Rapid determination of alkaloids in Macleaya cordata using ionic liquid extraction followed by multiple reaction monitoring UPLC–MS/MS analysis

Li, Linqiu; Huang, Ming-Yuan; Shao, Junli; Lin, Bokun; Shen, Qing

doi:10.1016/j.jpba.2016.12.016

Cited by 26 publications

(16 citation statements)

References 21 publications

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“…Pharmacological studies revealed that benzylisoquinoline alkaloids (BIAs) – sanguinarine (SAN), chelerythrine (CHE), protopine (PRO), and allocryptopine (ALL) – are the main bioactive constituents of the genus Macleaya. Due to their antimicrobial, antifungal, anti‐inflammatory, and antiproliferative activities, BIAs have attracted the attention of many researchers. Till now, 147 alkaloids have been isolated or identified, and benzyltetrahydroisoquinoline (I), aporphine (II), tetraprotoberberine (III), protoberberine (IV), N ‐methyltetrahydroprotoberberine (V), protopine (VI), dihydrobenzophenanthridine (VII), and benzophenanthridine (VIII) have been identified as the main isoquinoline alkaloids of Macleaya species.…”

Section: Introductionmentioning

confidence: 99%

Systematic identification of compounds in Macleaya microcarpa by high‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry combined with mass spectral fragmentation behavior of Macleaya alkaloids

Lin

et al. 2020

Rapid Comm Mass Spectrometry

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Rationale: Macleaya microcarpa (Maxim.) Fedde belongs to the genus Macleaya of the Papaveraceae family. Benzylisoquinoline alkaloids (BIAs) are considered the main bioactive constituents of M. microcarpa. Methods: Using high-performance liquid chromatography/quadrupole time-of-flight tandem mass spectrometry (HPLC/QTOFMS/MS) we identified BIAs in the aerial parts of M. microcarpa in the early flowering stage. Target profiling and identification of BIAs in the extracted samples from the fresh aerial parts of M. microcarpa were exclusively based on a personal, accurate, mass database of known compounds and the mass spectral fragmentation behavior of Macleaya alkaloids.Results: A total of 97 alkaloids, comprising 7 benzyltetrahydroisoquinolines, 1aporphine, 9 tetraprotoberberines, 3 protoberberines, 2 N-methyltetrahydroprotoberberines, 4 protopines, 47 dihydrobenzophenanthridines, and 24 benzophenanthridines, were identified from the fresh aerial parts of M. microcarpa, and 77 of these were detected for the first time in M. microcarpa. In addition, some of the screened alkaloids were related to the biosynthetic pathways of sanguinarine and chelerythrine. Conclusions:The integrated method is sensitive and reliable for screening and identifying trace or ultra-trace isoquinoline alkaloids and has contributed to a better understanding of BIAs in the fresh aerial parts of M. microcarpa.

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Section: Introductionmentioning

confidence: 99%

Systematic identification of compounds in Macleaya microcarpa by high‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry combined with mass spectral fragmentation behavior of Macleaya alkaloids

Lin

et al. 2020

Rapid Comm Mass Spectrometry

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“…Based on our previous experience in separating analytes in herbal medicines [27], a chromatographic method was developed and optimized to separate the target lignans in J. procumbens , which were eluted in the order of 6′‐hydroxy justicidin B (4.53 min), 6′‐hydroxy justicidin A (4.70 min), justicidin B (5.13 min), chinensinaphthol methyl ether (5.31 min), justicidin C (5.50 min), and neojusticdin A (5.63 min), as labeled in Fig. 4.…”

Section: Resultsmentioning

confidence: 99%

Development of a mesoporous silica based solid‐phase extraction and ultra‐performance liquid chromatography–MS/MS method for quantifying lignans in Justicia procumbens

