A strategy for characterization of triterpene saponins in Caulophyllum robustum hairy roots by liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry

Xia, Yueyuan; Li, Guoyu; Liang, Jun; Ortori, Catharine A.; Yang, Bing‐You; Kuang, Hai‐Xue

doi:10.1016/j.jpba.2014.07.024

Cited by 33 publications

(24 citation statements)

References 41 publications

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“…The analytical results of the sample showed the four‐step mining strategy was suitable for analyzing the major compounds in AF. Meanwhile, the fragmentation behavior discovered in this study has been widely found in other triterpenoid saponins of TCMs . So, the four‐step strategy could be applied in further research of AF and other TCMs.…”

Section: Discussionmentioning

confidence: 54%

“…The negative mode has higher sensitivity, more mass spectra peaks and lower background noise than the positive mode. However, in the positive mode, more information about the characteristic ions of aglycone fragments and the sugar chain constituents was obtained, which was also found for other TCMs . As an effective supplement to the negative mode, the positive ion mode was utilized for detection to completely represent the characteristics of the compounds.…”

Section: Resultsmentioning

confidence: 99%

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A four‐step filtering strategy based on ultra‐high‐performance liquid chromatography coupled to quadrupole‐time‐of‐flight tandem mass spectrometry for comprehensive profiling the major chemical constituents of Akebiae Fructus

Tan

Yang

et al. 2019

Rapid Comm Mass Spectrometry

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Rationale Akebiae Fructus (AF) is a traditional Chinese medicine (TCM) with antiphlogistic, analgesic, antineoplastic, diuretic, antirheumatic, antidepressant and antiobesity activities. Identification of chemical constituents from AF is helpful to discover the potential active ingredients and to control its quality. Methods The four‐step filtering strategy was as follows: (1) To extract the accurate mass by the different adduct ions. (2) To screen different types of the compounds using diagnostic ions. (3) By characteristic ion filtering, to confirm the substituted position and the sugar chain numbers. (4) Based on the neutral loss (NL), to identify the type of monosaccharide and the compositions of sugar chains of triterpenoid saponins and the structure of CGAs. Results A total of 94 compounds (85 triterpenoid saponins, 9 chlorogenic acids) were unambiguously or reasonably identified. Fifty constituents were discovered for the first time from AF. Nine types of triterpenoid saponins, including akebonoic acid (type I), norhederagenin (type II), oleanolic acid (type III), 2α,3β‐dihydroxy‐23‐oxo‐30‐norolean‐12,20(21)‐dien‐28‐oic acid (type IV), gypsogenin (type V), norarjunolic acid (type VI), hederagenin (type VII), 2α,3β‐dihydroxy‐23‐oxo‐olean‐12‐en‐28‐oic acid (type VIII), arjunolic acid (type IX), and two types of chlorogenic acid (mono‐CQA and di‐CQA), were identified in AF. Conclusions An ultra‐high‐performance liquid chromatography coupled to quadrupole‐time‐of‐flight tandem mass spectrometry with MSE (UPLC–QTOF‐MSE) analysis with four‐step filtering strategy was established and successfully applied to identify the chemical constituents of AF which can provide chemical support for further research and play an important role in the quality control of AF.

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Section: Discussionmentioning

confidence: 54%

Section: Resultsmentioning

confidence: 99%

A four‐step filtering strategy based on ultra‐high‐performance liquid chromatography coupled to quadrupole‐time‐of‐flight tandem mass spectrometry for comprehensive profiling the major chemical constituents of Akebiae Fructus

Tan

Yang

et al. 2019

Rapid Comm Mass Spectrometry

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“…Be different from ESI + ‐FT‐MS (1, 1) spectrum, a quite complex ESI + ‐FT‐MS (1, 2) spectrum was recorded in Figures S2B and S3B. This phenomenon could be explained because of the fact that weak stability of [M + H] + and [M + NH 4 ] + ion, which were easily fragmented under a small energy . Successive losses of sugar moieties one by one were commonly generated, producing rules to determine sugar numbers, positions and linkages.…”

Section: Resultsmentioning

confidence: 99%

Energy-resolved technique for discovery and identification of malonyl-triterpene saponins inCaulophyllum robustumby UHPLC-electrospray Fourier transform mass spectrometry

