Nebulosides A–B, novel triterpene saponins from under-ground parts of Gypsophila arrostii Guss. var. nebulosa

Arslan, İdris; Çelik, Ali; Melzig, Matthias F.

doi:10.1016/j.bmc.2012.12.036

Cited by 37 publications

(24 citation statements)

References 11 publications

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“…Regarding E, three mass intervals of 79.958 (sulphate group), 162.053 (glucose) and 242.011 (glucose + sulphate group) were observed in MS/MS spectra (Table S1). The base peak corresponded to the [α chain-H] -(monoacetylated and sulphated tetrasaccharide at m/z 707) which further undergoes cross-ring cleavages of the terminal acetylated fucose: 3,5 A0α (-100), 0,3 A0α (-116) and 1,3 A0α (-128) resulting in the ions at m/z 607.120, 591.127 and 579.124, respectively (Table S1)…”

Section: Fragmentation Patterns Of Gotcab References A-e By Lc-hrmsmentioning

confidence: 99%

“…1) and are among the highest glycosylated bidesmosides in advanced taxonomic groups Caryophyllidae, Rosidae and Asteridae. 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].…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Fragmentation Patterns Of Gotcab References A-e By Lc-hrmsmentioning

confidence: 99%

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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“…It has also been reported that G. paniculata and G. arrostii var. nebulosa saponins enhance the cytotoxicity of the type I ribosome – inactivating protein (RIP‐I) saporin from Saponaria officinalis (Weng et al ., ; Arslan et al ., ).…”

Section: Introductionmentioning

confidence: 97%

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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“…17,18) Some of these triterpenoids were reported to exhibit anti-tyrosine kinase activity. 19,20) Here we focused on a pentacyclic triterpenoid gypsogenin, 21,22) extracted from Gypsophila species, 23,24) which is widely distributed in the Eurasian continent. Previous studies have demonstrated anti-cancer activities of gypsogenin derivatives 1c, 1e and 1f ( Fig.…”

mentioning

confidence: 99%

The First Pentacyclic Triterpenoid Gypsogenin Derivative Exhibiting Anti-ABL1 Kinase and Anti-chronic Myelogenous Leukemia Activities

Çiftçi

Öztürk

Ali

et al. 2018

Biological & Pharmaceutical Bulletin

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SummaryThe discovery of the chimeric tyrosine kinase breakpoint cluster region kinase-Abelson kinase (BCR-ABL)-targeted drug imatinib conceptually changed the treatment of chronic myelogenous leukemia (CML). However, some CML patients show drug resistance to imatinib. To address this issue, some artificial heterocyclic compounds have been identified as BCR-ABL inhibitors. Here we examined whether plant-derived pentacyclic triterpenoid gypsogenin and/or their derivatives show inhibitory activity against BCR-ABL. Among the three derivatives, benzyl 3-hydroxy-23-oxoolean-12-en-28-oate (1c) was found to be the most effective anticancer agent on the CML cell line K562, with an IC 50 value of 9.3 µM. In contrast, the IC 50 against normal peripheral blood mononuclear cells was 276.0 µM, showing better selectivity than imatinib. Compound 1c had in vitro inhibitory activity against Abelson kinase 1 (ABL1) (IC 50 =8.7 μM), the kinase component of BCR-ABL. In addition, compound 1c showed a different inhibitory profile against eight kinases compared with imatinib. The interaction between ATP binding site of ABL and 1c was examined by molecular docking study, and the binding mode was different from imatinib and newer generation inhibitors. Furthermore, 1c suppresses signaling downstream of BCR-ABL. This study suggests the possibility that plant extracts may be a source for CML treatment and offer a strategy to overcome drug resistance to known BCR-ABL inhibitors. KeywordsGypsogenin, Abelson tyrosine-protein kinase 1, chronic myelogenous leukemia Biological and Pharmaceutical Bulletin Advance PublicationCancer is a worldwide health problem, and despite intensive research efforts over the last several decades, an effective cure has not been identified. 1)However, the recent discovery of molecular targeted drugs against cancer at the end of the 20 th century has led to promising results. 1,2) Imatinib (Fig. 1), which targets the chimeric tyrosine kinase breakpoint cluster region kinase-Abelson kinase (BCR-ABL), [3][4][5][6] was discovered based on the findings that chronic myelogenous leukemia (CML) is caused by a chromosomal translocation that results in the constitutively expressed and active BCR-ABL. 7,8) While imatinib can be initially effective in treating CML, some patients have shown drug resistance to imatinib. [9][10][11] Several new generation drugs with a different binding mode to Abelson kinase (ABL) have thus been developed. 6,[12][13][14][15][16] These drugs are artificial heterocyclic compounds, however, if widely distributed natural products and/or their derivatives show the inhibitory activity against BCR-ABL, it would be more convenient to get.Pentacyclic triterpenoids, a category of natural compounds, can be extracted from a variety of plants and show various activities. 17,18) Some of these triterpenoids were reported to exhibit anti-tyrosine kinase activity. 19,20) Here we focused on a pentacyclic triterpenoid gypsogenin, 21,22) extracted from Gypsophila species, 23,24) which is widely distributed in the Eu...

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Nebulosides A–B, novel triterpene saponins from under-ground parts of Gypsophila arrostii Guss. var. nebulosa

Cited by 37 publications

References 11 publications

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)

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)

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

The First Pentacyclic Triterpenoid Gypsogenin Derivative Exhibiting Anti-ABL1 Kinase and Anti-chronic Myelogenous Leukemia Activities

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