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Saponins - an overview | ScienceDirect Topics
Saponins are a diverse group of chemicals, which derive their name from their ability to form soap-like foams in aqueous solutions. Saponins consist of an aglycone unit linked to one or more carbohydrate chains Figure 1.
The aglycone or sapogenin unit consists of either a sterol or the more common triterpene unit. In both the steroid and triterpenoid saponins , the carbohydrate side-chain is usually attached to the 3 carbon of the sapogenin. Saponins possess surface-active or detergent properties because the carbohydrate portion of the molecule is water-soluble, whereas the sapogenin is fat-soluble.
The stability and strength of forage saponin foams are affected by pH, and this may have an effect on the development of bloat in ruminants.
Saponins are remarkably stable to heat processing, and their biological activity is not reduced by normal cooking. Isolation of saponins from plant material involves extraction with a polar solvent after removal of lipids, with petroleum ether or chloroform, followed by various purification techniques.
A number of chromatographic procedures have been used to separate individual saponins. The analysis of saponins is complex and potentially subject to considerable errors during their isolation, separation and quantification stages. Thus, many early reports of the saponin content of food plants and processed food should be treated with caution. The data presented in Table 1 were obtained using rigorous methodology and are the most reliable data available at present. More recent studies have shown that many legume seeds contain several saponins , e.
Saponins that are present in herbs and spices are likely to be present in such small quantities in the diet that they are unlikely to have any deleterious effect. Alfalfa has been selected by plant breeders to contain low levels of saponins. Similarly, quinoa Chenopodium quinoa seed, which is a minor Andean food crop, has reported saponin levels ranging from 0. This has allowed for the selection of low saponin genotypes.
In the Andes, in households, saponins are removed by soaking, washing, and rubbing to reduce the saponin levels in quinoa grain. Industrially, the seed is milled, or washed and milled.
Liwa 1 2 , Nwokocha 3 , in Pharmacognosy , Saponins are naturally occurring surface-active glycosides produced by plants, lower marine animals, and some bacteria. Saponins occur constitutively in a great many plant species, in both wild plants and cultivated crops. In cultivated crops, the triterpenoid saponins are generally predominant, while steroid saponins are common in wild plants used as herbs .
Plant saponins have been shown to inhibit cholesterol absorption from the intestinal lumen in experimental animals and consequently to reduce the concentration of plasma cholesterol. This may be the result of interactions with cholesterol in the digestive tract or a direct effect of plant saponins on cholesterol metabolism. For example, saponin fractions from garlic or ginseng were shown to decrease total and LDL cholesterol plasma concentrations without changing HDL cholesterol levels in hypercholesterolemic animal models [82,83].
Saponins comprise a large family of structurally related compounds containing a steroid or triterpenoid aglycone sapogenin linked to one or more oligosaccharide moieties. Despite the fact that saponins are widely distributed in the plant kingdom, only a small number of such plants are actually toxic to mammals.
It has long been recognized, however, that saponins , such as the glycoside of medicagenic acid 9 Figure 7 , which is found in alfalfa, is considered to have an adverse effect on the productive performance of nonruminant animals such as swine and poultry.
The negative effect of the saponins can be reversed, however, by the inclusion of dietary cholesterol, which interferes with the absorption of saponins by forming an insoluble complex with saponins. By the same token, dietary saponins may exert a positive effect by reducing cholesterol levels in the tissue and serum of experimental animals. Saponins are phytochemicals that produce a foam when dissolved in water.
Like soaps or detergents, saponins are large molecules containing a water-loving hydrophilic part at one end separated from a fat-loving lipophilic or hydrophobic part at the other. In aqueous solution, saponin molecules align themselves vertically on the surface with their hydrophobic ends oriented away from the water.
This has the effect of reducing the surface tension of the water, causing it to foam. For this reason, saponins are classified as surface-active agents. Similar to other surface-active agents, saponin molecules can align to form a spherical configuration within the water, creating a micelle.
Micelles have a lipophilic centre, and this creation of a fat-loving compartment explains why detergents can dissolve grease and oils. Saponins are glycosides the sugar part comprises the hydrophilic end.
Two classes are recognised based on the structure of their aglycone or sapogenin: Both of these have a glycosidic linkage, usually at carbon 3, and share a common biosynthetic origin via the mevalonic acid pathway.
Steroidal saponins are mainly found in the monocotyledons. Triterpenoid saponins are by far the most common. There are some unusual classifications; for example, the ginsenosides in ginseng are grouped with the triterpenoid saponins even though they exhibit a steroidal structure.
Steroidal saponins typically contain extra furan and pyran heterocyclic rings, which is not a feature of the ginsenosides. Furans and pyrans are respectively five- and six-membered rings containing oxygen. Saponins are consumed in many common foods and beverages including oats, spinach, asparagus, soya beans and other legumes, peanuts, tea and beer.
A bitter taste compound called saponin is located in the outer layers of quinoa seeds. This protects them from birds and insects.
Saponins are glycoside compounds which occur in two groups. According to the nature of the sapogenin moiety they are conjugated with hexoses, pentoses, or uronic acids.
The sapogenins are steroids C27 or triterpenoids C Using a gas chromatography method, the sapogenins oleanolic acid, hederagenin, o -methylspergulagenate, and phytolaccagenic acid are identifiable in sweet and bitter genotypes of quinoa.
Quinoa saponins are soluble in methanol or water. They have strong detergent properties which form very stable foam in water solutions, and reduce the superficial tension of aqueous solutions.
They also show hemolytic activity and are in general toxic to cold-blooded animals which obtain oxygen directly from water. Saponins are also present in common foodstuffs such as peanuts, asparagus, garlic, onion, and spinach.
