenty-one promising activities such as anticancer, antidiabetic, cardioprotective, anti-inflammatory, antioxidant, hepatoprotective, neuroprotective, and antibacterial. Eighty-two phytochemical studies have been summarized in this review which is majorly due to the presence of secondary active metabolites such as phenolics, flavonoids, terpenoids, steroid glycosides and coumarins along with minor constituents like polysaccharides, ketones, tannins, lignans, vitamins, amino acids, minerals, and essential oils. A critical assessment of the compiled scientific literature indicates serious efforts for systemic evaluation of the traditional claims and to identify, isolate and evaluate the phytoconstituents for nutritional and therapeutic potentials. Although the plant has immense potential in the health care system, still there is abundant need and avenues for commercialisation and awareness to society for the use of new health care products of bamboo.:The present review affirms that bamboo owing to its rich phytochemical spectrum is the epitome plant with a vast potential for the pharmaceutical, cosmeceutical, nutraceutical, and food industry.

Comparative phytochemical screening and antioxidant activity of lemon grass and sweet wormwood leaves extract

Sweet wormwood (Artemisia annua) and lemongrass (Cymbopogon citratus) leaves were extracted with methanol, evaporated to dryness and processed for antioxidant activity and phytochemical screening. Phosphomolybdenum Reagent was prepared using standard procedure. An aliquot mixture of 2mL of extract solution (1000µg/mL, 500µg/mL, 250µg/mL, 125µg/mL, 62.5µg/mL, 31.25µg/mL and 15.625µg/mL) was mixed with 1.8mL of reagent solution. The samples tubes were incubated at 95°C for 90 minutes. The absorbance of the aqueous solutions was measured at 695nm against blank. Antioxidant activities of the plants extract were also measured in terms of hydrogen donating radical scavenging ability using the stable DPPH method. Absorbance was recorded at 517 nm against blank using a UV-Vis spectrophotometer. The result of in vitro antioxidant potential of the methanolic leaves extract showed more increase in concentration the higher the absorbance. Qualitative Phytochemical Analysis of Lemon Grass and Sweet wormwood shows the presence of phytochemical in lemongrass and sweet wormwood such as flavonoid, tannin, steroid, saponins and cardiac glycoside. Â

New Triterpene Glycosides from the Far Eastern Starfish Solaster pacificus and Their Biological Activity.

Three new triterpene glycosides, pacificusosides A–C (1–3), and three previously known triterpene glycosides, cucumariosides C1 (4), C2 (5), and A10 (6), were isolated from the alcoholic extract of the Far Eastern starfish Solaster pacificus. The structures of 1–3 were elucidated by extensive NMR and ESIMS techniques and chemical transformations. Compound 1 has a novel, unique structure, containing an aldehyde group of side chains in its triterpene aglycon. This structural fragment has not previously been found in the sea cucumber triterpene glycosides or starfish steroidal glycosides. Probably, pacificusoside A (1) is a product of the metabolism of the glycoside obtained through dietary means from a sea cucumber in the starfish. Another two new triterpene glycosides (2, 3) have closely related characteristics to sea cucumber glycosides. The cytotoxicity of compounds 1–6 was tested against human embryonic kidney HEK 293 cells, colorectal carcinoma HT-29 cells, melanoma RPMI-7951 cells, and breast cancer MDA-MB-231 cells using MTS assay. Compounds 4–6 revealed the highest cytotoxic activity against the tested cell lines, while the other investigated compounds had moderate or slight cytotoxicity. The cytotoxic effects of 2–6 were reduced by cholesterol like the similar effects of the previously investigated individual triterpene glycosides. Compounds 3, 4, and 5 almost completely suppressed the colony formation of the HT-29, RPMI-7951, and MDA-MB-231 cells at a nontoxic concentration of 0.5 µM.

Ophiopogonin D Represses Transforming Growth Factor-β1-Induced Proliferation and Inflammation of Airway Smooth Muscle Cells by Inhibiting P65/Adenosine 5'-Monophosphate-Activated Protein/Nuclear Factor-Kappa B Signaling Pathway

Asthma, a common disease in children, is associated with proliferation and inflammation of airway smooth muscle cells. Ophiopogonin D is a bioactive steroid glycoside derived from the Japanese japonica rice root that has been shown to exhibit multiple biological activities through its antioxidant and anti-inflammatory properties. Herein, we report that ophiopogonin D inhibits TGF-β1-induced proliferation of airway smooth muscle cells through suppression of p65/AMPK/NF-κB pathway. We therefore conclude that ophiopogonin D is a promising candidate therapeutic drug for childhood asthma treatment.

Insights into the antitumor mechanism of ginsenosides Rg3.

