Quantitative determination of isoflavonoids in <i>Ononis</i> species by UPLC‐UV‐DAD

Gampe, Nóra; Nagy, É.; Kursinszki, L.; Béni, Szabolcs

doi:10.1002/pca.2995

Cited by 8 publications

(7 citation statements)

References 28 publications

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“…Based on these observations, it is hypothesized that pseudobaptigenin is transformed to onogenin and maackiain. These results show that the measured isoflavonoid content of wild grown samples (Gampe et al, 2020) does not necessarily reflect the isoflavonoid content of the living plant, as it changes with time after harvest. As different isoflavonoids can possess distinct biological effects, the age and the storage conditions can affect the medicinal value of the sample.…”

Section: Qualitative Characterization Of Phytochemical Composition Of Ononis Hrcsmentioning

confidence: 84%

“…However, the aim of this study was not to optimize the proliferation and isoflavonoid extractability, thus modifying the circumstances of cultivation can lead to better results. Moreover, the isoflavonoid profile of wild-grown samples markedly differed from the fresh and older samples, too (Gampe et al, 2020). The most characteristic compound produced by the HRCs was medicarpin glucoside (2.23-2.89 mg/100 mg in O. spinosa and 1.69-1.87 mg/100 mg in O. arvensis), followed by sativanone glucoside (0.56-1.14 mg/100 mg in O. spinosa and 0.13-0.20 mg/100 mg in O. arvensis) and pseudobaptigenin glucoside (0.12-0.20 mg/100 mg in O. spinosa and 0.09-0.16 mg/100 mg in O. arvensis) (Supplementary Tables 2, 3).…”

Section: Proliferation Of Hrcs and Comparison Of Biomass And Phenolic Compound Accumulationmentioning

confidence: 96%

“…Standard compound naringenin were purchased from Sigma-Aldrich (St. Louis, MO, United States), and formononetin, pseudobaptigenin, onogenin, sativanone, medicarpin, and maackiain were purified from hydrolyzed extracts of Ononis spinosa root in our laboratory. The isoflavone glucoside standards (formononetin-, pseudobaptigenin-, onogenin-, sativanone-, maackiain-, and medicarpin glucoside) were isolated in our laboratory, too (Gampe et al, 2020). High-performance liquid chromatography (HPLC) and Mass spectrometry (MS)-grade methanol and acetonitrile were purchased from Fischer Scientific Co. (Fair Lawn, NJ, United States); LiChropur formic-and acetic acid were obtained from Merck (Darmstadt, Germany).…”

Section: General Materialsmentioning

confidence: 99%

“…The collected supernatants were filled up to 25 ml, out of which 1 ml was filtered through a 0.22-µm PTFE filter (Nantong FilterBio Membrane Co., Ltd., Nantong, Jiangsu, China). From these, 200 µl were taken out and kept at 83 • C for 5 h prior to HPLC analysis in order to hydrolyze malonate esters (Gampe et al, 2020). Investigating the liquid media for possible exudation of isoflavonoids, it was filtered and analyzed directly.…”

Section: Sample Preparationmentioning

confidence: 99%

“…The samples were analyzed using the same phenyl-hexyl column as mentioned at the qualitative studies. Aiming at the determination of isoflavone derivatives, the same eluents were used, with the following gradient program: 0 min, 10% B; 15 min, 30% B; 17 min, 100% B; and 19 min, 10% B with 0.4 ml/min flow rate and 5 µl injected volume, and the column was heated to 40 • C. For quantification of the isoflavanone and pterocarpan derivatives, the following gradient was used: 0 min, 25% B; 5 min, 25%; 6 min, 29% B; 15 min, 29%; 17 min, 100% B; and 19 min, 25% B with 0.4 ml/min flow rate and 5 µl injected volume, and the column was heated to 27 • C (Gampe et al, 2020).…”

