Separation and characterization of homopipecolic acid isoflavonoid ester derivatives isolated from Ononis spinosa L. root

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

doi:10.1016/j.jchromb.2018.05.023

Cited by 18 publications

(19 citation statements)

References 19 publications

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“…Though, this group has been extensively studied in O. spinosa [ 19 , 20 , 21 , 22 ]. Peaks 8 ([M − H] − at m / z 459), 14 ([M − H] − at m / z 489), 15 ([M − H] − at m / z 459) and 16 ([M − H] − at m / z 515), were tentatively identified as spinonin- O -hexoside, pseudobaptigenin- O -hexoside, formononetin derivative and formononetin- O -malonyl-hexoside, respectively, based on its chromatographic characteristic, as also their fragmentation pattern, which has been previously reported by Gampe et al [ 5 ]. Although two of these compounds were found in trace amounts in the studied sample (peaks 8 and 16 ), it is important to highlight the relevance of isoflavonoids to human health, having already been intensively studied, mainly in legumes, for their effects to inhibit the proliferation of certain types of cancers or even against some neurodegenerative diseases [ 23 , 24 ].…”

Section: Resultssupporting

confidence: 65%

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Methanolic Extract of the Herb Ononis spinosa L. Is an Antifungal Agent with no Cytotoxicity to Primary Human Cells

et al. 2020

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Ononis spinosa L. is a plant traditionally used as folk remedy. There are numerous studies regarding chemical constituents and health beneficial properties of Ononidis Radix. The following study was designed to investigate chemical composition and antifungal potential of the methanolic extract obtained from the O. spinosa L. herb. Chemical analyses regarding phenolic compounds of O. spinosa were performed by liquid chromatography with mass spectrometry (LC-DAD-ESI/MSn). Antifungal activity, antibiofilm properties and antifungal mode of action of the extract were evaluated, as well as cytotoxicity. Chemical analyses revealed the presence of flavonoids, isoflavonoids and phenolic acids in O. spinosa, with kaempherol-O-hexoside-pentoside being the most abundant compound (5.1 mg/g extract). Methanolic extract was active against all of the tested microfungi with Penicillium aurantiogriseum being the most sensitive to the extract inhibitory effect at 0.02 mg/mL; and effectively inhibited biofilms formed by Candida strains. Minimum fungicidal concentrations of extract rose in the presence of ergosterol and leakage of cellular components was detected. The extract showed no cytotoxicity to human gingival fibroblast (HGF-1) cells. This study significantly contributes to overall knowledge about medicinal potential of O. spinosa herbal extract and enlightens previously unrevealed properties. O. spinosa aerial parts seem to be an interesting candidate for the development of antifungal preparations, non-toxic to human cells.

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Section: Resultssupporting

confidence: 65%

“…Ononis spinosa L. (Fabaceae), spiny restharrow an ethomedicinal plant [3], is widespread in almost all of Europe, western Asia and northern Africa [4,5]. European Pharmacopoeia has recorded O. spinosa dried roots as "Ononidis Radix".…”

Section: Introductionmentioning

confidence: 99%

Methanolic Extract of the Herb Ononis spinosa L. Is an Antifungal Agent with no Cytotoxicity to Primary Human Cells

et al. 2020

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“…The most intense peaks in the chromatogram in positive ionization mode were 12 , 13 , 14 , 17 , 20 , and 23 (Figure ). Based on our previous work, these compounds were identified as homopipecolic acid esters of isoflavonoid glucosides. These molecules are analogous structures to glucoside malonates, but instead of a malonic acid, the beta amino acid homopipecolic acid is involved in the esterification.…”

Section: Resultsmentioning

confidence: 99%

“…With the application of tandem mass spectrometry, the fragmentation patterns of isoflavonoid derivatives can be examined and compared. As isoflavonoids can be found in the form of glucosides, glucoside malonates, aglycones and beta amino acid glucoside esters, the similarity of their product ion spectra can be used to classify the derivatives with the same aglycone. In some cases, mass spectrometry on its own is not sufficient for the complete structural elucidation, so the application of NMR techniques is inevitable.…”

Section: Introductionmentioning

confidence: 99%

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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“…Boldine, the main active principle of Peumus boldus, revealed to be effective in inducing apoptosis in human bladder cancer cells, as well [18]. Ononis spinosa is a folk remedy used in the treatment of urinary tract infections and stones [19]. Analogous traditional uses have been described for Solidago virga-aurea, although the scientific literature reported anti-proliferative effects, possibly related to the presence of terpene and phenolic compounds, in the phytocomplex [20,21].…”

Section: Introductionmentioning

confidence: 99%

Phenolic Content and Antimicrobial and Anti-Inflammatory Effects of Solidago virga-aurea, Phyllanthus niruri, Epilobium angustifolium, Peumus boldus, and Ononis spinosa Extracts

et al. 2020

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Prostatitis is an inflammatory condition that is related to multiple infectious agents, including bacteria and fungi. Traditional herbal extracts proved efficacious in controlling clinical symptoms associated with prostatitis. In this context, the aim of the present study was to explore the efficacy of extracts from Solidago virga-aurea, Ononis spinosa, Peumus boldus, Epilobium angustifolium, and Phyllanthus niruri against bacterial (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus cereus) and fungi strains (Candida albicans; C. tropicalis) involved in prostatitis. Additionally, anti-mycotic effects were tested against multiple species of dermatophytes (Trichophyton rubrum, T. tonsurans, T. erinacei, Arthroderma crocatum, A. quadrifidum, A. gypseum, A. currey, and A. insingulare). Antioxidant effects were also evaluated in isolated rat prostates challenged with lipopolysaccharide (LPS), and phytochemical analyses were conducted to identify and quantify selected phenolic compounds, in the extracts. Finally, a bioinformatics analysis was conducted to predict putative human and microbial enzymes targeted by extracts’ phytocompounds and underlying the observed bio-pharmacological effects. The phytochemical analysis highlighted that rutin levels could be crucial for explaining the highest antibacterial activity of P. boldus extract, especially against E. coli and B. cereus. On the other hand, in the E. angustifolium extract, catechin concentration could partially explain the highest efficacy of this extract in reducing lipid peroxidation, in isolated rat prostates stimulated with LPS. Concluding, the results of the present study showed moderate antimicrobial and anti-inflammatory effects induced by water extracts of S. virga-aurea, P. boldus, E. angustifolium, P. niruri, and O. spinosa that could be related, at least partially, to the phenolic composition of the phytocomplex.

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Separation and characterization of homopipecolic acid isoflavonoid ester derivatives isolated from Ononis spinosa L. root

Cited by 18 publications

References 19 publications

Methanolic Extract of the Herb Ononis spinosa L. Is an Antifungal Agent with no Cytotoxicity to Primary Human Cells

Methanolic Extract of the Herb Ononis spinosa L. Is an Antifungal Agent with no Cytotoxicity to Primary Human Cells

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

Phenolic Content and Antimicrobial and Anti-Inflammatory Effects of Solidago virga-aurea, Phyllanthus niruri, Epilobium angustifolium, Peumus boldus, and Ononis spinosa Extracts

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