Countercurrent chromatography separation of saponins by skeleton type from Ampelozizyphus amazonicus for off-line ultra-high-performance liquid chromatography/high resolution accurate mass spectrometry analysis and characterisation

Figueiredo, Fabiana de Souza; Celano, Rita; Silva, Danila de Sousa; Costa, Fernanda das Neves; Hewitson, Peter; Ignatova, Svetlana; Piccinelli, Anna Lisa; Rastrelli, Luca; Leitão, Suzana Guimarães; Leitão, Gilda Guimarães

doi:10.1016/j.chroma.2016.12.053

Cited by 18 publications

(23 citation statements)

References 27 publications

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“…The peak with t R of 53.7 min was tentatively identified as Brandão et al (1992) and later reported in A. amazonicus (Figueiredo et al 2017). This correlation was possible due to the fragments generated in the MS 2 (Fig.…”

Section: Lc-dad-mssupporting

confidence: 62%

“…1). The use of electrospray ionization (ESI) is widely described in the literature for saponin analyses (Figueiredo et al 2017). However, in this work, the APCI source was selected because it is a good option to analyze complex mixtures containing pentacyclic triterpenes, which have low ionization in ESI sources (Nicolaus et al 2016).…”

Section: Lc-dad-msmentioning

confidence: 99%

“…However, these fragments related to sugar losses could also indicate the presence of jujuboside (3), described by Higuchi et al (1984) and Schühly et al (2000), since these two saponins have the same minimum molecular formula (C 46 H 74 O 17 ), comprising sugars and aglycones of the same molecular weight. Figueiredo et al (2017) reported the presence of two saponins with the same characteristics in A. amazonicus, a plant from the Rhamnaceae family: a molecular ion of [MH] -897.5 m/z, with product ions of 765, 735, and 603 m/z, corresponding to the same losses. An important highlight of jujuboside and the abovementioned saponin (bacopasaponin C, 5) is that both possess the same sugar residues.…”

Section: Lc-dad-msmentioning

confidence: 99%

“…S2) provided the annotation of 44 saponins, of which 40 were described for the first time for Z. joazeiro, with errors less than ± 10 ppm, using ESI as the ionization source. The described substances (Table S4 and Figure S3) were organized into four groups: hemolytic saponins (I), annotated non-hemolytic saponins previously described for Z. joazeiro or other species of the genus Ziziphus (II), other non-hemolytic saponins reported by Figueiredo et al (2017) in A. amazonicus (III), and known aglycones and triterpenes (IV). In group I (Table S4), thirteen saponins bearing an oleanane skeleton with deprotonated molecular ions corresponding to those described as hemolytic were found, and their hemolysis indexes are depicted (Voutquenne et al 2002).…”

Section: Hr-msmentioning

confidence: 99%

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Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Nascimento

Fonseca

Campos

et al. 2020

Rev. Bras. Farmacogn.

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Ziziphus joazeiro Mart., Rhamnaceae, is a plant native to northeast Brazil where it is known as "juazeiro." Its bark, rich in saponins, is widely utilized in folk medicine and as a supply to produce cosmetics. Aiming at the preservation of the species and the search for an alternative vegetal raw material, the phytochemical profiles of bark and leaves were compared by chemical techniques. The foaming index and gravimetric studies indicated that, in general, bark values were approximately twice than those of the leaves. The same occurred with the hemolysis indexes. Extracts were dereplicated by liquid chromatography with diode array detection coupled to mass spectrometry analyses using an atmospheric pressure chemical ionization source, which indicated that at least 5 saponins were common to all bark and leaf samples. The direct infusion high-resolution mass spectrometry analyses revealed at least 44 different saponins distributed between the bark and leaves of the analyzed plant, of which 40 were described for the first time. The data showed that there were similarities between the studied plant organs as demonstrated by mass spectrometry, foaming index, and hemolysis indexes. Therefore, with the application of a suitable standardization procedure the leaves could be a promising source for obtaining "juazeiro-type" saponins.