The amount of saponins present depends on the variety of quinoa. It is higher in bitter-flavor varieties than in sweet, or low-saponin, varieties. Quinoa comprises saponins from 0. The saponins of quinoa seeds are reduced to low levels after dry polishing and washing with water. These levels are apparently nontoxic to humans. The reduction of plasma cholesterol and bile salt concentration has been attributed to the presence of certain saponins in the diet.
However, some saponins can form insoluble complexes with minerals, such as zinc and iron, which make the minerals unavailable for absorption in the gut. Saponins consist of an aglycone with carbohydrate moieties. The number and type of carbohydrate moieties result in a considerable structural diversity of the saponins.
Most carbohydrates in saponins are hexoses i. Through the glycosylation of the hydrophobic aglycones, they can act as biological detergents and, when agitated in water, form foams, which gave rise to the name, saponin for this group of compounds. Saponins are widely spread throughout the plant kingdom, — and have been found in marine animals.
Exceptions are the sweet triterpenesaponin glycirrhicin from Glycirrhiza glabra , and diosgenin from Dioscorea yam , a steroidal saponin precursor for the synthesis of cortisone and progesterone. This makes their detection in complex samples containing other analytes, which absorb in this wavelength range, challenging.
Substantial work with LC—MS was performed on saponins from commercially significant plants, that is, black bean Vigna mungo , soybean Glycine max , — and ginseng Panax notoginseng.
These authors used an analytical 4. Eight triterpenoid saponins , namely, hederacholichiside F, prosapogenin CP11, clematichinenoside B, huzhangoside D, clematiganoside A, clematichinenoside C, huzhangoside B, and HN saponin H, were isolated from the whole plant of Clematis ganpiniana , independently characterized and employed as reference compounds.
This information provided structural insight into the carbohydrate sequence of the oligosaccharide chains and the mode of attachment of the aglycone of the saponins. As a consequence, these authors have tentatively identified two new compounds hitherto unknown for the genus Clematis.
This approach, employing C 18 silica phases with aqueous—organic mobile phases and volatile buffer additives is typical of the procedures followed for the analysis of saponins by HP-RPC and provides, in conjunction with online MS, the methodological framework for the discovery of new compounds. Table 6 lists examples that are representative of the approaches that have been used for the high-resolution chromatographic separation of saponins. Saponins are a diverse group of metabolic glycosides present in many higher plants.
Of importance to therapeutic and vaccine delivery is the ability of many saponins to potentiate systemic and oral delivery of antigens. Crudely processed saponin extracts may be too toxic for parenteral delivery in humans, yet crudely prepared saponins from the Q. Investigation of saponins as adjuvants during oral delivery suggests that saponin and ISCOMs are more rapidly transcytosed by APCs including DCs and macrophages compared to antigen alone, and are more rapidly transported to the draining lymph nodes than soluble protein .
Despite being already produced in plants and well tolerated orally, saponins and ISCOMs have been infrequently investigated in plant-vaccine trials, with only four trials using saponins delivered orally. When orally coadministered with a crudely purified plant-made measles virus H protein vaccine, food-grade Quillaja bark extract was a more efficient adjuvant than the nontoxic enterotoxigenic E.
This response may be due to a possible adjuvant role for saponins in increasing the permeability of the intestinal epithelium to facilitate transit of high molecular compounds across the mucosa. For low-cost oral vaccine purposes, it would be ideal to express an antigen complex in a host plant capable of direct or indirect modulation .
The principal saponin in unripe coperscium fruit and leaves is the glycoside alpha-tomatine, which exhibits diverse bioactivity similar to Quillaja -derived saponins , making it a potential candidate for oral vaccine formulation.
Alpha-tomatine has been shown to act as a potent adjuvant to steer oral and subcutaneous delivery of the Norwalk virus capsid protein expressed in tomato and delivered as a crude, dried preparation toward a Th1, IgG2a dominant response in rats Robert Shepherd, unpublished data.
Manish Gautam 1 , Saponins are a chemically heterogeneous group of steroid and triterpenoid glycosides present in a wide range of plant species. Notably, saponins can activate the mammalian immune system, which has led to a significant interest in their potential as vaccine adjuvants.
The lead candidate saponin adjuvants are Quil A and its derivative, QS The unique capacity of Quil A and QS to stimulate Th1 immune responses against exogenous antigens makes them ideal for use in vaccines against intracellular pathogens such as RSV cytomegalovirus Toxoplasma gondii , and visceral leishmaniasis and therapeutic vaccines such as cancer. Therefore, many saponins from other botanicals are being studied for their potential as vaccine adjuvants.
Notably, saponins represented by geninsenosides, notoginsenosides, and gypenosides were shown to display a slight hemolytic effect and enhance significantly a specific antibody and cellular immune response against OVA in mice. Adjuvant activity of Panax notoginseng saponin, ginsenoside was reported to increase an antigen-specific antibody and cellular response and elicit a Th1 and Th2 immune response by regulating production and gene expression of Th1 cytokines and Th2 cytokines.
The saponins from the root extract of Pelargonium grandiflorum increased specific antibody and cellular response against OVA in mice, and could be a promising balance between Th1- and Th2-directing immunological adjuvants.
Further purification of this extract afforded four adjuvant-active saponins , platycodin D, D2, D3, and platycoside E Platycodin D and D2 have recently proved to possess the adjuvant activities on recombinant hepatitis B surface antigen, Newcastle disease virus-based live attenuated vaccine, and fowlpox virus expressing the avian influenza virus H5 gene.