Section: Uhplc-uv-dad Conditions For the Quantitative Analysis Of Ononis Samplesmentioning

confidence: 99%

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Qualitative and Quantitative Phytochemical Analysis of Ononis Hairy Root Cultures

et al. 2021

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Hairy root cultures are genetically and biochemically stable, and they regularly possess the same or better biosynthetic capabilities for specialized (secondary) metabolite production compared to the intact plant. Ononis species are well-known herbal remedies in ethnopharmacology and rich sources of isoflavonoids. Besides isoflavones, less prevalent isoflavones and pterocarpans with valuable biological effects can be found in Ononis species as well. As these plants are only collected but not cultivated, biotechnological methods could play a role in the larger-scale extraction of Ononis isoflavonoids. Regarding this information, we aimed to establish Ononis spinosa and Ononis arvensis hairy root cultures (HRCs) and analyze the isoflavonoid profile of hairy root cultures qualitatively and quantitatively, in order to define their capacity to produce biologically valuable isoflavonoids. During the qualitative description, beside isoflavonoids, two new phenolic lactones, namely, bulatlactone 2″-O-β-D-glucoside and ononilactone, were isolated, and their structures were characterized for the first time. Altogether, 29 compounds were identified by the means of UPLC-Orbitrap-MS/MS. Based on UHPLC-UV-DAD measurements, the isoflavonoid spectrum of the Ononis HRCs differed markedly from wild-grown samples, as they produce a limited range of the scaffolds. The most abundant compounds in the HRCs were medicarpin glucoside and sativanone glucoside. The overall isoflavonoid production of the cultures was comparable to wild-grown O. arvensis and approximately twice as high as in wild-grown O. spinosa samples. As the overall content of wild-grown samples include more isoflavonoid derivatives, the HRCs contain structurally less divergent isoflavonoids but in higher quantity.

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Section: Qualitative Characterization Of Phytochemical Composition Of Ononis Hrcsmentioning

confidence: 84%

Section: Proliferation Of Hrcs and Comparison Of Biomass And Phenolic Compound Accumulationmentioning

confidence: 96%

Section: General Materialsmentioning

confidence: 99%

Section: Sample Preparationmentioning

confidence: 99%

Section: Uhplc-uv-dad Conditions For the Quantitative Analysis Of Ononis Samplesmentioning

confidence: 99%

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Qualitative and Quantitative Phytochemical Analysis of Ononis Hairy Root Cultures

et al. 2021

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Anti-adipogenic activity of maackiain and ononin is mediated via inhibition of PPARγ in human adipocytes

Mladenova¹,

Savova²,

Marchev³

et al. 2022

Biomedicine & Pharmacotherapy

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Comparative GC–MS based nutrients profiling of less explored legume seeds of Melilotus, Medicago, Trifolium, and Ononis analysed using chemometric tools

Fahmy,

El-Shamy,

Farag

2023

Sci Rep

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Exploring novel sources of plant protein for nutrition of both humans and animals is motivated mainly by its growing demand worldwide, besides identifying healthy alternatives for animal protein. The present study evaluates metabolome diversity within 15 legume seed species. The examined samples comprised three Melilotus, four Medicago, four Trifolium, and four Ononis seed species. A holistic approach for metabolites profiling using gas chromatography-mass spectrometry (GC–MS) led to the annotation and quantification of 87 metabolites comprising alcohols, free amino acids, aromatics, fatty acids/esters, nitrogenous compounds, organic acids, sugar alcohols, sugars, terpenes, and steroids. Fatty acids represented the major metabolite class represented by palmitic, stearic, oleic, linoleic, and linolenic acids. Sucrose and pinitol were the major sugars and sugar alcohols among seeds. Ononis seeds (OR, OS and OA) were the most abundant in fatty acids, sugars, sugar alcohols, and free amino acids, whereas Melilotus species (MO and MS) were least enriched in these key nutrients posing Ononis as potential food source for humans and animals. The examined seeds were generally low in sulfur-containing free amino acids and lacking many of the essential free amino acids. Multivariate data analysis aided in the identification of Ononis metabolite markers belonging to various classes i.e., (alcohol) glycerol, (sugar) allofuranose, and (sugar alcohol) pinitol, although the differentiation between Medicago, Melilotus, and Trifolium genera was not attained suggestive for other analytical platforms for its classification.

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Quantitative determination of isoflavonoids in Ononis species by UPLC‐UV‐DAD

Cited by 8 publications

References 28 publications

Qualitative and Quantitative Phytochemical Analysis of Ononis Hairy Root Cultures

Qualitative and Quantitative Phytochemical Analysis of Ononis Hairy Root Cultures

Anti-adipogenic activity of maackiain and ononin is mediated via inhibition of PPARγ in human adipocytes

Comparative GC–MS based nutrients profiling of less explored legume seeds of Melilotus, Medicago, Trifolium, and Ononis analysed using chemometric tools

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