Identification of Alkaloids in <i>Stephania hainanensis</i> by Liquid Chromatography Coupled with Quadrupole Time‐of‐flight Mass Spectrometry

He, Jiayong; Liu, Ying; Kang, Yun; Yang, Ping; Wang, Yaqin; Guo, Jinjun; Huang, Jianming

doi:10.1002/pca.2618

Cited by 28 publications

(41 citation statements)

References 20 publications

(71 reference statements)

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“…steporphine, ushinsunine, fibrecisine and roemeroline. Considering the hydroxy group present at C‐4 or C‐7 could easily be eliminated to form the intense [M + H−H 2 O] + ion at m/z 278.1187, compound 37 was tentatively identified as steporphine with the OH at C‐4 and/or ushinsunine with the OH at C‐7 (Semwal et al ., ; He et al ., ). The OH of compound 48 , however, was difficult to dissociate, and thus this compound was tentatively deduced as fibrecisine with the OH at C‐8 and/or roemeroline with the OH at C‐9 (Zhang and Rao, ; Semwal et al ., ).…”

Section: Resultsmentioning

confidence: 97%

Structural Characterisation of Alkaloids in Leaves and Roots of Stephania kwangsiensis by LC‐QTOF‐MS

Shangguan

Kang

et al. 2017

Phytochemical Analysis

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Section: Resultsmentioning

confidence: 97%

Structural Characterisation of Alkaloids in Leaves and Roots of Stephania kwangsiensis by LC‐QTOF‐MS

Shangguan

Kang

et al. 2017

Phytochemical Analysis

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“…The split of the [M + H] + ion led to the base peak fragment ion at m/z 107.0492, 30 Da lower than of compound 5 , thus indicating the presence of only one hydroxyl group on ring C. If the OH group was at C‐11, compound 8 could be identified as norcanelilline . However, if the OH group was at C‐12, compound 8 would be coclaurine or norjuziphine . According to data in the literature, benzylisoquinoline alkaloids without an oxygen functional group at C‐11 show benzyl fragments as the most intense fragment ions, which is due to their lesser ability to stabilise the benzyl leaving group .…”

Section: Resultsmentioning

confidence: 99%

“…15 However, if the OH group was at C-12, compound 8 would be coclaurine or norjuziphine. 16,17 According to data in the literature, benzylisoquinoline alkaloids without an oxygen functional group at C-11 show benzyl fragments as the most intense fragment ions, which is due to their lesser ability to stabilise the benzyl leaving group. 14…”

Section: Benzylisoquinoline Alkaloidsmentioning

confidence: 99%

Identification of structurally diverse alkaloids in Talguenea quinquinervia (gill. Et hook) by liquid chromatography/electrospray ionisation tandem mass spectroscopy and insecticidal activity

Quiroz-Carreño

Cespedes‐Acuña

Seigler

et al. 2019

Phytochemical Analysis

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Introduction Talguenea quinquinervia has been used in folk medicine and to dye wool, and the main constituents are alkaloids and triterpenes. Identification of these type of compounds in this specie is a necessary step to understand the biological properties. Objective To evaluate the relationship between the chemical composition of root from T. quinquinervia and its insecticidal properties using liquid chromatography electrospray ionisation tandem mass spectrometry (LC‐ESI‐MS/MS). Methods Alkaloids were extracted using Soxhlet extraction with methanol. Total extract was partitioned at pH 2 and 12 to enrich alkaloid constituents and to remove interferences. The separation of alkaloids in the Talguenea extract was performed on a C18 column using gradient elution and their tandem mass spectra were obtained by quadrupole time‐of‐flight tandem mass spectrometry (QTOF‐MS/MS) to perform accurate mass measurements of fragment ions for the alkaloid constituents. Results Several types of alkaloids were separated and identified by LC‐ESI‐MS/MS. The structural assignment of individual alkaloids was performed based on convergence of MS/MS spectral data, pH partitioning behaviour, LC retention behaviour, and accurate mass measurements. The pH partition of the extract provided structural information about unknown alkaloids extracted from T. quinquinervia. A total of 20 compounds were identified and tentatively characterised, and of these 15 alkaloids were reported for the first time in the investigated T. quinquinervia. Conclusion The chemical profiling of alkaloids in T. quinquinervia with different origins was performed for the first time and provided diagnostic ions for diverse alkaloids in T. quinquinervia. Insecticidal activity observed can be explain by the presence of alkaloid and pentacyclic triterpenes on the fractions assayed.

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“…Alkaloids from Papaver species possess significant biological activity [13,15], and the alkaloid content of Papaver plants varies greatly depending on their growth stage, conditions, and origin [4,12,16]. Rapid and reliable analytical techniques must be developed to facilitate identification and structural determination of alkaloids in complex extracts and medicine herbs [17][18][19][20][21][22][23]. To discover medicinally relevant compounds and potential alternatives to plants as the commercial source of valuable BIAs, metabolomic studies of the Papaver species have been reported by metabolomics with chemometric approaches and transcript profiling [13,15,[24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Identification and metabolite profiling of alkaloids in aerial parts of Papaver rhoeas by liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry

Lee

et al. 2018

J of Separation Science

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Papaver plants can produce diverse bioactive alkaloids. Papaver rhoeas Linnaeus (common poppy or corn poppy) is an annual flowering medicinal plant used for treating cough, sleep disorder, and as a sedative, pain reliever, and food. It contains various powerful alkaloids like rhoeadine, benzylisoquinoline, and proaporphine. To investigate and identify alkaloids in the aerial parts of P. rhoeas, samples were collected at different growth stages and analyzed using liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry. A liquid chromatography with mass spectrometry method was developed for the identification and metabolite profiling of alkaloids for P. rhoeas by comparing with Papaver somniferum. Eighteen alkaloids involved in benzylisoquinoline alkaloid biosynthesis were used to optimize the liquid chromatography gradient and mass spectrometry conditions. Fifty‐five alkaloids, including protoberberine, benzylisoquinoline, aporphine, benzophenanthridine, and rhoeadine‐type alkaloids, were identified authentically or tentatively by liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry in samples taken during various growth stages. Rhoeadine alkaloids were observed only in P. rhoeas samples, and codeine and morphine were tentatively identified in P. somniferum. The liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry method can be a powerful tool for the identification of diverse metabolites in the genus Papaver. These results may help understand the biosynthesis of alkaloids in P. rhoeas and evaluate the quality of this plant for possible medicinal applications.

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Identification of Alkaloids in Stephania hainanensis by Liquid Chromatography Coupled with Quadrupole Time‐of‐flight Mass Spectrometry

Cited by 28 publications

References 20 publications

Structural Characterisation of Alkaloids in Leaves and Roots of Stephania kwangsiensis by LC‐QTOF‐MS

Structural Characterisation of Alkaloids in Leaves and Roots of Stephania kwangsiensis by LC‐QTOF‐MS

Identification of structurally diverse alkaloids in Talguenea quinquinervia (gill. Et hook) by liquid chromatography/electrospray ionisation tandem mass spectroscopy and insecticidal activity

Identification and metabolite profiling of alkaloids in aerial parts of Papaver rhoeas by liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry

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