Enhancing the Membranolytic Activity of Chenopodium quinoa Saponins by Fast Microwave Hydrolysis (original) (raw)
Related papers
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 m...
Microwave-Assisted Desulfation of the Hemolytic Saponins Extracted from Holothuria scabra Viscera
Molecules, 2022
Saponins are plant and marine animal specific metabolites that are commonly considered as molecular vectors for chemical defenses against unicellular and pluricellular organisms. Their toxicity is attributed to their membranolytic properties. Modifying the molecular structures of saponins by quantitative and selective chemical reactions is increasingly considered to tune the biological properties of these molecules (i) to prepare congeners with specific activities for biomedical applications and (ii) to afford experimental data related to their structure–activity relationship. In the present study, we focused on the sulfated saponins contained in the viscera of Holothuria scabra, a sea cucumber present in the Indian Ocean and abundantly consumed on the Asian food market. Using mass spectrometry, we first qualitatively and quantitatively assessed the saponin content within the viscera of H. scabra. We detected 26 sulfated saponins presenting 5 different elemental compositions. Microw...
Phytochemical Analysis, 2000
Ion trap MS has been utilized in the structure elucidation of a saponin from Quillaja saponaria. With respect to the carbohydrate moieties, this technique allowed the elucidation of the sequence and branching, of six out of seven glycosidic linkages, the precise location of an appended O-acetyl group, and the ring sizes of three out of four nonterminal monosaccharide residues. The mass spectra could be recorded and interpreted within a day using approximately 1 mg of sample. The identities and absolute configurations of the constituent monosaccharides were determined using trimethylsilylated methyl glycosides and trimethylsilylated ()-2-butyl glycosides, respectively. Methylation analysis confirmed the MS data and yielded both the missing glycosidic linkage and the ring sizes. The identity of the aglycone-quillaic acidand the anomeric forms of the monosaccharide residues were established by NMR spectroscopy, while several structural features were confirmed. Ion trap MS proved to be attractive as a pre-NMR tool because it rapidly provided an overall idea of the structure, thereby considerably reducing the time required for interpretation of the NMR data. As a particular advantage, the structure as deduced from MS enabled facile NMR assignments in case of ambiguity due to overlapping signals.
Bioactivity of Triterpene Saponins from Quinoa (Chenopodium Quinoa Willd.)
Research & Reviews: Journal of Biology, 2016
Functional food is described as a food, even conventional, with special benefits to human health. Foods which includes particular functional nutrient by processing, enrichment or enhancement. Saponin in quinoa has been used as a many plant drug content and folk medicines for many centuries treatment of diseases. Quinoa seeds are naturally gluten free, high nutrient profile increasing attention has been given to these plants. Therefore, quinoa (Chenopodium quinoa Willd.), an Amaranthaceae plant of Andean region, recently became important for the researchers. Saponin has nutritional and pharmacological benefits. In addition to role in plant defense system, saponins possess various biological and pharmacological properties, including hemolytic, cytotoxic, immune modulatory, anti-inflammatory, and antitumor impact. The aim of this review is to plan a detail and recent report of quinoa pharmacological, phytochemical and nutritional aspects, while summary of late improvement link with the...
Biomedical and Pharmacology Journal
One of the known causes of cancer is imbalance production between reactive oxygen species (ROS) and antioxidant defense within the cell. Under oxidative stress conditions, excessive ROS production ultimately induces cell death via apoptosis or necrosis. Moreover cancer cells use glycolysis for energy production. Glycolysis inhibition will lead to cancer cell proliferation disruption. Quinones and saponins are chemical compounds that have anticancer properties. Saponin is one of the plant's metabolites, which also found in Indonesian medicinal plants. Preliminary studies in our lab showed that there were some species of medicinal plants in Indonesia that contained saponin, in which saponin known to have a good effect on inhibiting cancer cells. This study was aimed to know the anticancer activities from the compound that contains saponin and quinone as its active substance through the oxidative stress induction and glycolysis inhibition mechanism using in silico method. This research started by choosing the protein crystal structure of cytochrome p450 reductase (CYP450R) enzyme and pyruvate kinase M2 (PKM2) enzyme, then preparation of the protein with the help of Chimera 1.14.rc software, preparation of the ligands which belongs to cytotoxic molecule and optimization of their structure using Marvin Sketch software, and validation of molecular docking and docking process of the testing ligands on CYP450R and PKM2 enzymes using AutoDock Vina software. The results showed that testing ligands had affinity energy and good interaction with CYP450R and PKM2 enzymes, especially diosgenin. Testing ligands tended to interact with CYP450R rather than PKM2. Molecular interaction between testing ligands with the enzymes may provoke excessive ROS production and inhibit the glycolysis process in cancer cells. Compared to glycolysis inhibition, testing ligands had greater capacity in causing oxidative stress. Perhaps this study will motivate others for discovered the potential activity of medicinal plants in Indonesia.
Multi-stage mass spectrometric analysis of saponins in glycyrrhiza radix
Natural Product Communications, 2011
The fragmentation pathways of six triterpenoid saponins from Glycyrrhiza radix were investigated using LC-MS/MS. Depending on the structure and the substitution pattern, different molecular adduct ions, [M+NH4]+ or [M+H]+, were observed in the positive ESI spectra. In the positive MSn spectra from the molecular adduct ions, characteristic product ions corresponding to the loss of dehydrated glucuronic acid or glucuronic acid were detected and they indicated the type of substitution and structural modification. Fragment ions originating from the sapogenin moiety in the positive mass spectra were predominantly provided by saponins having an 11-oxo-12-ene structure. On the other hand, the saponins gave fragment ions corresponding to the sugar moiety in the negative mass spectra. These results indicate the specific property of saponins that have the 11-oxo-12-ene structure to localize positive or negative charge in the mass spectrometric ionization and fragmentation process. Information...
