Saponins from the roots of Chenopodium bonus-henricus L. with neuroprotective and anti-α-glucosidase activities

Six saponins of phytolaccagenin, bayogenin, medicagenic acid, 2β-hydroxygypsogenin, and 2β-hydroxyoleanoic acid from the roots of Chenopodium bonus-henricus L. were investigated for neuroprotective and anti-α-glucosidase activities. All tested saponins (10 µM) showed statistically significant neuroprotective activities on isolated rat brain synaptosomes using a 6-hydroxydopamine in vitro model. They preserved synaptosome viability as well as the reduced glutathione level. The bayogenin glycoside (Chbhs-05) possessed the most prominent neuroprotective effect. The anti-α-glucosidase activity of the tested saponins was established by measuring the levels of the released 4-nitrophenol using LC-MS. Bonushenricoside B (Chbhs-07) showed the highest inhibitory effect against α-glucosidase (44.1%) compared to the positive control acarbose (36.3%) at a concentration of 625 µM.

The Content of Biologically Active Substances in Crocosmia × crocosmiiflora ‘Lucifer’ Tubers after Treatment with GA3

This study was conducted to assess the influence of gibberellic acid (GA3) on the content of biologically active substances in Crocosmia × crocosmiiflora ‘Lucifer’ tubers. These tubers are a promising source of potential antioxidants, and their extracts can be used in pharmaceutical industry, as well as in cosmetics products and antifungal and antibacterial substances. Four groups of biologically active substances were determined from tubers: saponins, phenolic acid, flavonoids and carotenoids. The antioxidant activity of the extracts from tubers increased proportionally to the GA3 concentrations. GA3 at concentrations of 200, 400 and 600 mg dm−3 increased the content of medicagenic acid by 42.9–57.1% and the content of polygalic acid by 50% without affecting the content of medicagenic acid 3-O-triglucoside. The GA3 concentrations used in the experiment positively influenced the accumulation of caffeic acid, p-coumaric acid and gallic acid. The highest content of caffeic acid was noted in the tubers soaked in GA3 concentrated at 400 and 600 mg dm−3. GA3 at a concentration used in the study stimulated the accumulation of kaempferol by 15%, quercetin by 7–8.2%, quercetin 3-O-glucoside by 1.8% (when GA3 was applied at a concentration of 200 mg·dm−3) and by 4.1% and 3.6% (when GA3 was applied at concentrations of 400 and 600 mg·dm−3) and kaempferol 3-O-rhamnosylglucoside by 1.5–3.4%. The soaking of the tubers in GA3 increased the content of β-carotene by 7.9%, 5.2% and 7.9%, respectively, without affecting the content of crocin. For soaking of Crocosmia tubers, it is recommended to use GA3 at a concentration of 400–600 mg·dm−3.

Compound Characterization and Metabolic Profile Elucidation after In Vitro Gastrointestinal and Hepatic Biotransformation of an Herniaria hirsuta Extract Using Unbiased Dynamic Metabolomic Data Analysis

Herniaria hirsuta L. (Caryophyllaceae) is used for treatment of urinary stones and as a diuretic. Little is known about the active compounds and the mechanism of action. The phytochemical composition of H. hirsuta was comprehensively characterized using UHPLC-UV-HRMS (Ultrahigh-Performance Liquid Chromatography-Ultraviolet-High Resolution Mass Spectrometry) data. An in vitro gastrointestinal model was used to simulate biotransformation, which allowed the monitoring of the relative abundances of individual compounds over time. To analyze the longitudinal multiclass LC–MS data, XCMS, a platform that enables online metabolomics data processing and interpretation, and EDGE, a statistical method for time series data, were used to extract significant differential profiles from the raw data. An interactive Shiny app in R was used to rate the quality of the resulting features. These ratings were used to train a random forest model. The most abundant aglycone after gastrointestinal biotransformation was subjected to hepatic biotransformation using human S9 fractions. A diversity of compounds was detected, mainly saponins and flavonoids. Besides the known saponins, 15 new saponins were tentatively identified as glycosides of medicagenic acid, acetylated medicagenic acid and zanhic acid. It is suggested that metabolites of phytochemicals present in H. hirsuta, most likely saponins, are responsible for the pharmaceutical effects. It was observed that the relative abundance of saponin aglycones increased, indicating loss of sugar moieties during colonic biotransformation, with medicagenic acid as the most abundant aglycone. Hepatic biotransformation of this aglycone resulted in different metabolites formed by phase I and II reactions.

