Simultaneous characterization of quaternary alkaloids, 8-oxoprotoberberine alkaloids, and a steroid compound in Coscinium fenestratum by liquid chromatography hybrid ion trap time-of-flight mass spectrometry

Deevanhxay, Phengxay; Suzuki, Makoto; Maeshibu, Nariaki; He, Li; Tanaka, Ken; Hirose, Sohichi

doi:10.1016/j.jpba.2009.05.023

Cited by 69 publications

(50 citation statements)

References 26 publications

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“…The fragmentation pathways of dihydrosanguinarine and dihydrochelerythrine are proposed in Supplementary Fig. S6(B) (see Supporting Information), which agreed with the literature …”

Section: Resultssupporting

confidence: 86%

Structural speculation and identification of alkaloids in Macleaya cordata fruits by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry combined with a screening procedure

Qing

Cheng

Liu

et al. 2014

Rapid Comm Mass Spectrometry

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RATIONALE Alkaloids with significant therapeutic effects are the main active constituents of Macleaya cordata, which is a perennial herb plant in the Papaveraceae family. A systematic and novel method for speculating and identifying the structures of alkaloids in M. cordata fruits by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry (HPLC/Q‐TOF‐MS) with a screening procedure was reported. METHODS Investigation of mass spectral fragmentation of alkaloids was carried out based on the tandem mass spectrometry (MS/MS) data analyses of eight reference substances. The skeletons of alkaloids were determined by their ultraviolet spectra (UV) and MS/MS data. The substituent groups of the alkaloids were acquired through a screening procedure developed in our laboratory and MS/MS data. The substituent linkage sites were deduced by MS/MS fragmentation behavior, as well as biosynthetic pathways of related alkaloids. RESULTS The structures of 21 alkaloids were speculated in this study, 10 of which were reported for the first time in M. cordata. Furthermore, benzyltetrahydroisoquinoline and N‐methyltetrahydroprotoberberine‐type alkaloids were discovered, which indirectly proved that the biosynthetic pathways of benzophenanthridine alkaloids reported in Eschscholtzia california existed in M. cordata as well. CONCLUSIONS HPLC/Q‐TOF‐MS combined with a screening procedure was a systematic and reliable method for speculating and elucidating the structures of alkaloids. This study might be useful for the identification of other compounds in herbal medicines. Copyright © 2014 John Wiley & Sons, Ltd.

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“…The fragmentation pathways of dihydrosanguinarine and dihydrochelerythrine are proposed in Supplementary Fig. S6(B) (see Supporting Information), which agreed with the literature …”

Section: Resultssupporting

confidence: 86%

Structural speculation and identification of alkaloids in Macleaya cordata fruits by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry combined with a screening procedure

Qing

Cheng

Liu

et al. 2014

Rapid Comm Mass Spectrometry

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“…Peak 22 produced ion at m/z 192.1018 by RDA and at m/z 177.0778 followed by loss of methyl radical was identified as N ‐methyl tetrahydrocolumbamine (Guo et al, ; Sun et al, ). Peak 34 showed similar fragmentation pathways as of jatrorrhizine or columbamine along with consecutive loss of two CH 3 at m/z 324.0866 and loss of CO at m/z 296.0904 and was tentatively characterised as 8‐oxojatrorrhizine or 8‐oxocolumbamine as reported by Deevanhxay et al ().…”

Section: Resultssupporting

confidence: 67%

Analysis of phytochemical variations in dioecious Tinospora cordifolia stems using HPLC/QTOF MS/MS and UPLC/QqQ_LIT‐MS/MS

Bajpai

Singh

Chandra

et al. 2015

Phytochemical Analysis

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Phytochemicals in the stem of male and female Tinospora cordifolia showed significant qualitative and quantitative variations. LC-MS and MS/MS methods can be used to differentiate between male and female plants based on their chemical profiles and quantities of the marker bioactive alkaloids. This chemical composition difference was also evident during vegetative stage when there were no male and female flowers.

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“…Tetrahydroprotoberberine alkaloids : The characteristic fragmentation pathway of tetrahydroprotoberberine alkaloids was Retro‐Diels–Alder (RDA) rupture to produce the fragment A , and then a methyl radical ruptured in the case of a methyl group existing at C‐2 or C‐3. Losing a molecule of H 2 O could be seen after the methyl group rupture from fragment A due to the existence of a hydroxyl group at C‐1 (Table ).…”

Section: Resultsmentioning

confidence: 98%

Establishment of a search library about benzylisoquinoline alkaloids based on selective separation on the binaphthyl column and standard analysis on C18 column

Liu

Zhou

Wang

et al. 2012

J of Separation Science

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A search library about benzylisoquinoline alkaloids was established based on preparation of alkaloid fractions from Rhizoma coptidis, Cortex phellodendri, and Rhizoma corydalis. In this work, two alkaloid fractions from each herbal medicine were first prepared based on selective separation on the "click" binaphthyl column. And then these alkaloid fractions were analyzed on C18 column by liquid chromatography coupled with tandem mass spectrometry. Many structure-related compounds were included in these alkaloids fractions, which led to easy separation and good MS response in further work. Therefore, a search library of 52 benzylisoquinoline alkaloids was established, which included eight aporphine, 19 tetrahydroprotoberberine, two protopine, two benzyltetrahydroisoquinoline, and 21 protoberberine alkaloids. The information of the search library contained compound names, structures, retention times, accurate masses, fragmentation pathways of benzylisoquionline alkaloids, and their sources from three herbal medicines. Using such a library, the alkaloids, especially those trace and unknown components in some herbal medicine could be accurately and quickly identified. In addition, the distribution of benzylisoquinoline alkaloids in the herbal medicines could be also summarized by searching the source samples in the library.

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Simultaneous characterization of quaternary alkaloids, 8-oxoprotoberberine alkaloids, and a steroid compound in Coscinium fenestratum by liquid chromatography hybrid ion trap time-of-flight mass spectrometry

Cited by 69 publications

References 26 publications

Structural speculation and identification of alkaloids in Macleaya cordata fruits by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry combined with a screening procedure

Structural speculation and identification of alkaloids in Macleaya cordata fruits by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry combined with a screening procedure

Analysis of phytochemical variations in dioecious Tinospora cordifolia stems using HPLC/QTOF MS/MS and UPLC/QqQ_LIT‐MS/MS

Establishment of a search library about benzylisoquinoline alkaloids based on selective separation on the binaphthyl column and standard analysis on C18 column

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Simultaneous characterization of quaternary alkaloids, 8-oxoprotoberberine alkaloids, and a steroid compound in Coscinium fenestratum by liquid chromatography hybrid ion trap time-of-flight mass spectrometry

Cited by 69 publications

References 26 publications

Structural speculation and identification of alkaloids in Macleaya cordata fruits by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry combined with a screening procedure

Structural speculation and identification of alkaloids in Macleaya cordata fruits by high‐performance liquid chromatography/quadrupole‐time‐of‐flight mass spectrometry combined with a screening procedure

Analysis of phytochemical variations in dioecious Tinospora cordifolia stems using HPLC/QTOF MS/MS and UPLC/QqQLIT‐MS/MS

Establishment of a search library about benzylisoquinoline alkaloids based on selective separation on the binaphthyl column and standard analysis on C18 column

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Analysis of phytochemical variations in dioecious Tinospora cordifolia stems using HPLC/QTOF MS/MS and UPLC/QqQ_LIT‐MS/MS