Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.

Ghribi, Lotfi; Waffo-Téguo, Pierre; Cluzet, Stéphanie; Marchal, Axel; Marques, Jessica; Mérillon, Jean‐Michel; Jannet, Hichem Ben

doi:10.1016/j.bmcl.2015.07.076

Cited by 23 publications

(17 citation statements)

References 37 publications

(37 reference statements)

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…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%

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

et al. 2019

View full text Add to dashboard Cite

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.

show abstract

Section: Resultsmentioning

confidence: 99%

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

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Formononetin is a natural isoflavone found in many medicinal plants, including Pongamia pinnata (12), Astragalus membranaceus (13), Ononis angustissima (14) and Trifolium pretense (15). Studies investigating formononetin have demonstrated that it upregulates nitric oxide synthase (16), inhibits angiogenesis and tumor growth (17) and induces the apoptosis of human osteosarcoma cells (18).…”

Section: Introductionmentioning

confidence: 99%

Formononetin ameliorates mast cell‑mediated allergic inflammation via inhibition of histamine release and production of pro‑inflammatory cytokines

2017

Exp Ther Med

View full text Add to dashboard Cite

Abstract. Various allergic diseases cause allergic inflammation, which is mediated by mast cells. The current study investigated the anti-allergic inflammatory effects of formononetin and its mechanism of action in vitro using mast cells. Levels of histamine and pro-inflammatory cytokines, including tumor necrosis factor-α (TNF-α), interleukin (IL)-1β and IL-6, were measured to assess the effects of formononetin on allergic inflammation. The activation of intracellular calcium and nuclear factor (NF)-κB, as well as the activity of caspase-1, were assessed to determine the mechanism of action. It was determined that difference concentrations of formononetin (0.1, 1 and 10 µM) suppressed histamine release and secretion of TNF-α, IL-1β and IL-6. Further investigations indicated that the effects of formononetin were associated with a reduction of intracellular calcium, suppression of NF-κB activation and upstream IκKα phosphorylation and inhibition of caspase-1 activity. Therefore, the results of the current study demonstrated that formononetin ameliorated mast cell-mediated allergic inflammation.

show abstract

“…Beside isoflavonoid derivatives, special phenolic lactones (norneolignans) were detected in the forms of glucosides (9 and 11) and aglycones (15 and 23). These derivatives of puerol A and clitorienolactone B were known in Ononis species before (Ghribi et al, 2015;Addotey et al, 2018;Gampe et al, 2018b). Surprisingly, a compound (peak 26) with a different fragmentation profile and a rather unusual UV spectrum with two absorption maxima was also observed eluting with the aglycones (Figure 4).…”

Section: Qualitative Characterization Of Phytochemical Composition Of Ononis Hrcsmentioning

confidence: 95%

Qualitative and Quantitative Phytochemical Analysis of Ononis Hairy Root Cultures

et al. 2021

View full text Add to dashboard Cite

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.

show abstract

Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.

Cited by 23 publications

References 37 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

Formononetin ameliorates mast cell‑mediated allergic inflammation via inhibition of histamine release and production of pro‑inflammatory cytokines

Qualitative and Quantitative Phytochemical Analysis of Ononis Hairy Root Cultures

Contact Info

Product

Resources

About