Triterpenoid Saponins from Gypsophila altissima L.

Chen, Qing; Luo, Jian‐Guang; Kong, Ling–Yi

doi:10.1248/cpb.58.412

Cited by 18 publications

(9 citation statements)

References 8 publications

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“…This is consistent with the presence of two tertiary hydroxyl groups at C-3 and C-16 (Fig. 8), and the structure of quillaic acid, regularly identified in Gypsophila species in GOTCAB forms [30][31][32][33]. Quillaic acid was distinguished by its unique MS/MS fragmentation pattern including diagnostic ions at m/z 421.311 and 405.316 (Table S2).…”

Section: Type I -Gotcab Saponins With a C-28 Oligosaccharide (Tri- Tsupporting

confidence: 84%

“…One of them (10) was identified as reference A, while 19-22, 27/28 and 31 corresponded to its derivatives. Acetylated GOTCAB from type II (33)(34)(35)(36)(37) included reference B and its derivative 35 along with 37 (acetylated derivative of 32). Type III GOTCAB with sulphated pentose unit in the α chain was identified for the first time in the genus Gypsophila.…”

Section: Resultsmentioning

confidence: 99%

“…11 and 19-22 could be associated with saponins, identified in G. paniculata [30,31,35]. Recently, new GOTCAB saponins with C-28 acetylated ester chain were isolated from the roots of G. oldhamiana [28], G. repens [36], G. altissima [33], G. perfoliata [27] along with the GOTCAB references B, C and D from G. trichotoma [9]. Saponins 33 was previously identified in G. trichotoma (reference B), while related saponin of 34 was found in G. altissima.…”

Section: A Strategy To Screen and Characterize Gotcab Saponinsmentioning

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: Type I -Gotcab Saponins With a C-28 Oligosaccharide (Tri- Tsupporting

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: A Strategy To Screen and Characterize Gotcab Saponinsmentioning

confidence: 99%

See 1 more Smart Citation

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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“…Various Gypsophila taxa have been utilized for different purpose in folk medicine (Zheleva‐Dimitrova et al, ). For example, G. oldhamiana and G. paniculata have been widely used to lowering fever, treat consumptive disease, malnutrition syndrome, and diabetes (Chen, Luo, & Kong, ). G. elegans was reported to be used in immune disorders as well as liver diseases (Huang et al, ).…”

Section: Introductionmentioning

confidence: 99%

Preliminary phytochemical analysis and evaluation of in vitro antioxidant, antiproliferative, antidiabetic, and anticholinergics effects of endemicGypsophilataxa from Turkey

et al. 2019

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The phenolic contents and antioxidant, anticancer, antidiabetic, and anticholinergic potentials of four endemic Gysophila taxa (G. pallida, G. arrosti, G. tuberculosa, and G. eriocalyx) were investigated. The HPLC analysis showed that methanol extracts of all the tested species were richer in phenolics than water extracts. 3,4‐dihydroxybenzoic acid, p‐hydroxybenzoic acid, vanillin, syringic acid, and p‐coumaric acid were detected in all extracts. In parallel to the phenolic contents, methanol extracts displayed comparatively higher antioxidant activity than water extracts. Additionally, all extracts exhibited dose‐dependent antiproliferative activity on the cancer cell lines with lower IC50 values changing from 0.170 to 1.805 mg/ml. Moreover, the extracts impressively inhibited the acetylcholinesterase (0.63–26.04), butyrylcholinesterase (3.66–10.73), and α‐glycosidase (98.52–235.55) enzymes with very low IC50 (mg/ml) values. Together, the present results indicate that Gysophila taxa have various biological activities together with higher phenolic contents. Hence, these species hold good potential for use in the pharmaceutical industry. Practical applications Gypsophila taxa having numerous biological activities have been used for different purpose in folk medicine as well as their use in the food industry. The obtained results of the current study indicated that the extracts of Gypsophila taxa are rich in phenolics and flavonoids with powerful antioxidant and antiproliferative activity against different type of cancer cell lines. In addition, the extracts obtained from these taxa showed notable antidiabetic and anticholinergics effects. Gypsophila taxa could be used as a natural material to develop anticancer, antidiabetic, and anticholinergic drugs.

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“…The Gypsophila species are highly valued and important medicinal herbs widely spread in Asia and Europe, with application in traditional Chinese medicine to treat various ailments such as fever, malnutrition syndrome, diabetes (13), immune disorders or liver diseases (14)(15)(16). There are reports on the antioxidant potential of Gypsophila species related to C-flavonoid glycosides (14,15,17,18).…”

mentioning

confidence: 99%

Molecular networking-assisted flavonoid profile of Gypsophila glomerata extract in relation to its protective effects on carbon tetrachloride-induced hepatorenal damage in rats

et al. 2021

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The aim of the study was to provide an in-depth characterization of the methanol-aqueous extract from the aerial parts of Gypsophila glomerata Pall. Ex Adams (Caryophyllaceae) (EGG) and to assess its protective potential on carbon tetrachloride (CCl4)-induced liver and kidney damage in male Wistar rats. Twenty-two flavonoid C-, O- and C,O--glycosides in EGG were annotated by mass spectrometry--based molecular networking; nine of them are reported in this species for the first time. Fourteen-day oral administration of EGG at a dose 200 mg kg−1 bm prevented significantly CCl4-induced liver injury, discerned by an amelioration of the markers of oxidative stress (GSH and MDA) and transaminase activity. EGG decreased the serum level of urea and creatinine as well. The observed improvement of biochemical parameters was supported by histopathological observations. The protective hepatorenal effects of EGG, rich in 2“-О-pentosyl-6-С-hexosyl-apigenin/luteolin/ methylluteolin and their acetyl- and methoxycinnamoyl-derivatives, were comparable with the effects of the positive control silymarin.

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Triterpenoid Saponins from Gypsophila altissima L.

Cited by 18 publications

References 8 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)

Preliminary phytochemical analysis and evaluation of in vitro antioxidant, antiproliferative, antidiabetic, and anticholinergics effects of endemicGypsophilataxa from Turkey

Molecular networking-assisted flavonoid profile of Gypsophila glomerata extract in relation to its protective effects on carbon tetrachloride-induced hepatorenal damage in rats

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