Comparison of ultra-high performance supercritical fluid chromatography and ultra-high performance liquid chromatography for the separation of spirostanol saponins

Zhu, Li; Zhao, Yang; Xu, Yan; Sun, Qinglong; Sun, Xinguang; Kang, Liping; Ren, Yan; Zhang, Jie; Liu, Chao; B, Ma

doi:10.1016/j.jpba.2015.12.002

Cited by 32 publications

(8 citation statements)

References 45 publications

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“…Meanwhile, if the loss of a glucose unit is detected with the diagnostic ions at m / z 431, 413, 271, and 253 as well as an obvious neutral loss of 160 Da (C 8 H 16 O 3 ), these saponins are usually nuatigenin‐type aglycones. However, the presence of diagnostic ions at m / z 253, 271, or 287, 269, 251 indicates that the saponin is rarely present in the furost‐type aglycones typically observed in spirostanol saponins in the MS/MS ESI (+) mode . A strategy for characterizing steroidal saponin structures in P. polyphylla was then proposed (Figure S3, supporting information) and further verified by studying the reference standards of four diosgenin saponins.…”

Section: Resultsmentioning

confidence: 75%

“…With the aid of an in‐house chemical library of the genus Paris (Table S1, supporting information), 160 compounds—77 isospirostanols, 2 spirostanols, 19 furostanols, 10 pseudospirostanols, 6 cholesterols, 10 C 21 steroids, 5 insect metamorphosis hormones, 3 plant sterols, 6 five‐ring triterpenoids, 4 flavonoids, 8 fatty acids, 2 phenylpropanoids, and 8 other compounds—were successfully characterized from the extracts of PPY based on the common fragmentation pathways, reference standards, and comparison with the data in the literature . Their structures are shown in Figure S2 (supporting information).…”

Section: Resultsmentioning

confidence: 99%

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Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Wang

Fan

Xiang

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale: Paris polyphylla var. yunnanensis (Franch) Hand Mazz (PPY) is a traditionalChinese medicine with antitumor, antibacterial, hemostatic, and anthelmintic activities. Identification of the chemical composition in PPY is helpful to discover its active ingredients and can be used to establish its quality control protocols.Methods: The composition of PPY was identified using ultra-high-performance liquid chromatography combined with quadrupole time-of-flight mass spectrometry (UHPLC/QTOF-MS/MS) coupled with a molecular networking strategy. First, the UHPLC/QTOF-MS/MS approach was optimized for chemical compound profiling.Then, the MS data were processed using PeakView™ combined with an in-house database to quickly characterize the secondary metabolites. Finally, molecular networking excavated new molecular weights to discover unknown or trace natural products based on the characteristics of each cluster. Results:A total of 222 compounds, including 77 isospirostanols, 2 spirostanols, 19 furostanols, 10 pseudospirostanols, 6 cholesterols, 10 C 21 steroids, 5 insect metamorphosis hormones, 3 plant sterols, 6 five-ring triterpenoids, 4 flavonoids, 8 fatty acids, 2 phenylpropanoids, and 8 other compounds, were characterized in PPY by comparing their main fragmentation characteristics and pathways with the literature data, and 62 of them, 54 steroidals and 8 phenylpropanoids, were discovered or tentatively identified for the first time. Conclusions:This study extended the application of a molecular networking strategy to traditional herbal medicines and developed a molecular networking based screening approach with a significant increase in efficiency for the discovery and identification of trace novel natural products.Yumei Wang and Qian Fan contributed equally to this work as first authors. Paris polyphylla var. yunnanensis (Franch) Hand Mazz (PPY), calledChong Lou, is a well-known, valuable traditional Chinese medicine (TCM) that has been used to treat fractures, hemorrhages, snake bites, and abscess for many years. 1,2 PPY has been used as a main ingredient for the preparation of many TCMs, such as Yunnan Baiyao, Gongxuening capsules, and Jidesheng Sheyao tablets. 3 Phytochemistry studies have indicated that the dried rhizomes of Paris species contain steroidal saponins, triterpenoid saponins, flavonoids, phenylpropanoids, ecdysteroids, phenolic glycosides, and so on. 4-6 The glucosyl groups of steroidal saponins are normally attached to the steroidal aglycones through the hydroxyl groups at the C-3 and/or C-26 positions (and sometimes the C-1, C-21, C-23, and C-24 positions). Four types of steroidal sapogenins 6 (spirostanol, isospirostanol, furostanol, and pseudospirostanol) are considered major aglycones, and typical sugars are arabinose, xylose, apiose, fucose, rhamnose, glucose, and galactose. Comprehensive identification of ingredients in PPY is critical to understanding its biological mechanism and establishing quality control protocols. Because of the complexity of these components, their comprehensive...

