Systematic identification of alkaloids in Macleaya microcarpa fruits by liquid chromatography tandem mass spectrometry combined with the isoquinoline alkaloids biosynthetic pathway

Qing, Zhixing; Cheng, Pi; Liu, Xiubin; Liu, Yisong; Zeng, Jianguo

doi:10.1016/j.jpba.2014.11.002

Cited by 64 publications

(103 citation statements)

References 24 publications

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“…The product ions at m / z 189 and 188 were formed by the loss of the OH radical and H 2 O from m / z 206, respectively. These fragmentation patterns were also reported in the literature for Macleaya fruits …”

Section: Resultssupporting

confidence: 87%

“…The product ions at m / z 205 and 204 were formed by the loss of the OH radical and H 2 O from m / z 222, respectively. Therefore, AL3 was identified as an O‐methylated AL2 metabolite of muramine …”

Section: Resultsmentioning

confidence: 99%

“…The product ions at m / z 191 and 190 were formed by the loss of the OH radical (observed 17.0057 Da, predicted 17.0027 Da) and H 2 O from m / z 208, respectively. AL2 possessed the same [M + H] + ion and MS 2 spectrum as authentic 2‐demethylmuramine . Therefore, AL2 was identified as 2‐demethylmuramine.…”

Section: Resultsmentioning

confidence: 99%

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Identification of allocryptopine and protopine metabolites in rat liver S9 by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry

Huang

Xiao

Sun

et al. 2016

Rapid Comm Mass Spectrometry

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 99%

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Identification of allocryptopine and protopine metabolites in rat liver S9 by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry

Huang

Xiao

Sun

et al. 2016

Rapid Comm Mass Spectrometry

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“…They uncovered that the high‐abundance product ions below m/z 200 resulted from an RDA fragmentation reaction, which can be used to identify N ‐methyltetrahydroprotoberberine and protopine alkaloids. They further reported that tetrahydroprotoberberine, N ‐methyltetrahydroberberineand protopine alkaloids can be differentiated by the occurrence of the RDA reaction, the α‐cleavage and by the formation of water and methane losses (Qing et al, ). Wu et al reported that an RDA reaction plays a significant role in the skeleton fragmentation of two representative uleine alkaloids, alstilobanine, and undulifoline (Li et al, ).…”

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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“…For compounds 1 to 3 , product ion D formation is preceded by product ion C conversion to the intermediate C1 , from which a CO molecule is eliminated (Scheme ). Similar reactions to C1 decarbonylation to produce product ion D (ΔH C → D = 13.4‐22.2 kcal/mol) as well as product ion E formation from product ion D (ΔH D → E = 34.2‐47.5 kcal/mol) have been extensively described for natural products . In the product ion spectrum of compound 3 , the peak attributed to product ion D is the most intense.…”

Section: Resultsmentioning

confidence: 74%

Gas‐phase fragmentation reactions of protonated benzofuran‐ and dihydrobenzofuran‐type neolignans investigated by accurate‐mass electrospray ionization tandem mass spectrometry

et al. 2018

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We have investigated gas‐phase fragmentation reactions of protonated benzofuran neolignans (BNs) and dihydrobenzofuran neolignans (DBNs) by accurate‐mass electrospray ionization tandem and multiple‐stage (MSn) mass spectrometry combined with thermochemical data estimated by Computational Chemistry. Most of the protonated compounds fragment into product ions B ([M + H–MeOH]+), C ([B–MeOH]+), D ([C–CO]+), and E ([D–CO]+) upon collision‐induced dissociation (CID). However, we identified a series of diagnostic ions and associated them with specific structural features. In the case of compounds displaying an acetoxy group at C‐4, product ion C produces diagnostic ions K ([C–C2H2O]+), L ([K–CO]+), and P ([L–CO]+). Formation of product ions H ([D–H2O]+) and M ([H–CO]+) is associated with the hydroxyl group at C‐3 and C‐3′, whereas product ions N ([D–MeOH]+) and O ([N–MeOH]+) indicate a methoxyl group at the same positions. Finally, product ions F ([A–C2H2O]+), Q ([A–C3H6O2]+), I ([A–C6H6O]+), and J ([I–MeOH]+) for DBNs and product ion G ([B–C2H2O]+) for BNs diagnose a saturated bond between C‐7′ and C‐8′. We used these structure‐fragmentation relationships in combination with deuterium exchange experiments, MSn data, and Computational Chemistry to elucidate the gas‐phase fragmentation pathways of these compounds. These results could help to elucidate DBN and BN metabolites in in vivo and in vitro studies on the basis of electrospray ionization ESI‐CID‐MS/MS data only.

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Systematic identification of alkaloids in Macleaya microcarpa fruits by liquid chromatography tandem mass spectrometry combined with the isoquinoline alkaloids biosynthetic pathway

Cited by 64 publications

References 24 publications

Identification of allocryptopine and protopine metabolites in rat liver S9 by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry

Identification of allocryptopine and protopine metabolites in rat liver S9 by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry

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

Gas‐phase fragmentation reactions of protonated benzofuran‐ and dihydrobenzofuran‐type neolignans investigated by accurate‐mass electrospray ionization tandem mass spectrometry

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