A cytotoxic triterpenoid saponin from under-ground parts of Gypsophila pilulifera Boiss.&amp; Heldr.

Arslan, İdris; Çelik, Ali; Chol, Jang Hak

doi:10.1016/j.fitote.2012.02.005

Cited by 26 publications

(20 citation statements)

References 11 publications

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“…Gypsophila species roots are an extremely rich source of glucuronide oleanane‐type triterpenoid carboxylic acid 3,28‐ O ‐bidesmosides (GOTCABs), having a glucuronic acid moiety at the C‐3 hydroxyl group of the aglycone (Tan et al ., ; Henry, ; Bottger and Melzig, ; Zhang et al ., ). Previous reports have shown that saponins from G. oldhamiana and G. pilulifera display cytotoxic activity against different human cancer cell lines (Bai et al ., ; Arslan et al ., ; Zhang et al ., ). It has also been reported that G. paniculata and G. arrostii var.…”

Section: Introductionmentioning

confidence: 99%

Selective Profiling of Saponins from Gypsophila trichotoma Wend. by HILIC Separation and HRMS Detection

Gevrenova

Bardarov²,

Bardarov³

et al. 2017

Phytochemical Analysis

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Section: Introductionmentioning

confidence: 99%

Selective Profiling of Saponins from Gypsophila trichotoma Wend. by HILIC Separation and HRMS Detection

Gevrenova

Bardarov²,

Bardarov³

et al. 2017

Phytochemical Analysis

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“…Gypsophila L. species (Caryophyllaceae) have been shown to accumulate GOTCAB saponins [2][3][4][5]. Gypsophila GOTCAB are known to possess various pharmaceutical properties such as cytostatic and cytotoxic effects on malignant tumor cells [6][7][8][9], synergistic enhancement of the immunotoxines activity [10], adjuvant properties for vaccines as immunostimulatory complexes [11]. Since GOTCAB saponins usually are a mixture of structurally related forms with very similar polarities, their separation remains a challenge [1].…”

Section: Introductionmentioning

confidence: 99%

A new liquid chromatography-high resolution Orbitrap mass spectrometry-based strategy to characterize Glucuronide Oleanane-type Triterpenoid Carboxylic Acid 3, 28-O-Bidesmosides (GOTCAB) saponins.A case study of Gypsophila glomerata Pall ex M. B. (Caryophyllaceae)

Gevrenova

Bardarov

Bouguet‐Bonnet

et al. 2018

Journal of Pharmaceutical and Biomedical Analysis

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Glucuronide Oleanane-type Triterpenoid Carboxylic Acid 3, 28-Bidesmosides (GOTCAB) saponins are bioactive natural compounds spread in Caryophyllidae. The high complexity of GOTCAB occurring as closely related isobaric and positional isomers is a challenge in their separation and identification. A new liquid chromatography - high resolution Orbitrap mass spectrometry acquisition strategy would be important for the structural elucidation of GOTCAB in plant extracts. In this study, the fragmentation behaviors of GOTCAB from methanol-aqueous root extract of Gypsophila glomerata Pall ex M. B. (Caryophyllaceae) were investigated using ultra high-performance liquid chromatography (UHPLC) coupled with hybrid quadrupole-Orbitrap high resolution mass spectrometry (HRMS). A new saponin was isolated and its structure was established by 1D and 2D-NMR spectroscopic experiments as 3-O-β-D-galactopyranosyl-(1→2)-[α-L-arabinopyranosyl-(1→3)]-β-D-glucuronopyranosyl gypsogenin 28-O-α-L-arabinopyranosyl-(1→3)-[β-D-xylopyranosyl-(1→4)]-α-L-rhamnopyranosyl-(1→2)-β-D-fucopyranosyl ester. On the basis of the accurate mass measurements, fragmentation patterns in MS/MS analyses and comparison with previously isolated authentic references, a total of 41 GOTCAB saponins were identified or tentatively elucidated in G. glomerata roots, including 14 pairs of isobars. Possible fragmentation pathways for three groups of GOTCAB are suggested. The group I appeared to be GOTCAB of gypsogenin with two carbohydrate chains: a branched trisaccharide at C-3 and tri- to hexa-saccharide attached to C-28 of the aglycone through a deoxyhexose residue. Saponins with monoacetylated (group II) or sulphated (group III) C-28 chain were evidenced, as well as quillaic and oleanolic acid GOTCAB. Sixteen GOTCAB were previously not described. The content of Gypsophila prosaponins, gypsogenin 3-O-glucuronide (7.4079 ± 0.0723 mg/g dry weight, dw) and quillaic acid 3-O-glucuronide (4.4593 ± 0.1207 mg/g dw), was determined by solid phase extraction - high-performance liquid chromatography (SPE-HPLC). In this study is presented the first systematic investigation on the fragmentation patterns and diagnostic fingerprints of the fragment ions in the MS/MS spectra of the gypsogenin -, quillaic acid - and oleanolic acid - bidesmosides. A LC-HRMS Orbitrap acquisition strategy could give an insight in the GOTCAB containing taxa.

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“…We have previously reported that purification and structural elucidation of natural triterpenoidal saponins and their forceful activities, such as genotoxicological effects, enhance toxicity of type-I ribosome inactivating proteins (Arslan, 2014a(Arslan, , b, 2017Arslan et al 2012Arslan et al , 2013Arslan and Ili 2015).…”

Section: Occurrence Isolation and Identificationmentioning

confidence: 99%

N-triterpene Saponins in Cancer Therapy: a Review of Mode of Action

Arslan

Cenzano

2020

Rev. Bras. Farmacogn.

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A cytotoxic triterpenoid saponin from under-ground parts of Gypsophila pilulifera Boiss.& Heldr.

Cited by 26 publications

References 11 publications

Selective Profiling of Saponins from Gypsophila trichotoma Wend. by HILIC Separation and HRMS Detection

Selective Profiling of Saponins from Gypsophila trichotoma Wend. by HILIC Separation and HRMS Detection

A new liquid chromatography-high resolution Orbitrap mass spectrometry-based strategy to characterize Glucuronide Oleanane-type Triterpenoid Carboxylic Acid 3, 28-O-Bidesmosides (GOTCAB) saponins.A case study of Gypsophila glomerata Pall ex M. B. (Caryophyllaceae)

N-triterpene Saponins in Cancer Therapy: a Review of Mode of Action

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