LC–MSn characterization of steroidal saponins in Helleborus niger L. roots and their conversion products during fermentation

Duckstein, Sarina M.; Stintzing, Florian C.

doi:10.1016/j.steroids.2014.09.011

Cited by 18 publications

(14 citation statements)

References 39 publications

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“…roots and sapogenin products of their fermentative transformation were performed by means of LC-MS n [125]. The characterization of metabolite-saponins from fruit mesocarp, kernel, and root of Balanites aegyptiaca was also achieved through the use of LC-ESI/MS and matrix assisted laser desorption/ionization-time of flight-mass spectrometry (MALDI-TOF/MS).…”

Section: Methodsmentioning

confidence: 99%

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Jesus

Martins

Gallardo

et al. 2016

Journal of Analytical Methods in Chemistry

197

125

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Diosgenin, a steroidal sapogenin, occurs abundantly in plants such as Dioscorea alata, Smilax China, and Trigonella foenum graecum. This bioactive phytochemical not only is used as an important starting material for the preparation of several steroidal drugs in the pharmaceutical industry, but has revealed also high potential and interest in the treatment of various types of disorders such as cancer, hypercholesterolemia, inflammation, and several types of infections. Due to its pharmacological and industrial importance, several extraction and analytical procedures have been developed and applied over the years to isolate, detect, and quantify diosgenin, not only in its natural sources and pharmaceutical compositions, but also in animal matrices for pharmacodynamic, pharmacokinetic, and toxicological studies. Within these, HPLC technique coupled to different detectors is the most commonly analytical procedure described for this compound. However, other alternative methods were also published. Thus, the present review aims to provide collective information on the most recent pharmacological data on diosgenin and on the most relevant analytical techniques used to isolate, detect, and quantify this compound as well.

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Section: Methodsmentioning

confidence: 99%

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Jesus

Martins

Gallardo

et al. 2016

Journal of Analytical Methods in Chemistry

197

125

View full text Add to dashboard Cite

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“…Rudolf Steiner (1829–1910) assumed an anti-tumor activity [3]. Today, a broad pharmacological spectrum is ascribed to Christmas rose because of its multitude of compounds: anti-bacterial, anti-inflammatory, cholesterol- and blood glucose-lowering, neuroprotective, hepatoprotective and immune-modulating effects [2, 4].…”

Section: Introductionmentioning

confidence: 99%

Preclinical evaluation of safety and potential of black hellebore extracts for cancer treatment

Felenda

Turek

Mörbt

et al. 2019

BMC Complement Altern Med

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Background The therapeutic use of Helleborus niger L. is manifold due to its specific phytochemical composition. Two compound groups, the ranunculin derivates including protoanemonin and the steroidal saponins, are also associated with toxicity (genotoxicity, disintegration of membrane structures). Therefore, in vitro investigations were performed on safety aspects of a Helleborus niger aqueous fermented extract ( HNE ). In addition its therapeutic potential against various cancer cell lines was assessed to gain insight into the respective mechanisms of action. Methods To evaluate the safe use of HNE , Ames and hemolytic tests were carried out. Two angiogenesis assays in 2D and 3D design were conducted to assess the anti-angiogenetic potential, for which human umbilical vein endothelial cells (HUVEC) were chosen. A panel of tumor cell lines was used in 2D and 3D proliferation assays as well in the migration- and invasion-assay. All investigations were performed with HNE compared to reference substances. The 2D proliferation assay was additionally performed with isolated compounds of HNE (characteristic steroidal saponins). Results HNE did not exhibit any genotoxic potential. Concentrations up to 10 μl/ml were classified as non-hemolytic. HNE exerted anti-angiogenetic effects in HUVEC and anti-proliferative effects in five cancer cell lines, whereas hellebosaponin A and D as well macranthosid I did not show comparable effects neither singly nor in combination. Due to the inherent instability of protoanemonin in isolated form, parallel investigations with protoanemonin could not be performed. HNE (600–1000 μg/ml) inhibited the migration of certain cancer cells by > 80% such as Caki-2, DLD-1 and SK-N-SH. Conclusion HNE exhibit neither genotoxic nor hemolytic potential. The present investigations verify the anti-angiogenetic effects on HUVEC, the anti-proliferative effects and migration-inhibiting properties on tumor cells. The lower effect of the relevant steroidal saponins compared to the whole extract underlines the fact that the latter is more effective than a blend of isolated pharmacologically active components. Electronic supplementary material The online version of this article (10.1186/s12906-019-2517-5) contains supplementary material, which is available to authorized users.

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“…As previously discussed, galactosides elute before glucosides, so P'15 is assumed to be (3 β ,5 β ,25 S /R)- Spirostan-3- O -[ β - d -Glucopyranosyl-(1 → 2)-[ β - d -glucopyranosyl-(1 → 3)]- β - d -galactopyranoside] and P'19 is assumed to be Spirostan-3- O -[ β - d -Glucopyranosyl-(1 → 2)-[ β - d -glucopyranosyl-(1 → 3)]- β - d -glucopyranoside]. Exclusion of the furostanol possibility; Furost-20(22)-ene-3,26-diol; (3 β ,5 β ,25R)-form, 3-O-[ β - d -Glucopyranosyl-(1 → 2)- β - d -glucopyranoside], 26- O - β - d -glucopyranoside was based on the different mechanism of fragmentation of furostanols in positive mode, illustrated by the ion formation in MS1 which takes place by cleavage of the free and rather labile HO-C(22) group, which is absent in the spirostanol type, resulting in a prominent dehydrated pseudo-molecular ion, [(M-H 2 O) + H] + 54 .…”

Section: Resultsmentioning

confidence: 99%

LC–MS/MS and GC–MS profiling as well as the antimicrobial effect of leaves of selected Yucca species introduced to Egypt

Sayed

Basam

El-Naggar

et al. 2020

Sci Rep

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Few studies thoroughly investigated different Yucca species introduced to Egypt. As a part of our ongoing investigation of the Yucca species; Yucca aloifolia and its variety Yucca aloifolia variegata, Yucca filamentosa, and Yucca elephantipes (Asparagaceae) were extensively subjected to phytochemical and antimicrobial investigation. Yucca species cultivated in Egypt showed no antimicrobial effect. GC/MS of the lipoid contents of Y. aloifolia variegata was carried out. Twenty-six fatty acids were identified. Saturated fatty acids established almost twice the unsaturated ones and constituted 64.64% of which palmitic acid and palmitoleic acid signifying 58.28% and 30.98%, respectively. Hydrocarbons were 21 constituting 39.64% of the unsaponifiable fraction. Only three sterols 42.36% were detected, major was γ-sitosterol. LC–MS/MS comparison of the 4 plant extracts imply that Y.aloifolia variegata L extract was the richest, which was apparent through its superior biological activity. LC–MS/MS analysis of the total alcoholic extract (Alc) of the leaves of Y.aloifolia variegata L. was performed using MS-techniques at different voltages; equal to 35 and 135 eV. Negative and positive-ion modes analyses at low fragmentation energy allowed the tentative identification of 41 and 34 compounds, respectively. The LC–ESI–MS/MS analysis in the positive mode proved to be better in the identification of saponins.

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LC–MSn characterization of steroidal saponins in Helleborus niger L. roots and their conversion products during fermentation

Cited by 18 publications

References 39 publications

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Diosgenin: Recent Highlights on Pharmacology and Analytical Methodology

Preclinical evaluation of safety and potential of black hellebore extracts for cancer treatment

LC–MS/MS and GC–MS profiling as well as the antimicrobial effect of leaves of selected Yucca species introduced to Egypt

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