Isoflavonoids with inhibiting effects on human hyaluronidase-1 and norneolignan clitorienolactone B from Ononis spinosa L. root extract

Addotey, J; Lengers, Isabelle; Jose, Joachim; Gampe, Nóra; Béni, Szabolcs; Petereit, Frank; Hensel, Andreas

doi:10.1016/j.fitote.2018.08.013

Cited by 17 publications

(21 citation statements)

References 18 publications

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confidence: 84%

“…The identity of the aglycones was investigated using calycosin as standard substance and its retention time and MS/MS spectrum matched with the later eluting peak ( 34 ). As Addotey et al isolated calycosin D from O. spinosa , which differ only in the position of a methyl group (see Figure ), it was hypothesized that the major peaks ( 4 , 16 , and 34 ) are the derivatives of this molecule. To verify this hypothesis, the firstly eluting relative larger peaks ( 2 and 11 ) were isolated and investigated by NMR.…”

Section: Resultsmentioning

confidence: 99%

“…Nevertheless, the authors drove to the conclusion that spinonin contained a 2,3‐dihydro‐3‐oxofurane ring instead of a 2,3‐dihydro‐2‐oxofurane, like the puerol derivatives. Puerol A and its 4′‐ O ‐methylated form, puerol B, along with their 2′‐ O‐ glucosides were isolated from O. angustissima L. by Ghribi et al but another O ‐methylated derivative of puerol A (clitorienolactone B) was isolated from O. spinosa by Addotey et al (See Figure S8). Puerol B and clitorienolactone differ only in the position of a methyl substitution.…”

Section: Resultsmentioning

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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confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

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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“…Also, the European Medical Agency recommends the use of restharrow extracts for flushing of the urinary tract as an adjuvant herbal material during minor urinary complaints due to its diuretic effects [2,3]. The diuretic effect is based on an inhibition of human hyaluronidase-1 (Hyal-1) by the isoflavone sativanone [4].…”

Section: Introductionmentioning

confidence: 99%

“…In vitro investigations indicated inhibitory activity of the extract and, particularly, the pterocarpan medicarpin against 5-lipoxygenase and leukotriene B4 formation [7]. Recently, it has been shown that aqueous and dichloromethane extracts significantly reduce the release of IL-8 and TNFα from human neutrophils, which was related to the presence of the norneolignan clit-orienolacton B [4] and the triterpene onocerin. These anti-inflammatory effects were due to a significant inhibition of TLR4-mediated signaling [8].…”

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confidence: 99%

Aqueous Root Extract from Ononis spinosa Exerts Anti-adhesive Activity against Uropathogenic Escherichia coli

2020

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Extracts from Ononis spinosa are traditionally used for urinary tract infections due to diuretic and anti-inflammatory activity. A potential influence on the virulence of uropathogenic Escherichia coli has not been investigated until now. The following study aimed to investigate the influence of an aqueous O. spinosa extract on uropathogenic E. coli and uropathogenic E. coli host cell interaction. A hot water extract from the roots of O. spinosa (O. spinosa extract) was characterized by LC-qTOF-MS. The influence of O. spinosa extract on the proliferation of uropathogenic E. coli UTI89 and on cell viability against human T24 bladder cells was investigated. Anti-adhesive activity of O. spinosa extract was assessed by flow cytometry, evaluating the adhesion of fluorescent-labelled UTI89 to T24 bladder cells. Internalization of uropathogenic E. coli into T24 cells was monitored by an invasion assay. O. spinosa extract was characterized by the presence of isoflavones, isoflavanones, licoagrosides, pterocarpans, tartaric acid derivatives, and saponines. O. spinosa extract had no influence on the proliferation of uropathogenic E. coli (125 – 1000 µg/mL) and did not influence the cell viability of T24 cells. Bacterial adhesion to T24 cells was significantly (p > 0.001) inhibited by O. spinosa extract in a concentration-dependent manner (125 – 1000 µg/mL) during coincubation. Preincubation of uropathogenic E. coli or T24 cells with O. spinosa extract reduced bacterial adhesion, but to a lower extent than during coincubation. Consequently, the reduced bacterial adhesion also leads to a reduced internalization of uropathogenic E. coli uropathogenic E. coli into the host cell. O. spinosa extract does not interact with FimH-mediated uropathogenic E. coli adhesion to host cells. From these data, the traditional use of O. spinosa extracts for urinary tract infections seems to be rationalized.

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

Gampe

Nagy

Kursinszki

et al. 2020

Phytochemical Analysis

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Introduction: The root of the Ononis species has been used internally and externally in ethnomedicine for centuries and contains biologically valuable isoflavonoid compounds. Therefore, it is important to obtain quantitative information about the isoflavonoid profile of these plants.Objectives: In this article we aimed to develop an optimised sample preparation protocol alongside a validated method for the quantitative measurement of isoflavones, isoflavanones and pterocarpans in the form of glucosides and aglycones, in order to compare the specialised metabolites of Ononis spinosa L. and O. arvensis L.Material and methods: Quantitative determination was carried out by the means of ultra-performance liquid chromatography coupled with ultraviolet diode-array detection (UPLC-UV-DAD).Results: An optimised sample preparation method was developed to transform malonyl glucosides to their glucosidic forms. Chromatographic methods were created for the baseline separation of isoflavones, isoflavanones and pterocarpans alongside with their glucosides. Altogether 12 compounds were evaluated quantitatively in samples of O. spinosa and O. arvensis. Conclusion:As a result, no characteristic change could be observed between the two species regarding their isoflavonoid pattern.

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Isoflavonoids with inhibiting effects on human hyaluronidase-1 and norneolignan clitorienolactone B from Ononis spinosa L. root extract

Cited by 17 publications

References 18 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

Aqueous Root Extract from Ononis spinosa Exerts Anti-adhesive Activity against Uropathogenic Escherichia coli

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

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