Panax ginseng, an ancient herb, belonging to Chinese traditional medicine, is an important herb that has a remarkable impact on various diseases. Ginsenoside Rg3, one of the most abundant ginsenosides, exerts significant functions in the prevention of various types of cancers with few side effects. In the present review, its functional molecular mechanisms are explored, including the improvement of antioxidant and anti-inflammation properties, immune regulation, induction of tumor apoptosis, prevention of tumor invasion and metastasis, tumor proliferation and angiogenesis, and reduction of chemoresistance and radioresistance. On the other hand, metabolism, pharmacokinetics and clinical indications of Rg3 are also discussed. The biological functional role of ginsenoside Rg3 may be associated with that it is a steroid glycoside with diverse biological activities and many signaling pathway can be regulated. Many clinical trials are highly needed to confirm the functions of ginsenoside Rg3.

Three novel furospirostanol glycosides and a steroidal alkaloid glycoside from the bulbs of Fritillaria camtschatcensis (L.) Ker Gawl., and their cytotoxicity

Three novel steroidal glycosides (1–3) and a previously described steroidal alkaloid glycoside (4) have been isolated from the bulbs of Fritillaria camtschatcensis (L.) Ker Gawl. (Liliaceae). The structures of novel compounds 1–3 were characterized based on NMR spectroscopy and chemical transformations. Compounds 1–3 are furospirostanol glycosides bearing a (3S)-3-hydroxy-3-methylglutaryl moiety at C-26 in the aglycone. Compounds 1–4 were evaluated in terms of their cytotoxic activities toward HL-60 human promyelocytic leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human lung small cell carcinoma cells. Only 4 showed moderate cytotoxicity against HL-60, A549, and SBC-3 cells with IC50 values of 22.9, 13.3, and 11.9 µM, respectively. Compound 4 was found to cause necrotic-like cell death in HL-60 cells.

Suspension Cell Culture of Dioscorea deltoidea—A Renewable Source of Biomass and Furostanol Glycosides for Food and Pharmaceutical Industry

Dioscorea deltoidea is a medicinal plant valued for its high content of steroidal glycosides (SG)—bioactive compounds with cardioprotective and immunomodulation actions, also used to treat reproductive system disorders. To overcome the limitations of natural resources of this species, a suspension cell culture of D. deltoidea was developed as a renewable and ecologically sustainable source of raw biomass and SG. Cell culture demonstrated stable and intensive growth in the laboratory (20 L) and industrial (630 L) bioreactors operated under a semi-continuous regime (specific growth rate 0.11–1.12 day−1, growth index 3.5–3.7). Maximum dry weight accumulation (8.5–8.8 g/L) and SG content (47–57 mg/g DW) were recorded during the stationary phase. Bioreactor-produced cell biomass contained inorganic macro (K, Ca, Mg, Na) and micro (Zn, Mn, Fe, B, Al, Cu, Cr, Se, Co, Ni) elements in concentrations within the safe range of dietary recommendations. Acute toxicity test showed no or insignificant changes in organ weight, hematological panel and blood biochemistry of laboratory animals fed with 2000 and 5000 mg/kg dry biomass. The results suggest that cell culture of D. deltoidea grown in bioreactors has great potential to be used as functional foods and a component of specialized dietary supplements in complex therapy of reproductive system disorders and mineral deficiency.

Magnetic analogue-imprinted polymers for the extraction of ginsenosides from the Panax ginseng callus

Ginsenosides, which are naturally produced steroid glycosides and triterpene saponins, are thought to have a number of beneficial pharmacological activities and are thus an attractive target for novel extraction methods. Ginsenosides can be isolated from various parts of plants of the Panax genus, but are usually isolated from the roots, and can be purified by column chromatography. In this work, molecularly imprinted polymers were developed for the extraction of ginsenosides, using the ginsenoside analogue lanosterol as a template for the imprinting of magnetic lanosterol-imprinted polymers (MLIPs). Poly(ethylene-co-vinyl alcohol)s, with various ethylene ratios of were used to form MLIP nanoparticles by phase transformation. Magnetic lanosterol-imprinted polymer compositions were then characterized for the absorptivity of ginsenosides, finally, calluses of ginseng were cultured and extracted with magnetic lanosterol-imprinted polymers, and ginsenosides Rg1 and Rb1 can be successfully extracted.

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.

New steroidal glycosides from the roots of Asparagus cochinchinensis

Steroidal saponins were the main active constituents of the traditional medicinal herb Asparagus cochinchinensis. A phytochemical investigation of A. cochinchinensis roots led to the isolation of nine new steroidal glycosides (1–9) and seven known analogues (10–16). Their structures were established by spectroscopic analyses as well as necessary chemical evidence.

Steroid Glycosides Hyrcanoside and Deglucohyrcanoside: On Isolation, Structural Identification, and Anticancer Activity.

