Triterpenoid Glycosides from Leaves of Medicago arborea L (original) (raw)
Related papers
A Review on Saponins from Medicinal Plants: Chemistry, Isolation, and Determination
Journal of Nanomedicine Research, 2019
Saponin isolated from medicinal plants is a naturally occurring bioorganic molecule with high molecular weight and its aglycone (water non-soluble part) nucleus having 27 to 30 carbon atoms besides one or two sugar moieties (water soluble part) containing at least 6 or 12 carbon atoms respectively. The complexity of saponin chemistry maybe considered as a gap for many scientists and researchers to understand the relationship between the chemical structure and its medical or pharmaceutical behavior. Recently, the increase in demand of saponin applications was observed due to various biological, medicinal, and pharmaceutical actions. Therefore, this present review article provides detailed information about the chemistry of saponin, especially triterpenoid saponin. Classifications, chemical structure, the possible traditional isolation ways, qualitative, and quantitative determination of saponins were included exclusively. Examples of mono and bidesmosidic structure of oleanolic acid and hederagenin also outlined. Structural differences between triterpenoid, steroid, and alkaloid glycosides were summarized according to their atoms, rings, and functional groups.
Medicinal Aspect of Saponins shows their wide range of Pharmacological/Biological activities
2010
Saponins (saponosides) belong to a group of secondary metabolites, widely distributed mainly, but not exclusively, among plants. The saponins are naturally occurring surfaceactive glycosides. They are reported to occur in over 500 species from over 90 families of both edible and nonedible plants. Chemically, saponins are glycosides consisting of a sugar moiety and non-sugar aglycone, called also sapogenin. Depending on the number of sugar chains attached to the aglycone, mono-, biand tridesmosides are distinguished. According to the structure of aglycone, saponins are classified into steroidal and triterpenoid. Saponins have a high ability to bind to cell membrane sterols, which is responsible at least in part for their biological activities. They reveal also strong haemolytic properties, which differ depending on the saponin type and its aglycone structure. Saponins exhibit a wide range of biological properties and are believed to be one of the key biologically active constituents ...
Chromatographic determination of plant saponins—An update (2002–2005)
Journal of Chromatography A, 2006
The developments during 2002-2005 in the methods used for saponin analyses in plant material are presented. There were number of papers published on isolation and identification of new saponins by chromatographic techniques. Some new developments can be found in separation techniques or solid and mobiles phases used. Separation of individual saponins is still complicated and time consuming. This is due to the fact that in most of the plant species saponins occur as a multi-component mixture of compounds of very similar polarities. Thus, to isolate single compound for structure elucidation or biological activity testing, a combination of different chromatographic techniques has to be used, e.g. first separation of the mixture to simpler sub-fractions on reversed phase C18 has to be followed by further purification on normal phase Silica gel column. Especially difficult is determination of saponins in plant material as these compounds do not posses chromophores and their profiles cannot be registered in UV. Most HPLC methods apply not only specific registration at 200-210 nm, but these methods are not applicable for determination of many saponins in plant material at levels lower than 200-300 mg/kg. Some new or improved techniques for quantification of saponins in plant material were published in reviewed period. These include further progress in the application of evaporative light scattering detection (ELSD) for saponin profiling and quantification, which is also not only specific but also more sensitive in comparison to 200-210 nm detection. Some progress in development of new applications for liquid chromatography-electrospray mass spectrometry (LC/ESI/MS) for saponin determination has also been done. This method gives highest sensitivity and on line identification of separated saponins and should be recommended for specialized analyses of extracts and pharmaceutical formulas like the validation of a new assay. From non-chromatographic techniques for saponin determination, a sensitive and compound specific ELISA tests for some saponins were developed.
Antimicrobial activity of saponins fromMedicago sp.: structure-activity relationship
Phytotherapy Research, 2006
The antimicrobial activity of saponins from Medicago sativa, M. arborea and M. arabica against a selection of medically important yeasts, Gram-positive and -negative bacteria was investigated. Structure-activity growth inhibitory effects of related prosapogenins and sapogenins are also described. Increasing antibiotic activity was observed going from the saponin extracts to the sapogenin samples, suggesting that the sugar moiety is not important for the antimicrobial efficacy. Activity was especially high against Gram-positive bacteria (Bacillus cereus, B. subtilis, Staphylococcus aureus and Enterococcus faecalis) with M. arabica being the species showing a broader spectrum of action. Discrete antifungal activity was also observed, mainly against Saccharomyces cerevisiae. The observed antimicrobial properties of M. sativa and M. arborea were related to the content of medicagenic acid, while hederagenin seems to contribute to the bioactivity of M. arabica total sapogenins. The present study reports on the in vitro antibiotic activity of saponins from M. sativa L., M. arborea L. and M. arabica (L.) Huds. against a selection of medically important yeasts, and Gram-positive and Gram-negative bacteria. The structure-activity growth inhibitory effects of related prosapogenins and sapogenins are also described. METHODS Plant material. Roots and tops from M. sativa L. (syn. M. media Pers.) and M. arabica (L.) Huds., and tops from M. arborea L. were used for saponin extraction. M. sativa and M. arborea were grown at the Istituto Sperimentale per le Colture Foraggere, Italy; M. arabica was grown at the Institute of Soil Science and Plant Cultivation, Poland. Ground desiccated (40°C) plant material was used in the successive extraction procedures.
