Characterization and identification of isoflavonoid glycosides in the root of Spiny restharrow (Ononis spinosa L.) by HPLC-QTOF-MS, HPLC–MS/MS and NMR

Gampe, Nóra; Darcsi, András; Lohner, Szilvia; Béni, Szabolcs; Kursinszki, L.

doi:10.1016/j.jpba.2016.01.058

Cited by 51 publications

(38 citation statements)

References 16 publications

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“…The two intense fragment ions at m/z 163.0388 (C 9 H 7 O 3 ) and 135.0440 (C 8 H 7 O 2 ) could be attributed to [M + H‐B‐ring] + and [M + H‐B‐ring‐CO] + (Figure B). This typical fragmentation pattern was in agreement with our previous results; consequently, the peaks were tentatively identified as the 7‐ O ‐glucoside ( 24 ), the 4″ and 6″‐ O ‐glucoside malonates ( 29 and 36 ), and the aglycone ( 45 ) of sativanone (Figure ). The molecular formula of peaks 22 , 28 , 33 , and 41 (Figure F) differed from the corresponding ones of sativanone in that of an extra oxygen and the lack of the two hydrogens which could be a consequence of a methylenedioxy substitution instead of a methoxy group.…”

Section: Resultssupporting

confidence: 91%

“…All the former discussed isoflavonoids, dihydroisoflavonoids, and pterocarpans were already known for O. spinosa ; however, peak 43 showed a m/z value for the aglycone which was not mentioned in Ononis species before. The formula calculated from the HR‐MS data was C 17 H 14 O 5 (Table ), which could refer to known compounds afrormosin, cladrin, or 2′‐methoxy formononetin.…”

Section: Resultsmentioning

confidence: 89%

“…All the former discussed isoflavonoids, dihydroisoflavonoids, and pterocarpans were already known for O. spinosa 10 (Figure 6). Consequently, it can be deduced that the mass difference arose from the substitution pattern of the B-ring, meaning that beside a methoxy group an additional methylenedioxy group is localized on it.…”

Section: Identification Of the Rare 2′-methoxy Isoflavonoidsmentioning

confidence: 99%

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Phytochemical analysis of Ononis arvensis L. by liquid chromatography coupled with mass spectrometry

et al. 2019

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Ononis arvensis L. can be found overall in Europe and is used to treat infections of the urinary tract and skin diseases in ethnopharmacology. Flavonoids, hydroxycinnamic acids, oxycoumarin, scopoletin and scopolin, phytosterols, lectins, and some selected isoflavonoids were identified in O. arvensis till date; however, there is a lack of the detailed investigation of the isoflavonoid profile of the plant. With the application of high‐resolution tandem mass spectrometry, the fragmentation patterns of isoflavonoid derivatives found in O. arvensis roots and aerial parts were investigated and discussed. Isoflavonoid glucosides, glucoside malonates, aglycones, and beta amino acid derivatives were characterized, among which homoproline isoflavonoid glucoside esters were described for the first time. Besides the known isoflavonoid aglycones described earlier in other Ononis species, two 2′‐methoxy isoflavonoid derivatives were detected. The presence of licoagroside B was verified, and its structure was also corroborated by NMR experiments. Altogether, the high‐resolution fragmentation pattern of 47 isoflavonoids and glycosides is presented, and their relative quantity in the roots and the aerial parts can be evaluated. Based on this information, the chemotaxonomic relation of Ononis species and the biosynthesis of their compounds could be comprehended to a greater depth.

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Section: Resultssupporting

confidence: 91%

Section: Resultsmentioning

confidence: 89%

Section: Identification Of the Rare 2′-methoxy Isoflavonoidsmentioning

confidence: 99%

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Phytochemical analysis of Ononis arvensis L. by liquid chromatography coupled with mass spectrometry

et al. 2019

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“…In the MS/MS spectra, the [M+H] + ion exhibited fragment ions at m/z 225.0381, 197.0444, 169.0491 and 115.0254. Similar fragment ions were found from pseudobaptigenin . As a result, M3‐5 was identified as pseudobaptigenin.…”

Section: Resultssupporting

confidence: 62%

Application of ultra‐performance liquid chromatography coupled with quadrupole time‐of‐flight mass spectrometry in identification of three isoflavone glycosides and their corresponding metabolites

Xin-hui

Liang

2018

Rapid Comm Mass Spectrometry

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A selective, sensitive and rapid method was established for detecting and identifying three isoflavone glycosides and their metabolites using UPLC/QTOF-MS. The established method can be used for further rapid structural identification studies of metabolites and natural products. Furthermore, the proposed metabolic pathways will be helpful for understanding the in vivo metabolic process of isoflavone.

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“…Many species of the genus Ononis are a source of therapeutic agents such as essential oils, flavonoid glycosides, and tannins. One of the representatives of this genus is O. arvensis L. The ingredients of this plant are used in traditional folk medicine for the treatment of various diseases, e.g., those connected with bladder and kidney (Kirmizigul et al 1997; Suntar et al 2011; Gampe et al 2016). Based on the potential value of the Ononis species, we decided to collect and characterize 29 strains associated with O. arvensis , using different approaches including phenotypic as well as genotypic characteristics for their potential use as PGPB.…”

Section: Introductionmentioning

confidence: 99%

Diversity and plant growth promoting properties of rhizobia isolated from root nodules of Ononis arvensis

Wdowiak-Wróbel

Marek-Kozaczuk

Kalita

et al. 2017

Antonie van Leeuwenhoek

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This is the first report describing isolates from root nodules of Ononis arvensis (field restharrow). The aim of this investigation was to describe the diversity, phylogeny, and plant growth promoting features of microsymbionts of O. arvensis, i.e., a legume plant growing in different places of the southern part of Poland. Twenty-nine bacterial isolates were characterized in terms of their phenotypic properties, genome fingerprinting, and comparative analysis of their 16S rRNA, nodC and acdS gene sequences. Based on the nodC and 16S rRNA gene phylogenies, the O. arvensis symbionts were grouped close to bacteria of the genera Rhizobium and Mesorhizobium, which formed monophyletic clusters. The acdS gene sequences of all the isolates tested exhibited the highest similarities to the corresponding gene sequences of genus Mesorhizobium strains. The presence of the acdS genes in the genomes of rhizobia specific for O. arvensis implies that these bacteria may promote the growth and development of their host plant in stress conditions. The isolated bacteria showed a high genomic diversity and, in the BOX-PCR reaction, all of them (except three) exhibited DNA fingerprints specific only for them. Our studies showed that restharrow isolates formed effective symbiotic interactions with their native host (O. arvensis) and Ononis spinosa but not with Trifolium repens and Medicago sativa belonging to the same tribe Trifolieae as Ononis species and not with Lotus corniculatus, representing the tribe Loteae.

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Characterization and identification of isoflavonoid glycosides in the root of Spiny restharrow (Ononis spinosa L.) by HPLC-QTOF-MS, HPLC–MS/MS and NMR

Cited by 51 publications

References 16 publications

Phytochemical analysis of Ononis arvensis L. by liquid chromatography coupled with mass spectrometry

Phytochemical analysis of Ononis arvensis L. by liquid chromatography coupled with mass spectrometry

Application of ultra‐performance liquid chromatography coupled with quadrupole time‐of‐flight mass spectrometry in identification of three isoflavone glycosides and their corresponding metabolites

Diversity and plant growth promoting properties of rhizobia isolated from root nodules of Ononis arvensis

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