Cardiac glycosides (CGs) represent a group of sundry compounds of natural origin. Most CGs are potent inhibitors of Na+/K+-ATPase, and some are routinely utilized in the treatment of various cardiac conditions. Biological activities of other lesser known CGs have not been fully explored yet. Interestingly, the anticancer potential of some CGs was revealed and thereby, some of these compounds are now being evaluated for drug repositioning. However, high systemic toxicity and low cancer cell selectivity of the clinically used CGs have severely limited their utilization in cancer treatment so far. Therefore, in this study, we have focused on two poorly described CGs: hyrcanoside and deglucohyrcanoside. We elaborated on their isolation, structural identification, and cytotoxicity evaluation in a panel of cancerous and noncancerous cell lines, and on their potential to induce cell cycle arrest in the G2/M phase. The activity of hyrcanoside and deglucohyrcanoside was compared to three other CGs: ouabain, digitoxin, and cymarin. Furthermore, by in silico modeling, interaction of these CGs with Na+/K+-ATPase was also studied. Hopefully, these compounds could serve not only as a research tool for Na+/K+-ATPase inhibition, but also as novel cancer therapeutics.

CNS Acting Potential of Natural Products with Special Reference to Family Solanaceae

Solanum species belong to the family Solanaceae, with over 1500 species, worldwide. This type of species also contains medicinal plants such as tomato, potato, eggplant, bell, chilli, peppers and many species such as tropical Mapple, aquatic soda apple and sea walnut etc. Plants in this type of species, the family are usually rough hairy and often prickly, with a distinctive part of plants like flower, seed and fruits, and these numerous types of plants occurring from Solanaceae made up of rich sources of biotin, minerals, vitamins, iron and potassium salts. Mainly Solanum species plants contain steroidal glycoalkaloidal constituents and they are responsible for the various effectiveness in disease and disorders, most of plants contain solasodine and solamargine and both are possessing anticonvulsants effects. During the study of many review and research, most of solanum plants contain steroidal glycosides and they exert the anti-seizure effect because of the solasodine, solmine, solamarginine etc. which inhibit the increment of sodium voltage ions which is responsible for the convulsion.

THE EFFECT OF LEAF TYPE AND SOLUTION ON THE RENDER OF PAPAYA SAPONINDA EXTRACT (CARICA PAPAYA LINN.)

Food safety issues can not be separated from the microbial pathogens that can cause health problems and food spoilage. Their presence in food product should be prevented and controlled. One of the efforts to improve food safety is the utilization of antimicrobial compounds, that can inhibit the growth of pathogenic microbes and food spoilage microorganism like Saponin. Saponins are triterpenic or steroidal glycosides which have many biological properties, and largely distributed in papaya leaves abundantly grown in Indonesia. This research aimed to compare the extraction procedure of saponin from papaya leaves by the difference of papaya leaves (young and old) and solvent (methanol, ethanol) that be used.The results showed that extraction by etanol provided higher yields (5.7 %) than by metanol (3.2 %). The yields of saponin-rich-extract from young and old leaves were not significantly different.

Chemical constituents of Ngoc Linh ginseng leaves (Panax vietnamensis Ha et Grushv.)

Ngoc Linh ginseng or Vietnamese ginseng (Panax vietnamensis Ha et Grushv.) of the Araliaceae family, a endemic plant in Ngoc Linh mountain, is the 20th type of ginseng found in the world (1985). The content of saponin of Ngoc Linh ginseng is much higher than that of other ginsengs in the world such as Panax ginseng (Korean ginseng), anax quinquefolium(American ginseng) and anax notoginseng (Chinese ginseng). Until now, from roots, rhizomes and leaves of Ngoc Linh ginseng, there are 63 saponin which were isolated and determined structures. In addition, polyacetylenes, polyphenols, fatty alcohols and amino acids were also reported. Some of them showed diverse biological activities. In this research, from Ngoc Linh ginseng leaves, six compounds were isolated and structural elucidated by 1D and 2D NMR, MS spectroscopic methods and comparison of the spectral data with those in literature. They were one triterpene, squalene (1), one quinone terpenoid, a-tocopherolquinone (2), two fatty alcohols, tetradecanol (3), docosanol (4) from the -hexane extract and a steroid glycoside, daucosterol (5) and one flavonoid, kaempferol (6) from the methanol extract. All six compounds were reported for the first time from Ngoc Linh ginseng leaves.

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.

Chemical Synthesis of Saponins.

Saponins are a large family of amphiphilic glycosides of steroids and triterpenes found in plants and some marine organisms. By expressing a large diversity of structures on both sugar chains and aglycones, saponins exhibit a wide range of biological and pharmacological properties and serve as major active principles in folk medicines, especially in traditional Chinese medicines. Isolation of saponins from natural sources is usually a formidable task due to the microheterogeneity of saponins in Nature. Chemical synthesis can provide access to large amounts of natural saponins as well as congeners for understanding their structure-activity relationships and mechanisms of action. This article presents a comprehensive account on chemical synthesis of saponins. First highlighted are general considerations on saponin synthesis, including preparation of aglycones and carbohydrate building blocks, assembly strategies, and protecting-group strategies. Next described is the state of the art in the synthesis of each type of saponins, with an emphasis on those representative saponins having sophisticated structures and potent biological activities.