Shen

Wang

et al. 2020

Electrophoresis

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Justicia procumbens is a food and medicine homologous variety, popularly used for making vegetable soups. In this study, a novel mesoporous silica was synthesized and used as the sorbent of SPE for the purification of lignans from J. procumbens. A laboratory‐made SPE cartridge was packed with 100 mg of mesoporous silica, which was washed with 10% methanol and eluted using 0.8 mL acetonitrile after sample loading. Afterward, the extract was analyzed by ultra‐performance liquid chromatography (UPLC) and MS/MS. All the lignans were efficiently separated in 6 min with the noise level in the range of 50–150 cps. 6′‐Hydroxy justicidin B, 6′‐hydroxy justicidin A, justicidin B, chinensinaphthol methyl ether, justicidin C, and neojusticdin A were identified to be the dominant molecular species in J. procumbens with contents of 0.065−0.37 mg/g in three tested sample batches from different geographic origins. In conclusion, the proposed mesoporous silica based SPE UPLC–MS/MS method is efficient in linearity (R2 = 0.9989−0.9996), sensitivity (LOD ≤0.13 μg/kg and LOQ ≤0.42 μg/kg), precision (RSDintra‐day ≤3.12 and RSDinter‐day ≤4.56), and recovery (83.42−96.11%, RSD ≤2.88%).

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“…They are well-known for their very extensive application value and great exploitation foreground as well as pesticide, veterinary drug, medicinal ones in North America, Europe, China, which are directly associated with the multifarious alkaloids and their significant biological activities. A variety of alkaloids from M. cordata, such as sanguinarine, chelerythrine, protopine, allocryptopine, and others, exhibit anti-microbial, anti-inflammatory, insecticidal, analgesic, anticancer activity, have irreplaceable pharmacological effects [2][3][4]. However, systematic researches on the phytochemical composition of M. microcarpa are few.…”

Section: Introductionmentioning

confidence: 99%

Isolation and identification of alkaloids from Macleaya microcarpa by UHPLC–Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo

Sai

Wang

et al. 2020

BMC Chemistry

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Background: Extensive bioactivities of alkaloids from the genus Macleaya (Macleaya cordata (Willd.) R. Br. and Macleaya microcarpa (Maxim.) Fedde) have been widely reported, as well as more and more concerned from the scientific communities. However, systematic research on the phytochemical information of M. microcarpa is incomplete. The aim of this study was to rapidly and conveniently qualitative analyze alkaloids from M. microcarpa by ultra-performance liquid chromatography/quadrupole-time-of-fight mass spectrometry (UHPLC-Q-TOF-MS) using accurate mass weight and characteristic fragment ions, furthermore separate and identify the main alkaloids, test antitumor activity in vitro and antiangiogenic activity in vivo. Results: A total of 14 alkaloids from fruits of M. microcarpa were identified by UHPLC-Q-TOF-MS, including 5 protopines, 2 benzophenanthridines, 1 dimer, 1 dihydrobenzophenanthridines and 5 unknown structure compounds. Two major alkaloids were isolated by various column chromatographic methods. Their structures were determined by NMR data and related literatures. The two major alkaloids were evaluated for intro cytotoxic activities against HL-60, MCF-7, A-549, and in vivo antiangiogenic activity using transgenic zebrafish. Conclusions: Current qualitative method based on UHPLC-Q-TOF-MS technique provided a scientific basis for isolation, structural identification, and in vitro or in vivo pharmacological further study of alkaloids from M. microcarpa in the future.

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Rapid determination of alkaloids in Macleaya cordata using ionic liquid extraction followed by multiple reaction monitoring UPLC–MS/MS analysis

Cited by 26 publications

References 21 publications

Systematic identification of compounds in Macleaya microcarpa by high‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry combined with mass spectral fragmentation behavior of Macleaya alkaloids

Systematic identification of compounds in Macleaya microcarpa by high‐performance liquid chromatography/quadrupole time‐of‐flight tandem mass spectrometry combined with mass spectral fragmentation behavior of Macleaya alkaloids

Development of a mesoporous silica based solid‐phase extraction and ultra‐performance liquid chromatography–MS/MS method for quantifying lignans in Justicia procumbens

Isolation and identification of alkaloids from Macleaya microcarpa by UHPLC–Q-TOF-MS and their cytotoxic activity in vitro, antiangiogenic activity in vivo

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