Triterpene saponins from the roots of  Acacia albida  Del. (Mimosaceae)

Tchoukoua, Abdou; Tabopda, Turibio Kuiate; Uesugi, Shota; Ohno, Misa; Kimura, Ken; Kwon, Eunsang; Momma, Hiroyuki; Horo, Ibrahim; Çalişkan, Özgen Alankuş; Shiono, Yoshihito; Ngadjui, Bonaventure T.

doi:10.1016/j.phytochem.2016.12.019

Cited by 16 publications

(13 citation statements)

References 12 publications

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“…Beside these two families, macrocyclic topologies are also known and correspond to molecules with single oligosaccharide chains attached at two sites of the aglycone. These topologies require extensive purification and subsequent NMR experiments to be identified . In the context of our development of MS‐based methods for saponin characterization, we here consider IMMS, in association with computational chemistry, for the distinction between saponins presenting different topologies.…”

Section: Introductionmentioning

confidence: 99%

“…These topologies require extensive purification and subsequent NMR experiments to be identified. [44][45][46] In the context of our development of MS-based methods for saponin characterization, we here consider IMMS, in association with computational chemistry, for the distinction between saponins presenting different topologies. For the present study, we select the sea cucumber Holothuria forskali, the common soy Glycine max, and the quinoa Chenepodium quinoa as saponin sources, since their saponin extracts are known to be constituted by monodesmosidic saponins, 16,25 a mixture of mono-and bidesmosidic molecules, 29,47,48 and bidesmosidic structures only, 33,49 respectively.…”

Section: Introductionmentioning

confidence: 99%

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Ion mobility mass spectrometry of saponin ions

Decroo

Colson

Lemaur

et al. 2018

Rapid Comm Mass Spectrometry

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Rationale Saponins are natural compounds presenting a high structural diversity whose structural characterization remains extremely challenging. Ideally, saponin structures are best established using nuclear magnetic resonance experiments conducted on isolated molecules. However, saponins are also increasingly characterized using tandem mass spectrometry (MS/MS) coupled with liquid chromatography, even if collision‐induced dissociation (CID) experiments are often quite limited in accurately determining the saponin structure. Methods We consider here ion mobility mass spectrometry (IMMS) as an orthogonal tool for the structural characterization of saponin isomers by comparing the experimental collisional cross sections (CCSs) of saponin ions with theoretical CCSs for candidate ion structures. Indeed, state‐of‐the‐art theoretical calculations perfectly complement the experimental results, allowing the ion structures to be deciphered at the molecular level. Results We demonstrate that ion mobility can contribute to the structural characterization of saponins because different saponin ions present significantly distinct CCSs. Depending on the nature of the cation (in the positive ion mode), the differences in CCSs can also be exacerbated, optimizing the gas‐phase separation. When associated with molecular dynamics simulations, the CCS data can be used to describe the interactions between the cations, i.e. H+, Na+ and K+, and the saponin molecules at a molecular level. Conclusions Our work contributes to resolve the relationship between the primary and secondary structures of saponin ions. However, it is obvious that the structural diversity and complexity of the saponins cannot be definitively unraveled by measuring a single numerical value, here the CCS. Consequently, the structural characterization of unknown saponins will be difficult to achieve based on IMMS alone. Nevertheless, we demonstrated that monodesmosidic and bidesmosidic saponins can be distinguished via IMMS.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ion mobility mass spectrometry of saponin ions

Decroo

Colson

Lemaur

et al. 2018

Rapid Comm Mass Spectrometry

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“…Four new oleanane-type saponins, macrostachyaosides A, B, C, and D (1)(2)(3)(4) were isolated from the roots of Acacia macrostachya. Their structures were elucidated on the basis of extensive 1D-and 2D-NMR data and HR-ESI-MS analyses.…”

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confidence: 99%

“…As part of an ongoing search for bioactive saponins from Cameroonian medicinal plants, 4) four new triterpene saponins, macrostachyaosides A, B, C, and D (1)(2)(3)(4) were isolated from the roots of Acacia macrostachya. This paper describes the isolation and structure elucidation of these new compounds.…”

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confidence: 99%

“…The HPLC of their retention time and optical rotation with standard sugars. 4) The downfield shift of aglycone (Agly) C-3 and the upfield shift of Agly C-28 indicated that 1 was a bidesmosidic saponin of machaerinic acid. Based on the 1 H-, 13 C-NMR spectral data, and literature, 7) the anomeric configurations of the sugar moieties were determined as β for galactose and xylose, and α-configuration for arabinose and rhamnose.…”

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confidence: 99%

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New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)

Tchoukoua

Tabopda

Usukhbayar

et al. 2017

Bioscience, Biotechnology, and Biochemistry

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Saponins as cytotoxic agents: an update (2010–2021). Part II—Triterpene saponins

et al. 2022

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Saponins make up an important group of natural glycosidic compounds which are distinguished by triterpene or steroidal aglycone. Although widely distributed in terrestrial flora, especially higher plants, they can also be found in some marine organisms. Cytotoxic activity is one of the most frequently reported from a wide array of pharmacological activities known for these metabolites. The current review is an update of our previous paper—Saponins as cytotoxic agents (Podolak et al. Phytochem Rev 9:425–474, 2010), and covers studies that were since published (2010–2021). This part refers to triterpene saponins and complements the first, which was devoted solely to steroidal saponins (Sobolewska et al. Phytochem Rev 19:139–189, 2020). Cytotoxic activities in vitro and in vivo are presented with a main focus on structure-activity relationships and molecular mechanisms of action.

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Triterpene saponins from the roots of Acacia albida Del. (Mimosaceae)

Cited by 16 publications

References 12 publications

Ion mobility mass spectrometry of saponin ions

Ion mobility mass spectrometry of saponin ions

New triterpene saponins from the roots of Acacia macrostachya (Mimosaceae)

Saponins as cytotoxic agents: an update (2010–2021). Part II—Triterpene saponins

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