Journal of Agricultural and Food Chemistry, 2005
Triterpene saponins from aerial parts of Medicago truncatula cv. Jemalong A-17, M. truncatula Gaertn. var. longispina Urb., and M. truncatula Gaertn. var. truncatula were profiled and quantified using reverse-phase liquid chromatography with on-line photodiode array detection and electrospray ionization mass spectrometry (LC-PDA/ESI/MS/MS). The determination was based on standard curves obtained for the 18 available saponin standards, previously isolated from Jemalong A-17. Aerial parts of all three subspecies contained 17 saponins previously identified and also a substantial amount of astragaloside VIII (3-GlcA-Xyl-Rha soyasapogenol B), not previously reported in M. truncatula. The compositions of saponin mixtures were very similar in the three subspecies with three dominant groups, recognized as zanhic acid, medicagenic acid, and soyasapogenol glycosides. Relative proportions of these three groups were also similar in the three subspecies: var.
An improved method for thin layer chromatographic analysis of saponins
Food Chemistry, 2012
Analysis of saponins by thin layer chromatography (TLC) is reported. The solvent system was n-butanol:water:acetic acid (84:14:7). Detection of saponins on the TLC plates after development and air-drying was done by immersion in a suspension of sheep erythrocytes, followed by washing off the excess blood on the plate surface. Saponins appeared as white spots against a pink background. The protocol provided specific detection of saponins in the saponins enriched extracts from Aesculus indica (Wall. ex Camb.) Hook.f., Lonicera japonica Thunb., Silene inflata Sm., Sapindus mukorossi Gaertn., Chlorophytum borivilianum Santapau & Fernandes, Asparagus adscendens Roxb., Asparagus racemosus Willd., Agave americana L., Camellia sinensis [L.] O. Kuntze. The protocol is convenient, inexpensive, does not require any corrosive chemicals and provides specific detection of saponins.
International Journal of Pharmacy and Pharmaceutical Sciences, 2015
Saponins are the potential bioactive compounds secreted by plants, endophytic fungi and marine organisms. Saponins are the glycosides containing non sugar portion, aglycone (sapogenin) attached to sugar moiety by glycosidic linkage. Depending on the chemical nature of aglycone, saponins are of triterpenoid and steroid saponins. The present review gives an overview of the biosynthesis pathway of triterpenoid saponins and mechanism of the biosynthesis. The review discusses the biomedical and pharmaceutical importance of triterpenoid saponins as they possess different activities including antimicrobial, haemolytic, hypolipidemic, immunomodulating and cytotoxic activities. The review also focuses on the mechanism of their action towards various activities.
Isolation, identification and toxicity of saponin from different legumes
Food Chemistry, 1994
Saponin extracts were prepared from peas, beans and soya bean seeds by four different methods. Two biological assays were developed for measuring toxicity of crude saponin extracts based on haemolytic activity and fish mortality. The results indicated that saponin extracts were able to lyse red blood ceils with different velocity. The haemolytic activity of bean extracts were significantly higher (P < 0.05) than those of soya bean and pea extracts. Sensitivity of blood ceils to crude saponin extracts was detected by sheep and rabbit blood cells. The highest haemolytic activities of sheep and rabbit blood cells were 30-0 and 6.24 mg saponin equivalent/g legume sample, respectively. As well as being potent haemolysins, saponin extracts were lethal to guppy fish. The lethal dose (LDs0) of saponin to guppy fish was 150 /xg/ml. The ethanol/water (1 : 1) extracts showed the highest toxicity as revealed by both assays. Thin-layer chromatography (TLC) of crude saponin extract from beans separated it into six fractions, whereas pea and soya bean were separated into seven and six fractions, respectively. The TLC pattern of standard saponin indicated the presence of two main spots with Rf 0.75-0.85. Further purification of crude saponin extracts from legumes by silica gel column chromatography increased the haemolytic activity of the active principle 5.7, 5.1 and twofold for bean, soya bean and pea extracts, respectively.