2012
Saponins are a group of amphiphilic glycosides containing one or more sugar chains linked to a nonpolar triterpene or steroid aglycone skeleton, which are believed to be responsible for the pharmacological activities of many Chinese medicinal herbs. The purpose of this paper is to summarize the contemporary knowledge of the absorption, disposition, and pharmacokinetics of some important saponins, including ginsenosides, licorice saponins, dioscorea saponins, astragalosides, and saikosaponins. Poor intestinal absorption of saponins is mainly due to their unfavorable physicochemical traits, such as large molecular mass ( > 500 Da), high hydrogen-bonding capacity ( > 12), and high molecular flexibility ( > 10), that underlie poor membrane permeability. Rapid and extensive biliary excretion is another primary factor that limits the oral bioavailability of most saponins. However, several saponins, including ginsenosides Ra3, Rb1, Rc, and Rd, and dioscin, are excreted slowly into the bile and in turn have significantly long elimination half lives (7-25 h in rats). These longcirculating saponins may be used as pharmacokinetic markers to substantiate systemic exposure to the ingested herb extracts. In addition to biliary excretion for elimination of most saponins unchanged, renal excretion may also be important for certain saponins. Saponins can be hydrolyzed by the colonic microflora. After absorption, the deglycosylated aglycones undergo phase I and/or II metabolism by the host. In line with the poor permeability, saponin concentrations in most rat tissues are lower than the concurrent plasma level and the brain level is usually very low. However, the liver concentrations of many saponins, as well as the kidney levels of certain saponins, can be quite high, which involves transporter-mediated uptake mechanisms. Repeated p.o. ingestion of glycyrrhizin appears to be able to induce CYP3A in rodents and humans, while several deglycosylated products of ginsenosides can moderately inhibit CYP activities in vitro with IC50 values of 10-50 μM. More research is required for elucidation of the absorption, disposition, and pharmacokinetics of multiple saponins to enhance understanding which saponins are most likely to exert pharmacological effects in vivo, as well as influence of complex herb matrix. In addition, research is also needed to characterize the microbiotal deglycosylation and the subsequent aglycone metabolism by the host for a broader range of saponins, as well as the hepatobiliary transporter phenotyping for and the interaction with saponins. Furthermore, in vitro and in vivo studies of saponin-based herb-drug interactions are also warranted.
Molecules
An immunoadjuvant preparation (named Fraction B) was obtained from the aqueous extract of Quillaja brasiliensis leaves, and further fractionated by consecutive separations with silica flash MPLC and reverse phase HPLC. Two compounds were isolated, and their structures elucidated using a combination of NMR spectroscopy and mass spectrometry. One of these compounds is a previously undescribed triterpene saponin (Qb1), which is an isomer of QS-21, the unique adjuvant saponin employed in human vaccines. The other compound is a triterpene saponin previously isolated from Quillaja saponaria bark, known as S13. The structure of Qb1 consists of a quillaic acid residue substituted with a β-d-Galp-(1→2)-[β-d-Xylp-(1→3)]-β-d-GlcpA trisaccharide at C3, and a β-d-Xylp-(1→4)-α-l-Rhap-(1→2)-[α-l-Arap-(1→3)]-β-d-Fucp moiety at C28. The oligosaccharide at C28 was further substituted at O4 of the fucosyl residue with an acyl group capped with a β-d-Xylp residue.
Saponin production from Quillaja genus species. An insight into its applications and biology
Scientia Agricola, 2021
Quillaja genus (Quillajaceae family) is endemic to South America, where is represented by two species, Quillaja saponaria and Quillaja brasiliensis. One outstanding characteristic of these forest tree species is their production of saponins, a family of amphipathic glycosides, involved in the defensive response of plants against biotic and abiotic factors. Saponins are metabolites of economic importance due to their chemical and physical properties. Basic and applied research efforts performed during the last decades, mainly on Q. saponaria, have placed these compounds as an important raw material in industrial areas, such as food and beverage, cosmetics, vaccine production, biopesticides, among others. In this review, we summarize information on saponins from Quillaja species during the last years, analyzing current developments by application areas, as well as their chemical composition and properties. We also describe the general advances in revealing saponin biosynthesis pathways, related genes and Quillaja genomes, as well as the conservation status, domestication processes, and perspectives in the context of implementing genetic improvement programs.
Preparation and characterisation of quillaja saponin with less heterogeneity than Quil-A
Vaccine, 2000
Immunisation against pathogens remains one of the most eective ways of preventing or reducing losses due to infectious diseases in animal husbandry. When inactivated vaccines are used, adjuvants are most often required to obtain satisfactory immune responses. One such type of adjuvant is saponin derived from the bark of Quillaja saponaria Molina, a tree of the rose family. A few dierent commercial sources exist, but due to the structural complexity and heterogeneity of these saponin preparations, it has been dicult to establish exactly which components are responsible for the adjuvant activity. By carefully selecting the bark source, we have succeeded in preparing a much less heterogeneous preparation of quillaja saponin. In this report we describe the preparation, in terms of structural complexity, hemolytic activity, adjuvant activity, and its ability to form ISCOM matrix. This new preparation could have implications for use per se, or as starting material for more eective preparation of pure substances. 7