Xia

Liang

et al. 2016

J. Mass Spectrom.

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Malonyl-triterpene saponins (MTSs) attract scientific attentions because of their structural diversities and valuable bioactivities. However, its thermal instability brings a huge amount of challenges for isolation and purification of this class of compounds. To our best knowledge, there has been no report on isolation and analysis of MTSs from genus Caulophyllum. In this study, a strategy combining data acquisition using an energy-resolved technique and the narrow widow extracted ion chromatograms as data mining method was developed for discovery and identification of MTSs in Caulophyllum robustum hair roots by ultra high liquid chromatography coupled to electrospray ionization Fourier transform mass spectrometry. The method was performed at an independent MS full scan using our bottom-up energies by in-source collision induced dissociations with 0, 25, 50 and 100 eV in both positive and negative modes. Precursor ion as well as fragment ion information was simultaneously collected from four energy-resolved MS spectra in a single run of 18 min. The fragmentation pathways of intact deprotonated, protonated and sodium ions of MTSs were proposed for the structural elucidation of Caulophyllum MTSs. A flowchart involving a stepwise procedure based on key fragments from ESI /ESI -FT-MS to MS spectra was constructed for the identification of structural elements in the MTSs. As a result, a total of 23 MTSs were discovered and tentatively identified, which had not been reported from Caulophyllum species before. All of these were potentially new compounds. This study provides an excellent example for discovery and identification of MTSs in herb medicines. Copyright © 2016 John Wiley & Sons, Ltd.

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“…Peak identification and assignment in HPLC fingerprints were made on the basis of the reference substances in the chromatogram, and a total of nine characteristic peaks were identified, shown in Figure 1 and Table 10 [26,27]. …”

Section: Resultsmentioning

confidence: 99%

Spectrum-Effect Relationships between Fingerprints of Caulophyllum robustum Maxim and Inhabited Pro-Inflammation Cytokine Effects

Lü

Dong

et al. 2017

Molecules

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Caulophyllum robustum Maxim (CRM) is a Chinese folk medicine with significant effect on treatment of rheumatoid arthritis (RA). This study was designed to explore the spectrum-effect relationships between high-performance liquid chromatography (HPLC) fingerprints and the anti-inflammatory effects of CRM. Seventeen common peaks were detected by fingerprint similarity evaluation software. Among them, 15 peaks were identified by Liquid Chromatography-Mass Spectrometry (LC-MS). Pharmacodynamics experiments were conducted in collagen-induced arthritis (CIA) mice to obtain the anti-inflammatory effects of different batches of CRM with four pro-inflammation cytokines (TNF-α, IL-β, IL-6, and IL-17) as indicators. These cytokines were suppressed at different levels according to the different batches of CRM treatment. The spectrum-effect relationships between chemical fingerprints and the pro-inflammation effects of CRM were established by multiple linear regression (MLR) and gray relational analysis (GRA). The spectrum-effect relationships revealed that the alkaloids (N-methylcytisine, magnoflorine), saponins (leiyemudanoside C, leiyemudanoside D, leiyemudanoside G, leiyemudanoside B, cauloside H, leonticin D, cauloside G, cauloside D, cauloside B, cauloside C, and cauloside A), sapogenins (oleanolic acid), β-sitosterols, and unknown compounds (X3, X17) together showed anti-inflammatory efficacy. The results also showed that the correlation between saponins and inflammatory factors was significantly closer than that of alkaloids, and saponins linked with less sugar may have higher inhibition effect on pro-inflammatory cytokines in CIA mice. This work provided a general model of the combination of HPLC and anti-inflammatory effects to study the spectrum-effect relationships of CRM, which can be used to discover the active substance and to control the quality of this treatment.

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A strategy for characterization of triterpene saponins in Caulophyllum robustum hairy roots by liquid chromatography with electrospray ionization quadrupole time-of-flight mass spectrometry

Cited by 33 publications

References 41 publications

A four‐step filtering strategy based on ultra‐high‐performance liquid chromatography coupled to quadrupole‐time‐of‐flight tandem mass spectrometry for comprehensive profiling the major chemical constituents of Akebiae Fructus

A four‐step filtering strategy based on ultra‐high‐performance liquid chromatography coupled to quadrupole‐time‐of‐flight tandem mass spectrometry for comprehensive profiling the major chemical constituents of Akebiae Fructus

Energy-resolved technique for discovery and identification of malonyl-triterpene saponins inCaulophyllum robustumby UHPLC-electrospray Fourier transform mass spectrometry

Spectrum-Effect Relationships between Fingerprints of Caulophyllum robustum Maxim and Inhabited Pro-Inflammation Cytokine Effects

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