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Wang

Fan

Xiang

et al. 2020

Rapid Comm Mass Spectrometry

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“…Analysis of spirostanol saponins is usually performed by ultra-high performance supercritical fluid chromatography (UHPSFC) and ultra-high performance liquid chromatography (UHPLC) [ 10 ], which are not suitable for mass preparation. Until now, successful preparation examples for (25 R / S )-spiromeric epimers were accomplished by SFC isolation [ 11 , 12 ] usually.…”

Section: Discussionmentioning

confidence: 99%

Separation and Bioactive Assay of 25R/S-Spirostanol Saponin Diastereomers from Yucca schidigera Roezl (Mojave) Stems

Ruan

et al. 2018

Molecules

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In order to find a simple, generic, efficient separation method for 25R/S-spirostanol saponin diastereomers, the liquid chromatographic retention behaviors of C12 carbonylation and C12 unsubstituted 25R/S-spirostanol saponin diastereomers on different stationary phases (C8, C18, C30 columns) and different mobile phases (MeOH-1% CH3COOH and CH3CN-1% CH3COOH) were investigated. A C30 column was firstly found to offer the highest efficiency for the separation of this kind of diastereomers than C8 and C18 columns. Meanwhile, the analysis results indicated that both CH3CN-1% CH3COOH and MeOH-1% CH3COOH eluate systems were selective for C12 unsubstituted 25R/S-spirostanol saponin diastereomers, while MeOH-1% CH3COOH possessed better selectivity for C12 carbonylation ones. Using the abovementioned analysis method, six pairs of 25R/S-spirostanol saponin diastereomers 1a–6a and 1b–6b from Yucca schidigera Roezl (Mojave) were isolated successfully by using HPLC on C30 column for the first time. Among them, three pairs were new ones, named as (25R)-Yucca spirostanoside E1 (1a), (25S)-Yucca spirostanoside E1 (1b), (25R)-Yucca spirostanoside E2 (2a), (25S)-Yucca spirostanoside E2 (2b), (25R)-Yucca spirostanoside E3 (3a), (25S)-Yucca spirostanoside E3 (3b), respectively. Moreover, 3a, 5a, 6a, 3b–6b showed strong inhibitory activities on the growth of SW620 cell lines with the IC50 values of 12.02–69.17 μM.

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“…continued the advantage to avoid hydrolysis of ginkgolides that occur during RP-HPLC with aqueous eluents and without the need for derivatization of the ginkgolic acids as it is necessary prior to GC analysis. Only recently, Zhu et al [45] compared the separation of 20 different spirostanol saponins by UHPSFC and UHPLC underlining the complementarity of both techniques. While UHPSFC showed to be advantageous for the separation of spirostanol saponins with the same aglycone and a different sugar residue, UHPLC was preferable for the resolution of saponins with the same sugar residue and different aglycones.…”

Section: Terpenesmentioning

confidence: 99%

Supercritical Fluid Chromatography in Natural Product Analysis – An Update

2017

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The wide chemical diversity of natural products has challenged analysts all over the world and has been a driving force for the development of innovative technologies since decades. In the last years, supercritical fluid chromatography (SFC) has finally emerged from the shadow of liquid chromatography (LC) and gas chromatography (GC) and has become a powerful tool in modern natural product analysis. Whereas in the past the technique had mainly been restricted to a small group of nonpolar compounds, it has largely expanded its suitability in the last years and has demonstrated possibilities without boundaries. This mini-review, focused on the latest applications, provides a brief update on the current status of SFC in natural product analysis with the aim to demonstrate its applicability for both polar and nonpolar plant constituents. The approaches cover the whole range of polarity, including carotenoids, flavonoids, water-unstable ginkgolides, and even highly polar triterpene saponins with several sugar residues.

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Comparison of ultra-high performance supercritical fluid chromatography and ultra-high performance liquid chromatography for the separation of spirostanol saponins

Cited by 32 publications

References 45 publications

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Structural characterization and discrimination of Paris polyphylla var. yunnanensis by a molecular networking strategy coupled with ultra‐high‐performance liquid chromatography with quadrupole time‐of‐flight mass spectrometry

Separation and Bioactive Assay of 25R/S-Spirostanol Saponin Diastereomers from Yucca schidigera Roezl (Mojave) Stems

Supercritical Fluid Chromatography in Natural Product Analysis – An Update

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