Hepatoprotective activity of a purified methanol extract and saponins from the roots of Chenopodium bonus-henricus L.

An ultra-high-performance liquid chromatography-high-resolution mass spectrometry based profiling of a purified MeOH extract (PME) from the roots of Chenopodium bonus-henricus L. (Amaranthaceae) tentatively identified 15 saponins of six sapogenins. The PME exerts hepatoprotective and antioxidant activities comparable to those of flavonoid complex silymarin in in vitro (1 and 10 μg/mL) and in vivo (200 mg/kg/daily for 7 days) models of hepatotoxicity, induced by CCl4. The main constituents of PME, respectively saponins bonushenricoside A (1), 3-O-β-D-glucuronopyranosyl-bayogenin-28-O-β-D-glucopyranosyl ester (2), 3-O-β-D-glucuronopyranosyl-medicagenic acid-28-O-β-D-xylopyranosyl (1→4)-α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl ester (3), 3-O-β-D-glucuronopyranosyl-2β-hydroxygypsogenin-28-O-β-D-glucopyranosyl ester (4), 3-O-α-L-rabinopyranosyl-bayogenin-28-O-β-D-glucopyranosyl ester (6) and bonushenricoside B (8) (3 μg/mL each), compared to silymarin (5 and 50 μg/mL), significantly reduced the cellular damage caused by CCl4 in rat hepatocytes, preserved cell viability and glutathione level, decreased lactate dehydrogenase leakage and reduced lipid damage. The experimental data suggest that the glycosides of phytolaccagenin, bayogenin, medicagenic acid, 2β-hydroxygypsogenin, 2β-hydroxyoleanoic acid and oleanoic acid are a promising and safe class of hepatoprotective agents.

Isolation and chemical characterization of saponins from lucerne seeds (Medicago media Pers.)

Saponins of lucerne seeds have been prepared by two different methods. It was found by thin-layer chromatography that these glycosides consist of at least four components with one dominant. Soyasapogenols B, C and E were identified in acid hydrolysate of these saponins and in carbohydrate moiety glucose, galactose, rhamnose, small quantity of arabinose and xylose and glucuronic acid. It was established that saponins of lucerne seeds do not haemolyse red blood cells, contrary to top, root and blossom saponins. That may be due to the lack of medicagenic acid glycosides.

Studies on Medicago lupulina saponins. 1. Isolation and identification of sapogenins from M. lupulina tops

Saponins from <em>M. lupulina</em> tops were investigated for the first time. Eight aglycones were found in the acid hydrolysates of saponins. All of the aglycones were isolated. On the basis of chromatography, mass spectrometry and infrared spectrometry the aglycanes were identified as soyasapogenols B, C, D, E, F and medicagenic acid. Two new aglycones were also isolated and identified as pentacyclic triterpens of β-amyrin structure. Both possess a methyl ester group which is rarely present in nature.

Isolation, chemical characterization and biological activity of alfalfa (Medicago media Pers.) root saponins

Saponins from alfalfa (<em>Medicago media</em> Pers.) roots were isolated and their acid hydrolysis revealed several aglycones that were obtained in crystalline form and characterized. Medicagenic acid, hederagenin and soyasapogenols A. B, C. D, E and F were found. Crude saponins were separated into cholesterol-precipitable and nonprecipitable fractions. The precipitable fraction consisted of medicagenic acid glycosides: glucose, arabinose, xylose and rhamnose were found as their sugar chain components. The nonprecipitable fraction was a mixture of hederagenine and soyasapogenol glycosides, and glucose arthinose. xylose. galactose and glucuronic acid were found in the sugar component,. 7 he medicagenic acid glycosides made up 6% of root dry matter and showed high biological activity. They cuased red blood cells lysis (haemolytic index 3000), completely inhibited <em>Trichoderma viride</em> growth at the concentration of 2.5 Mg. 100 cm^-3 of growth medium and retarded wheat seedling growth at concentrations as low as 100 ppm. The cholesterol-nonprecipitable fraction caused no blood cell lysis and fungus growth inhibition, although it did inhibit seedling growth, but to a much lesser extent than medicagenic acrd glycosides. The detrimental effect of alfalfa root saponins on winter wheat crop after alfalfa is discussed.