Identification of saponins from sugar beet ( Beta vulgaris ) by low and high-resolution HPLC–MS/MS

Mikołajczyk-Bator, Katarzyna; Błaszczyk, Alfred; Czyżniejewski, Mariusz; Kachlicki, P.

doi:10.1016/j.jchromb.2016.06.038

Cited by 29 publications

(29 citation statements)

References 22 publications

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“…Losses of m/z 132, 146, 162 and 176 were observed, corresponding to pentose, deoxyhexose, hexose and uronic acid moieties, respectively. Three different aglycone moieties were observed with fragment ions at m/z 543.33234, 541.31787 and 501.32074, corresponding to acetylated medicagenic acid, zanhic acid and medicagenic acid, respectively [25,26].…”

Section: Identification Of Compoundsmentioning

confidence: 99%

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

et al. 2020

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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.

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Section: Identification Of Compoundsmentioning

confidence: 99%

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

et al. 2020

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“…Similar concentrations of saponins have been detected in the filtration residues and molasses. In Polish research laboratories, several triterpene-based saponin structures have been isolated and characterized [24]. Given the scale of worldwide sugar production from sugar beet, this plant can be considered as an industrial source of saponins [25].…”

Section: Application and Characterization Of Surfactantsmentioning

confidence: 99%

Saponin-Based, Biological-Active Surfactants from Plants

Kręgiel¹,

Berłowska²,

Witońska³

et al. 2017

Application and Characterization of Surfactants

123

106

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Plants have the ability to synthesize almost unlimited number of substances. In many cases, these chemicals serve in plant defense mechanisms against microorganisms, insects, and herbivores. Generally, any part of the plant may contain the various active ingredients. Among the plant, active compounds are saponins, which are traditionally used as natural detergents. The name 'saponin' comes from the Latin word 'sapo,' which means 'soap' as saponins show the unique properties of foaming and emulsifying agents. Steroidal and triterpenoid saponins can be used in many industrial applications, from the preparation of steroid hormones in the pharmaceutical industry to utilization as food additives that exploit their non-ionic surfactant properties. Saponins also exhibit different biological activities. This chapter has been prepared by participants of the Marie Sklodowska-Curie Action-Research and Innovation Staff Exchange (RISE) in the framework of the proposal 'ECOSAPONIN.' Interactions between the participants, including chemists, physicists, technologists, microbiologists and botanists from four countries, will contribute to the development of collaborative ties and further promote research and development in the area of saponins in Europe and China. Although this chapter cannot provide a comprehensive account of the state of knowledge regarding plant saponins, we hope that it will help make saponins the focus of ongoing international cooperation.

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“…The fragmentation pattern of this compound indicated the presence of pentose (product ion at m/z 631 [M-132-H] -) and uronic acid (product ion at m/z 455 [M-132-176-H] -) in the structure. According to data found in the literature, in triterpene saponins, uronic acid is typically attached to the C-3 hydroxyl group of the aglycone [Mikołajczyk-Bator et al, 2016b]. However, based on the MS/MS data alone, it is impossible to reliably detect whether hexuronic acid is attached to C-3 hydroxyl or C-28 carbonyl of the aglycone.…”

Section: Characterization Of Saponin Structuresmentioning

confidence: 99%

“…Consequently, appropriate methods needed to be established for the qualitative and quantitative analysis of saponins in complex plant matrices. Mass spectrometry (MS), as an extremely sensitive and specific analytical technique, providing qualitative and quantitative data, is an essential tool for saponin characterization [Foubert et al, 2010;Ge et al, 2017;Gómez--Caravaca et al, 2011;Kowalczyk et al, 2011;Mikołajczyk--Bator et al, 2016a, 2016b]. In the current study, we used ultra--performance liquid chromatography (UHPLC) coupled with quadrupole-time-of-flight mass spectrometry (QTOF-MS/MS) that has recently been widely applied to characterize natural compound structures, including saponins [Alara et al, 2018;Mikołajczyk-Bator et al, 2016a;Onlom et al, 2017].…”

Section: Introductionmentioning

confidence: 99%

Determination of Saponins in Leaves of Four Swiss Chard (<i>Beta vulgaris</i> L.) Cultivars by UHPLC-CAD/QTOF-MS/MS

Mroczek¹,

Klimczak²,

Kowalczyk³

2021

Pol. J. Food Nutr. Sci.

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Swiss chard is a vegetable valued not only for the taste of its leaves but also because of its health-promoting properties. To date, nothing is known regarding the occurrence of saponins in the Swiss chard plant, even though they could be at least partially responsible for the nutraceutical activities of this plant. This research aimed to describe saponins from the leaves of four Swiss chard (Beta vulgaris L.) cultivars. Saponin structures were analyzed by UHPLC-CAD/QTOF-MS/MS. Based on the fragmentation patterns, we tentatively identified 16 triterpene saponins in B. vulgaris, including two that had not been detected previously. The observed compounds were glycosides of five different, tentatively identified aglycones, i.e., oleanolic acid, hederagenin, gypsogenin, akebonoic acid, and serjanic acid. Moreover, the structure of four saponins detected in Swiss chard leaves included dioxolane-type and six acetal-type substituents. Eleven, eight, eleven, and eight saponins were observed in saponin fractions obtained from Rhubarb, Bulls Blood, Perpetual Spinach, and White Silver cultivars, respectively. Furthermore, the content of all identified triterpene derivatives in the investigated cultivars was estimated using a method based on the UHPLC coupled with QTOF-MS/MS and charged aerosol detector (CAD). The analyzed cultivars differed in the total and individual saponin content. The total saponin content ranged from 125.53 to 397.09 μg/g DW.

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Identification of saponins from sugar beet ( Beta vulgaris ) by low and high-resolution HPLC–MS/MS

Cited by 29 publications

References 22 publications

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

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

Saponin-Based, Biological-Active Surfactants from Plants

Determination of Saponins in Leaves of Four Swiss Chard (<i>Beta vulgaris</i> L.) Cultivars by UHPLC-CAD/QTOF-MS/MS

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