Analysis of triptophenolide and its related compounds from Tripterygium wilfordii Hook.f by electrospray ionization tandem mass spectrometry

Li, Rui; Peng, Aihua; He, Chunmei; Li, Linyu; Shi, Jianyou; Chen, Lijuan; Wei, Yuquan

doi:10.1016/j.ijms.2008.08.007

Cited by 12 publications

(4 citation statements)

References 19 publications

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“…Similar H rearrangement was reported by Li et al. (2008). The high‐abundance fragment ion at m/z 243 in low mass range was formed by the cleavage of ring C from m/z 441 produced by sequential elimination of CH 3 radical from m/z 471.…”

Section: Results and Disccussionsupporting

confidence: 90%

Analysis of sesterterpenoids from Aspergillus terreus using ESI‐QTOF and ESI‐IT

Fang

Han³

et al. 2010

Phytochemical Analysis

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ABSTRACT:Introduction -Biosynthesis of terretonin was studied due to the interesting skeleton of this series of sesterterpenoids. Very recently, López-Gresa reported two new sesterterpenoids (terretonins E and F) which are inhibitors of the mammalian mitochondrial respiratory chain. Mass spectrometry (MS), especially tandem mass spectrometry, has been one of the most important physicochemical methods for the identification of trace natural products due to it rapidity, sensitivity and low levels of sample consumption. The potential application prospect and unique skeleton prompted us to study structural characterisation using MS. Objective -To obtain sufficient information for rapid structural elucidation of this class of compounds using MS. Methodology -The elemental composition of the product ions was confirmed by low-energy ESI-CID-QTOF-MS/MS analyses. The fragmentation pathways were postulated on the basis of ESI-QTOF-MS/MS/MS and ESI-IT-MSn spectra. Common features and major differences between ESI-QTOF-MS/MS and IT-MS n spectra were compared. For ESI-QTOF-MS/MS/MS experiments, capillary exit voltage was raised to induce in-source dissociation. Ammonium acetate or acetic acid were added into solutions to improve the intensity of [M + H]+ . The collision energy was optimised to achieve sufficient fragmentation. Some fragmentation pathways were unambiguously proposed by the variety of abundance of fragment ions at different collision energies even without MS n spectra. Results -Fragmentation pathways of five representative sesterterpenoids were elucidated using ESI-QTOF-MS/MS/MS and ESI-IT-MS

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Section: Results and Disccussionsupporting

confidence: 90%

Analysis of sesterterpenoids from Aspergillus terreus using ESI‐QTOF and ESI‐IT

Fang

Han³

et al. 2010

Phytochemical Analysis

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“…This observation suggested that triptolide (1) and triptonide (2) shared a similar fragmentation pattern. The fragmentation of triptophenolide (6) and other related diterpenoids has been studied with ESI-QTOF-MS by Rui Li et al [26]. A similar approach of conducting the MRM optimization was applied to triterpenoids obtained from T. wilfordii.…”

Section: Resultsmentioning

confidence: 99%

Simultaneous Quantification of 18 Bioactive Constituents in Tripterygium wilfordii Using Liquid Chromatography-Electrospray Ionization-Mass Spectrometry

et al. 2013

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A liquid chromatography-electrospray ionization-mass spectrometry method with multiple reaction monitoring was established for simultaneous quantification of 18 bioactive constituents from the stem and root of Tripterygium wilfordii Hook. f. collected from different places in China and various commercial preparations. The chromatographic separations were achieved on an Agilent Poroshell SB-C₁₈ column (150 × 4.6 mm, 3.5 µm) with gradient elution using acetonitrile and 0.03 % formic acid aqueous solution in 45 min. Detection was performed in the positive ionization mode by monitoring the precursor-product combination. The validation of the method included tests of linearity, sensitivity, precision, repeatability, stability, and accuracy. All calibration curves showed good linearity (r > 0.9990) within the test range. The established method showed good precision and accuracy with intraday and interday variations of 2-5 % and 1-4 %, respectively, and recoveries of 95.5-104.5 %.

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“…Guo et al reported that the RDA reaction occurring in triterpenoids from Ganoderma lucidum depends on the substitution pattern at C‐7, 12, 15 (Yang et al, ). Chen et al indicated that the RDA reaction plays an important role in the fragmentation of the [M − H] − ion of some triptophenolide and related compounds isolated from Tripterygium wilfordii Hook.f using ESI‐QTOF (Li et al, ). Madhusudanan et al found that lithium cationization of irinoids, such as loganin, epi ‐loganin and ketologanin, opens dissociation pathways of RDA reaction (Madhusudanan, Raj, & Bhaduri, ).…”

Section: Characteristic Fragmentation Patternsmentioning

confidence: 99%

Recent (2000–2015) developments in the analysis of minor unknown natural products based on characteristic fragment information using LC–MS

Cai

Guo

et al. 2016

Mass Spectrometry Reviews

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Liquid chromatography-Mass Spectrometry (LC-MS) has been widely used in natural product analysis. Global detection and identification of nontargeted components are desirable in natural product research, for example, in quality control of Chinese herbal medicine. Nontargeted components analysis continues to expand to exciting life science application domains such as metabonomics. With this background, the present review summarizes recent developments in the analysis of minor unknown natural products using LC-MS and mainly focuses on the determination of the molecular formulae, selection of precursor ions, and characteristic fragmentation patterns of the known compounds. This review consists of three parts. Firstly, the methods used to determine unique molecular formula of unknown compounds such as accurate mass measurements, MS spectra, or relative isotopic abundance information, are introduced. Secondly, the methods improving signal-to-noise ratio of MS/MS spectra by manual-MS/MS or workflow targeting-only signals were elucidated; pure precursor ions can be selected by changing the precursor ion isolated window. Lastly, characteristic fragmentation patterns such as Retro-Diels-Alder (RDA), McLafferty rearrangements, "internal residue loss," and so on, occurring in the molecular ions of natural products are summarized. Classical application of characteristic fragmentation patterns in identifying unknown compounds in extracts and relevant fragmentation mechanisms are presented (RDA reactions occurring readily in the molecular ions of flavanones or isoflavanones, McLafferty-type fragmentation reactions of some natural products such as epipolythiodioxopiperazines; fragmentation by "internal residue loss" possibly involving ion-neutral complex intermediates). © 2016 Wiley Periodicals, Inc. Mass Spec Rev 37:202-216, 2018.

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Analysis of triptophenolide and its related compounds from Tripterygium wilfordii Hook.f by electrospray ionization tandem mass spectrometry

Cited by 12 publications

References 19 publications

Analysis of sesterterpenoids from Aspergillus terreus using ESI‐QTOF and ESI‐IT

Analysis of sesterterpenoids from Aspergillus terreus using ESI‐QTOF and ESI‐IT

Simultaneous Quantification of 18 Bioactive Constituents in Tripterygium wilfordii Using Liquid Chromatography-Electrospray Ionization-Mass Spectrometry

Recent (2000–2015) developments in the analysis of minor unknown natural products based on characteristic fragment information using LC–MS

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