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Section: Lc-dad-mssupporting

confidence: 62%

Section: Lc-dad-msmentioning

confidence: 99%

Section: Lc-dad-msmentioning

confidence: 99%

Section: Hr-msmentioning

confidence: 99%

See 2 more Smart Citations

Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Nascimento

Fonseca

Campos

et al. 2020

Rev. Bras. Farmacogn.

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show abstract

“…There is a precedence for using CCS fractionation in the first chromatographic dimension along with LC–MS in the second chromatographic dimension to identify low abundance compounds from complex matrices. CCS x LC–MS has been used in evaluation of bioactive secondary metabolites [23–28]. CCS x LC–MS has also been applied in determination of Alternaria mycotoxins in wine [29] and toxaphene metabolites in polar bear adipose tissue [30].…”

Section: Introductionmentioning

confidence: 99%

Countercurrent separation assisted identification of two mammalian steroid hormones in Vitex negundo

Fan

Liu

Kulakowski

et al. 2018

Journal of Chromatography A

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Countercurrent separation (CCS) has been widely used for the separation of high abundance compounds. However, the identification of low abundance compounds, such as mammalian steroid hormones, from natural sources is still a challenging task. A mixture of 14 human steroid hormone reference compounds was prepared for the development of a CCS enrichment strategy. The TLC-based GUESS (Generally Useful Estimate of Solvent Systems) method along with partitioning experiments were implemented to develop a process for the enrichment of these low abundance compounds with CCS. The application of CCS to the steroid hormone enrichment of Vitex negundo extracts was demonstrated by the identification of progesterone and estriol. This method provides a CCS-driven strategy to mine plant sources for low abundance compounds.

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Mass spectrometry as a tool for the dereplication of saponins from Ampelozizyphus amazonicus Ducke bark and wood

Mendonça

Simas

et al. 2020

Phytochemical Analysis

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Introduction Mass spectrometry in natural products research has been used as a first step to identify possible chemical structures and to guide subsequent efforts to isolate novel compounds. Preparations of Ampelozizyphus amazonicus Ducke (AA) are known for their high content of saponins, especially dammarane‐type triterpenoid aglycones. In the Amazon, where it is known as “saracura‐mirá”, roots and bark are widely used for the treatment and prevention of malaria, while the wood is discarded. The extract prepared from the wood is also saponin‐rich, but its exact chemical composition has not been described. Objective This study provides information on the chemical profiling and tentative structural identification of the major compounds (saponins) present in aqueous and ethanol extracts of bark and wood of AA by mass spectrometry. Methods The strategy used to identify compounds present in all samples was ultra‐high‐performance liquid chromatography with an ultraviolet detector coupled to tandem mass spectrometry (UHPLC‐UV‐MS/MS) for the analysis of fragmentation patterns through product ion scan using MZmine 2 software. Also, direct sample injection and electrospray ionisation combined with high‐resolution mass spectrometry (DI‐ESI‐HRMS) measurements were performed. Results The extracts showed chemical similarity, and 95 saponins were tentatively identified in AA wood and bark, including 73 which are described for the first time as tentative structures for this plant species. Conclusion This research describes a useful method for the fast and simultaneous tentative identification of major saponins in AA, contributing to the study of the chemical properties of this genus and family. Furthermore, it demonstrates the importance of the qualitative dereplication process, allowing a straightforward way to propose the tentative identification of compounds.

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Countercurrent chromatography separation of saponins by skeleton type from Ampelozizyphus amazonicus for off-line ultra-high-performance liquid chromatography/high resolution accurate mass spectrometry analysis and characterisation

Cited by 18 publications

References 27 publications

Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Ziziphus joazeiro, a Saponin-Rich Brazilian Medicinal Plant: Pharmacognostic Characterization of Bark and Leaves

Countercurrent separation assisted identification of two mammalian steroid hormones in Vitex negundo

Mass spectrometry as a tool for the dereplication of saponins from Ampelozizyphus amazonicus Ducke bark and wood

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